Conflict Resolution & Second Date Wait


No matter how amazing any relationship is, there will always be conflict. It’s inevitable. As humans we are going to have differences of opinions, emotions, or beliefs at least occasionally.  In the end, it’s how you navigate through the tough times that will ultimately determine the longevity of your relationship.

That’s why Jayson Gaddis, relationship teacher and the host of The Relationship School podcast, is here to share his methods for navigating conflict in dating and relationships.


Will those viral ‘36 questions’ actually lead to love?:

After having been around for years, an article from The Conversation is bringing the 36 Questions of Love back on our radars for discussion. If the 36 Questions don’t ring a bell for you, let us give you a little backstory. These 36 Questions of Love were first published in 1997 as part of scientific research into relationships. But you might actually recognize them from the 2015 New York Times essay written by Mandy Lynn Khatron, To Fall In Love With Anyone, Do This. Originally, there was a researcher named Arthur Aaron who, along with his colleagues, had a group of strangers ask each other a series of questions that became progressively more intimate in context. According to the study’s results, they found that through the gradual increase in disclosure between strangers, they also increased in closeness. And following the study, there were participants who actually fell in love and kept the friendships they’d made. Fast forward to 2015, the NYT essay then asked – if we applied these questions to people looking to fall in love, what would happen? If you ask a stranger these 36 questions, would you know enough about this person to actually fall in love with them?


So what are some examples of the 36 questions? The questions are actually structured into 2 sets which increase in intensity. Set #1 has questions like “what do you feel most grateful for in your life?” Set #2 includes ones like “what’s your most treasured memory?” And Set #3 ends with the hard hitters, like “when did you last cry in front of another person?”

According to The Conversation, the 36 questions don’t lead to love and were never intended to lead to love. But what they DO do, is they help us figure out what is really important to disclose in a relationship. Damona summarizes that you can develop intimacy with a person more quickly through the kinds of questions that you ask. And hopefully, she says, you will not be afraid when you are on a date to get to the heart of what the other person’s values, beliefs, and goals for the future are. “We tend to stay away from conflict when we’re in a new relationship. But it’s so revealing. It can really teach you how you communicate, and it can show you how to be a better listener and to be more authentic in the relationship.” And most of all, as good as it is to be open and vulnerable when getting to know someone, remember that your information needs to be earned.

(P.S. If you want a real blast from the past, check out this show Damona hosted in 2017 called A Question of Love, where the contestants asked similar questions as the 36 Questions of Love to quickly figure out if they were compatible with their partner.)


Ready to test your compatibility and find your match? Let Damona help you redesign your dating profile with the Profile Starter Kit to get you online easily and on to your dating success story. Get yours for free HERE!



Jayson Gaddis is an author, podcaster, speaker and “personal trainer for relationships”.

Jayson started off as a Licensed Professional Counselor with a private practice, and since then he has founded The Relationship School – a company dedicated to helping people work out their differences to improve their relationships. 

Today he hosts The Relationship School podcast where he teaches people how to build street-level relationship skills.  His book “Getting to Zero: How to Work Through Conflict in Your High Stakes Relationships” is out now!

(11:26) Getting down to zero:

Since his book completely revolves around the different types of conflict, Damona asks Jayson for his definition of conflict. According to Jayson, conflict = a rupture, a disconnection, or an unresolved issue between two people. His book, Getting to Zero, is targeted toward high stakes relationships, which include family partnerships, business partnerships, every relationship where we have a lot to lose if we can’t resolve the conflict. And the way that we resolve conflict is what Jayson calls “getting to zero.” He evaluates our triggers based on a 1-10 scale, and the further we are from zero, the more activated we are in our nervous system. Meaning, the more we tend to act out and react in ways that aren’t helpful for resolving conflict. “And it’s through that process of getting to zero getting back to a good place, over and over, that builds security in long term relationships.”


Damona wonders what happens when you are consistently at a 9 on the trigger scale at work, and how this can impact our relationships at home. Because let’s face it – we’re all pretty stressed out these days. “If we’re in a good place [with our partner], then no problem. Our partner can help resource us and they can be a safe place for us to vent and get support. But some of us go home to a shitty, crunchy relationship, and then we’re dealing with even more stress… So many of us are living with a lot of chronic, low grade stress, we don’t even notice the water we’re swimming in. Some of us even grew up in households that were at a 4. And that was considered zero. But it’s not good for us. Again, it creates long term health problems, if we’re living in that chronic environment all the time.”

(15:37) Addicted to the drama:

Damona mentions that people can become addicted to the drama of a relationship. So much so, that finally moving into something more secure feels boring, or like there’s something wrong with the relationship. Jayson adds that growing up in hostile or intense environments can add to that level of addiction, because it messes with your hormone release – messy ends up feeling familiar and safe. Jayson recalls working with a client with the same issue, and having to really ask the client to become comfortable with himself, and become more accustomed to his own fears and discomforts. “I was like, ‘Look, do you want a relationship where you have to leave yourself behind in that volatility, to protect yourself? Or would you rather have a relationship where you get to keep yourself, but you might lose the relationship?’ So we’re helping him deepen and enhance his relationship with himself, so that it kind of weeds out the people that try to seduce him into this up and down thing.”


() The 5 most common fights:

In his book, Jayson outlines the five most common types of fights people have. The five are: surface fights, value difference fights, projection fights, resentment fights, and security fights. Surface fights revolve around the little things (i.e. not washing the dishes, leaving dirty clothes on the floor), but are never really about the little things. Surface fights almost always lead into one of the other four types of fights.

A value difference fight is a dealbreaker for some people. Those are the types of agreements such as being pro-vaccine and someone else is anti-vaccine, wanting kids or not, moving to the east coast or west coast – these are very large value differences that are pretty hard to work out. “If we don’t know how to accept each other’s values and work with them in a relationship, we’re going to want the other person to come over to our values. And that alone creates a lot of fighting, tension, and feeling judged and criticized.” Jayson also highlights a value difference that is not commonly talked about, which is being willing to work through conflict. If there is a relationship in which one person wants to go to couples therapy and grow and develop, and the other person believes that there’s nothing to fix, that will create problems. You can’t get to zero with someone who doesn’t want to learn how. Damona adds that being clear on your own values is extremely important, because not knowing just contributes to the conflict and lack of clarity on how to resolve the issue.


Next you have projection fights, which revolve around childhood projections. We tend to find ourselves with people in a long term relationship that remind us of our family of origin, usually our parents or caregivers. And we then project onto them, which will often trigger us. These kinds of fights can be particularly difficult if you don’t realize that you are actively projecting.

Fourth are resentment fights. This is where one partner tries to get the other to change themselves in some way. “If I don’t conform when you want me to change, you’ll resent me. If I do conform when you want me to change, I’ll resent you.” And lastly, you have security fights. According to Jayson’s book, “if any of your four relational needs – feeling safe, feeling seen, feeling soothed, and feeling supported and challenged – is unstable in any way, it will impact your sense of security, and every surface conflict will be more intense because of the unresolved security issue.”

(24:17) Tools for defusing conflict:

When in the middle of conflict, Jayson has a couple of acronyms he shares in his book that will help you move towards resolution. The first is called LUFU, which Jayson describes as being a commitment to listen to the other person until they feel understood – Listen Until you Feel Understood. “In that process there’s eight steps. But the three that matter most to me are I want to take responsibility for anything I did in the listening process. I want to not defend myself, I’m gonna say ‘Yeah, got it, I did that thing.’ So I take ownership. And then I want to empathize. I imagine the impact on you, and it makes sense. That’s the validation part. The last step, ‘it makes sense’ – three words. That’s the easiest way to validate someone. ‘That makes sense that you feel that way, that you feel hurt, that you felt scared, and that you’re upset now.’ I continue to stay in my listening seat until you feel like I’m understanding you. And then eventually, you’re hopefully also going to be generous with me, and you’ll listen to what happened for me.”


Also in Jayson’s repertoire is the acronym SHORE – Speak Honestly and Openly in order to Repair Effectively. “If you take responsibility for what you did or didn’t do, that alone is going to help the other person’s nervous system chill out big time. And a lot of us don’t do that. We speak, we lead with what the other person did wrong, and how we’re right, and how they made us feel. I think it’s just more efficient to lead with, ‘are you open to having a conversation? I just want to say I messed up there. Yep, I did that thing again that really upsets you, and it makes sense you’re upset. I just want to know how you feel.’”

But as many tools as we may acquire, the one thing to have above all is a willingness to be a team player, to make sacrifices, and collaborate with your partner. 

(31:14) But what if I can’t get to zero?:

Getting to zero and working through conflict typically requires two people to work together – but what if only one of you is willing to work at it? Jayson states that family is an easy place to identify those kinds of relationships, where certain members may be particularly closed minded or unable to see their own role in a conflict, not to mention where value differences come into play. But luckily, Jayson maintains that you can get to zero on your own (there’s a whole chapter dedicated to this in his book). And sometimes you have to, because the other person will never come to the table. “I don’t want to stay angry at this person my entire life. I just don’t, it’s energy draining. So how can I get to either gratitude or appreciation, or just appreciating myself at the very least, and sort of letting go of that relationship forever?”


You can follow Jayson on Instagram @jaysongaddis, and you can learn more about his school at Plus, be sure to check out his podcast by the same name – The Relationship School.


If you liked what Jayson had to say, check out his book, Getting to Zero, HERE!



Submit your questions on  Instagram, Twitter, or Facebook and hear our answers live on the show! Here’s what our listeners asked about this week:

  • IG Message from Lisa – Hi Damona! I recently went on a date with a guy and we really seemed to click on the date. The conversation flowed well and we had a lot in common; we even talked about going to the driving range on a second date. I knew he was going out of town for 2 weeks the day after our date for a work trip, but 2 weeks is a long time to wait between the first and second date. We’ve texted a few times about how his trip is going and I’ve asked a few ‘would you rather’ questions. He’s answered all my texts, but isn’t asking me anything back. I’m having a hard time telling if he’s still interested and I’m not sure if my texts are just boring to him. How do I keep the momentum going during these 2 weeks? Should I call or suggest a video date while he’s out of town? Any advice is appreciated. Thank you!



Vulnerability & The Sleepover Talk


Warning! This episode uses more colorful language than usual. So if your kids are nearby, make sure to avert their eyes from the screen…


Damona is a big believer that vulnerability is the key to true connection. But as we know, at times it can be difficult to let others in and to know when to give a f*ck about what they say. (A swear word in the intro?? Oh yeah, you better believe it’s that kind of episode.)

This week, Damona is chatting with behavior scientist and lifestyle design coach Gianna Biscontini, the author of the new book F*ckless: A Guide to Wild, Unencumbered Freedoms. They’ll be discussing how vulnerability can lead to emotional depth and better opportunities for connection.



Scientifically speaking, what does it actually mean to click with someone?:

Inc Magazine recently came out with an article tackling the science behind the feeling of “clicking” with someone. The article uses a new study published in The Proceedings of the National Academy of Sciences, in which researchers out of Dartmouth, used 322 conversations between strangers to get a sense of how participants rated their level of connection with each other (i.e. how much they clicked). The researchers made a point to pay attention to the gaps between responses in the conversation. And after all their observation, a clear pattern emerged – the quicker the response times during the conversation, the more the two parties reported feeling like they clicked.

The researchers also looked at the conversations from an outsider’s perspective. They edited the videos to make it look as though there were shorter response times between participants. As a result of the editing, the observers actually rated the conversational partners as being more closely connected.

On average, there’s about a quarter of a second gap between turns during a regular conversation. But when people felt like they were finishing each other’s sentences and really clicking, they closed that gap. So basically, clicking with someone comes down to how much the conversation flows without long pauses or awkward brakes.


Although this article gives us a window into how we naturally think, Damona highlights two of the key flirting tools she teaches clients that actually involve slowing the pace of the conversation down. “Whether or not you can close that quarter of a second gap in a conversation does not actually relate to long term compatibility. So I’ve actually encouraged you on the show before to take more time to allow more of the pauses, and not be in such a rush to fill the pause.”

Damona recommends seeing what happens if you allow the pause to happen, which also takes the pressure off of yourself to be witty, charming and quick with your answers. The second tip Damona gives is to pay attention to that person’s speaking pattern. “One thing that happens when you’re connecting with someone, when you’re really actually connecting with someone, is you start to naturally mimic their body language, their intonation, their inflection, their pacing.” She continues that attempting to speed up the natural flow of conversation could actually signal to the other person that you’re not on the same page as them. Instead, try to match their pacing rather than trying to change it for the both of you. Prioritize the full body context of the other person, not just how quick and witty they are. Because if we continue to search for for that witty or rapid delivery, we may end up missing that juicy, deeper level connection.


Ready to click with your person? Let Damona help you redesign your dating profile with the Profile Starter Kit to get you online easily and on to your dating success story. Get yours for free HERE!



Damona sits down with lifestyle design coach and Board-Certified Behavior Analyst Gianna Biscontini! She is the author of F*ckless: A Guide to Wild, Unencumbered Freedoms – which will be released on May 17th!

Gianna has been featured in publications such as Forbes Magazine, and she has a roster of A-list clients including Christina Schwarzenegger and Simon Sinek (you know, the Start With Why guy).

(9:04) Choose what you care about:

Jumping right into her book title, Damona asks Gianna – what does it really mean to be f***less? Gianna responds that it’s not whether you care or not (i.e. whether you give a f***), it’s what you care about. “F***s are our opinions, beliefs, expectations, fears, or advice from other people that don’t belong to you. All of us carry some level of other people’s bullshit, whether it’s from our parents who love us very much, whether it’s from a professor who was working out some anger through us, society, the entertainment industry, whatever. We’re given these messages, and we take them on as if they are true for us. And then you hit your 20’s, your 30’s, your 40’s, your 50;s. And you go, ‘Oh shit, that’s actually not true for me.’”


Damona brings up the point that although it can be overwhelming nowadays (especially for women) to be told what we’re supposed to care about, there also exists the reality that we’re in a much broader place of choice than many of our ancestors. So there really is a responsibility to be mindful of choosing what you care about. Gianna recounts times in her life where she had no choice but to stay in an unhappy relationship because she couldn’t afford to live on her own. And that the reality of women who are financially independent is quite different, because their choices are led by their wants, not their needs. 

“In the book, I ask questions like – Is this a good time for you to be in a relationship? What are the stories that you’ve been told as a woman about being in a relationship? What do you think being in a relationship and having a partner will do for you? What might it hold you back from? …I think that with some thoughtful inquiry, we can tease apart the needs from the wants, and the stories that are just f***s that aren’t true for us, and the things that we truly believe in.”

