Tag Archive for: dating offline

Summer Dating & SET It Up


It’s 4th of July, Independence Day here in the States! And while people might say summer isn’t a great time for romance, we beg to differ.

This week 20 years ago, Damona actually had her first date with her husband Seth, and has since made many matches for her clients over the summer.

Summer takes people out of their normal routines. Think about it – there’s travel, summer work schedules, wanting to be out and about enjoying the good weather with friends. It’s switching up the mundane that gets you to take chances, say yes to new things, and bring new people into your orbit. And THAT is precisely the energy we want you to harness if you’re single this summer.

The other thing that makes this summer unique is this is the first time we are officially not in a pandemic in 3 years!!! Everyone has had their lives deeply impacted since Covid-19, which has prompted people to enter into dating with a new mindset and drive for true connection.

So let’s get down to it. Here are the 3 ways you can take advantage of your single status this summer…

  • (2:00) Adopt an attitude of yes.
  • (2:25) Embrace the apps – here’s how.
  • (4:00) S.E.T. it up! (AKA Smile, Eye Contact, & Touch)

Ready for Damona’s 201 Flirt School class? She recently created an entire Guide on Flirting in the Blinkist app!

Blinkist allows you to hear or read the key points from books and podcasts, and they invited Damona to share her biggest flirting tips and favorite books that will help you with your flirting skills. Download Blinkist today and look for Damona’s Guide on Flirting. 😘

Argument Styles & Dr. Orna Guralnik


It is NO secret that we love television shows about relationships and dating, but one Damona holds particularly dear to her heart is Showtime’s “Couples Therapy.”

If you don’t already know about the show, the documentary TV series is a deep dive into the authentic and visceral experience of weekly therapy where couples confront each other AND themselves. Spicy, but also, incredibly deep. It’s the best.

Leading the sessions for all three seasons is our guest today, Dr. Orna Guralnik! She’ll be sharing how she leads couples to some extraordinary breakthroughs, the best and worst ways to show up in a partnership, and what she has learned along the way.


How to figure out your partner’s “argument style”:

Refinery29 came in clutch with a recent article about how identifying your argument style can help your relationship dynamics in a similar way to knowing your love language, attachment style etc. 

The article lays out four common argument styles: Attacking, Defensive, Withdrawing, and Open (AKA the “holy grail” of argument styles). 

The author also points out that identifying the feelings or sensations that arise in your body during an argument can be key in directing you towards your argument style. Damona refers to this act of noticing as interoception, and explains how this can help you tune into your intuition and use it to improve your relationship communication.


Dr Orna Guralnik is a Clinical Psychologist and Psychoanalyst practicing in New York City. She lectures and publishes on the topics of couples treatment and culture, as well as culture & psychoanalysis.  

Her article – “I’m a Couples Therapist. Something New Is Happening in Relationships.” – was featured in the New York Times in May. And, of course, she is the host of the hit Showtime television series, Couples Therapy.

(11:24) How do you get people to reveal themselves?

As a renowned couples therapist, Orna seems to have the magic touch when it comes to helping couples open up. Orna states, “The whole therapeutic profession is based on the idea that if you create space, people will want to walk into it. People want to share space, people want to connect.” 

She also mentions that she is listening to the less conscious registers of what is troubling someone. This includes details relating to early family dynamics, personality structure, trauma, attachment styles, and the overall societal issues that affect how a couple is interacting with each other.

(17:30) What are the biggest elements that are shifting for relationships today?

Referencing her infamous article “I’m a Couples Therapist. Something New Is Happening in Relationships,” Damona asks Orna about the biggest elements that are shifting for relationships today. “With the recent social justice movements, we’re all learning what it means to understand ourselves in relation to systemic issues and how these issues are running through us… This helps us understand what’s governing the dynamic of a couple.”

Orna also points out how the consciousness of privilege is shifting the way we look at relationships (and let alone communicate). “When you really understand privilege, how privilege shapes the way we experience the world and how people differ in terms of how much they walk around the world with or without, something really fundamental changes inside you.”

(25:40) We gotta go to the hard, scary places.

As most of us can presume, any type of therapy will only work as much as you are willing to open up and go deep. Damona wonders how one might handle a situation where one partner in a couple is willing to go deeper, but the other isn’t ready? Orna responds, “The person who’s not in pain is out of touch in some way that they’re not well in the relationship, so it’s just a matter of time in how to gain access to that part of the person.” 

Orna adds, as the therapist, that there’s a level of “the client is always right” – if she can’t get through to someone, Orna believes she needs to figure out what is being blocked and adjust her approach. But this is always made easier if the client is willing to be as open as she is.

(32:25) Becoming a better partner starts with being yourself.

Damona asks what advice Orna can give to single folks on being a better partner, and her primary advice is to “show up as yourself and not someone else.” She also believes that a good reason to get into a relationship is to expand beyond who you are, not just pull someone into what you already are and know. And if that’s your motivation, then it’s going to get wonderful, complicated, and really interesting.

Orna also shares how you can get motivated to do the hard self-work, and reframe it so it’s not scary (hint: stay curious about yourself).


Be sure to follow Dr. Orna on Instagram @OrnaGuralnik and check out Couples Therapy on Showtime!


