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.


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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?


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