(13:40) Being chosen:

At times we may silence ourselves and our opinions because we want to ensure the happiness and comfort of those around us by avoiding confrontation and anger. Damona says that most of us would rather be liked and be likeable (which may not even be conscious). Gianna describes how this applies to one of the “f***s” she addresses in her book, called “be chosen.” Gianna grew up constantly envying the endless freedom bestowed upon boys. To her observation, they got to make mistakes and sleep around, while girls’ lives tended to orbit around them. “Men do the choosing and women are chosen, and so we have to just really be mindful about these stories and understand that we have the power to change them.” 


In terms of dating, Gianna notes how much she used to base her decisions on the approval of men. For instance, she would hold back on going on larger adventures on her own because she wanted her life choices to be compatible with whoever she might date in the future.  She says she was doing two things wrong. “Number one, I was making the wild assumption that there would be someone in the future to begin with.  And number two, I was already orbiting around someone in my future that didn’t even exist.” 

After choosing to leave her marriage, Gianna spent the whole of 2020 and 2021 committed to being single and following that experience (which ended up being really easy, thanks to the global pandemmy). “Dating is all about choosing and not choosing, and getting to know each other. And sometimes you date for a couple of weeks and you say, ‘No, I’m good. This isn’t for me.’ And sometimes you just, you know, Sunk Cost Fallacy. You just keep choosing because you already invested so much time and energy, which is a whole other thing.”


(19:00) There is no destination to be reached:

Damona reads the quote from Gianna’s website, “Life is not linear. It’s filled with events that require us to restore, calibrate, and head back out into the world with clarity.” Damona describes coming to the recent conclusion in her life that there is no actual destination to be reached because as soon as you get to one destination, another appears or there’s something more to be learned.

Gianna jumps in, “You know, you’re talking about mindfulness. It’s that Buddhist concept of non-attachment. How many times have you said, ‘Okay, here’s the plan. And this is what’s going to happen. And I’m going to control it. And I’m gonna go through steps one through five, and then this will be the result.’ And it alerts something in the universe, and it comes in with a wrecking ball, like ‘Oh, that’s precious that you’re trying to plan when you’re gonna get married.’ … We have to just be in that place of mindfulness, live from within, and be open to the things that are around us.” Being present is all that we can really control, which involves checking in with yourself and asking clarifying questions – who am I? What are my values? How am I serving myself? How am I building and designing this life?

(21:23) What should we give a f*** about?:

Gianna speaks to one of the other f***s in her book, called “be everything.” Just as it describes, this is trying to be everything to everyone all the time, and letting what you want take a backseat. “When we hesitate and when we stall, and when we want something, but reel it back in, that’s a moment where we have to go, ‘Oh, I’m living on someone else’s terms.’ …And so when women start to try and be everything to everyone, the first question is why? Second question, where did that story come from? The real work comes in actually behaving differently and dropping the fact that you have to be liked, that everyone has to pat you on the back and reward you and validate you for everything that you do.”


Gianna adds that letting go of what others think shouldn’t come from a place of disrespect.  She says that we can learn to hear the opinions of others, and give their opinions back with grace by saying “I can see why you want that for me. But that just doesn’t work for me right now.”

(23:25) Reframing success:

Damona is a big fan of dating apps, but she recognizes that they come with many micro choices. She believes that we have to reframe our relationship with the “rejection” that shows up on dating apps. “People will say to me, Gianna, ‘I tried the dating apps. They didn’t work for me. You know, I only went out with somebody for three months and then it didn’t work.’ No, no, it did work. It did work for that time. And it worked until it didn’t.” It’s all about our perception of success.

Gianna brings up a great question, which seems obvious but gets overlooked: are you on dating apps to be validated, or are you looking for a partner? “We have two needs as people. We have the need to show up in the world as our truest, most authentic self. And, we need to do that in a world or a friend group or a family or a society that accepts it, and loves it, because of who we are… You’re curating a group of people. You’re curating friends, you’re curating who you’re dating, and you’re teaching yourself what’s important to you and what you’ll accept. And that takes, unfortunately, a really long time.”



Look out for Gianna’s book F*ckless: A Guide to Wild, Unencumbered Freedoms, on shelves May 17th – order your copy HERE

And be sure to follow her on all the socials @giannabiscontini.



Submit your questions on  Instagram, Twitter, or Facebook and hear our answers live on the show! Here’s what our listeners asked about this week:

  • Email from Ginny – What do you think of a guy who tells me before a phone conversation or date, that if I’m someone who waits 3-6 dates before a sleepover we’re not a match? I think he was hiding something, which became obvious after a while. He claimed he wanted to take things slow and that he wanted a long term relationship, like I did, but then pressured me to answer how many dates till we sleep together. I told him ‘you are putting the cart before the horse, as we haven’t even met yet. Besides, taking things slow means not discussing this in the first conversation.’ He was evasive about other things, like he told me he worked for a large well known company, which shall remain nameless. I felt he was very opinionated, almost belligerent. When I told him I was open minded, he asked what that meant. Well, I guess you’re not then. I think he was using a burner phone too. Questionable!



New Mindset & LinkedIn Love

You’ve heard Damona say on the show before that mindset is everything when you begin your dating journey. You have to know who you are and what you’re looking for, and it helps to have mindset tools in place to support and keep you going when things get tough. And we know it gets tough.

That’s why Case Kenny, Instagram sensation (quite literally) and host of the New Mindset, Who Dis? Podcast, is joining Damona today to discuss how his methods of mindfulness will benefit you in dating and relationships.


Are you looking for love in all the wrong places?

According to the latest in Insider Magazine, people are using Tinder not to find love… but to sell insurance policies. This article tells the story of a guy who matched with a gal on Tinder, they went out for coffee. He thought that sparks were flying, but then she started pulling out all of these insurance packets and proceeded to try and sell him an insurance policy!! She was literally just using Tinder as a way to get clients. The experts in the article suggest that this is due to the “blurred nature of the online world” (although Tinder has been pretty clear that promotion or solicitation is a violation of their community guidelines).


On the flip side, while people are using Tinder to reel in customers, others have been using LinkedIn to find dates. There are a lot of people on the site who have blogged about finding their significant other through the platform, despite being a professional networking site. But putting all the community guidelines aside, this behavioral trend begs the question – why do we try to control the platforms that we’re on? Speaking to the blurred nature of the online world, once a platform is created, it kind of takes on its own identity and its own nature of possibility. The reality of all of these platforms, whether it’s Twitter or Tik Tok or LinkedIn, is that they’re actually created for connection. Just because a platform is created with a certain purpose, doesn’t mean that that is the meaning it will take on later down the road.

Damona adds, “When we look at it in the offline world, it’s actually kind of ridiculous. Like, you don’t say, “I intended to meet someone in a bar. So I can’t go to a bar unless I’m there to hook up or to date or to meet someone. We don’t do that offline. Why are we doing this online?” So given how fluid online forums will continue to be, the more we can stay open to possibility and stay present, the sky’s the limit on the connections and the conversations that you’re able to create.


Not ready to try dating on LinkedIn? Let Damona help you redesign your dating profile with the Profile Starter Kit to get you online easily and on to your dating success story. Get yours for free HERE!



Damona is bringing us an interview with Case Kenny, Instagram sensation and host of the New Mindset, Who Dis? Podcast.

Case is also the Founder and Editor-in-Chief of – “a quirky, no BS mindfulness email that feeds your soul.”

(7:42) A love for mindfulness:

Although Case is often asked to talk about relationships and give relationship advice, he hasn’t quite gotten used to it yet. He shares how this was not by design, since he originally started his podcast as a means to share his love for mindfulness and how to take an optimistic, self-aware approach to life. “For a long time, I never touched relationships because I thought, ‘Who am I to give relationship advice? I’m a single guy in my 30s.’ But you know, more and more I talk to people and they’ve said, the area of life where we need mindfulness most is relationships. So I started to give my thoughts, not my advice. Not ‘here’s what’s right’ and ‘here’s what’s wrong’. But just my thoughts on exactly what you said, what can you take from dating experiences that aren’t necessarily great? And I started to do that, and I just realized that there was a lot of power in it.”

(9:28) Not afraid of a good cliché:

One of the things Case is most notable for are his extremely relatable and shareable Instagram posts, in which he holds up mindfulness quotes against urban or cityscape backgrounds. (An example of one of his recent quotes is “sometimes the only closure you need is deciding you are worthy of mutual effort and respect.”) 


So where does Case get the inspo for his content? He states that the majority of what he posts are obvious truths, but that our life experiences can sometimes cause us to forget these truths. “I think a lot of times we confuse ourselves, we overthink. Life beats us up to the point where we no longer believe these things that at some point were fundamental to us. Namely, you don’t chase people who aren’t interested in you, you can’t force someone to love you. Y’know, you shouldn’t ever want to do these things. But I think life, you know, adds up over time, and we forget these things. So I am not afraid of a good cliche, I’m not afraid of stating the obvious, because I think it’s my mission in life to remind people of the things that we know…”

Case mentions that another part of his inspiration, which he also describes as one of his favorite pastimes, is asking older generations what they regret in life. “It’s like a weird, seemingly downer thing to do. But I’ve learned so much from observation and deep thinking, I spend all day every day thinking about these topics.” Damona adds that she often asks her clients to find a relationship role model for themselves. Because you might not have come from a family where healthy relationship dynamics were modeled for you, but that doesn’t mean you can’t gain that knowledge, insight and wisdom through the people you interact with.

(13:02) Be more you-specific:

And when you’re someone who gives relationship advice, you know that you’re going to be asked about relationship red flags. As Case details, the reason talking about red flags is so popular is because, as humans, we gravitate towards absolute truths (although life isn’t always this straightforward). Case recently did an episode on his podcast about red flags, and actually spoke about the red flags his younger self had been putting out while dating. And the biggest one for him was lack of clarity – dating without a reason to date. He adds that this is actually a hurdle that is pretty rampant in today’s dating climate as well (makes a lot of sense, since ‘situationship’ is now practically a colloquialism). 


Case then speaks about the book he wrote that tackles this issue: “I wrote a book called Single Is Your Superpower, and Chapter One was to sit down and ask yourself, why are you dating? And most people were like, ‘What do you mean? Of course, you’re supposed to date, you’re not supposed to be alone. I want to start a family. I want to leave a legacy.’ Very like biological, societal things. And I think those are fine answers. But I think we need more intentional specific-to-you answers… I don’t think it’s an over standard to say I expect someone else to know why they’re dating.”

Damona asks Case to speak a little more about why he himself used to back away from partners who expressed clarity with him. “I’d say two quick things. One, that was a reflection of my lack of maturity, for sure. Like not knowing what I wanted, but continuing to date without knowing that and then being scared off by someone who knows what they want. That’s immaturity… But I think a bigger part of that is lack of awareness around conditioning, lack of awareness around things like attachment styles.” Case ends with the biggest revelation he had being that in dating, there is always going to be some amount of discomfort. And that can show up in different ways – discomfort from being single for a long time, discomfort from having a routine to bringing someone into your life, etc. A lot of people see that discomfort as a sign to back up, but everyone feels that discomfort. “I think any great, rewarding compatible relationship requires that both people challenge the discomfort and engage in the discomfort rather than seeing discomfort as a sign to back up.”

(18:14) Patterns are only patterns:

Damona brings up one of Case’s favorite bites of knowledge, which is “patterns are only patterns until they stop becoming patterns.” Case explains how he believes “the greatest things are on the other side of tremendous friction and frustration, and discomfort and lessons learned. And if we understand that, then hopefully we can empower ourselves to see the ups and downs – and the downs, and the downs – in a way that empowers us rather than pulls us back.” So instead of being a victim to your circumstances (which then may lead to patterns that you get stuck in), ask yourself how you can flip negative observations and experiences into things that empower you rather than lower your standards. Case notes that it’s very tempting to come back to negative assumptions about ourselves, and when we look for the lessons in our negative experiences, we are able to break out of our negative cycles and take our power back.


(20:18) Sitting with discomfort:

Speaking of taking our power back, Damona once again brings up the idea of discomfort and how it’s such a necessary feeling, because it is the feeling of change happening. Damona then inquires if Case has any exercises on hand for getting more comfortable with discomfort. In the context of dating, Case says “the question is, is this person capable of loving me? Like, that’s always the question… It’s like one thing to go on a couple dates and be like, this is great. But like, is this capable of turning into something real? You look at it through the lens of, is this person willing to embrace the discomfort that’s going to come? Or are they going to back up from that discomfort?” On the flip side, negotiating discomfort in dating isn’t always an issue with the other person. You may then have to ask yourself, am I willing to embrace discomfort to know what I have to do? And more immediately, you may ask yourself, am I willing to embrace the discomfort of stating my intention on day one? Am I willing to embrace the discomfort from what could be rejection, judgment, maybe a weird look? If you can ask yourself these questions and work towards being more comfortable with discomfort, then you unlock a whole new realm of possibilities.

(22:47) Fact or Feeling:

In another recent episode of his podcast, Case tackles the idea of honoring your feelings, but not trusting them. Now what does that mean, exactly? Basically, it’s recognizing and remembering that your feelings are not facts. We can acknowledge the things we tell ourselves or the negative thoughts that come up without fully putting our faith in them. “It’s the ultimate balancing act, right? Like your feelings are your greatest friend, but also can be your greatest enemy. Like, your intuition is so powerful.”


So how do we know when to trust our emotions or intuition? Case gives Damona an exercise he likes to use called Facts or Feelings. “What I think is really helpful is to establish a list of facts for yourself. Those are facts that you fundamentally believe, and you compare those to your feelings. So for instance, like you come up with a list of facts – I believe that my hard work will pay off. I believe that I am worthy of honesty and kindness, whatever it may be. Those are the facts. When you have a feeling that isn’t aligned with that, you should always listen to it. You shouldn’t ignore, you shouldn’t exist outside of your feelings. But I found it really powerful to take a look at the feeling and compare and contrast that with the fact, and then realize that facts are permanent in your life. The facts are non-negotiable. The feelings are temporary.” Remember that whatever facts you choose, these are the statements that you will never negotiate on when it comes to your worth or what you believe, or how you see the world.

