We all like to think we understand attraction, have a specific type, and know what we want. But in reality, our dating experiences and behaviors have been shaped over a lifetime by the people and ideas around us. We are products of our environments, but the messages we’ve received aren’t always the most helpful in charting our path to happiness and fulfillment.
This week, we have master-certified life coach Kara Loewentheil joining us! She will use an analytical, feminist lens to explore our dating culture and how old stories may be affecting our decisions in love.
Plus, we’ve got a squeaky-clean Dating Dish for you—discover what singles prioritize most in a surprising social experiment. And don’t miss our Dear Damona question: Is there a match-and-no-response loop?
DATING DISH (3:10)
It’s spring cleaning time, not just for your household but for your dating profile, too! NBC News reports that 83% of single online daters plan to refresh their profiles this spring. The big question is, what should you include to attract the right matches?
A recent survey by Whirlpool, revealed that swapping out typical “thirst trap” photos for ones showcasing household care—like doing dishes and folding laundry—led to more connections and relationships.
How many of those men are now in LTRs? The answer may surprise you!
7:06 Kara Loewentheil
Kara Loewentheil, JD, is a master certified life coach, founder of the School of New Feminist Thought, and host of the podcast Unstuck Your Brain: Feminist Self-Help for Everyone.
Kara is no slouch; she’s a Yale and Harvard Law School graduate who went on to join a think tank at Columbia Law School. She’s also the author of the critically acclaimed book *Take Back Your Brain: How a Sexist Society Gets in Your Head and How to Get It Out*.
9:10 What is a brain gap?
Kara shares the “brain gap” concept, which illuminates the disparity between our desired thoughts and feelings and our actual ones, especially concerning societal norms around gender roles and romantic connections.
From early on, we absorb implicit and explicit messages about what’s desirable or worthy, molding our perceptions of ourselves and others.
In Kara’s words: “So that is the brain gap. Those two different thought patterns really can’t reconcile themselves. We have to intervene to reshape our thinking to bridge them actively.”
20:11 The romantic socialization traps
You don’t want to fall into any of Kara’s “four traps of romantic socialization.” The traps of romantic socialization contribute to unhealthy dating mindsets, especially for women taught their value hinges on male partnership.
Kara shares, “Society gives women because it makes women settle for any relationship. ” This scarcity mindset, coupled with ingrained insecurity around being “chosen,” breeds fixation and rumination where “some part of your brain thinks finding a partner is what is going to keep us safe and part of the tribe.”
34:10 What about societal messages?
Are you ready for a deep dive into the impact of societal messages on our beliefs about relationships, gender roles, and self-worth?
Kara traces the evolution of these narratives, highlighting how media, culture, and institutions shape our perceptions. The romanticization of marriage? Changing the dynamics of gender roles? All covered and more…
37:27 On rewriting the Fairy Tale
Damona asks Kara about her checklist when looking for her life partner, citing the List Myth from her book F the Fairy Tale.
Despite having a specific checklist and vision for her ideal life partner, Kara fell for someone whose circumstances didn’t match her criteria.
This allowed her to rewrite her own fairy tale narrative and unexpectedly find fulfillment by prioritizing substance over superficial factors.
Follow Kara on Instagram @KaraLoewentheil and be sure to grab a copy of her new book, “Take Back Your Brain: How A Sexist Society Gets In Your Head and How To Get It Out.”
43:38 DATING DISH
Submit your questions for our Dear Damona segment on Instagram, X, TikTok, or Facebook, and hear Damona’s answers live in a future episode!
IG Voice Memo from Jack:
Hi Damona, how long should I wait before moving on from a match? After we’ve matched, and exchanged a couple of words and then the kind of ball is in their court for responding to a match. I’ll ask something about their profile. We’ll talk a little bit, exchange a couple of messages on the app, and then they’ll kind of go cold.
So, I’m wondering if you have any recommendations. Do I dive back into those conversations to try to get their attention again? Is there something I’m doing wrong? Maybe, you know, should the first course of action not be to try to talk and just ask them out on a date instead, without trying to warm up to anything? Or should I just move on? Any advice you could give on this would be awesome, and I’d really appreciate it.
Thanks! Love your show, Jack.