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:


  • Voicemail from S – Hi Damona! I’m a finishing PhD student and I’m getting ready for a big cross country move in the next 6 months. As you can imagine, I have a lot on my plate. I am curious about short term dating, but I could use some advice. On the one hand, I think it would be good practice. That way when I get into this new environment I’m ready to dive in feet first. But on the other hand, with everything that’s going on, I don’t know if it’s going to be a good distraction or if it’s just going to add more stress. I would love to get your advice on how to go about short-term casual dating or anything about dating right before a big move. Thank you so much for your time and your advice, looking forward to hearing what you have to say!


Unsure if your question is right for Dates & Mates? Check out our recent all-Dear Damona episode to get a taste of what our listeners are thinking. 📝 

Truths and Myths & Reality Gays


In reality, love is all around us! No, seriously. We see it in shows like Love Is Blind, Married at First Sight, The Bachelor, Too Hot To Handle, and so so so many more. 

At Dates & Mates, we are HERE for this reality dating renaissance. (Damona has even hosted some reality dating shows herself). They are both a window into the current landscape of dating and a mirror reflecting many of the same dating experiences that we’ve all been through.

They also give us an opportunity to learn through the contestants’ experiences, and it’s a heck of a lot of fun to watch too. So today, we will be doing an ALL-Dating Dish episode to examine the latest TV trends, some new data, and hot headlines on dating and relationships. And we’ll be joined by one of Damona’s BFF’s and host of Reality Gays, Matt Marr.


Matt is one of the hosts of the mega-hit podcast, Reality Gays. But what some people don’t know is he’s also trained as a psychotherapist, so he knows all about why we do the wacky things we do in love. 

Plus, Damona and Matt will be celebrating Pride Month Reality Gays style.

(5:05) Not celebrating Pride Month? Here’s how to be a solid Ally. 🏳️‍🌈

Although we often focus on the “out and proud” aspects of Pride Month, there is always room for clarity on how to be a great ally. This recent headline about Abbott Elementary star Tyler James Williams is the epitome of how to do just that. After rumors started circulating about his sexuality, Williams stepped in to highlight how overanalyzing someone’s sexuality “contributes to the anxiety a lot of queer and queer questioning people feel when they fear living in their truth.” 

Matt and Damona weigh in on Williams’ statement and the importance of coming out on your own terms.

(11:25) Love Is Blind & relationship timelines…

If you watched Love Is Blind Season 3 (one of the shows Matt consistently covers on his podcast), you may remember one of the season’s most controversial couples – Matt and Colleen. The two did get engaged at the end of the season, but decided to prolong moving in together. And after two years of marriage, they’re finally doing it!!! 

Damona and Matt recall the couple’s emotional history, and dive deeper into breaking conventional relationship timelines. (Check out Damona’s thoughts on when couples should have the moving-in-together talk…)

(18:00) Once a cheater, always a cheater??

After coming across this article from The Guardian, Damona and Matt shed some light on some controversial relationship myths. Including, should you ever go to bed angry? Can a relationship really survive an affair? Once a cheater, always a cheater? And – *drumroll please* – is it possible to have a good sex life FOREVER?

(26:15) The state of Matt Marr.

Matt spills the tea on his own relationship status, diving into the embrace of his anxious attachment style and how thinking you’re “good with being alone” may actually be a reaction to some inner codependency. 

After a rocky relationship that ended in a lot of mistrust, Matt also shares some of the concrete steps he took that helped him learn to trust himself in dating again.


Be sure to follow Matt on Instagram @TheMattMarr and check out Reality Gays wherever you listen to Dates & Mates!



There is no Dear Damona this week, but you can submit your questions on Instagram, Twitter, or Facebook and hear your answers during a future episode of Date & Mates!

Single on Purpose & Second Date Decision


Going through stretches of singlehood is part of the dating process, but when the stretches run long, we can begin to lose our motivation. We may begin to doubt ourselves or question if we can create the kind of future we had in mind.

But what if we told you that these periods of singlehood were actually your greatest opportunities for growth and discovery? A time to confront your past and emerge into the world with a new perspective.

It might feel counterintuitive, but our guest today and good friend of the show, John Kim (AKA The Angry Therapist), is here to help you see the light. He will be joining Damona to talk about how you can transform being single into a joyous, exciting period of personal growth. Plus he’ll share some of the tips and exercises from his new workbook, 31 Days of Single on Purpose.


Here’s how long it takes most people to decide on a second date:

According to a new survey covered by the New York Post, the average dater knows whether or not they’d like to see someone again at the 19-minute mark of their first date. The article also noted some of the main traits folks pay attention to on a first date (manners, conversation skills, etc), as well as taboo first date topics and the main contributors to the end of a relationship. 

As for Damona’s take? Although we may have made up our mind about someone at the 19-minute mark, your best first date should be 1 HOUR LONG. We break it all down on Damona’s blog here…

JOHN KIM (9:10)

John Kim is a Licensed Therapist & Life Coach, best-selling author and the host of The Angry Therapist podcast. His books include It’s Not Me, It’s You; Single On Purpose; I Used To Be A Miserable F*ck and more.

John’s latest book, a workbook, 31 DAYS OF SINGLE ON PURPOSE, is out now!

(11:30) Why a workbook, why now?

Although having written several books, “31 Days of Single On Purpose” is the first workbook John has published. He shares that he always found workbooks kind of cheesy, but what became his main source of inspiration was the aspect of being a community builder, and creating a venue for singles to help each other out using the workbook.

John says that singlehood is the soil most fertile for growth and that finding community or groups of people you resonate with is huge. 

(16:30) What does it really mean to be single on purpose?