(26:33) Is mindfulness a form of meditation?:

With so much information on how to be mindful in everyday life, could one say that practicing mindfulness is basically meditation? On the contrary, Case believes that meditation is a form of mindfulness. To his interpretation, Case sees being mindful as being self-aware, and in turn being self-aware is to be radically honest with oneself. “Radical Honesty is defined by the practice of asking yourself why, and answering it. So I consider mindfulness the practice of why – a three letter word, very powerful. That’s why I think meditation is a form of asking why. It’s a form of, why are my mind and my body in two different places? Why am I allowing this thought to absorb my energy? Whatever it may be.” 


When you make it a habit of asking yourself “why,” Case says that you begin to experience two things – closure from the past, and clarity in the present. And when you’re operating from a place of closure (or rather, from a place of peace), the answers to all your “why” questions become infinitely clearer. 


Check out Case’s podcast New Mindset, Who Dis? And follow him on Instagram @case.kenny for your daily dose of mindfulness. 



Submit your questions on  Instagram, Twitter, or Facebook and hear our answers live on the show! Here’s what our listeners asked about this week:


  • IG Message from A – I’m usually an anxious-avoidant and working on it. I’m 33 and my new mate is 36. It all started when I was visiting NYC about a month ago and I matched with him on Bumble. We went on a first date and it felt really good – like, long-term potential good. What was meant to be a hookup developed and I really felt like I wanted to see him again. So, a few weeks later I flew back to NYC. Our time together was INCREDIBLE. Now he is coming to see me (and stay with me) at the end of this month for a couple of days. I realize this intense romantic phase fades, but since we’re across the nation it feels like a special situation and we want to make the most of our time together. I told him I’d like to talk more about deeper things and text less so we can develop more closeness. Last night via video chat, we spoke about both wanting a long term partnership with the right person. Next he asked me if I wanted kids (he wants them). Having kids terrifies me because I didn’t have good examples growing up, but things shift and maybe it could happen with the right person. It got a little awkward and I felt really anxious after we wrapped (I felt like I overshared). On one hand it kind of feels quick, but on the other hand it feels amazing that we are genuinely connecting. But I know my brain is on love drugs, so I am having a hard time thinking of this objectively. I read some articles that say I should avoid oversharing and moving too quickly in the beginning because things can blow up if we skip the ‘getting to know each other’ phase. How do I identify if we are going too fast and should I attempt to slow things down? And if we are going too fast, how do I slow it down without seeming unstable or like I’m holding back out of fear, when all my heart wants is to lean in?


Dating with Anxiety & The Newly Single Scene

Many people find the uncertainty experienced in dating and relationships stressful, but is anxiety keeping you from meeting your match?

New York Times Best-selling author Allison Raskin, co-host of the Just Between Us podcast, is here to discuss how coming to understand her anxiety and OCD have helped her to approach dating from a new perspective.


The opposite of jealousy:

What is the opposite of jealousy? Well according to Psych Central, it’s a feeling called compersion. To give y’all a definition, compersion is our wholehearted participation in the happiness of others. It is the sympathetic joy we feel for somebody else, even when they’re positive experience does not involve or benefit us directly. Thus, compersion can be thought of as the opposite of jealousy and possessiveness. To add some historical context, this term was first coined by the Karissa Commune in San Francisco, which was actually a polyamourous community! This new definition was meant to encapsulate the feeling that you got when you saw your partner with another partner, and made you feel joy rather than jealousy. The article addresses a question you’re probably wondering – is it possible for monogamous people to feel compersion as well? And it definitely is! Monogamous couples may already be experiencing joy for their partners through experiences such as their close friendships or work wins.

Damona suggests that compersion may actually be an opportunity to visualize the kind of partner we want to be in a relationship with, and how we want to feel when we’re with them. Turning your feelings of jealousy into compersion could also act as an opportunity to experience a stronger feeling of connection and oneness with your partner. Psych Central gives some tips on ways to practice compersion in your relationship. The first tip, although counterintuitive, is to acknowledge your feelings of jealousy instead of pushing them away – when you first recognize that the feelings are there, it relieves any tension or judgment you may have around experiencing jealousy in the first place. 


Another suggestion of accessing compersion is to practice it first in non-romantic relationships.  Practice compersion when a family member or friend is experiencing joy. And if you are having a hard time shifting your feelings of jealousy to joy, not to worry – the article states that it is definitely possible to feel compersion and jealousy at the same time. Regardless, keep an open mind to how practicing compersion may help you find greater compassion for your romantic partner, as well as every other relationship in your life.


Ready to find your match?  Let Damona help you out with the free Profile Starter Kit to get you online easily and on to your dating success story. Get yours for free at HERE!



Damona sits down with Allison Raskin, New York Times bestselling author and co-host of the Just Between Us podcast.

Allison is the author of “Overthinking About You: Navigating Romantic Relationships When You Have Anxiety, OCD, and/or Depression.” Additionally, she has developed shows with FX, Netflix, MTV, YouTube Red and 20th Century Television.

(10:52) A hard time with uncertainty:

Before writing her book, Allison was truly surprised that a book hadn’t yet been written on the experience of what it’s like to date with anxiety and OCD. She recounts that mental health has always been a prevalent part of her life, since she was diagnosed with OCD at four years old. “I don’t think I’ve recognized how my anxieties and my different mental health struggles made dating really hard. I think I really viewed them as two separate things that I have mental illness. And also, I’m bad at dating.” Allison shares that the uncertainty of dating was the most challenging part. She felt stuck in this loop of forever trying to lock things down, trying to define what things were and trying to get reassurance that the relationship was leading somewhere. So when she began dating in a healthier way, she felt extremely curious that this kind of change was possible. One of Allison’s missions in her book is to address the changes you can make to date in a healthier way.


(15:08) When is the time for intervention?:

Allison explains that in order to date in a healthy way, you have to be in a stable enough place to do so. “There have been times in my life where I’ve just not been stable enough to date. And that didn’t stop me from dating, and then it was a disaster. But I think the ability to really check in with yourself is important.” Be sure to keep tabs on yourself, and your reactions to different dating scenarios. For instance, Allison mentions that if your date were to cancel plans with you at the last minute, there are two very different reactions that could be had. The first is to feel rightly annoyed and shake it off, and the second is to spiral into self-deprecating thoughts. Both of these reactions can help to let you know where your head is at, and how much your external circumstances are affecting your internal reality.

(17:13) The value of diagnosis:

Damona asks Allison about weighing the difference between having anxious thoughts while dating, versus having an actual diagnosis such as Generalized Anxiety Disorder (which Allison has herself). “It’s interesting, because there’s a lot of debate within the mental health community about the value of diagnosis. A lot of people don’t really think there’s much value in diagnosing people. And instead, it’s more important to just work with the individual and their personal symptoms and making their daily life better.  The value in diagnosis often gives us a common language and vocabulary. So if I go from one therapist, to another therapist, and I say, ‘I’ve been diagnosed with OCD,’ they have a general idea of what that means.”


So, when is the right time to reveal your diagnosis to your partner or the person you’re dating? Allison expresses that it’s really important to pay attention to what stage you’re at in the relationship versus how long you’ve known the person. “So for some people on a first date, you might dive into some really deep topics.  Some people are just naturally more open and vulnerable… And so when you are talking about the more intimate things, then it becomes a little tricky to omit the mental health of it all. But if you’re in a stage of dating where it’s pretty casual, you’re just talking about work friends and what movies you saw, and you haven’t really deep dived into the bigger life stuff, then I don’t think that you need to share it yet… Because it’s not just about ‘Oh god, I’m sharing this thing. I hope that they don’t reject me because of it.’ It’s also how does this person receive this information. It is a great opportunity for you to see if this person is even worth your intimacy and your vulnerabilities.”

(21:58) Is dating with OCD a big deal?:

Dating with OCD or another diagnosis is one thing, but how do you navigate your mental health once you are in a relationship? Allison affirms that if your diagnosis impacts your day to day life, it’s going to impact the day to day life of whoever you’re with. Because of this fact, communicating with your partner is key. “Really understanding the way that your brain works, and then being able to have the language to explain that to another person is uncomfortable, it’s vulnerable. But it’s going to serve you so much. It’s so important to get there.” Letting your partner or date know when you’re struggling can give them the insight to know why you’re reacting the way that you are.

If being very forward with your partner about your diagnosis sounds scary, Allison recommends roleplaying – “If you have somebody in your life that you trust, that maybe already knows this stuff about you, you can have a roleplay conversation with them. When you know that you’re starting to date somebody and you’re getting ready to tell them [about your diagnosis], you can practice out loud with someone else, what you want to say and how you want to say it… Because then in the moment, you have that to fall back on, versus the potential anxiety of not knowing what to say, which will then impact the way that you say it.”


(26:09) From fiancé to boyfriend:

Although Allison is currently living with her new boyfriend, the end of her book includes personal anecdotes having to do with her previous partner, her fiancé to be exact – so what changed? Allison recounts that when she was writing this book, she was living with a different person who eventually proposed to her in May of 2020. “It was basically my dream come true. I’m somebody who has always wanted to be married, always wanted a life partner. And it was also like, ‘Oh, great. I’m writing this book about how to date in a healthy way. And I won, I got engaged! By the time the book comes out, I’ll be a married woman and I’ll be able to speak from a level of expertise I’ve never had before and all this stuff.’” (When writing the book post-proposal, the last chapter had a whole interview between Allison and her ex-fiancé.) 

Later that year in November 2020, on a very random night, Allison’s ex told her that the relationship was over, that something was missing. “He didn’t want to work it out, he didn’t want to do anything. He had unilaterally decided that the relationship was unsalvageable. And for an anxious mind, it can be really harmful to try to fill in what is that something. Because then you can start to go, ‘Oh, I’m ugly. They don’t find me attractive anymore. I’m annoying. They think I’m a bad mother. They think that my OCD will ruin his life, like you fill in that blank because they didn’t give you any answers.’ It was very ironic, because I kind of became the first guinea pig of the book’s messaging, where I was able to have this huge heartbreak without also having a mental breakdown. And I remember feeling in my gut, this is so awful. This is so painful, but I know I’m going to be okay.”


(30:42) Leading with optimism:

We won’t spoil all the juicy parts of Allison’s book, but Damona remarks how the last line Allison leaves readers with is “don’t give up on yourself, and don’t give up on love.” Even after having experienced devastating heartbreak, Allison remembers how she made the decision to not let her ex control her life. “If I didn’t start dating again and if I gave up on this lifelong dream of having a partner, then not only was he robbing me of the future I thought we were gonna have together, he was robbing me of any good future I could have for myself. And so I really decided I had to take the power back. And for me, taking the power back meant not letting it prevent me from the type of life I wanted… And so I kind of dove back in [to dating] pretty quickly, because I could tell that if I waited a long time, I was going to be too afraid.”

Allison adds how a big part of moving forward from heartbreak was learning to be okay with the gray, instead of always needing things to be very clearly black and white. “It felt really uncomfortable for me to be dating somebody while I was still in love with my ex-fiancé. That process took a long time, and a lot of the beginning of our relationship was me getting over somebody else. I credit myself for being able to tolerate that discomfort. And I also really, really credit John for giving me the space to do that, and not making me feel like I had to hide my thoughts about it.”

(35:34) Come from a place of love:

Damona asks for Allison’s thoughts on what to do if you are the partner of someone with a diagnosis, and how to best support them? Allison answers with another of the book’s vital themes – you need to be your primary helper, and then your partner is your secondary helper. “When somebody is suffering with these various disorders, I get that you want to help them and you want to be a support system. But for it to be a healthy dynamic, they have to be their own primary helper. If you develop into a pattern where it’s all on you to help them and they’re not doing things to help themselves, that can be really problematic. But if you have a partner who has the language and the ability to say, ‘Hey, I’m noticing that my depression is getting worse. I’m going to go back to therapy, I’m going to start exercising more regularly for the dopamine.’ Then you can say, ‘Great, thank you for telling me. Now I know that the reason that we’ve been off is because you’re off, but it’s not a reflection of how you feel about me. Thank you for that clarity. Let me know how I can support you in helping you get better.’”


Along with being a secondary helper, Allison says that it’s always important to come from a place of love versus accusation. That can show up in many ways, for instance instead of stating your feelings as fact, observing “Hey, I’ve noticed that, it seems like maybe your anxiety is a little more present than it’s been in other times. Does that feel true to you?” Or reminding your partner that they’ve gotten through these episodes before, and they’ve gotten themselves back up. 


Check out Alison’s podcast Just Between Us, and you can follow her on Instagram @allisonraskin

And be sure to order your copy of Overthinking About You, on shelves May 3rd!


Submit your questions on  Instagram, Twitter, or Facebook and hear our answers live on the show! Here’s what our listeners asked about this week:

  • IG Message from Wanda – Hi Damona! I am a 55 year-old woman who has been permanently separated for the past 9 years from a 28 year marriage. I am interested in dating, but the truth is, I don’t know how. I come across as an extroverted person, I am a portrait photographer and nurse. I married someone from my neighborhood to reduce any challenges in my world. But even more than marrying that way, I stayed in the marriage! Now fast forward, we are in the time of online dating and I have no idea how it works. I meet men and I freeze, I don’t know what to say or do. Please help me, thanks!



Deeper Dating & Comfortably Single

Most of us are looking for love, but is it possible some of us are doing it all wrong?

Psychotherapist Ken Page of the podcast Deeper Dating is here to share how self empowerment and a deeper understanding of oneself can lead to deeper and more optimistic dating.


(1:30) A new term for our Dating Dictionary:

This article in InStyle Magazine describes how “hesidating” is running rampant among singles right now. Plenty of Fish coined this new term, since a recent study of theirs showed how 70% of singles are unsure about their relationship status, and whether they want something serious or more casual. So in other words, they are hesidating (hesitating to date).

The article and Damona both agree that this heightened hesitancy is a downstream effect of the pandemic,  considering how none of us are sure when the pandemic will really subside. Damona brings up another article she spotted in the New York Times, which dove into the experience of languishing (which similarly mirrors the feelings behind hesidating). According to this article, languishing is this feeling of not quite being depressed, but not really being excited and optimistic. You’re just languishing – you’re in the middle. As a result, it just creates all of these icky feelings that bleed over into other areas of our lives.


Damona recounts all the highs and lows we in the dating scene have experienced as a result of the pandemic. When Covid first hit in the Spring of 2020, singles were using dating apps as a tool to connect amidst all the separation. Then there was the first Summer of Uncertainty, which bled into the Fall Haze (where languishing started to develop). By the following Summer (aka Hot Girl Summer), people were pulling away from dating apps and dating in general because of the Delta surge. Now, singles continue to hesitate in dating because all of the restrictions keep changing. Although we are still unsure how safe it is to be dating out in the streets, Damona states that partnerships and relationships are the things that fuels so much else, and could potentially be the key to moving on from languishing.