365 Love Practices & AI Dating Concierge
Why do we treat love as a one-time-only adventure?
We often associate love with grand gestures and monumental moments, but those only scratch the surface of what love truly entails. Love is not a one-time event; it’s a continuous journey requiring dedication, effort, and practice.
Daily love isn’t always easy—life’s challenges can distract us and fear can hold us back. That’s why I’ve brought in Dr. Alexandra Solomon, whose new book, “Love Every Day: 365 Relational Self-awareness Practices to Help Your Relationship Heal, Grow, and Thrive”, helps develop a daily love practice.
Plus, we have a futuristic dating dish: Could an AI dating concierge fix your dating life? And our Dear Damona question this week: Is it a red flag if my match doesn’t ask me any questions about myself? Let’s dive in!
DATING DISH (3:40)
Get ready for a heated debate!
NBC News claims AI personas are the future of dating, but Bumble’s founder Whitney Wolfe Herd isn’t fully convinced. We’re diving into this buzzy and controversial topic.
Could AI dating concierges that pre-screen matches be the answer to relentless texting and unfulfilling first dates? Or is the idea of robots handling your romantic life a step too far?
11:19 Dr. Alexandra Solomon
Dr. Alexandra Solomon, PhD, is a couples therapist, speaker, and professor at Damona’s alma mater, Northwestern University.
She’s the host of the Reimagining Love podcast and the author of two books, “Taking Sexy Back” and “Loving Bravely”. And now her newest book, “Love Every Day 365 Relational Self-awareness Practices to Help Your Relationship heal, grow, and Thrive” is on shelves now.
13:10 Love as a Daily Practice
Shattering the fairy tale myth of effortless love, Dr. Alexandra said “I really like this framing of love every day being okay, so what am I going to do? Because I have the power to shape the dynamic between myself and my partner.”
She’s dropped major truth bombs about making love an ongoing daily practice through small, intentional actions.
15:30 You Have to Shake the Snow globe in Relationships
When you find yourself falling for someone new, brace yourself – your emotional baggage is about to get shaken up like a snow globe!
Dr. Alexandra Solomon has an enlightening take on how diving into a romantic partnership can inadvertently kick up repressed feelings and patterns, even ones you thought you’d worked through. Instead of feeling ashamed, she reframes this as an opportunity for powerful self-discovery alongside your partner.
24:13 Is There a Ghost in the Room?
When triggered by your partner, do you feel the “ghost in the room” – that fear of becoming someone you don’t want to be, like your rageful father or doormat mother?
Dr. Alexandra said to shine a light on these knee-jerk reactions from past wounds. Recognizing these “ghosts” allows you to consciously navigate conflicts alongside your partner rather than just reacting defensively. She shared a powerful exercise to help you reframe your thinking.
Follow Dr. Alexandra on Instagram @Dr.Alexandra.Solomon and grab a copy of her new book, “Love Every Day: 365 Relational Self-Awareness Practices to Help Your Relationship heal, Grow and Thrive”
48:24 DEAR DAMONA
Submit your questions for our Dear Damona segment on Instagram, X, TikTok, or Facebook, and hear Damona’s answers live in a future episode!
Question from Debbie:
Hi Damona. My name is Debbie. I’m new to dating apps. I find when I reach out to a match and ask a question, he will respond—the majority of the time. My match doesn’t ask a question about me and return. Is this a lack of interest? Thank you.
LAist – Who Should Make The First Move When It Comes To Dating?
Things are getting interesting in the dating world!
During her recent appearance on LAist radio, dating coach Damona Hoffman, host of the Dates & Mates podcast and author of “F the Fairy Tale: Rewrite the Dating Myths and Live Your Own Love Story”, shared her insights on Bumble’s new feature “Opening Moves” and the growing dating burnout.
As the New York Times reports, this shift comes at a tough time for dating apps, with many people feeling dissatisfied overall. So, if we’re all feeling burnt out and tired of the dating app scene, who should be making the first move? How has that evolved over the decades? And what’s your experience been? Damona dives into these questions and more in her discussion with LAist.
Listen to Damona’s interview on LAist!