Inspired by his book of the same name, John recently began a podcast collective called Single On Purpose (check out Damona’s episode here). But what does it really mean to be single on purpose? 

After having coached many singles who lost themselves in their relationships, John states “it just means to find yourself first.” So when you build a relationship with yourself, you go into relationships with a foundational sense of self.

Mantras and meditation also play a huge role in John’s definition of being single on purpose. There’s so much power in language, and “if we don’t have an intentional mantra, we return to distorted thinking.” 

John continues that being single on purpose isn’t an easy feat, and shares his own struggles with his journey.

(25:10) “I’m not lonely, I’m experiencing loneliness.”

John and Damona dive into one of the hardest aspects of singlehood, which is remembering that everything is temporary. “When you’re single, the big fear is, is this going to be forever?” 

John notes it’s important not to internalize your feelings of loneliness as a permanent state of being and instead remember it is a feeling that will pass. Just like Day 23 of his workbook states, remember that your experiences do not define you.

(30:45) How do you know you’re relationship-ready?

The whole concept of being “ready” for dating or a relationship is a slippery slope. Sometimes we may be ready but we don’t know it yet, or we may think we want to get out there but still have some necessary work to do. 

John and Damona note that you might realize you’re ready when you meet a certain person, or some people even find “ready” while they’re dating. Of course, it’s all up to your discretion. But Johns says “it’s like having children – at some point you just take the leap.”


Be sure to follow John on Instagram @TheAngryTherapist and grab a copy of 31 Days of Single on Purpose by visiting TheAngryTherapist.com.



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 P – Hey Damona, I’m a single mom and have struggled to find love… I thought I found it in my most previous relationship but I was so wrong because I became a mistress and now I keep attracting that. I want my own relationship and I’m wondering if that’s what I’m putting out? I don’t want to jump into the wrong relationship because I have to protect myself and my child.

Language of Love & DM Dating

Are you using all of the available tools to find your match? We know about dating apps. We talked recently about singles parties. And, we’ve even talked about letting your friends set you up. But have you tried flirting on Instagram?

Okay, that last one may feel forward but with so much of our time spent online these days, it actually makes sense. Even still there’s a right way and a wrong way to do it and that’s why my guest today is the perfect person to be joining us. She and her boyfriend have been together for over a YEAR and it all started with a casual DM she sent.

Joy Ofodu is a celebrated voice actor and the host of Dating Unsettled! She will be sharing her IG love story and her top tips for how YOU can use Instagram to find your match. 


How to Fall in Love When You Don’t Speak the Same Language:

In this deep dive from the Atlantic, this article author spoke to different couples all around the globe who were in relationships with someone who spoke a different native tongue. Multilingual relationships are more possible today than ever, with translation apps and learning resources like Duolingo. There are also numerous pros, as well as some obvious obstacles, to dating someone who speaks another language. 

Damona breaks it down, including the unexpected ways speaking different languages can actually benefit your relationship.

JOY OFODU (9:50)

Joy Ofodu is a Creative Executive and voice actor whose voice can be heard in her partnerships with HBO Max, Adult Swim, Netflix, Refinery 29, Meta, Credit Karma, DIRECTV, Upenndo! and more!

She has drawn over 30M views to her original digital comedy content and countless more to inclusion-centered, global marketing campaigns at Instagram. 

Joy is also the host of Dating Unsettled, an audio show designed to validate women daters, available now on all podcast platforms. 

(12:50) What’s happening in these dating streets??

Joy breaks down some of the most common missed opportunities in online dating, including how she ended up with her current partner through a spur of the moment direct message. In her words – “I’m gonna make some people mad. Online dating is the best, quickest, most efficient way to find somebody that you are compatible with on multiple fronts that you can actually kind of control.”

(20:50) Leave some room for grace.

We all know ghosting has been kind of rampant in dating culture as of late, but Damona points out that as a result, we are becoming more quick to cut someone off at the first sign of flakiness. Is there room to give people some grace and remember that nobody’s perfect? 

Joy points out that someone else’s dating rules or deal breakers will not always work for you, and that’s okay. She gives some other pointers on navigating your own dating journey, most importantly to remember to listen to your intuition.

(25:40) The voice note is our dating superpower.

Being a voice actor herself, Joy is the first to recognize there’s something about the power of the human voice. “I think it kind of simulates what you would be experiencing on the date before you even get there, without giving them a full plate. So it’s a teaser. It’s romantic. It’s exciting.”

(32:20) Hardcore Instagram flirting hacks…

On her own podcast, Joy is all about giving her listeners actionable dating advice. She goes over her top IG flirting hacks, including taking advantage of your Close Friends story and making the most of their newest “status” feature.


Be sure to follow Joy on Instagram @joyofodu and listen to Dating Unsettled wherever you listen to Dates & Mates!



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 Sean – Hi Damona. In your opinion, who should ask if the relationship is “official or exclusive”? The man or the woman? Also in your episode with Lauren Zoeller, you say not to put all the eggs in one a basket until 60-90 days. Does this mean the two should NOT think about becoming exclusive until at least 3 months? Thanks!

Dear Damona: Rubbish Texter & Dating Racism


We have covered a LOT of topics over the last 5 months – from building your own relationship with columnist and author Dan Savage to the challenges faced in interracial dating with Rachel Lindsey of the Bachelorette.

At this point, we can confidently say that if there is one thing Damona has in common with you all, it’s a thirst for knowledge. And boy, does that manifest in the number of emails, DM’s and voice memos we get from all of you.