You can be on the apps… but if you’re not really present with your swiping and are continuing to hesitate, it is wasting your time and energy. We have spent so much time behind our screens, cornered away in our own little worlds. It will take decisive action, not indecision, to move forward. It is okay to only be seeking casual dating right now (and maybe it’s the answer to move you out of languishing) – own that, embrace it. But if you want something more serious, lead with that in your dating profile and on your in-person dates. Figure out what you need to shore up emotionally to come to the table as a whole person, because dating will bring out all your stuff. 



Need help expressing your relationship goals in your dating profile? Downloading my Profile Starter Kit may be the first step for you! Get your free kit HERE.


KEN PAGE (8:30)

Damona is here with Ken Page – LCSW, renowned psychotherapist, and host of the Deeper Dating Podcast. 

Ken is the co-founder of, an online dating experience for single people to meet in an environment that’s kind, respectful and inspiring. He’s been featured in Oprah Magazine, The New York Times, Cosmopolitan, Fox News, and is also the author of Deeper Dating: How to Drop the Games of Seduction and Discover the Power of Intimacy.

Ken is passionate about helping people understand the search for love as one of the greatest spiritual adventures in life.


(9:42) Our core gifts:

Before learning how to date successfully and finding his life partner, Ken notes how he carried the inherent belief that he was not attractive enough, and therefore wasn’t confident enough, to attract the attention of other men. He went on this intense journey of becoming extremely buff and physically in shape (believing his “attractive” problem was fixed), only to find that it had made no difference in pulling in the kinds of people he wanted to date for a serious relationship.

Damona asks Ken what shifted in order for him to meet his husband. “The thing that made the difference was that an innate quality of goodness in me, that I had been embarrassed about my entire life – I finally learned to honor and dignify and treasure, and take it really seriously. And when that happened, that’s when everything changed. And that made me begin to think, maybe there’s a pattern here. The pattern being that there are places of passion and vulnerability that we think we need to hide to find love, because we’re either not enough, or we’re too much. Those parts are what I call our core gifts. And when we start to treasure those, and then we make this shift, we say I am only going to look for someone who treasures those qualities in me, and where it’s mutual. And that is it. When we make that change, our world changes. And hope comes back because we start to see things change.”


(13:20) Attractions of deprivation vs inspiration:

Ken often speaks of “becoming a student of your attractions” – meaning, instead of focusing on becoming irresistible to quality people, you have to become irresistible to the kind of person who is looking for someone just like you by being you. “The focus is on how to become more attractive. But the deeper focus is, who am I attracted to? What are my attraction patterns? And how can I begin to shift those?”

Damona then brings up another concept that Ken teaches, called Attractions of Deprivation vs Attractions of Inspiration. The idea here is that we cannot force our attractions, but we can educate them (although this process takes time). Ken lists two changes you can make regarding these attractions that will set you up for profound change: “The two changes I think are embracing those authentic qualities that we talked about… And the second is to choose your attractions of inspiration and saying no to your attractions of deprivation.”

So how does Ken define both of these attractions? “Attractions of deprivation are the people who almost are able to commit, who almost treat you like they treasure you consistently. But no, they don’t. They can’t… And when you’re hooked, then there’s this feeling of the person pulling away or not being there, which triggers an ancient response of ‘I cannot lose this person.’ So this feels like love. But it’s not love… It’s an attraction of deprivation.” Once Ken started to honor and champion his own core gifts, he developed more of a pull towards attractions of inspiration. “I realized I could also be attracted to people who were kind, decent, and smart and were available… It would be a different kind of attraction. It might not be as white hot as first, but something in my heart and soul would feel really good.” 


In order to find your attractions of inspiration, Ken suggests asking yourself this question: “Does my deep heart feel safe with this person? And if the answer is pretty much consistently yes, you’ve got something to go on. Then all the other stuff follows.”

(23:24) The wave of distancing:

Damona ponders how an Attraction of Inspiration might also feel more like a slow burn, rather than an instant spark. Ken expands into what he calls “the wave of distancing, which I think is the single greatest destroyer of healthy new love.” The wave of distancing is the process of meeting someone who feels like an attraction of inspiration to you, and they are available and ready to build a relationship. Then out of the blue, things about them start to seem less exciting and not as desirable. “What that is, is a spasm of fear, in many cases, because you finally met someone that really could be available and that’s scary as hell… But by not pressuring myself and giving myself space for this kind of thing that I have, that many people have, it went away.”


(26:00) Valuing kindness in the scope of dating:

One of Ken’s core values as a coach revolves around valuing and practicing kindness in one’s dating life. He details that when you slow down and look for the goodness in someone, you create more space to notice the things about people that resonate with you simply for who they are. You begin to operate less from a fight or flight/sex vs flight/romance vs flight kind of place, because your values will change as well. And in turn, Ken says that you will make better choices overall when you practice kindness. Ken also continues with how dating apps can tend to hold us back: “When you’re doing that quick thing of just swiping, you actually will be much more prone to choosing your scratch-the-itch type, which, according to a lot of couples theory, are the people who embody both the best but also the worst characteristics of your primary caregiver… Your ego wants to go back to the scene of the crime to finally get the perpetrator to love you, right. And that does not work so well… By making these deep shifts, you’re actually going to notice different people, different sensors get activated, and they’re much better sensors. [These] will lead you to a much happier future.”


Check out Ken’s podcast Deeper Dating and follow him on IG for more advice!


And if you’re curious, head over to Ken’s website for more info on working with him.



Submit your questions on  Instagram, Twitter, or Facebook and hear our answers live on the show! Here’s what our listeners asked about this week:

  • VIP Question from T – I have trouble identifying what value I bring to a relationship – do you have prompts to help? I have some complacency arising, feeling “comfortably single” when I think about taking action towards dating and the relationship I want – what’s that about and how do I overcome it?


  • Download the OkCupid Dating App for free today!
  • Click here to try Damona’s free First Date Starter Kit!

Financial Intimacy & Reset Relationships

Successful relationships thrive on compatibility, vulnerability and intimacy. But, talking to your partner about your finances can be downright scary.

Don’t worry. Financial therapist Amanda Clayman is here to put your fears to rest. She’ll illuminate how money fears show up in dating and relationships and give us the tools to have a healthier outlook on finances for ourselves and our partners.


(1:30) Feel like something is missing? Maybe it’s time for a “reset relationship”:

Stylist magazine suggests that a “reset relationship” could help you rediscover the spark you’ve been missing. According to the article, it turns out that a lot of us want to make what they call big life changes, such as quitting a job and ending a relationship. In fact, a new study from Bumble and Plenty of Fish said that almost half of single people are craving a reset in their dating life, and 72% desire for life to change significantly rather than go back to how it was before COVID 19.


So what is a relationship reset? Basically, It’s a relationship that is all about serving your own need to refresh your life and get yourself out of a funk. It’s not that different from a rebound relationship (except in this case, you’re rebounding from this pandemic). But Stylist mentions how reset relationships aren’t only a pandemic phenomenon – rather that they actually can happen at any time in your life when you feel stuck. 

If you’re thinking about diving into a reset relationship of your own, Damona suggests that you don’t look at it as a temporary thing. Look at it as a mindset shift that is potentially going to change the entire trajectory of your life. Now, don’t get panicked. This sounds like a lot, but you can make these changes in small incremental steps. For instance, try opening up your search preferences in your dating app to include qualities you hadn’t thought about before. After all, to go someplace mentally that we’ve never been, we have to do something we’ve never done (or date someone we never thought we’d be open to).

Another way you can prep for your reset relationship is to question the rules and requirements you’ve made for the people you’re dating. Who wrote these rules? Did you write these rules? Did society write these rules? Do these rules still apply to you? Really focus on your must haves and deal breakers, and look at them through the lens of your future. Because maybe if you explored a little bit more, that reset in your dating life could lead to a tremendous reset in the way that you live the rest of your life.


Are you looking for your reset relationship? Then maybe you need the Profile Starter Kit to get you online easily, and moving forward in your dating success story. 

Download yours for free here.



Damona is so excited to welcome financial therapist Amanda Clayman! Amanda specializes in the cognitive, emotional, and behavioral aspects of our financial well-being (hence, financial therapist). 

She is the host of the recurring Death, Sex & Money podcast series Financial Therapy with Amanda Clayman, and authored several financial wellness courses for LinkedIn Learning. Amanda’s advice has been featured in CNBC, Fox News, The New York Times, The Wall Street Journal, REAL SIMPLE, Forbes, and more.

Amanda’s passion for financial wellness began with a dramatic styling mishap, which she will share with Dates & Mates listeners today. 

(11:00) Universal financial red flags:

Damona mentions how she’s received the question from a client, if she should date someone with significant debt. Amanda brings up the idea that for some people, if a potential partner does have debt, that makes them feel incredibly vulnerable about their own security – “and anything that makes us feel vulnerable is obviously our business and something that we can set boundaries around.” Although Amanda declares having significant debt isn’t universally a red flag on its own, it might be a red flag or deal breaker for some based on their own relationship with financial vulnerability.


Damona inquires if there are any universal red flags, and Amanda responds: “When I think about red flags, I think about them more in terms of process… like if a person is really secretive and they won’t disclose things even when you ask them to, that’s a red flag for me. Because that shows me something about how that person is going to be open to the kind of partnership that I have in mind for my potential mate.” Amanda also adds how someone who won’t engage with you and discuss both your needs and wants around money is definitely a red flag – communication is key.

(13:13) What does it mean when you’re withholding spending money?: 

Damona brings up a story about a friend of hers who grew up with money and a stable job, but weirdly enough was always so insecure about her spending. Damona continues to ask, what does it signify to have extreme frugality with money? “So I love in the example with your friend, the characterization [you used] was that something was outside of her comfort zone, or that everything it seemed like was outside of her comfort zone. And so she was bringing in this kind of anxious intensity to what maybe should have been a simpler choice… And absolutely, this is where our inner set of experiences and sort of strategies that make sense to us [come into play], where sometimes it feels like our insides are not quite matching the outside.”  

Amanda uses the quality of frugality as a specific example. She describes how we can differentiate between frugality being a strategy (i.e. being really careful with your means and your resources and a way of paying extra close attention), or we can think of frugality as a rigid behavior (i.e. where the caution is not matching the circumstances). But for the person inside of the behavior, frugality may have a totally other purpose. For example, Amanda describes how people who foster a high degree of control in their financial lives do so because they think control is the antidote (most likely for anxiety). So if someone has significant anxiety, then exerting control in their finances is sort of a continuous loop in that person’s mind – and that’s being expressed in their relationship with money.


(15:46) Self-indulgence & money:

Have you ever experienced guilt over treating yourself to something you knew you didn’t need? Or tried to buy something self-care oriented, only to counterintuitively feel like you were indulging yourself? Amanda addresses this anxiety – “What I would like to say to everyone is that we all have money ‘stuff’. So I think stepping back and being like, this is all very personal, how do I want money to work for me? Take the decision making into a clear and neutral place.”

When Amanda says ‘neutral place,’ she is speaking to the way we direct our money outside of those times when old stories and old obstacles jump up in the way, and tell us that we can’t or we’re bad or we’re not worth it. Taking your relationship with your finances to a neutral place, if only for a few moments, is where you can engage more neutrally with the tool properties of money, such as organization, allocation and negotiation.  “We can focus on those aspects to try to program self-care into our budget.  We experience ourselves as being able to use money effectively, to nurture, grow, take care of ourselves.”


(17:15) The $19,000 Haircut:

Amanda’s journey to financial wellness all started with what she poeticizes as a $19,000 haircut. “I took on a lot of my parents’ anxiety about money without knowing it, since my parents had experienced real deprivation in their childhoods… And when they came into adulthood, they always felt like the wolf was at the door…And I didn’t have the ability to know if that was true or not true in terms of danger… But when I got to be a grown up, I noticed that I had a really hard time paying attention to money, that anytime I was trying to look at my cash flow, look at my expenses, even to make a deliberate decision about money, I just couldn’t do it. I would get so triggered by it.”

Amanda persists that because of her financial triggers, she became increasingly impulsive with her spending habits – doing a lot of emotional spending, bouncing checks just to get by, and later moving to New York with nothing in the bank. She says everything came to a head when she asked her mom to give her a (what turned out to be terrible) haircut, because she had bounced a check at her hairdresser and couldn’t go back. 

Damona clarifies, “and you were at that point $19,000 in debt, yes? All of those checks that you were writing finally caught up to you.” Amanda responds, “I look at myself, like who is that person who just moved from Michigan to New York, like it’ll all work out? And the fact is, it did. Financial problems and consequences can be very, very real. But where we can, I think that we should appreciate that there’s a lot of on the job learning when it comes to money.”


(24:35) The Pillars of Financial Intimacy:

Amanda often speaks to the idea of ‘financial intimacy’ and the Five Pillars that help foster financial intimacy in a relationship. She gives us a rundown of each quality below: 

  1. Equality. “Meaning that both partners have equal decision making power.” 
  2. Inclusivity. “That means that both partners have to show up to this process, there’s no opting out by one person, there’s no pushing out by the other person.”
  3.  Transparency. “This is how we make sure that both partners have access to the information that they need. And it doesn’t mean that we can’t negotiate areas for privacy, but even those areas of privacy still have boundaries. Like we might say, both partners have to agree not to open new accounts without talking to the other person, or any expenditure above a certain point is going to get discussed.”
  4.  Flexibility. “Flexibility means that we allow ourselves to change, we allow our decisions to evolve that a level of sort of exposure and vulnerability that may not feel right for you at one period in the relationship, may become more right for you as time goes on… The point is, we can change all of these things, there’s no right or wrong thing that we have to stick to.”
  5.  Sustainability. “Sustainability is like, it just has to work enough for both of you. Like if one person is feeling like everything is wonderful, and the other partner is like, ‘I cannot stand to live under this tyranny’. Your money may look okay, but trust me – that is showing up somewhere else in the relationship.”


Connect with Amanda on IG @amandaclayman, or visit her website to learn more about private coaching and courses.



Submit your questions on  Instagram, Twitter, or Facebook and hear our answers live on the show! Here’s what our listeners asked about this week:

  • VIP Question from D – What are the rules of thumb for continuing a conversation after the person takes a long time to respond back? For example, I finally got a response to a basic message that I sent this past June. Should I respond right away or should I wait a few days? I’ve also had people respond back recently after I sent an initial message… in 2019. I’ve also had a person respond to my initial message, then ghost me for about a year, start talking again and then ghost me again. Any suggestions?