Take Back Your Brain & The Texting Trap
We all like to think we understand attraction, have a specific type, and know what we want. But in reality, our dating experiences and behaviors have been shaped over a lifetime by the people and ideas around us. We are products of our environments, but the messages we’ve received aren’t always the most helpful in charting our path to happiness and fulfillment.
This week, we have master-certified life coach Kara Loewentheil joining us! She will use an analytical, feminist lens to explore our dating culture and how old stories may be affecting our decisions in love.
Plus, we’ve got a squeaky-clean Dating Dish for you—discover what singles prioritize most in a surprising social experiment. And don’t miss our Dear Damona question: Is there a match-and-no-response loop?
DATING DISH (3:10)
It’s spring cleaning time, not just for your household but for your dating profile, too! NBC News reports that 83% of single online daters plan to refresh their profiles this spring. The big question is, what should you include to attract the right matches?
A recent survey by Whirlpool, revealed that swapping out typical “thirst trap” photos for ones showcasing household care—like doing dishes and folding laundry—led to more connections and relationships.
How many of those men are now in LTRs? The answer may surprise you!
7:06 Kara Loewentheil
Kara Loewentheil, JD, is a master certified life coach, founder of the School of New Feminist Thought, and host of the podcast Unstuck Your Brain: Feminist Self-Help for Everyone.
Kara is no slouch; she’s a Yale and Harvard Law School graduate who went on to join a think tank at Columbia Law School. She’s also the author of the critically acclaimed book *Take Back Your Brain: How a Sexist Society Gets in Your Head and How to Get It Out*.
9:10 What is a brain gap?
Kara shares the “brain gap” concept, which illuminates the disparity between our desired thoughts and feelings and our actual ones, especially concerning societal norms around gender roles and romantic connections.
From early on, we absorb implicit and explicit messages about what’s desirable or worthy, molding our perceptions of ourselves and others.
In Kara’s words: “So that is the brain gap. Those two different thought patterns really can’t reconcile themselves. We have to intervene to reshape our thinking to bridge them actively.”
20:11 The romantic socialization traps
You don’t want to fall into any of Kara’s “four traps of romantic socialization.” The traps of romantic socialization contribute to unhealthy dating mindsets, especially for women taught their value hinges on male partnership.
Kara shares, “Society gives women because it makes women settle for any relationship. ” This scarcity mindset, coupled with ingrained insecurity around being “chosen,” breeds fixation and rumination where “some part of your brain thinks finding a partner is what is going to keep us safe and part of the tribe.”
34:10 What about societal messages?
Are you ready for a deep dive into the impact of societal messages on our beliefs about relationships, gender roles, and self-worth?
Kara traces the evolution of these narratives, highlighting how media, culture, and institutions shape our perceptions. The romanticization of marriage? Changing the dynamics of gender roles? All covered and more…
37:27 On rewriting the Fairy Tale
Damona asks Kara about her checklist when looking for her life partner, citing the List Myth from her book F the Fairy Tale.
Despite having a specific checklist and vision for her ideal life partner, Kara fell for someone whose circumstances didn’t match her criteria.
This allowed her to rewrite her own fairy tale narrative and unexpectedly find fulfillment by prioritizing substance over superficial factors.
Follow Kara on Instagram @KaraLoewentheil and be sure to grab a copy of her new book, “Take Back Your Brain: How A Sexist Society Gets In Your Head and How To Get It Out.”
43:38 DATING DISH
Submit your questions for our Dear Damona segment on Instagram, X, TikTok, or Facebook, and hear Damona’s answers live in a future episode!
IG Voice Memo from Jack:
Hi Damona, how long should I wait before moving on from a match? After we’ve matched, and exchanged a couple of words and then the kind of ball is in their court for responding to a match. I’ll ask something about their profile. We’ll talk a little bit, exchange a couple of messages on the app, and then they’ll kind of go cold.
So, I’m wondering if you have any recommendations. Do I dive back into those conversations to try to get their attention again? Is there something I’m doing wrong? Maybe, you know, should the first course of action not be to try to talk and just ask them out on a date instead, without trying to warm up to anything? Or should I just move on? Any advice you could give on this would be awesome, and I’d really appreciate it.
Thanks! Love your show, Jack.
DREW CREW: How to Catch a Catfish
How to Catch a Catfish!!