But hey, we are NOT complaining! While we love bringing you the most up to date and helpful information on all things dating, our favorite thing is still answering your questions directly. And that’s why we’ve decided to do an all Dear Damona episode today! 🎉



(3:42) Voicemail from Alexis: Hi, Damona. My name is Alexis. So really, I have a big problem with moving past a scarcity mindset. So how do I remain positive that there are people out there, especially considering that I haven’t had much experience in dating? In addition to that, the past three years have been pretty rough with the pandemic. I’m also still figuring out my career. Really what it boils down to is I don’t feel successful enough really to be dating. I want to focus more on my career. But at the same time, I also want to make up for lost time that I spent not dating prior to the pandemic. How can I feel successful enough to feel comfortable dating?


If you want to dive a little deeper on building self-love and confidence, check out Damona’s episode with author and life coach Michelle Elman.


(10:35) Voice Memo from C: What do you do when you’re in the early stages of dating and he seems keen in every other way, except for the fact that he’s a rubbish texter? Now, he is a doctor who works shift work. So I’ve been inclined to give him a little bit of a pass. But we could be having a conversation, he’s texting back, and then all of a sudden it takes him like two or three days to reply, which seems a bit crappy. So what do you do there? Do you just kind of continue to go on the dates but just have lower expectations? Do you keep exploring other options, or do you playfully call him out on it?


This question is a doozy – but if you want more texting tips, Damona did a recent interview with fellow dating coach Blaine Anderson. Damona and Blaine also go into more detail about how to avoid the Texting Trap.



(17:10) Voicemail from B: Hey Damona! I just got back onto Tinder after a breakup a couple months ago, and it’s going pretty well. I had three solid first dates with three different guys this past weekend. And yet, I’m still curious about some of these other guys I’ve matched and had communication with on the app. I live in a huge city with tons of options, which can be obviously a blessing and a curse. So how do you know when to stop looking? And then beyond that, do you just go on second dates with all of these people, assuming that they’re actually into you? And then do you disclose this to them? Is that type of transparency respectful or is it unnecessary?


Getting back on the apps after a hiatus? Then you’ve GOT to download Damona’s Profile Starter Kit – only free for a few more months!!


(23:50) Voice Memo from B: Hi Damona, I have a question. So there’s this guy that I met through Facebook. We follow each other on a couple of different social media platforms. And we flirt and we text back and forth sometimes, but he’s never asked me on a date. So to me, I was kind of thinking I was friendzoned. Well, he just invited me to his 40th birthday party. And now I’m a little bit nervous about going because it would be our first time meeting each other with all of his family and friends there. Do you have any advice? Am I thinking too much into it? So anything you have to say would be helpful.



(28:45) Voicemail from Cautiously Open: Hi Damona! So as a black woman, I have always found beauty in all ethnicities, but have always felt more comfortable with black men. As of late, I’ve been really feeling like maybe I should expand my horizons and be open to dating outside of my race. But the one race that kind of scares me to be in a relationship with is white men. While I’ve met some really nice white men, with everything that has gone on in the political arena in Charlottesville, it has really scared me. To the point where I’m just like, well, what if he’s okay, but his friends or his family are racist? How do I fully open myself up to the idea of being in a relationship with a white man, knowing that there’s a possibility that I would be encountering racist people? I’m open to being with whomever or whatever ethnicity, but that’s the one thing that scares me. I also find that when I’m out, those are the men that look at me. So if white men are finding me attractive, I don’t want to reject them for fear of my assumption. How do you navigate that?


(37:35) Voicemail from Ms. M: Hi Damona, I’m a 43 year old pansexual cisgender female. I spent the last eight months not dating to become very clear about what I want going forward. I listen to Dates & Mates every week and read Myisha Battle’s This Is Supposed To Be Fun. Right now I’m looking for respectful and empathetic folks with aligned values that I can go on fun dates with as well as explore my sexuality with. Ultimately, I would love to find a Shibari partner. For me practicing Shibari means getting to know someone and establishing trust. This will not happen within the first few dates. I don’t want first date sex or hookups, however, I also don’t want a long term relationship. I want a lover I can continue to explore with. How do I convey this in my profile? I found that if I write I like Shibari, my matches tend to take the in-app convo to a very sexual place before meeting IRL. I’ve thanked and released a few of these matches already. Damona, I want to practice slow love and explore my kinks and sexuality. Is this possible? Also can you explain slow love some more? Is sex on date five within three weeks of meeting too fast? I know it’s different for everyone. Thank you so much!

Submit your questions on Instagram, Twitter, or Facebook and hear your answers live on a future all-Dear Damona, or another episode of Dates & Mates!

Multiamory & Short King Spring


Look, relationships aren’t one size fits all. We each have unique needs and desires, origin stories and goals. And with so many people out in the world today, there seems to be a match (or two, or three) for everyone out there. That coupled with the fact that relationships are no longer solely a financial commitment means you really can build your own. That’s part of the beauty in dating today, we have choice.

We can choose to be in a monogamous relationship, to be multiamorous OR to be lifelong bachelors and bachelorettes. And of course, there are even lifestyles in between. We get to choose the relationship types that best suit our lifestyles and the futures we have in mind. 

Whatever YOU choose, it all comes down to communication. That is what will determine how well you and your partner, or partners, connect and build trust. And that is why we have Dedeker, Emily and Jase, the hosts of the Multiamory Podcast, joining us today to talk about how to identify what you need from a conversation, how to use microscripts to manage difficult topics, and how to make repairs after things get heated.