  • Download the OkCupid Dating App for free today!
  • Click here to try Damona’s free First Date Starter Kit!

Rom-Com Romance & 15th Anniversary

Welcome to another hot, romantic episode of Dates & Mates! Did you know that April is Couple’s Appreciation Month? It’s great timing for this episode because this week is Damona’s 15th wedding anniversary!

Which begs the question: what is the secret to a long lasting relationship?

Damona says that for her and her husband Seth, it’s growth – looking at your partner as a mirror who can illuminate your flaws and celebrate your gifts and using that to grow into the best version of yourself.

Okay, that was sappy.  Let’s change gears and get silly with the hosts of The Rom-Com Room Podcast, Kendra Okereke and Mercedes Gonzales-Bazan! They’re here to dissect the rom-com genre, how it affects dating and relationships, and what we can take away from our favorite movies.


(2:30) How to use constructive feedback in your relationship to your advantage:

A recent article from The Conversation has shed some new light on the importance of giving feedback to others. The article centers around a study published in the Journal of Personality and Social Psychology. The study looked at a broad range of scenarios and how willing people were to give feedback within them. In one (very telling) part of the study, less than 3% of people were willing to share with one of the researchers that they had a smudge on their face. The researchers hypothesized from this instance that we are reluctant to give feedback potentially because we don’t realize how valuable the feedback is to the person receiving it


Researchers looked at another scenario that involved pairs of friends, roommates or romantic partners providing genuine feedback. While less than half of the feedback givers wanted to provide feedback when given a choice, 86% of the participants wanted to receive the feedback. 

Damona points out how we can use our relationships, both romantic and otherwise, as learning tools and as safe spaces to practice some of these really important interpersonal communication techniques. And more importantly, she says to take the opportunity to give feedback to your partner in ways in which it will impact your own satisfaction in the relationship. 

This complimentary article from The Center for Mental Wellness spills tips on how to give constructive feedback to your partner (criticism got canceled in 2019, so let’s stick with feedback):

  1. Talk about behavior, not personality.
  2. Focus on how the behavior affects you – use “I” language.
  3. Be specific – tell your partner exactly what you’re upset about.
  4. Stick to the present – don’t bring up the past.
  5. Consider: “Am I the problem?”
  6. Pick a neutral place and time – don’t bring something up when you’re angry.
  7. Make a habit of giving positive feedback – this will make it easier for your partner to listen when you have a complaint.
  8. Make some ground rules for how to act during conflict – come to the table knowing what to expect from your behavior and the other person’s behavior. Additionally, come to the table with the goal of finding resolution.



Damona is here with the hosts of The Rom-Com Room Podcast!

Mercedes Gonzales-Bazan is a writer researcher and the co-host of Meet Cute’s The Rom-Com Room. She’s done editorial work for women in Hollywood and the Call Your Girlfriend podcast. Plus, she has a BA in rom-coms and an MA in memes. 

Kendra Okereke is a 29 year-old solo traveler from Los Angeles. She is the creator and moderator of the Late Bloomer Support Group, a Facebook group for people who identify as late bloomers in life. And of course, she’s also the co-host of Meet Cute’s The Rom-Com Room.

(11:30) How did this collab come to be?:

Turns out Mercedes and Kendra went through a substantial casting process to end up on The Rom-Com Room together. After several rounds of chemistry reads with other co-host candidates, Mercedes and Kendra were selected.  Their chemistry was undeniable! (Funny enough, they’ve actually never met in person.)

Damona asks the co-hosts when their passion for rom-coms started to blossom. Kendra starts, “I am the biggest hopeless romantic. All of those cheesy moments in rom-coms, that’s what I live for… I also identify as a late bloomer, so I’m a person who’s older who just has little to no romantic experiences… I really do believe in true love. I believe in soulmates, I believe that there is one person out there for everyone. And I love that rom coms just kind of let me live that out.” 


And the origin of Mercedes’ love for rom-coms? “My love of rom-coms started with my mom, so it has that nostalgia factor. For me, this is what we watched growing up. I also have a background in Media Studies, and specifically pop culture. So I really loved watching rom-coms as kind of a cultural artifact to look at different eras of history, and how there are different expectations set up for couples… I also love just seeing joy at the end of the film. So many dramas have harm-based stories for women, so I like seeing stuff that’s really focused on women and celebrates them.”

(15:48) “Love is not designed for the cynical”:

Damona comments how as a dating coach, she is often asked how romantic comedies affect her business. Although rom-coms do give people hope, Damona ponders how they can simultaneously set up grandiose relationship expectations. 

Kendra responds with her belief that “love is the one thing in life that you have to be 100% optimistic and hopeful in for it to happen. One of my favorite musical artists is Dermot Kennedy, and he has this line in this song that says ‘love is not designed for the cynical.’ And it’s so true. Like, in order for love to come in, you have to be open to it… I feel like if you are cynical, and you’re always out here thinking of the negative, that’s what you’re going to attract… And so I feel like with rom-coms, for me specifically as a hopeless romantic, they inspire me in a way. They keep that hope alive.”


Damona adds to Kendra’s idea of faith in love, remembering that when she first met her husband, she had no idea that someone like Seth could even be out there. 

Mercedes says that a lot of the criticism around rom-coms has to do with their being a specific formula to them, always making them predictable. “But that’s the challenge, right? Like they’re convincing you that this [story is] compelling anyway, and they’re making it interesting despite you knowing what’s going to happen. And that’s also like, the fun of dating, getting to know someone and going through the process.  That’s the exciting part, like, okay, what’s gonna be different about this time.”

(18:43) My Best Friend’s Wedding:

I think we’re all wondering… as a self-identified rom-com cynic, what is Damona’s favorite romantic comedy? Damona’s pick is the 1997 film My Best Friend’s Wedding, with rom-com darling Julia Roberts. She notes how it’s kind of an anti rom-com. Spoiler alert: “She doesn’t get the guy, but she’s not supposed to get the guy and I kind of love that. She goes through the experience and then realizes she’s okay even in spite of that outcome, right? It’s like the feminist rom-com.” 


Using her BA in pop culture, Mercedes reevaluates the meaning of the film. “It’s so great because it’s this love story of two cowards who won’t admit it to each other. And if they don’t have that communication, of course it’s not gonna work. Neither of them are brave enough to [express their feelings for each other], so obviously he’s going with someone that’s easier in that realm per se.”

(20:44) The elements of a great wedding:

Recounting her own wedding highlights, Damona asks Kendra and Mercedes what they think are the most important elements of a great wedding. Kendra kicks it off – number one, music! Be sure to have a good DJ with a solid playlist, and include a mix of all-around favorites like “Cha Cha Slide,” plus some nice slow-dance jams. Number two, food. There is something about having really good food at your wedding that will make everyone remember the occasion. Mercedes adds that most people only envision elements of their wedding as being for themselves – but a big part of a wedding is creating a good time for all the attendees, as well. 


(23:30) Fav wedding rom-coms:

In honor of Damona’s upcoming anniversary, she asks The Rom-Com Room co-hosts about their favorite wedding-themed movies. Being a Justin Long superfan, Kendra gives a shoutout to the 2017 indie rom-com Literally Right Before Aaron. Justin Long’s character attends his ex-girlfriend’s wedding, and spends the entirety of the event trying to convince himself and everyone else that he is truly happy for her. 

Mercedes jumps in with a cult classic. “To me, I can’t think about wedding movies without My Big Fat Greek Wedding. I think it goes under the radar a lot. And when it comes to big ethnic families, it’s so relatable… And the fact that he doesn’t shy away from her family either, like it’s not a deterrent. He’s there for the long haul. And that’s so appreciative to me, just because I’m so close to my family.”


Damona ends with a controversial take – “I’m not a rom-com girl. But I will say… I have a really love-hate relationship with 500 Days of Summer. I actually went to school with Zooey Deschanel, but I frickin’ hated her character! Because I thought, she’s the villain.” Kendra strongly agrees, and comes in with receipts. “If you set boundaries, that’s one thing. But you cannot set boundaries, and then keep pushing those boundaries and expect the person to still respect the boundaries that you set. Like, it just doesn’t work like that.”


Look out for The Rom-Com Room on Apple Podcasts, or wherever you like to listen. 

 Be sure to follow Kendra and Mercedes on the socials, @ken10hollywood and @merdedesgb11.



Submit your questions on  Instagram, Twitter, or Facebook and hear our answers live on the show! Here’s what our listeners asked about this week:

  • IG Message from N – I’m a pretty young 52, very active, typically I have dated 15 years younger but I feel it’s time to move on from there. For activity levels, goals, interests and appearance I’m finding women, give or take 10 years younger, are more fit for a companion, but I am finding a lot are not interested in a 50+ male. I see women’s profiles where they say they are younger to get the ideal matches but in their descriptions they reveal their real ages (targeting younger men). What are your thoughts on changing your age on your general profile to attract what you would feel to be a suitable mate. But revealing your actual age in your self description. Side note, typically I have no need or desire to lie about my age IRL. People are often surprised when I reveal I’m 52, but I’m proud of who I am, my accomplishments and my appearance for my age.


  • Download the OkCupid Dating App for free today!
  • Get 10% off BetterHelp at
  • Click here to try Damona’s free First Date Starter Kit!

Dating Tok & Fashion Therapy

I don’t know about you, but lately it’s been feeling like love is in the air. Spring is here, the flowers are blooming, we’re doing all our spring cleaning… so why not also think of spring cleaning your dating wardrobe?

If you’ve never thought about having a dating wardrobe, you’re in luck. Damona’s guest today, Stephanie-Gisondi Little (also known as the “fashion therapist”) will tell you why it’s so important and how to create one – even if you’re on a budget.


(2:30) Feeling disorganized in your love life?:

We’ve all heard of attachment styles, right? Well Allure Magazine explains in this article how disorganized attachment became the most misunderstood (and forgotten) attachment style. If you’re not familiar with attachment theory, it’s a method of analyzing and understanding how our childhood influences our relationships in adulthood. There are three primary attachment styles that are most often utilized by mental health professionals – secure, anxious and avoidant. And when you don’t fall under any of those categories, that’s where disorganized attachment comes in.


According to professionals in the article, about 20-40% of adults have a disorganized attachment style. It can present itself as fear of abandonment or of getting emotionally close to someone.  In extreme cases, it can emerge when a child grows up in an abusive household, which makes sense – you grow up in chaos, so then you bring chaos to your future relationships. Here are some signs that you may have a disorganized attachment style:

  • Anxiety about abandonment or rejection
  • Emotional or physical hostility (which shouldn’t be showing up in any relationship)
  • Constant mistrust in a partner
  • Someone who goes through intense periods of connection and detachment
  • Struggling with dysregulation like substance abuse or out of control behaviors
  • And if you’re dating someone who sounds a little bit like this, it may be difficult to engage with them because their behavior can feel chaotic or unpredictable.

Damona believes that we move through these attachment styles differently in different relationships. Think about it – different people bring out different elements of your personality, and they trigger different things from your past. So it may not just be about being in a relationship with someone who’s securely attached, or moving towards a secure attachment yourself. You can be multiple things at the same time, as long as you are getting the right support from the right people to help you navigate your behaviors.

(7:03) Could an A.I. predict your relationship red flags?: 

Wouldn’t it be nice if we could have a third POV in our relationships to spot any red flags, before we start to introduce our new partners to friends and family? As it turns out, A.I. (artificial intelligence) technology could be that third POV. This fascinating article in Screenshot Media gives us all the deets on A.I. dating apps. A recent study titled Loving the Age of AI Dating Apps surveyed people on how they would feel about working with an A.I. dating app. Nearly half of the respondents admitted that they would join an advanced A.I. powered dating app if it meant having more chances at finding a long term partner. But when they were asked what they would do if an A.I. dating app did suggest they break up with someone, only 7% said that they would end the relationship immediately.


Damona is a little skeptical that A.I. could predict the end of a relationship, but believes that it could be used to find better matches for the participant overall. Honestly, so many of our behaviors that we think are random, are actually more predictable and pattern-based than we realize. According to the article, the main input that the A.I. would use to determine the success of your relationship, was your in-app user behavior – conversations with matches that had gone silent, changes in conversation based on keywords, and frequency of conversations. And if the A.I. could recognize when you acted in a way that could potentially threaten the relationship, they might be able to tell you in advance.

Now of course, there’s always issues, right? With A.I., it would be difficult to know what information to feed the A.I. from outside the app to get a strong enough understanding of the relationship. So basically, folks, we’re not there yet. But there is even more potential as to how an A.I. could predict your best matches before you have even had a conversation. Using A.I. in dating apps is only a proposal at this point, but I suppose only time will tell which direction dating app technology will be heading in next…



Damona is thrilled to welcome Stephanie Gisondi-Little, the Fashion therapist, to the Dates & Mates family!

Stephanie began her career in the fashion industry working between New York and LA, with top designers like Emanuel Ungaro and Nicole Miller. Her advice has been featured in Marie Claire, In Style, The Hollywood Reporter, and more. 

Stephanie also works to style clients and their closets from many different backgrounds, warranting her the title of ‘fashion therapist.’

(14:00) Why are you the ‘fashion therapist’?:

First things first, why does Stephanie call herself a fashion therapist? “I call myself a fashion therapist because having worked in retail wholesale garment industry, and having had my own ecommerce website, I realized that it’s not just about clothes at all right? The clothes are the fun part. But it’s really about how the clothes make you feel. In addition to being a personal stylist, I also work as a wardrobe organizer and closet organizer. And when you see how difficult it is for people to let go of certain things, the reasons why we hang on to them, you start to see that it’s just it really is about so much more than just clothes. And there’s a lot of emotional stuff that goes with just getting dressed.” 


Stephanie believes that clothes are a tool to express our core essence, and a great way to start conversations. She also recognizes the stigma around clothes only being about fashion, but there are trends for every body and every budget. “The thing that I realized is that you can either love clothes, or you hate clothes. But in our society, one has to get dressed, right? So the best thing to do is to figure out what works for you.” 

(16:55) How to prep for the occasion:

Damona asks Stephanie, when prepping for a date or an event, what are the questions we should be asking ourselves? “I think the first question to ask yourself is, what time is it happening, where is it happening, and how do you want to show up as your favorite self?” And your favorite self for going on a first date may be a different self than the one that gets dressed for a business meeting or a wedding. Stephanie suggests looking into the kind of feeling you want to have. Maybe you want to feel more armored up, so you wear a motorcycle jacket or padded shoulders. Or maybe you want to feel more free and flowey, so you choose to wear that sundress you always get complimented on or a certain kind of fabric. But regardless of how you dress, make sure that your attire is appropriate to the time and location, and that you wear something clean. This is a big one for Stephanie, because even if you don’t have the fanciest outfit, showing up in stainless clothes and looking polished shows that you have respect for yourself, and respect for the person that you’re showing up to meet. That can’t be bad for a first impression, right?