It’s another fun episode of the Drew Barrymore show! The Drew Crew dish on Damona’s book “F the Fairy Tale: Rewrite the Dating Myths and Live Your Own Love Story”.
Then they explore how to detect a Catfish! An audience member share her experience with a catfish on a dating app while Damona helps point out the warning signs to watch out for.
ACCESS DAILY: Bumble’s Opening Moves and Moving Dating Offline
Things got real entertaining when relationship expert Damona Hoffman stopped by Access Daily with Mario and Courtney Lopez to dish on all the wild trends happening in the dating world lately!
From Bumble shaking things up by letting guys respond first now, to singles ditching the apps and trying bold moves like passing out actual “dating business cards” to make connections IRL (that’s “in real life” for you, Mario!).
But the real fun was playing Damona’s red flag/green flag game, debating whether giving away TV show endings is a deal-breaker or if being a bad dresser is fixable. Courtney and Damona had Mario sweating with their “Saved by the Bell” fandom throwing some friendly shade his way too.
Check out the video above!!
Mind Your Manners & Bumble Bummer
What does it take to navigate the world of modern romance with poise and grace?
Well, get ready to upgrade your dating game because we’ve got a special treat for you! Sarah Jane Ho, etiquette expert extraordinaire and host of Netflix’s “Mind Your Manners”, is joining us on the Dates & Mates podcast this week.
From first impressions to meeting the parents, Sarah’s here to share her invaluable insights on how we can all be our best selves in any situation.
Of course, we also have a delectable Dating Dish straight from Bumble, and don’t forget about Dear Damona: How long should my first date last if I am traveling a distance to meet my match?
Get ready to ditch the old rulebook and embrace a fresh perspective on modern dating etiquette. It’s time to elevate your love life to new heights with Sarah Jane Ho! So, grab your favorite beverage, settle in, and let’s dive into the world of modern romance.
DATING DISH (2:38)
In case you missed it, Bumble has undergone some major changes lately, shaking up the original dynamics of their app. Women don’t have to make the first move anymore!!
With the introduction of Bumble’s “opening moves,” women no longer carry the weight, but will this really solve the problem of connection fatigue, or is there more to the story?
We explore the ins and outs of Bumble’s latest feature upgrades and discuss how they might impact your dating journey. From revamped profile badges to highlighting common interests, there’s a lot to unpack, and we’re here to guide you through it all.
Sara Jane Ho (10:43)
Sarah Jane Ho is an etiquette expert and the founder of China’s first finishing school. Today, she’s the host of Netflix’s Daytime Emmy-nominated series Mind Your Manners. She also joins me as a Drew Crew member on The Drew Barrymore Show.
Back in February, Sarah Jane became the co-founder and CEO of Antevorta Labs, an intimate care line inspired by traditional Chinese medicine. Her book “Mind Your Manners: How to Be Your Best Self in Any Situation” is on shelves now!
Etiquette is for more than fine dining (11:38)
While many might associate etiquette with formal dining or workplace interactions, Sara Jane reveals how it permeates every aspect of our lives, including the intricate dance of dating and relationships.
From knowing how to behave to understanding the subtle nuances of misbehavior, Sara Jane’s insights make you rethink how you approach love and connection.
This is why she says dating and relationship etiquette deserve its own spotlight and that embracing these principles can transform your romantic life.
How does empathy figure into dating? (13:41)
“Empathy is about sensing somebody’s energy, understanding where they’re coming from, and feeling what they’re feeling.” Sara Jane shared. In Eastern culture, empathy is very energy-based.
When you are on a date, you are reaching out to connect with someone, to understand where they are coming from, and to learn about them. This insight helps to underscore the significance of empathy in dating.
Practice makes perfect (15:33)
Sara Jane uses role-playing and scripts in her etiquette classes to help her students gain confidence. Mastering it in a low-pressure environment will make the action seem natural on a big date.
Tricks of the trade?
Is it time to meet the family? (27:10)
Navigating the etiquette of introducing your significant other to your home and family can be a delicate dance, but Sara Jane offers invaluable advice to ensure smooth sailing.
From briefing your partner on household quirks to steering clear of contentious topics during family gatherings, preparation is key to setting everyone up for success. Sara Jane reassures us that it’s not as daunting as it seems.