Why has height become such a significant factor in dating?:

If we’re being honest, height has ALWAYS been a significant factor for folks in dating. But this recent article from Glam Magazine helps break down the exact origins of our height biases, how our instinct for survival plays a factor, and how this all plays into our perception of gender roles. Damona further explains why what we’re attracted to doesn’t just “happen.”


Jase, Emily, and Dedeker created the Multiamory Podcast in 2014 to raise awareness, provide approachable resources, and combat the stigma faced by people in non-traditional relationships. 

Together they have been featured in numerous publications, including NPR, Vice, Huffington Post, Oprah Daily, Cosmopolitan, and Elle. In addition to their national tours, they have presented at the Google campus in Seattle and have been keynote speakers and presenters at numerous conferences.

Their new book “Multiamory: Essential Tools For Modern Relationships” is out now!

(17:55) Origins of the Multiamory Podcast…

Fun fact: before they launched their podcast exploring relationship archetypes and nonmonogamy, Jase, Emily, and Dedeker were in a relationship quad with another partner. 

Although the quad eventually broke up, Jase, Emily and Dedeker decided to launch the Multiamory Podcast. At that time (around 9 years ago), there wasn’t NEARLY as much research about non-monogamy or alternative relationship models out there as there is today. 

Dedeker continues that “over time, we started to find that a lot of this advice was about good relationships in general. Whether you’re monogamous, non-monogamous, sometimes even going beyond whether you’re in a romantic relationship or not.”

Jase also dives deeper into how the perception around non-monogamy has shifted over the years, and the biggest misconceptions about this relationship model.

(23:30) The Triforce of Communication

Having researched it so much, Jase, Emily, and Dedeker are ready to share their biggest insights on what makes great communication. Emily starts, “I think it’s really important to be able to look inward at your own history with how you communicate with others. And that’s from your childhood or the way that your parents may have communicated with you, and the ways that may translate to how you communicate with your partner.” 

Emily and the gang bring up a concept from their book called the Triforce of Communication and how to use it to gain clarity on what you need from your partner (or another person) in a conversation.

(32:05) Let’s talk about neurodivergence.

Dedeker mentions that when diving deeper into the non-monogamous community, you will find a lot of non-neurotypical people. “Often people who are different flavors of neurodivergent really appreciate clear structure, a clear sense of the rules of engagement for how we’re going to engage in this conversation, for people’s intentions to be very clearly laid out.” 

Dedeker then shares her experience with being on the neurodivergent spectrum, specifically dealing with some significant PTSD.

Jase and Dedeker also explain how they worked through their gaps in communication, using something they refer to as personalized “micro-scripts.”

(42:30) What should we keep in mind when establishing boundaries?

Many of us often conflate boundaries with rules or limitations on our partner, but Emily asserts that boundaries are necessary because they allow us to advocate for ourselves in a relationship – “it’s not something you’re doing to punish a partner, but rather something you’re doing to keep yourself safe.” Dedeker adds that the power of boundaries is all about what you can do to change your own behavior, because that’s the thing we have the most control over.

Jase then describes another concept for repairing conflict in their book called “SHOP” and how it works.


Be sure to follow them on Instagram @multiamory_podcast and grab a copy of their new book, Multiamory: Essential Tools For Modern Relationships, by visiting Multiamory.com/book.


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 S – Hi Damona, I’m trying to get my brother back into the dating pool. After a failed marriage, and 3 kids later, he feels that he won’t ever find love or have a family again. He feels he’s not going to find someone who will want a man with 3 kids. He is also afraid to be used, and that people will only want him for his money. How do I approach this conversation to tell him that love is out there just waiting for him, when he is so down on himself and being negative?

Chaotic Singles Party & The Silent Treatment


Are you ready to party?! Okay, not really, but we are changing things UP today.

Y’all know that Damona talks A LOT about dating apps. It’s how she met her husband and how she has helped so many others to find love.

But even still, Damona will be the first to tell you that online dating is just one tool you can use in your search. It shouldn’t be your ONLY strategy.  You can also let your friends set you up on a date, try a matchmaker or pick up a new hobby to meet people. 

We all know that chatting with strangers can seem overwhelming but it is a great opportunity to find love and that’s why we have Cassidy Davis, the founder of Chaotic Singles Party, joining us to talk about how to meet your match IRL.


It’s time to embrace the awkward silence:

As this recent article in The Atlantic says, uncomfortable silences have always existed. But they’re harder to avoid today than ever before. Our newfound reliance on Zoom also highlights the way awkward silences can permeate conversations through lag time, glitches, and not knowing who should speak first in a Zoom room full of people. Not to mention, coming out of the pandemic hasn’t helped with practicing social skills. 

Damona dives into what makes silence feel awkward, shares her perspective on why we can all benefit from reframing the awkward pause to just be a “natural pause.”


Cassidy Davis is an actor, producer and the creator/host of the Chaotic Singles Party. Cassidy hosts parties monthly in LA and NYC.

She has been featured on Good Morning America, Insider, and the Wall Street Journal and on a little program that is near and dear to our hearts, The Drew Barrymore Show.

(10:30) What is a Chaotic Singles Party?

It all started when Cassidy was feeling “really sadly single for five years” and she had the idea for her and her friends to each invite someone single to a house party. But in a last minute panic, Cassidy invited 65 additional strangers off of Tinder to come to this party too! 