(20:06) Dress how you want to be perceived:

Damona mentions her strong belief in presenting yourself the way that you want to be seen. Particularly in dating profile photos, people are developing an impression of who you are in a split second based on the way that you’re presenting. Stephanie adds, “I take it back to the cave brain, where we are hardwired to be kind of on alert to say ‘are you from my tribe or are you not from my tribe?’ So we are making these instantaneous micro decisions. And for better or worse, they do affect what people think of us.” We don’t have control over a lot of things that happen to us in life. But one of the things we can control, and have a surprisingly large amount of control over, is how we are perceived. “I always say we all have multiple facets to our personalities and thank goodness your wardrobe can and maybe should reflect that.” 

In terms of first dates, having a couple of go-to pieces for how you want to make a first impression is a great strategy. “It’s nice to know that you have at least one thing that fits you, feels like you like your current self, and you’re physically comfortable in it. What you don’t want to be doing is sitting around adjusting your bra straps, or thinking ‘my feet are killing me in these shoes’ or ‘this shirt makes me sweat buckets.’ You know, that’s not a cute feeling to be having while you’re trying to make nice conversation and get to know somebody.” Damona adds that so much energy already goes into preparing for dates emotionally and mentally, so having your wardrobe already decided helps to set you up for success even more so.


(24:15) Stay adaptable:

Damona continues with something some people often have a hard time doing, which is staying flexible in your wardrobe – our wardrobes evolve just as we evolve over time. So keeping those pieces of “aspirational clothing” in your closet, i.e. clothes that you keep because one day you’ll be able to fit into them again, actually takes up more mental energy than we realize (not to mention closet space). Stephanie hits Damona with one of her favorite facts – “The average person makes 10,000 micro decisions every day. We’re not thinking about all of them, but we’re doing them. So there is energy that you’re expending before you’re even out the door if you’re looking into a closet that is not seasonally appropriate.”

Stephanie agrees that we all evolve in life, so having a closet that is equally as adaptable matters. “It’s worth populating what you have with one or two fresh things [every so often], even if you have a uniform of a kind that you wear all the time… If you can look around and say, ‘what’s one piece that’s on trend that I think would feel comfortable or look good on me,’ just try something! Whether it’s a brighter color or shoe style or what have you. There’s just so many ways to kind of pop what you already own.”

(27:28) Enclothed cognition:

Stephanie shares with Damona a concept in social psychology called “enclothed cognition,” which essentially states that you become what you wear. “I think we all instinctively know that when we get dressed, we get called for an interview, or a first date, you dress differently. And it makes a huge difference, what you feel once you start to get intentional in thinking about that. Damona remarks that you can also change the way you feel based on what you wear under your clothes, and this may even have a stronger effect since the undergarments you wear would only be for you.


Damona mentions that tailoring is also a tool to help you feel your best in your clothing, and even take a piece that you may have felt frumpy into feeling like a completely different person. Stephanie states, “Totally agree. I think we’re all fed this continual diet of how everything should fit perfectly, and it should just be easy, breezy… And the other thing to bear in mind is that you know one brand’s 8 is another brand’s 10 is another brand’s 12.”

(33:11) Having a dating capsule wardrobe:

If you’ve never heard the term before, a “capsule wardrobe” is a small collection of clothing items designed to be worn together which are synchronized in color and line. The main point of a capsule wardrobe is to be able to have many outfit options without needing an excess of garments. So if you’ve never thought about creating a capsule wardrobe exclusively for dating, this may be a game-changing move for you. Stephanie gives some tips on how to get the most out of your dating collection. 

I recommend getting better quality wherever possible. You can get that more easily these days second hand, in very good condition. And it’s a little easier to source because there are so many great places… But I would rather have fewer pieces of better quality.” She recommends checking out classic pieces such as a well-fitting blazer, black ballet flats, a good white t-shirt, and a good pair of jeans. For men, she even recommends extending your capsule wardrobe by using the jacket from a 2-piece suit as its own blazer. Damona also points out that red is a good color to have somewhere in your capsule wardrobe, because it’s a color that we are biologically predisposed to be attracted to, and it naturally catches our attention.


When creating your wardrobe for dating, also consider adding some conversation pieces. These are useful for dating because not only can they break awkward silences and inspire conversation, they have a story behind them which you can speak with more passion and presence. This can be anything from jewelry, to a bright red lip, or a cool graphic tee. Fun, printed socks or button-downs are also a great way to set the tone that you are playful and don’t take yourself too seriously. And to top it off, Stephanie adds that comfort is key – “You got to be comfortable. I always like to think, do your outsides match your insides? You know, are you dressed in a way that doesn’t really reflect who you are at all? Maybe you’re dressing too conservatively, and that’s not really who you are inside. Or maybe it’s vice versa? But comfort is key. It shouldn’t be that hard to get around in the clothes. I want folks to be comfortable and have a good time and be able to focus on the things that are far more important than just clothes.”


Be sure to follow Stephanie and her company on Instagram at @composed_co

If you’re interested in learning more about fashion therapy, you can work with Stephanie virtually or in person through her website


Submit your questions on  Instagram, Twitter, or Facebook and hear our answers live on the show! Here’s what our listeners asked about this week:

  • Email from H – Do you have any suggestions on how to deal with the societal pressure to find someone? As a single guy in my mid-twenties, I’ve felt behind in finding a partner. This feeling is amplified whenever I see my friends enter or maintain long term relationships and even get engaged or married. I know that this thought is completely false, and that I can develop a satisfying long-term relationship at any age. I just struggle with feeling like I need to achieve this milestone ASAP.
  • Email from T – For online dating, do you have any tips to get a guy to ask you questions? When I’m on dating apps, I feel like I’m the person always asking the questions and moving the conversation forward. I would like for the guy to ask me questions too.



  • Download the OkCupid Dating App for free today!
  • Click here to try Damona’s free First Date Starter Kit!

Google Sleuthing & Elephant in the Room

From West Elm Caleb to The Tinder Swindler to Kim and Kanye we’ve got digital safety and online etiquette on the brain. Damona mentions one study that predicted that if Cyber Crime continues at its current rate of growth, it’ll cost 10.5 Trillion dollars globally by 2025.

This isn’t to scare you, because a lot of these scams, crimes, and sticky situations can be avoided if you know the signs to look for. So today, Burton Kelso will tell us how to stay protected in our search for love and in our relationships.


(2:33) Is Grimes and Elon Musk’s relationship the wave of the future?:

According to our friends at Metro UK, Grimes and Elon Musk’s fluid relationship is joining the hall of fame for unconventional celebrity romances (including Dolly Parton to Will Smith and Jada Pinkett Smith).

If you haven’t heard, the couple *secretly* welcomed a baby together in December 2021 via surrogate, even though they had officially separated that September. In a recent interview with Vanity Fair following the announcement of their new child, Grimes then said that they were maybe kind of together, like he was her boyfriend she guesses? But they don’t live together and they don’t follow a traditional relationship model. 

Not only is it becoming more and more common for modern-day couples to edge away from stereotypical relationship norms, but it’s also becoming increasingly visible in celebrity relationships as well. Which, all in all, is kind of an awesome thing! If we are able to be more flexible in our expectations of what a healthy relationship looks like, then this widens the bracket for people to feel more content in their own relationships, and not have their happiness be dependent on cultural validation.

So maybe it’s time for us to start looking towards the celebrity couples and role models in our lives that resemble the kind of relationship we want, not the one we think we should have.


(5:55) Vulnerability is the new black: Well it’s official – Pure Wow confirmed in this recent article that vulnerability may be the new foreplay. The article starts with an anecdote from the author who had a very honest groundbreaking conversation with her partner. And through her partner’s vulnerability, she actually found herself feeling connected and… maybe a little turned on?

Award winning somatic sexologist, Jaiya, elaborated on this – she says that vulnerability is a powerful ingredient to creating alignment between two people who wish to get their true desires fulfilled and their needs met. But basically, it’s a way of exposing the most authentic you.

So how do we even open the door to be vulnerable? Well, Jaiya says to gauge your partner’s willingness and responsiveness when you choose to be vulnerable. This will also vary depending on how serious your relationship is. If you’ve just started dating, try to avoid any kind of emotional dumping – give them a little appetizer of the relationship to hang on to and be invested in before you hit him with the hard stuff. Additionally, in the early relationship stages, try to allow a ratio of making sure that you’re both sharing, and then listening to the other. If there’s a reciprocal share, then you know you’re both getting to a place of mutual vulnerability and authenticity.


A lot of times when we go to vulnerability, our instinct can be to fix something. But this article really shows that it’s the act of vulnerability – of just the share – that can be really bonding for two people. Once you get into the relationship, it triggers a whole other series of emotions and levels of connection. And according to another study mentioned in the article, researchers found that oxytocin is released into our bloodstream whenever we experience true and authentic vulnerability (that’s the same chemical that’s essential to arousal). So although it can definitely be scary to be vulnerable, the payoff is evidently greater than we thought.


Damona is here with tech expert, TV personality, speaker, and entrepreneur Burton Kelso. Burton is currently the Chief Tech Expert of the award-winning tech service company Integral, based in Kansas City. He is regularly featured on local ABC, NBC, CBS & FOX morning shows, speaking about internet safety.

Burton’s passion is to help people make sense of, and get the most use out of, the digital world they live in.


(13:16) Hit us with some dating safety: It seems like we’re living in a period right now where digital romance scams are on the rise (although part of this may just be Tinder swindler hype). Regardless, it’s never a bad idea to brush up on our online dating safety. Burton says that one of the main improvements in online safety is the existence of live video. In the past, if you wanted to see what someone looked like, you just had to trust that the glamor shot they sent you was actually what they looked like (and maybe there wasn’t as much of an instinct to question that they would be lying).

Nowadays online dating creates “watering holes” for people looking for connection, and so scammers are more likely to be on dating apps because that’s where the bodies are. But Damona confirms that although our access to potential scams has widened, our arsenal of tools to combat scamming has grown even more so, i.e. the ability to Facetime, researching their identity on the internet.

(15:18) Avoid getting socially engineered: Burton gets right down to the facts – he says that if you get into a relationship online, and your partner starts asking you for money or gifts soon after, that’s a red flag (especially large amounts of money upfront). Another red flag is if you read something they’ve texted you, and it seems vague enough that it could have been sent to anyone, there is a likelihood they could have copy-pasted the message to multiple people. Burton adds, “it’s so easy to do this, and they can carry on multiple conversations and have multiple people that they’re grooming at the same time. And technology just makes it so easy. You can do it from a computer, you can do it from a smartphone, so you can be anywhere and just send whatever you want, whenever you want.”


Damona brings up a concept Burton has mentioned before, which is how scammers are able to “socially engineer” their subjects. Basically, social engineering is when a scammer takes a look at a situation or person and finds out what their weak spots are. And with social media allowing us to post our thoughts and emotions online daily, it doesn’t take long for a scammer to figure out what they can say to peak your interest. A common symptom of this is if the person you’re talking to makes you feel extremely special, like you’re the only one for them. Damona concludes that “people like to blame the dating apps, but it’s really the communication and that digital communication. Everybody wanting to move to text, wanting it to be more efficient, that has pushed us in this direction.”

(19:16) What’s up with your digital hygiene?: Let’s clarify – what are the precautions we should be taking online to avoid getting socially engineered by scammers? “The best thing to do is to use common sense and slow your roll, slow down when you’re in these online relationships. Because usually, in about six months, someone’s going to reveal who they are. We can only fake it for so long.” Another red flag Burton has clocked is if someone did not want to meet face to face in a safe location. This is a pretty reasonable request (especially as a woman), so if there is resistance in meeting for the first time in a way that’s comfortable for you, then there’s probably something going on with that person that you don’t need to deal with.

So what information should we avoid putting onto the internet altogether? Damona points out how she never “checks in” on any of the apps (i.e. attaching your location to a post you make, or updating the check-in feature on Facebook). Burton proposes avoiding giving out your real cell phone number when possible, because there is a way that your partner could gain access to your service provider and hack into your voicemail (if they become ambitious enough). Instead, Burton suggests getting a number with WhatsApp or Google Voice to hand out to people that you’re dating. That way if they become a nuisance, you can change your number within the app. Lastly, if you are nervous about your information being too public, go to your Google preferences, and indicate that you don’t want your information shared via Google. Be sure to turn off some of those personal-data sharing features within your Google or Microsoft account.


(26:39) Internet sleuthing 101: Now that we know how to spot scammer red flags, how can we fact-check our suspicions? Burton remarks that Google is a good and very basic place to start if you want to become an internet sleuth. In addition, everyone’s on social media and even more people are on LinkedIn, which often gets lost in the shuffle as a resource. “If someone is employed they’re going to have a LinkedIn profile, because they want to keep their options open. Maybe they’re an entrepreneur and they want to connect with more people. So I definitely would check on both Facebook, and of course, LinkedIn. LinkedIn has got about 850 million users now – they have more users than Tik Tok.” Damona mentions that if they’re not on LinkedIn themselves and they are part of a business or corporation, it’s bound to have a website. Or if they’re on the board of some kind of charity, the website will often have a list of all the board members and essential persons.

But we couldn’t talk about sleuthing without mentioning the unsung hero of fact-checking – Google Image search. This is where you can drag and drop a photo from online into the Google search bar, and Google will then scour the internet for all instances in which that photo pops up. “Even on social media, you want to make sure someone isn’t using a headshot from Pixabayor Wix or Squarespace, that they haven’t used just some random dude that they posted on their social media platform.” If you want to do an image search, go to the main page of Google and at the top, click the little tab that says “images.” And Damona says to make sure that the photo you use is taken directly from the website or profile, screenshots will not work.


(31:32) Beware of airtags: Airtags (or smart tags, for Samsung users) have been giving everyone a spook lately, so let’s nail down exactly what they are and how to avoid them. Basically, airtags are a tracking device keychain created by Apple to act as a key finder to help find lost items. But unfortunately, scammers have been using air tags and smart tags to track people by slipping them into an individual’s purse or pocket without them knowing. Sometimes, scammers will actually attach airtags to your car. So if a notification pops up on your device that says there’s an unknown airtag or smart tag nearby, definitely pay attention to the alert and disable its access. Damona does point out the bright side of airtags, which is that you can use these so your family and friends can keep track of your location, and even as a safety precaution the next time you go out on a date.