Be sure to follow Sara Jane on Instagram @SaraJaneHo and grab a copy of her new book, ““Mind Your Manners: How to Be Your Best Self in Any Situation”.
39:20 DEAR DAMONA
Submit your questions for our Dear Damona segment on Instagram, X, TikTok, or Facebook, and hear Damona’s answers live in a future episode!
IG voice memo from Aya:
My name is Aya, and I live in New York City. I’ve greatly appreciated listening to your podcast for the last year and did a lot of reflection as I read for the fairy tale.
Well, I haven’t met that someone yet. I feel like the quality of men I’ve been dating recently has been much better. Since working on my dating mindset and clarifying what I’m looking for. So thank you. Now, my question. I know that you generally recommend that the first date should be about an hour long. Occasionally, I match up with men in New Jersey and if we were to meet, the travel would be time-consuming, pending a good screening phone call. If a person is traveling more than usual for a first date. How long would you recommend that date to last?
NPR – Women No Longer Have to Make the First Move on Bumble
In a recent NPR interview, Damona shared her insights on Bumble’s latest update: Women no longer have to make the first move!
With the introduction of Opening Moves, Bumble is shifting the dynamics of online dating, offering female users a new way to initiate conversations without the pressure of always making the first move. This is after years of their policy of women having to make the first move.
This change not only empowers women but also addresses the growing issue of dating-app fatigue. As Damona highlights, this innovation reflects a broader trend in the dating world, where platforms are adapting to meet the evolving needs of their users. Check out the NPR article: Women no longer have to make the first move on Bumble. Will it make the app better?
Speaking of dating fatigue check out our recent episode of Dates & Mates featuring Julie Krafchick, & Yue Xu: Dating with Intention & Taking a Break
Addicted to Drama & I Can Fix Him
Have you ever caught yourself rehearsing arguments in your mind before they’ve even happened? Or riding an emotional roller coaster day in and day out? Is forgiveness feeling like an uphill battle?
Could it be that you’re addicted to drama? It’s a tough question, but fear not, because our esteemed guest, and new BFF, Doctor Scott Lyons, has the answers. He’s done the legwork, folks, and he’s here to unpack his enlightening book, “Addicted to Drama: Healing Dependency on Crisis and Chaos in Yourself and Others.”
But before we dive into that, we’ve got a delectable Dating Dish for you: HuffPost serves up insights on why we’re prone to trying to fix our partners and what we should do instead.
And, of course, we can’t overlook our Dear Damona question of the week: “How can I attract more culturally open matches?”
We don’t know about you, but we’re positively thrilled about this week’s episode! So, without further ado, let’s dive right in and start dishing!
DATING DISH (1:36)
A recent HuffPost article addressed a pressing question: Why Do We Try To ‘Fix’ People In Our Relationships? They kick off with a nod to Taylor Swift’s iconic line, “I Can Fix Him (No, Really I Can).”
But can you? And should you? We’ve all felt that pull to rescue our partners at some point. But why? Maybe it’s the feel-good factor of helping someone out. Or perhaps it’s about grasping a sense of control in a chaotic world. But here’s the kicker: our well-meaning efforts can sometimes do more harm than good. It’s a slippery slope, folks. What starts as noble intent can quickly morph into something unhealthy – hello, codependency
To learn more about codependent relationships, tune into one our favorite past episodes on the topic with Kylie McBeth and Mark Groves: Codependent Patterns & Are We Dating The Same Guy
9:52 Dr. Scott Lyons
Dr. Scott Lyons is a licensed psychologist, educator, and author of the best-selling book “Addicted to Drama Healing Dependency on Crisis and Chaos in Yourself and Others”. He is the host of the Gently Used Human Podcast, a delightfully delightful exploration of what it is to be human, and also a renowned body-based trauma expert and mind-body medicine specialist.
13:32 The Drama Lure
We’ve all been there – caught up in the whirlwind of emotional highs and lows that drama brings into our lives. But why are we drawn to drama in the first place? Dr. Scott starts off with a fascinating explanation of the psychological underpinnings of this addiction. He shares that, for some, drama can provide a sense of excitement and intensity that may be lacking in other areas of their lives. It’s a temporary escape that can make us feel alive.