It was such a success (AKA no creeps, no robberies) that Cassidy began hosting these parties monthly. One year later, business is still booming. As Cassidy mentions, “it’s better than going on dates alone, let’s date together as a unit.” 

Cassidy also shares some of her favorite CSP success stories.

(14:15) Making the “meeting IRL” fantasy a reality.

Cassidy says, “My best tip to find success is to really lean into it. It might be way out of your comfort zone to go to a singles event, it might be way out of your comfort zone to start approaching people at the singles event. But the most successful people really just embrace the chaos.”

Cassidy also details why your hobbies (or finding new hobbies) are the key to meeting someone IRL.

(24:10) The ultimate opener…

So you get to the singles event, you’ve got your drink… now what? 

Damona asks for Cassidy’s ideas on good openers for starting a conversation. She states that a compliment can always go a long way. Or if someone is wearing a unique piece of jewelry or a graphic tee (what Damona would call “conversation piece clothing”), point it out!

Damona continues that we can get too caught up in saying the perfect thing to make a lasting impression, and sometimes the simplest move can lead to the biggest payoff. That being said – Damona and Cassidy share the topics you should avoid talking about too much at a singles ever or on a first date.


Be sure to follow Cassidy on Instagram @cassidynashdavis and learn more about her events at chaoticsinglesparty.com.


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:

Text from Anya – Hi Damona! You totally changed the way I date and so far, so good, except – I met this guy on a matching app, and we get along SO WELL. We are both creative and have tried to live off our creativity so we both know the struggle. Even on other topics we agree on almost everything. On paper this guy is like, perfect. However, I’m not physically attracted to him! At all!! I’m a pretty sexual being but I don’t feel like touching him in any way, let alone having sex…? Nope. He just feels like my brother or best friend and that’s it. Should I trust my gut and tell him that? Or keep on dating him and see physical attraction grow out of… nothing? He is really a nice guy and I don’t want to lead him on if someone he is meant to be with is out there, waiting for him. I also know myself to be hopelessly romantic and because of that, I wonder if I’m waiting for that butterfly to happen if I meet the “right” person. We just had 2 dates and he hasn’t suggested anything intimate. So part of me hoped for him to say, he also doesn’t feel the chemistry… ugh I. Don’t. Know!! Help!!

Jewish Matchmaking & 5 Date Challenge

Are you dating in reverse?! It’s easy to get caught up in appearances while you’re doing your swiping but in the end does focusing on looks get you your dream partnership?

Probably not. You may have heard Damona mention her four pillars of long-term compatibility in previous episodes – common values, shared goals, trust and healthy communication. These are the things you SHOULD be basing your partner search on.

But shifting your focus is easier said than done, especially in a world that centers on appearances so much (hello Instagram). Luckily, there is plenty of inspo out there for how to date against the grain. We see it reflected in tv shows like Love Is Blind and Married At First Sight.

And, it’s happening again in the newest series to tackle the quest for true love, Netflix’s Jewish Matchmaking. The show stars matchmaker Aleeza Ben Shalom, as she helps Jewish singles find love across the US and Israel.

We’re excited to share that Aleeza will give us her matchmaking tips, some secrets from the show, and a 5-Date Challenge that’s going to blow your mind. 🤯


Modern dating only feels worse because we keep saying it is:

According to online publication The Face, four out of five US adults have emotional fatigue from online dating and three quarters of UK singles are burnt out from unrewarding interactions. Now, this isn’t necessarily a new stat. But the article makes a crucial point – what we consume becomes our reality. So could it be that going on about how romance is rare, only makes it rarer? 

Damona goes over how to rewrite your “dating samskaras” (AKA our belief patterns about dating) and why we need to stop screenshotting our dating app conversations.


Aleeza Ben Shalom is a soulmate clarity coach, speaker, and author of two books, Get Real, Get Married, and Virtual Dating. She has appeared everywhere from BBC World News to NPR to HuffPost. 

Aleeza also trains dating coaches and matchmakers through her company Marriage Minded Mentor, and has helped over 200 singles manifest their soulmate. 


(14:40) Not all Jewsish matchmaking is the same…

Aleeza breaks down how matchmaking for Jewish families plays out with different communities. “Jewish matchmaking as a concept is the foundation, but the people that we work with are from all different backgrounds. So we do have a couple that’s Orthodox, we have somebody who’s traditional, somebody who’s kind of middle of the road, we have people that are secular… we’re taking the traditional Jewish wisdom of matchmaking, and we’re bringing it to whatever dating world our people are in.” 

Aleeza also divulges her biggest challenges with her clients on Jewish Matchmaking.

(19:30) Aleeza’s 70/30 rule.

Relationships are built between two individuals, so there is always bound to be compromise. But Aleeza believes 70% of a relationship between these individuals needs to be aligned and balanced on its own. As for the other 30%, this can be where the work and communication comes into play. But all in all, Aleeza states that ZERO percent needs to be a potential dealbreaker, “because one deal breaker breaks the entire deal.”

(23:50) The infamous 5-Date Challenge!

Aleeza compares her experience matchmaking with clients as playing on a playground, giving them challenges here and there. And thus the 5-Date Challenge was born (which you can download here)! 

“First of all, if you’re gonna go out on one date, I want you mentally committing to 5 dates. You bothered to pick the person, you bothered to say yes. Get to know them! Can you break it off before five dates? If it’s an absolute deal breaker.” 

The most controversial thing about the challenge? No touching for those 5 dates.