Check out more of Burton’s advice at and be sure to follow him on all the socials @BurtonKelso.



Submit your questions on  Instagram, Twitter, or Facebook and hear our answers live on the show! Here’s what our listeners asked about this week:

  • IG Message from Maria – Dear Damona, I chose to only filter in partners who don’t drink alcohol or only drink sometimes. I’ve been talking to a woman who seems lovely, has done some inner work, and has come out of an abusive/toxic relationship last may. She has on her profile that she drinks sometimes, yet she messaged me late the other day saying that she was just out of her ‘little bar job to help her friend out.’ Alarm bells went off inside, and I asked the next day ‘when you say you drink sometimes, what does that mean? As I’m looking for someone who preferably doesn’t drink or drinks occasionally.’ She didn’t reply to this specific message. I said again “I asked you this question and you didn’t answer me, I just want to make sure that we’re aligned with each other’s values’ and she didn’t reply again, and said that the conversation wasn’t feeling good and we briefly cut contact. We both decided to carry on talking, yet I feel that there’s an elephant in the room now. Please advise.
  • Email from J – What is a kind and graceful way to end a relationship if you decide it isn’t working out? I am terrible at ending relationships and I often end up letting things linger way past their expiration date. I often tell myself, “He’s not so bad. He’s a nice guy.” But deep down I know that it isn’t going to work out. This year I’m focused on creating better boundaries, so I want to learn how to be better at this skill.



  • Download the OkCupid Dating App for free today!
  • Click here to try Damona’s free First Date Starter Kit!

The 7 Love Styles & Doppelbangers

Are you still using the “5 Love Languages” to understand the relationships in your life? Well, it’s time to put an end to that! A lot has changed since the 80’s, including the ways we give and receive love.

In this week’s episode, Damona is joined by Molly Owens, the CEO and founder of Truity, a provider of research-backed personality tests which help people better understand themselves at home, at work and in relationships.

Molly will walk us through Truity’s newest research, which indicates that there are actually 7 love styles experienced in modern day relationships. Plus, Damona will share her own results from the “Seven Modern Love Styles test” – and oh boy, is this system good.



(2:42) The new dating trend that’s dawned on daters: The Independent recently covered a new trend called ‘dawn dating,’ and you can probably guess what this means: it’s going on dates in the morning. According to data from dating app Badoo, which surveyed 1,000 of its users, 71% of single people on the app said they would be impressed if someone asked them to go on a date in the morning.

So why has dawn dating been trending? Here’s the deal. It’s no secret how much alcohol is intertwined with dating culture, and many singles have changed their dating habits to take alcohol out of the equation – also called ‘dry dating’. Similarly, almost half of the people surveyed enjoy the fact that on a morning date, there’s no expectation to drink alcohol on the date. Plus, when you’re on a morning date, you don’t have to worry about setting a drink maximum for yourself (unless you’re going for brunch and mimosas).

Singles from Badoo’s data also mention that dawn dating is an optimistic and fun way to start the day, and that they feel like they’re more refreshed in the mornings and can get to know their dates on a deeper level.

Damona comments that she’s all about challenging dating norms and shifting your habits to see the different results. Dawn dating shows us that you don’t have to delete your dating apps, get a crazy haircut, or buy a whole new wardrobe to shake things up. Instead, you can use your experiences to craft your dating life in a way that really supports you, and helps you feel like your best self.


(5:32) Could you be dating your ‘doppelbanger’?: Are you dating someone who looks kind of… or exactly like you? According to the Daily Mail, you may be dating your ‘doppelbanger.’

The term is used mostly in the LGBTQ community when somebody is dating someone who bears a big resemblance to themselves. But if we step back and look at this pattern overall, there is something going on in attracting someone who shares similar features to yourself.

The article mentions research that was conducted by Hungarian scientists around physical attraction. They found that women were inclined to choose partners whose faces resemble those of their fathers, and men of their mothers. Another 2012 study by Institut des Sciences de l’Evolution in France, discovered that a third of men were attracted to images of women that had been digitally manipulated to resemble their own features.

Now all this begs the question – is there something biological that causes us to seek out visual similarities? Is it that we trust those who reflect our own features back to us, or look like our caregivers? And even further, with all this article touches on, can we still say that opposites attract? The next time you find yourself making eyes at a potential match, take a moment and see if you observe any parallels in your features. You may look more alike than you think…



Molly Owens is the CEO & Founder of Truity, one of the leading providers of research-backed personality tests. She is a former therapist, with a Master’s Degree in Counseling Psychology. Molly is also a contributor to INC. Magazine and recently appeared on Bloomberg TV.

Molly is here to share research which builds upon the original “5 Love Languages.”  She will explain how Truity’s new “Seven Love Styles” framework addresses the changes we have come to see in modern day love styles.

(11:34) What exactly are love languages?: As popular as love languages have become in recent years, it’s funny to think that most of us don’t even know their origins. Molly gives us the scoop that the 5 love languages were originally developed in the 80s by a marriage therapist named Dr. Gary Chapman.

His hypothesis was that people express and receive love in different ways. So if you’re doing something that you think is very loving for your partner, and you’re thinking, “oh, I’m doing a great job of showing them how much I love them,” it won’t translate in the same way if what you’re doing doesn’t align with their love language. Chapman idealized that if you could teach couples about the 5 love languages, they would then have the language to explain what they want and need from each other in a relationship.

Molly explains that as helpful as the love languages were as a foundation for emotional communication between couples, Chapman’s research was actually done on a pretty homogenous sample of people. Since Dr. Chapman was a marriage therapist, he conducted his research on his straight, married Christian clients. 

So in Truity’s research to see if the love languages held up, they looked at a more current sample and more diverse sample of people. Truity collected data from over 500,000 visitors to their website, asking them what made them feel loved and how they like to express love to their partners. The results showed that in modern-day relationships, people’s “love styles” actually fell between 7 categories – a reflection of how relationships have really changed since the 80s.


(15:25) The Intellectual Love Style: Damona and Molly start with the Intellectual love style, which Molly mentions is a love style that wasn’t really talked about at all in the original 5 love languages. So what does it really mean to have this love style? Molly describes that “it’s all about respect. It’s all about connecting on a mental level. It’s all about having that discourse with your partner, having those discussions, respecting their opinions, getting thoughtful advice, really thinking about what’s going on mentally, and having that mental match.” 

Molly adds that a “red flag” for this love style (or rather, an indication that this may be yours), is if you’re very quickly turned off by someone who you can’t have a stimulating conversation with. Damona mentions how she definitely defines herself as having this love style, since what really attracted her to her husband was that he could keep up with her in conversation.


(16:30) The Emotional Love Style: Molly comments that the Emotional love style parallels the Intellectual one, in that they are both newer styles that accommodate the shifts in modern-day relationships. On top of that, these two love styles are the most popular love styles. “The Emotional love style has to do with supporting your partner through hard feelings, through difficult times, and really showing empathy to your partner,” Molly reports (and Damona remarks how this aligns with her own support for “empathetic dating”).


(20:50) The Activity Love Style: If this love style sounds familiar or appealing to you, Molly explains this is because the Activity love style pretty much matches the Quality Time love language in the original system. Although, rather than spending any kind of time together, the Activity love style focuses more specifically on sharing leisure activities and hobbies with your partner. Molly notes that this showed up in their data as couples often traveling, going on trips, and learning new skills together. 

Uniquely, this love style also includes sharing a hobby with your partner, or at least sharing the interest of your hobbies with your partner. Damona also observes that many of the people she coaches often put an emphasis on shared activities as being core to their relationship. And while quality time is important, Damona believes that some of the other love styles are more crucial for long term compatibility.


(24:42) The Physical Love Style:

Now this one sounds pretty much like a given, right? Damona ponders how there is more to the Physical love style than meets the eye, since the physical aspects of a relationship tend to change over time as familiarity and closeness grow between two people. Molly agrees, and expresses that the Physical love style “really combines both the kind of sex side of things, that attraction and intimacy, and also just the sort of snuggly huggy stuff that we like. We found that the two did often go together for people, so that’s why it’s not separate.” 

So what should you look for in a partner if you have a Physical love style? Molly suggests when you’re starting out in a relationship, to look for signs that the other person has the same, or at least roughly the same tolerance level, for physical closeness. “This is one where we have sort of a biological need, and it’s a little bit harder to overcome it if you’re really kind of off kilter with the person that you’re with. And that’s true for sex drive, as well as kind of just that physical closeness.”


(26:52) The Practical Love Style: The Practical love style has another parallel within the original 5 love languages, which is Acts of Service. But interestingly, this love language has a bit of a loaded history. “We found the acts of service concept to be pretty gendered… So in Dr. Chapman’s book The Five Love Languages, usually when he talked about housework, he framed it as a woman’s job. And if a man did it, then he was helping out his wife, which really doesn’t fly anymore.”

Molly and Damona agree that nowadays, there is some wiggle room for what “act of service” is. For instance, if your partner has a Practical love style, you can take the car to the car wash versus doing it yourself. This is still considered a practical expression of love, considering you went out of your way to make your partner’s day easier.


(29:54) The Financial Love Style: In a way, you could categorize this love style under the same umbrella as the Acts of Service love language. But more specifically, the Financial love style is really about “being there for the other person, and saying ‘I have these resources and I’m going to share them with you.’” Molly continues that expressions of financial love don’t necessarily have to be bougie – it could be as simple as stepping in to pay your partner’s phone bill when they can’t, or supporting them when they feel financial stress.


(31:00) The Appreciation Love Style: Much like the Words of Affirmation love language, “people who have the Appreciation love style really want to hear verbal positive feedback. They want to hear ‘you did a great job, I really appreciated that, thank you for all that.’ That rah-rah sort of verbal feedback.” One difference between this love style and that of its 80’s counterpart, Molly says, is that Truity found more people nowadays need that congratulatory aspect from their partners. So instead of just the verbal recognition, people with this love style may crave the emotional recognition.


Curious about your own love style? Be sure to take Truity’s 7 Love Styles quiz here.



Submit your questions on  Instagram, Twitter, or Facebook and hear our answers live on the show! Here’s what our listeners asked about this week:

  • IG Message from J – Hi! I love your podcast and have been a listener for about a year now and have learned so much. I’m seeing someone new, it’s been a few weeks and it’s going very well so far. She has all the things I’m looking for, there’s chemistry, it’s great. So this “problem” is most likely just a me thing BECAUSE there are times she doesn’t text back for a day or day and a half. Before, she would text me at least once a day or even call me when she knows I’m not at work yet or just clocked out. I have an anxious/preoccupied attachment style and am fully aware of it, so when she doesn’t text back for a while, I assume the worst. I’m fully aware the worst case scenario may not be happening, but because of my attachment style I can’t help it. I’m afraid of asking for too much of her or looking like I’m emotionally unstable or something. I just feel like if it was just one text saying good morning or that she’s thinking of me or if she called, that would be great. I know she’s actually a very busy person and I appreciate the time she makes for me, but when I don’t hear back from her for two days and we haven’t made plans for our next date yet, I get super nervous that she’s about to ghost me. I’ve been ghosted so much. But I really really like her so…please help! Last thing I’ll say is that this is the most interest someone has shown me. She even gave me this GIANT bouquet of flowers on our second or third date, and even introduced me to her friends twice. So it’s because she’s everything I’m looking for AND she seems to really like me too, that I just don’t want to mess this up. I’m generally an open book but when it comes to sharing my attachment style, I feel weird about it. Should I tell her about my anxious attachment style in hopes she’ll accommodate it? For context, this is a lesbian relationship, in case that effects your answer at all. Thanks again and love the podcast!
  • Email from T – Dear Damona, I’ve done a lot of work on removing internal barriers through listening to your podcast over the past year so thank you so much for the content you put out! I’ve improved my profile, opened up my filters and gone on fun dates. My one issue is however, how can I figure out whether I’d be okay to move to a different city away from my friends, family and current job to be in a relationship? My problem is that I hesitate at the idea of being far removed from them but I also know I’m potentially restricting myself if I only look for people within a 10 mile radius. For context, due to religious reasons I wouldn’t move in with my partner without being married, so I wouldn’t be able to test the idea before fully committing to it if that makes sense.  Culturally, women are expected to move to their husband’s location too so it’s unlikely that someone would move to be with me.What can I do to help me figure out if I’d be okay moving? I’m tired of spiraling every time I see a person’s location or not knowing how to answer when I’m asked about relocating. Hope this makes sense!



  • Download the OkCupid Dating App for free today!
  • Click here to try Damona’s free First Date Starter Kit!

Design Your Relationship & The Talking Stage

Do you ever feel like traditional dating and relationships just won’t work for you? Or maybe they do work for you, but the timeframe when you can date and connect is narrow? Does it hold you back?

Well, today’s guest is Damona’s good friend – freelance writer and Certified Life, Love and Dating Coach, Deb Besinger. She is here to let you know that times are a changin’ and that now’s the time to “design your own relationship.”


(1:36) Is the economy what’s actually keeping you single?: Business Insider dropped some knowledge on us in this recent article, explaining how our economy is really set up to more highly benefit married couples over singles. 


So let’s get educated. The article points out the many aspects of life in which married couples have advantages – tax breaks, social security savings, and even social circles (when you’re single, you spend more money on your own going out with friends or buying gifts for loved ones). They also drop some recent data on home ownership provided by Bank of America, stating that about 65% of single women said that they would rather not wait until they were married to buy homes. 

In terms of dating, some single women are even worried that owning their own home sends a message to men that they don’t have space for them in their life, because home ownership must mean they’ve already got everything figured out. And all this isn’t even taking into consideration the wage gap between men and women, and then further between white women and women of color. All of these factors not only reflect societal standards from a rather bygone era, but they add up to one upsetting deficit on behalf of singles – lack of financial control. 

Considering all this, Damona states that you don’t necessarily need to be married or in partnership, to have someone to lighten the load. She proposes that women and other singles join to form single pods, where you can buy things in bulk (hello, Costco) and split the cost of other expenses. This also gives you more power to choose the people that you spend time with and decide to make a part of your single life.


(7:10) The newest form of dating torture: Glamour Magazine came out with an article last week describing the talking stage.  According to this article, the talking stage is a label coined by Gen Z to describe a maddening, undefined early stage in many relationships. 