14:14 How Do I Know if I am a Drama Addict?
Of course, Dr. Scott has a quiz to take to see the signs that someone might be addicted to drama in his book “Addicted to Drama Healing Dependency on Crisis and Chaos in Yourself and Others”. He mentioned behaviors such as constantly seeking out conflict, overreacting to minor issues, and thriving on the chaos that drama creates. It was a moment of self-reflection for many of us as we considered whether these patterns resonated with our own experiences.
18:09 Relationship Ripples
Dr. Scott made it clear that an addiction to drama can have profound effects on our relationships: “We’re not looking for relationships. We’re attached to the action of getting there.” He pointed out that when we’re addicted to drama, we often create unnecessary conflict, leading to a cycle of emotional turmoil and instability. This can strain even the strongest of bonds and leave us feeling disconnected from our partners.
39:30 Growth Beyond the Chaos
How do we break free from the grip of drama addiction? Dr. Scott provides practical advice and strategies for reducing drama in our lives. He emphasizes the importance of self-awareness, setting healthy boundaries, and nurturing inner peace. It’s about finding equilibrium and learning to appreciate the tranquility as much as the chaos.
Dr. Scott shares insight into five key milestones for healing from drama addiction. Drawing from the experience of someone who has successfully overcome this addiction, Dr. Scott highlights the shift from using stress as a social adhesive to cultivating a sense of belonging and connection with others without relying on chaos and drama to fulfill that need.
Want to know about Dr. Scott Lyons? Follow him on Instagram @DrScottLyons and grab your copy of Addicted to Drama: Healing Dependency on Crisis & Chaos In Yourself & Others today!
46:58 Dear Damona
Submit your questions for our Dear Damona segment on Instagram, X, TikTok, or Facebook, and hear Damona’s answers live in a future episode!
Text from Angelo:
Hi, Damona. First off, thank you for your wonderful book. I enjoyed reading it and took some very valuable things away. I have a question for you. I’m a very culturally mixed person. I grew up with parents from opposite sides of the globe. I’m finding that in the dating world, I’m often defined by being mixed in communities I’m part of. I’ve gone on first dates where things go well, we keep talking, and right before our scheduled second date, it’s postponed or canceled. And eventually, I get a text saying I’m looking for someone more X or you’re 2XX being one element of my heritage, or even I prefer tall and white. How do I keep attracting those who can’t see past heritage?
Since When Did People Treat Dating More Like a Business Pitch? – Popsugar
As dating app culture becomes increasingly frustrating, people are shifting their focus to unconventional tactics, borrowing from the world of networking and job hunting. From creating personal dating websites to crafting first-date pitches on PowerPoint, dating is taking on a more strategic, business-like approach. Damona shares her take on this trend in this fun article from Popsugar!
Popsugar is where it’s at! Head over there and read about this unique take on dating and see what you might be able to put to work for you in your own love life!
Be the boss of your own love life! Check out this Dates & Mates episode with our special guest, author and spiritual life and business coach, Morgana Rae: Manifest Love & Slay Monsters
Things Your Date Immediately Notices About You – BuzzFeed
Experts Are Sharing The 7 Things Your Date Immediately Notices About You, And Its Need-To-Know Info For Your Next Coffee Or Dinner Date
It’s time to get ready for your date…are you stressing out about things your date may immediately notice about you? What should I wear? What will I say? Will they like me?? We get it and so do the dating experts. BuzzFeed brought together 7 dating experts, including our own amazing Damona Hoffman, to share what your date is likely, and unlikely, to notice right off the bat!
Head over to BuzzFeed and read the article. We are sure you will find some surprising stuff in there!
Still nervous about that first date? Lucky for you Damona has a First Dates Master Class on the Dates & Mates Podcast!! Check it out!
His Move & Love After 50 – Dear Damona
There’s been A LOT of talk this year about dating burnout and swipe fatigue. And while we know that the frustration is real, the ultimate takeaway is people are STILL dating or else they wouldn’t have the experiences to complain about.