(32:35) Recommendations on how to incorporate families into the matchmaking process?

We’ve all gotten ourselves on a dating app at some point. But when it comes to matchmaking, many of us don’t even consider incorporating our families into the process. This is a huge aspect of how Aleeza collects her clients’ options, as the wants and needs of the family are often weighed just as heavily as the client. 

With all her experience, Damona asks Aleeza how she navigates this dynamic and how others can begin including their family in the process if they so choose.


Be sure to follow Aleeza on Instagram @AleezaBenShalom and check out Jewish Matchmaking on Netflix! And if you want to take on Aleeza’s 5-Date Challenge, you can find it on her website MarriageMindedMentor.com.


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 T – Dear Damona, love your podcast! Can people be single for too long? Are there people who just are too set in their ways to meet and keep a significant other?

Empathic Listening & Single Male Loneliness

While scoping out the latest and greatest in dating news, we came across a stat that just about blew our minds – 54% of men say they’d rather play video games than have sex on a given day.

Say what?! The pandemic has without a doubt left many of us feeling lonely and isolated, but we found this info utterly shocking. It comes out of a study on Single Male Loneliness conducted by fellow dating coach, Blaine Anderson. 

The study is jam packed with so many fascinating findings that Damona just HAD to have Blaine on this week’s episode to break it all down. Plus, Blaine is one of the top dating coaches on texting (and you know how passionate Damona gets on the topic). Blaine will be sharing tips for everybody on how to be a better texter, how to send a first message that gets a response, and how to be in integrity in your dating life.


How Drew Barrymore gave us all a masterclass on empathic listening:

If you’ve ever heard Damona talk about empathetic dating, then here’s a headline that will hit home. Huffpost recently published an article taking a deep dive into Drew Barrymore’s interview style on her daytime talk show – but more specifically, how she demonstrates “empathetic listening.” Besides her iconically open and friendly nature, Drew engages in empathetic listening by simultaneously remaining curious and open to her guest’s own experiences. Drew also is big on self disclosure, often candidly sharing info with her audiences about her love life or struggles with addiction. Damona further breaks down why it’s important to be curious and empathetic in our dating lives.


Blaine Anderson is a dating coach for men and her mission is to curb the increasing isolation they are experiencing globally. She has been featured in major publications such as The New York Times, Forbes, Psychology Today, NYPost, and Vice i-D.

Blaine offers one-on-one coaching, practical online courses, and relatable dating content via her fast growing company, Dating By Blaine.

(13:45) Going into the stats…

Damona asks Blaine to break down her study on Single Male Loneliness – a big aspect being that men have given up on or see dating as too much effort. Blaine mentions that this is a huge symptom of our addiction to instant entertainment (re: the stat from the intro), and how “human instinct often is to pick the path of least resistance… so you really have to be intentional and motivated to go get your entertainment out in the real world.” Blaine and Damona also share strategies to navigate your dating life phone-free, and easing back into your dating journey after a period of loneliness.

(22:20) The profile photo is EVERYTHING.

So what is the biggest challenge for men when it comes to dating apps? Blaine has a few theories. But first and foremost, you’ve GOT to have a good set of pictures. Your profile photos are a chance for potential matches to see what it would be like dating you, so be sure to include some pics featuring your favorite hobbies and showcasing your interests. 

Blaine then explains the reality of dating app experiences for men vs women based on her findings, PLUS the reality of making the first move…

(34:45) How to avoid the quicksand (AKA the Texting Trap)

If you’ve listened to Dates & Mates before, you’ve probably heard Damona talk about The Texting Trap – essentially, this is when you get stuck chatting with your match solely over text, never making plans to meet IRL. Blaine points out that while it’s important to build a certain amount of trust with your match before meeting up, “it’s much easier to text yourself out of another date than into one.” Blaine additionally shares the most common texting mistake she sees from her clients when leading up to a date.

Blaine and Damona end by answering your most burning texting questions in a round of Yay or Nay: Texting Edition.

Be sure to follow Blaine on Instagram @DatingByBlaine and visit her website DatingByBlaine.com to learn more!



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:

  • Text from M – Hi Damona! I have been online on and off since my divorce in 2018. I have met a lot of wonderful men and have had a few relationships, but I’m still seeking my life partner. I have noticed myself swiping left on men who make a point of mentioning the importance of chemistry in their profiles even though I am a very sexual woman. Is this a mistake? I’ve been treating it as a red flag because it feels like they either don’t value compatibility or they haven’t put much thought into what they want beyond sex. Am I overthinking this?

Love Letters & Undefined Relationships

You all know Damona has been in this game for a minute – and by a minute, we mean like 17 years. Damona has spent her career as a love expert reading, studying, and analyzing all of the trends and stories out there on dating and relationships, so you can chart yourself to the love life you want and deserve.

And there are a handful of people who we’ve been tracking for a while. Folks who share this same passion for stories, for relationship trends, and for love. Meredith Goldstein is one of those people and it’s a special delight for us to share her interview today. Meredith will be sharing insights from her long-running Boston Globe advice column, Love Letters, and her podcast of the same name. 

You know how JLo once said “my love don’t cost a thing”? Well, Meredith and Damona will also be examining the actual cost to be single vs coupled and how it’s far more expensive to be in the wrong relationship! 