Damona thinks this is really cute because Gen X and millennials have been saying “talking” forever. But regardless of your age, you get it right. This is like, “we’re talking, but we’re not dating.”

Although Glamour makes this phase of dating seem unbearable and confusing for most people, Damona believes that “the talking stage” is actually a very necessary part of the dating process, and one that you shouldn’t run away from. “This is more what I call the screening stage to the people who are in my program. But the screening stage then has to move into some sort of definition.” 

The article also makes mention of another relationship buzz word, which is the “situationship.” Although a situationship may be more defined and have some level of commitment (because you technically have to be *in* a situationship), what further separates this from “the talking stage” is that a situationship is something you don’t want to be in. 


So Damona votes that we all skip over the situationship phase, and that we get to a period of definition after the talking stage more quickly. Embrace defining the relationship and leaving the ambiguity behind, and this may mean embracing a different definition than any relationship you’ve had in the past. 

Additionally, be sure to have clarity on three questions: what do I want, what do they want, and have we talked about it. You are in control of your dating destiny. So if you dislike ambiguity, end it. 


Check out Damona’s Free Profile Starter Kit here, to take more control of your dating destiny.



Deb Besigner is a freelance writer and Certified Life, Love and Dating Coach. She is the founder of Kiss of Perspective, her coaching program where she teaches clients how to “design their own relationship.”

Deb is also the author of Bound and Gagged by Christianity and the Sins that Set Me Free – her personal story of leaving fundamental Christianity and finding the religion of love.

(14:05) People’s relationship goals are shifting:  Deb has been in the business of romantic coaching for eight years and she has seen a shift in how singles are dating. Deb says that many people are finding empowerment in learning how to be alone and that this process may have been sped up by the pandemic and the resulting lockdowns. 


Deb explains how she sees people becoming more conscious and realistic about the amount of time they have to date intentionally.  She reveals how she fosters this in her 10 week coaching program by asking members not to date for the first 8 weeks.  That’s right, y’all read that right, the first 8 weeks.

Deb talks about how so many people feel pressured by traditional relationship timelines.  Her goal is to help people slow down and become more aware of what life with a partner ideally looks like to them – in your perfect world, how do you spend your time? And how does the partner factor into that? Do you want to share a friend group, or are you okay having separate circles of friends? What works for you?

(17:09) Design the relationship you want:

Wait… Deb’s clients don’t date for the first 8 weeks of her 10 week program? What do they do in the meantime? 

Deb lays out for Damona that “they’re getting really clear on what they want, what makes sense for them, what they have to offer, and getting rid of the stories in their head… “In my program, we’re really taking the steps to get you in that ideal place and to get really clear on what you want. And part of that is asking, what kind of relationship do you think is going to work for you?” 

Damona brings up a recent article in the New York Times, about the relationship concept of “living apart together,” where couples don’t necessarily need to live together in the same space, or even the same country, to be together long-term. This idea totally aligns with Deb’s philosophy of leaving conventional relationship models behind.  She says that “designer relationships” (meaning you forge your own relationship model) are becoming more common. “We’ve all gotten very used to video chatting whether we wanted to or not these last couple years, including planning a virtual date –  you can still do that with a partner that’s far away.” 


Deb does note that designer relationships do take a bit more intentionality and emotional intelligence to really make them work, since the distance makes it necessary to communicate more and keep checking in. But if we have the capacity to create the life we want, why wouldn’t we have the power to create the relationship we want in the same way?

(22:52) The feminine and the masculine:  Along with goals and values, people’s exploration of gender roles and identities have been expanding as well. Deb believes that letting go of traditional gender dynamics is also key to attracting a match who will like you for your authentic self.

Deb goes on to say that many of her male clients identify or lean towards demisexual, meaning they need the emotional connection before they can get intimate with someone. But because society has told them that prioritizing emotion invalidates their masculinity, it’s hard to let that authentic part of themselves thrive. 


Deb continues, “one thing I say often when that subject comes up is, if women were all feminine all the time, and men were all masculine all the time, the men would beat each other up and kill each other, and the women would be in puddles on the floor crying.  We all have to balance both of these things all the time… to say that just because you were born a certain way, you therefore have to have these characteristics, is ridiculous.” 

Bottom line: we have more freedom now than ever to explore what feels authentic to us. So take advantage of the opportunity, and don’t be afraid to listen to your gut.

(27:20) Turning up the heat:

Damona adds, “I believe there’s value in understanding the various parts of ourselves. And sometimes we need to turn up the volume on certain parts. And sometimes we need to turn down the volume on others.” 

For instance, if you decide to go on a lunch date during your work day, your mind would most likely still be in work mode. You might be thinking about what you will have to go back to. Although this is technically presenting an authentic part of yourself, it’s not ideal when you’re getting to know a potential partner.


So, If you have to make the transition from work to a date, Deb recommends having a jam song that you can sing at the top of your lungs beforehand (even if it’s in the car on the way there). On top of that, Deb suggests changing one thing about your appearance – maybe take a tie off or change your shirt, or put on your best lipstick and jewelry. Both of these tips help your brain to recognize that you’re shifting into a different mode of energy.

(29:19) Bound and gagged by Christianity:

Deb’s book, Bound and Gagged by Christianity, is all about navigating her own path of life and love after leaving her fundamentalist Christian Church. Deb recounts getting married very young at 23 years old, and that this marriage was sort of an arranged marriage.  She explained that in her community,  you didn’t really date anyone unless you thought that you were going to marry them. 

Divorce was also a concept that the church thoroughly rejected. “It took my ex-husband being really bold and brave to say, you know, we just can’t keep on. And I’m grateful for that, actually, because I decided that I could redesign my life.” 

Another thought remained in Deb’s head after her divorce – “Gosh, I’d really like to have sex”. Her strict upbringing had prevented Deb from exploring her sexuality.  Her husband was the only person she had ever been intimate with. She needed to unlearn the stories the Church had taught her about purity and consent. Doing this for herself led Deb to her current religion, which is the religion of love. 



Check out all of the dating help Deb offers, plus more info on private coaching, on her website



Submit your questions on  Instagram, Twitter, or Facebook and hear our answers live on the show! Here’s what our listeners asked about this week:


  • Email from S – Hi Damona. My question for you is, when is the best time to come forward and tell a man that I’m Dyslexic? It’s no joke, it’s been a struggle my whole life. I’m no dummy but just a slow reader and an awful speller (thank God for spell-check and audiobooks). I am a professional Esthetician and have been self employed for 20 years. I know how to work around it and most of my clients don’t have a clue, but when it comes to an intimate relationship I can’t hide it. I feel like I’ve explored every option – not telling is definitely a bad idea, but telling too soon can be a slippery slope. I’ve never been married and I always feel like this Dyslexia has put off some dates & a couple of ex-boyfriends. I would love to meet a man that will be understanding and patient. I took the last two years off after a ugly breakup and now I feel like trying. At 51, I have shied away from starting any dating apps because of setting up my online profile and fast past of texting.

Email from N – What if you connected on your first date, and then spent the night together? At 50 I feel old enough to make a decision like this. Is it bad to not slow down? Does it always blow the relationship? What’s the statistic? What’s a good timeline and what do you say to that person?


  • Download the OkCupid Dating App for free today!
  • Click here to try Damona’s free First Date Starter Kit!

Dr. Drew & The Big 400

It’s our 400th episode special of Dates & Mates! We’ve been collecting messages from Dates & Mates listeners who shared why they listen to the show. They’ll be sprinkled throughout the episode, including two very special messages from the Hoffman household.

That is not the only thing that makes this episode special. When Dates & Mates started 9 years ago, there weren’t many other shows like this around. But there was one show (and one person in particular) that gave Damona a roadmap for how she wanted to share her voice and knowledge with the world. That show was Loveline, and that person was Dr. Drew Pinsky – who will be the honorary guest on today’s episode!



Dr. Drew co-hosted the radio show Loveline for over 30 years and offered advice on dating, relationships and so much more. In addition to his career as a TV and radio personality, Dr.  Drew is a doctor of internal medicine and an addiction specialist. He continues to treat patients to this day.  

Dr. Drew and his wife, Susan, have been married for 30 years and they currently work together to produce the podcast, Ask Dr. Drew. Today he joins us to share the story of their 7-year courtship and his secrets for a long-lasting relationship.

(4:30) How Dr. Drew met his wife Susan:

Dr. Drew sets the record straight on his marriage origin story. It’s 1982 – Dr. Drew had finished his second year of medical school, and he and his friend went out to a bar to blow off some steam from studying.

When they arrived, they were surprised to find that a fashion show was being held at the bar, and it was at that moment that Dr. Drew spotted his now-wife at the mic MC-ing the show. He recalls having this weird, cosmic feeling of “I have to talk to this person.” Buuuut this apparently wasn’t reciprocated, since she blew him off pretty hard.


Two years later, Dr. Drew was in the studio hosting Loveline when Susan appeared.  She was at the radio station as a guest to promote another fashion show. Dr. Drew describes how he felt a powerful attraction to her again, and he explains how he did something he had never done before.  He knew that she was in a relationship, but he still asked her to please take his phone number, no strings attached. He says he just “had” to do it.

Susan eventually did give Dr. Drew a call, and it wasn’t until a year later that they both realized their paths had crossed before. They continued to date off and on for seven years, until finally staying together. “I think it’s Eastern philosophers like Chinese philosophers that have a saying about the important people in your life entering more than once,” mentions Dr. Drew. “They come around a few times typically.”

(10:23) Good stretches and bad stretches:

Damona asks Dr. Drew about why he and his wife were off and on over the years, and how he knew when it was the moment to pursue the relationship head-on. “It’s more that I knew when it wasn’t the moment. I knew that if I got married or committed myself to somebody, let’s say five years into our relationship of on-and-off again, I’d blow it if I was not ready.” 


He continues that readiness, and having a sense of when you’re ready for something, is such a personal compass. Part of this process is accepting how you may need to let go of the right person if it’s the wrong time, which can be hard to swallow. 

Damona also inquires Dr. Drew’s thoughts on “doing the dance” of dating (i.e. when should I text them, is it too early/late to call, I have to wait for them to reach out first). Dr. Drew is very clear that men will never play games with you, they are wired to see things very simply.

And if a guy IS playing games with you, it’s either to keep you from getting too deep into the relationship, or to keep themselves out of the relationship. Bottom line: the more direct and honest you can be, the better it will be for both parties.


(14:36) One day at a time:

Dr. Drew gives a piece of sound relationship advice that parallels the work he does in long-term recovery from drug addiction – take it one day at a time. He states that if you are happy today, you will most likely be happy the next. Take the time to express gratitude for your partner and let them know that you appreciate them.

But if you are not happy today, the negative feelings will continue to build up. This is when you need to pay attention and hone in on what is missing for you. Damona adds that much like Dr. Drew’s advice, a relationship is just a constant choice. “You get to choose to be committed to the relationship. And it’s this constant process of recommitting.”

Damona also brings up the elements of communication and conflict resolution in a relationship, which can be very layered. She points out that if your model for relationships has been a dysfunctional one, then having clear and honest communication can feel wrong. In these cases, fighting or a lack of communication will feel comfortable and familiar, however unhealthy it may be.


Dr. Drew says the remedy is learning how to fight fairly. “One of the ways to think about it is when there’s a winner, the relationship loses. The fighting should not be gratifying, it should not be interesting. It should be something you just want to understand and move past and not let it escalate in any way.”

(19:56) When people are ready, they’re ready:

Damona brings up one final point with Dr. Drew – what can I do if my partner doesn’t show up to do the work? Put simply, Dr. Drew answers that you can’t force somebody to show up to do the work, they have to make the choice. But when someone motivates themselves to step up to the plate on their own, they will be ready.

Dr. Drew indicates that he’s a big fan of EFT, or Emotionally Focused Therapy, because it’s all about supporting both people in a deep context. He adds that most people usually feel heard and understood, and come out having clarity about what’s creating the conflict and what each other is experiencing.


EFT also helps you to listen with your whole body (wait, what?). “It’s really the difference between hearing the words, and listening with your whole body. Your body is the instrument of what you’re listening to. You hear it to your toes, and you feel it, hear it, and process the information as it’s coming in.”

You can hear more of Dr. Drew’s amazing advice and insightful conversations on his podcast, Ask Dr. Drew.


Submit your questions on  Instagram, Twitter, or Facebook and hear our answers live on the show! Here’s what our listeners asked about this week:

(24:57) “Waiting For Chemistry” asks: My new date seems a lot more interested in me than I am, but I’m not feeling it yet! He lacks that sexual spark for me and I admit it’s from comparing him to my past lovers. However, he meets all my must-haves and seems devoted to a real relationship. I don’t want to lead him on, but how long should I continue to show him my undivided attention in terms of going out and showing physical affection? I’ve already slept with him, partly because I wanted to see if that changed the chemistry between us – it hasn’t.

(28:10) Anonymous asks: The last couple of months, especially over the holidays, have been very challenging emotionally, mostly due to the continued isolation and living alone with the day-to-day anxiety during covid. I’ve done EMDR, and I’m likely going to start taking medication soon to help me through this very difficult time. Something I struggle with now is finding the time, energy, and mindset to even check the apps or have a phone call or in-person date. When will I know I’m ready to date? And how do I get back out there?

(31:23) Anonymous asks: How does one handle dating with a disability that is only occasionally visible but yet can’t be denied?

(31:23) R asks: I’m still looking young at 34 years old, but I just find myself in a single place – others in my life already have families and now are even married. Coming from a Latino based family, I get asked by Aunts and Uncles when am I going to find my match, and it’s just killing me inside. Especially that I’ve been through so much in my life since I am epileptic and have had more than 6 brain surgeries now. When women see me, they ask me about my scars on my head, and I will always feel it’s not their business to know about my medical condition. But will they just run away like always?

(37:21) Dani asks: Why do I want physical intimacy and touch when I think about the person I am going on a date with, but when I am there with them in person, my instinct is to pull back and I often feel uncomfortable with affectionate contact? I understand it takes a while to warm up to someone, but it can feel really frustrating to want to run towards something in my head only to end up running away from it in person.

(41:03) Anonymous asks: I am going through something really painful. I caught my boyfriend of 5 years in a lie and he revealed that he loves another woman. This was via text and he hasn’t contacted me since. I would love it if you have any advice or pointers. I feel so lost right now.

(43:20) Anonymous asks: When I am out in social settings, I have been told I am unapproachable or intimidating. How can I appear more approachable?


  • Download the OkCupid Dating App for free today!
  • Try Damona’s free First Date Starter Kit at