So what if we reframe our dating troubles and see them as learning opportunities? What dating doors might open for you then? What power could you snatch back from the jaws of dating apps, or ghosting, or other forms of fatigue or burnout?It’s time to hop back in the driver’s seat of your dating life and that’s exactly why we’re serving up an extra-special “all Dear Damona” episode today!
Dear Damona (2:25)
3:00 Text from A
Is it generally a good idea not to message someone on the app if the last message was sent by me, meaning it’s now his move? I matched with someone last weekend. He expressed that he was extremely interested in getting to know me and that I seemed to have the strong character he’s looking for in a partner.
Side note: I don’t have a bio written yet. I’m new to this, and yes, I will put up a bio soon. So he was making this call, but my strength of character was purely on my photos, basic info, and interests. I thanked him for the compliment, then directly asked him, with so little to go on, what had given him a sense of my character; he explained that having practiced medicine for so many years, he learned to read people and look for cues that others might not see. He’s not wrong. I am all those things. But let’s just say I was cautiously impressed but also suspicious by his observations. I asked him a little about his work, which he answered without hesitation. And then, after my last two messages, which confirmed what he’d explained, he didn’t message back. That was three days ago. Should I assume that this thing has already fallen flat on its face? Before we even had a chance to meet? My friend told me to wait, and he probably gets hit on by a million nurses, so I should be the cool one.
11:53 Email from Gary
Hi, Damona, I enjoyed your conversation on NPR. I started dating after healing from a relationship, but I struggle to manage and set expectations for potential partners. Could you please shed some light on this scenario and provide advice?
17:13 Instagram DM from Vernee
Dear Damona, I’m curious about dating up. I have habitually dated men who made less than me because it didn’t matter to me, and often, in these relationships, I found myself taking care of them in ways that they could not reciprocate.
Anyway, I’m fresh off of a breakup. Oof! Long story. Incoming. But the week before the breakup, my ex-boyfriend asked me how much money I made. He had previously told me what he had made a few times, and I never felt the need to share, but we had plans to move in together, so I didn’t see the harm at this point. I told him how much I make. He seemed a bit surprised, and he said, “Oh, you make comfortably more than me.” I said, yes, I do. I think it’s possible that he felt some type of way about that from an ego standpoint. Many men still carry that provider thing, and I’d like to be taken out sometimes or suggest places where we can split the bill or buy our own tickets to a nice event. I’m not asking to be spoiled, and I believe in sharing costs, but what can we do when they make less than you and have poor money management? My ex would pay for some of our meals out, but I’m pretty sure most of that went onto credit cards that his parents would pay for.
And then, after a year together, my ex told me that he wasn’t in love with me, even though all of his behavior said otherwise. So I told him goodbye. I know I’m not the only woman to go through this. My heart can’t handle any more fixer-upper men. Where did all the grown men go? So many of us are stuck with Peter Pan on one level or another.
27:50 Text from Tasha
Dear Damona, I love your story. I just recently discovered your podcast. Have you helped many singles in their 50s? I am 54 and just really am wondering if it’s too late. Isn’t it more difficult to find love after 50?
Send Us YOUR Questions (33:04)
Don’t be shy! If you’ve got a burning question about love, dating, or relationships! You can reach out on Instagram, TikTok, or Facebook, or even give us a ring or text us at 424-246-6255. We absolutely adore hearing your voices, so don’t hold back! Whether it’s a whisper or a shout, your input help us tailor the best dating advice for you. Drop us a voicemail or slide into our DMs with a voice memo – we can’t wait to hear from you!
Keep Listening!
If you enjoyed this all Dear Damona episode, you would really like our recent episode with the host of the “I Thought it Was Just Me” podcast, Lane Moore: Tinder Love & Love Don’t Cost a Thing
7 Black Books Changing How We Think About Love – Hello Beautiful
Hello Beautiful Shares F the Fairy Tale as a Black Authored Book that is Changing How We Think About Love!
Exciting news! “F the Fairy Tale; Rewrite the Dating Myths and Live Your Own Love Story” just snagged a spot in Hello Beautiful’s Top 7 Black-authored books shaking up the relationship scene.
Head over to Hello Beautiful and check out the other amazing black authors on this list! There is a treasure trove of love advice!
Think this was an amazing shout out? Check out what Mashable had to say about the Dates & Mates Podcast!