How do undefined relationships impact your mental health?:

At this point, we’ve all heard the terms “ghosting” and “situationship” floating around, and Forbes recently published an article spelling out the effects of undefined relationships on mental health. The article first defines a situationship – “a relationship of romantic or sexual nature that exists without commitment and the expectations of such” – and mentions the details of a 2022 YPulse survey, revealing that 16% of Millennials have been involved in a situationship and 35% of Gen Z individuals prefer an undefined relationship rather than one with a label.

Damona further explains why undefined relationships and ambiguity can work against us, and dissects another Time Magazine article written by friend of the pod, Myisha Battle, stating that “situationships are the future of dating, and that’s not a bad thing.”

(Check out Myisha’s Dates & Mates interview!)


Meredith Goldstein is an associate editor and advice columnist for The Boston Globe. Her column, Love Letters, is a daily dispatch of wisdom for the lovelorn that has been running since 2009. She also hosts the popular Love Letters podcast. 

She is the author of the memoir “Can’t Help Myself: Lessons and Confessions From a Modern Advice Columnist,” 

(19:34) Some of the best advice is the wrong advice…

Both Meredith and Damona were questioned when beginning their careers as to why they should be the ones giving others advice. Meredith elaborates, “I always used to tell people – if I was a trained mental health professional, I would not be telling people what to do in 300-word responses, that’s not really what happens. And so much of the process is about hearing an opinion from someone like you or me, and then saying, ‘Well, wait, that’s actually not it.’ Sometimes my best advice is the wrong advice. Because someone says, ‘oh, Meredith, I’m not going to do that. And here’s why.’”

Meredith also shares her own current experience with dating in her 40’s, and what she has learned about the metropolitan dating scene from those 40+ who write to her.

(26:30) Every story is really about money.

In her most recent season of the Love Letters podcast, Meredith decided to center her stories and interviews around the idea of money. “I started to realize that every story we’ve ever told was kind of about money. Like you could call it a story about how to meet someone, but it was about the cost of dating. You could talk about a breakup, but it was about the trip the person took after the breakup or running to the hairstylist to get bangs.”

Damona and Meredith discuss the gray area of dating during inflation, while Meredith relives an interview she did with a man who decided to buy himself a giant ball pit in his mid-fifties.

Be sure to follow Meredith on Instagram @MeredithGoldstein and check out her podcast, Love Letters, wherever you listen to Dates & Mates!




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:

  • Text from Dale – Dear Damona, I’m currently on Match and am finding that the majority of men that are interested in me I’m not interested in. The men that I look at their profile and think “oh you could be interesting”, don’t seem interested in me. Maybe that’s just normal, like that there are only a few folks of real interest… I tried really going out with pretty anyone who expressed interest and that just led to nowhere. So basically I’ve stopped dating. Suggestions welcomed.

Sweet 16 & Couples Challenge

What do wax and serving trays have in common? Besides having been everywhere during Damona’s recent family trip to Colonial Williamsburg, they are both traditional gifts for a 16th Wedding Anniversary, which is PERFECT timing, since Damona and her husband Seth just celebrated their Sweet 16(th Anniversary).

To celebrate, our guest today is none other than Seth Hoffman! Seth isn’t *technically* an expert in love, but he’s taught Damona a heck of a lot about what partnership really means. The two will be sharing their most important lessons, favorite memories, and will be taking a stab at the infamous Couples Challenge.


The social experiment that wants to end dating apps:

According to a recent article in Interesting Engineering, the Pear Ring is the real-life social experiment looking to make IRL connections easier for singles. The Pear Ring is advertised as “the opposite of an engagement ring,” and wearing the green-colored accessory signals to others that you’re single and looking for a match. Although an altruistic idea, there are some caveats to wearing something that advertises you’re open to being approached. Damona goes over these caveats, as well as some intriguing stats on engagement rings – for example, while both men and women are more likely to wear a wedding ring today than in previous generations, those under 40 are also more likely to remove it


Seth Hoffman has written on tv dramas you know and love, including House, Prison Break and The Walking Dead. But his most important creations are certainly Damona’s two children.

(12:30) Love will find you when you least expect it.

We’ve all been on the receiving end of unsolicited relationship advice at one point or another, and there are definitely phrases that float around in the zeitgeist of romantic advice. But do these suggestions really check out over time? Damona and Seth ponder over and debunk some classic pieces of relationship advice, including “happy wife, happy life” and “never go to bed angry.” 

(18:05) The memory jar exercise.

If you’re an avid watcher of The Drew Barrymore Show, you may have seen Damona featured in an episode honoring the newest issue of Drew Magazine. Drew brought together her cohost Ross Mathews, his husband Wellington, and Damona to deliberate whether soulmates were real. In this same episode, Damona mentioned an exercise she and Seth have done called The Memory Jar – you write down your favorite memories together, place them in the jar, and continue to add to it over time. (You can see a clip from the segment on Damona’s Instagram!) Seth shares the proper origin story of the memory jar, and how their daughter Addie played a vital role.

(28:50) The Couples Challenge!

You know that the truth comes OUT during a couples challenge. And in Damona and Seth’s version, we get answers to questions like: Who is more likely to talk to a stranger? Who is stricter with the kids? Who steals the bed covers more? Who would die first in a zombie apocalypse? Who is usually right? And who’s the better kisser?

Want to hear more reflections from Damona and Seth? Be sure to check out their previous Dates & Mates interview here!



Submit your questions on Instagram, Twitter, or Facebook and hear our answers live on the show! There was no Dear Damona this episode, so listen in next week to see if Damona addresses your question. 👀