Tag Archive for: dating tips

Main Character Energy & Moving Too Fast

Are you bringing “Main-Character Energy” to your dating life? A thriving dating life doesn’t just boost your joy; it lays the groundwork for lasting, meaningful relationships. 

While we know it takes intentionality, many of you have asked about the steps in between. That’s why we have Lily Womble, host of the Date Brazen podcast, here today to share insights from her new book, “Thank You, More Please.” She’s on a mission to help singles navigate the dating world with eyes wide open and a little main-character energy. Plus, she will share when it’s time for a dating detox. 

But first, we have the Dating Dish, which features Tinder’s new Green Flags Study on Dating Assumptions. Our Dear Damona question this week is: How fast is too fast when dating a new match? Let’s keep it positive as we kick off with the dish!


Tinder released a New Green Flags Study that uncovers some surprising dating truths.

Turns out, men and women actually want the same things in relationships more often than we thought. One surprising fact that the study highlights is that many women believe most men are seeking casual flings, but the reality is quite different. 

Do we need to rethink our assumptions about gender roles in dating? Maybe! By focusing on genuine connections instead of outdated stereotypes, we can navigate the dating world more effectively and spot those all-important green flags.


12:23 Lily Womble

After moving to NYC in 2015 and starting as a matchmaker, Lily Womble quickly became a top matchmaker, setting up 399 dates. 

In 2018, Lily founded Date Brazen, her dating coaching company, helping hundreds of women create joyful, resilient love lives with her intersectional feminist approach. 

Today she also hosts the Date Brazen podcast and has just released her debut book, “Thank You More, Please: A Feminist Guide to Breaking Dumb Dating Rules and Finding Love.”

14:00 Are Dating Apps a Scam?

Lily went viral in June 2022 with her TikTok video, “Dating Apps Are a Scam,” which sparked the creation of her book, “Thank You More, Please.”

As a former top matchmaker, Lily saw the emotional toll dating apps can take on users. She highlights how these apps are designed like games, which can lead to mindless swiping without intention.

Lily encourages us to approach dating apps with a clear plan and boundaries. By using them thoughtfully, we can protect our mental health and focus on building genuine connections.

22:10 Date with Main Character Energy

Lily shares how to date with “main character energy,” breaking it down into three key skills: permission, self-trust, and massive, messy action. 

She explains, “Permission is a powerful tool to reclaim your agency.” By giving yourself permission to be imperfect, trusting what you want, and taking bold actions—even if they’re messy—you can transform your dating life.

Main character energy isn’t just for a select few; anyone can develop it. Embrace these steps to attract the right people and become unstoppable in your dating journey.

42:25 Do You Need A Dating Detox?

Damona and Lily explore the idea of a dating detox, which involves taking a break from active dating, avoiding bad dating advice, and addressing dating worries.

Lily emphasizes the benefits of a 30-day intentional pause to reset your mindset and calm your nerves. By detoxing from unhelpful advice and reframing negative thoughts, you can approach dating with a clearer, healthier perspective.

It’s all about being intentional and mindful to improve your overall dating experience.

Catch up with Lily on Instagram @DateBrazen and grab your copy of Thank You, More Please: A Feminist Guide to Breaking Dumb Dating Rules and Finding Love” today!


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 message from Megan:

I met someone and we really like each other to the point of talking about being exclusive. We’ve only known each other for about 20 days, had eight dates. Everyone says this is fast. What are your thoughts? It feels a bit fast, but I’m also not concerned about it, and I’m excited to see where this goes.

First Dates & Old Flames

First dates are gateways to new possibilities, blending excitement and apprehension. 

They offer a unique chance to make a lasting impression, showcase your true self, and gauge compatibility with someone new. More than just an outing, first dates set the stage for potential relationships and define the path of your dating journey. No pressure…right?

Luckily for you, we’ve got dating coach Mat Boggs to guide you through first-date essentials—from spotting red flags to conversation tips and time investment. Mat will help you learn to release that pressure and make the most of your first dates!

But first, let’s dive into a hot topic: has dating culture become selfish? Plus, our Dear Damona question of the week tackles family versus gut instinct in rekindling old flames. 


Is dating culture becoming selfish?? Mashable thinks so!

A recent article says dating culture is becoming selfish, leaving many feeling insecure about finding love.

Frustration often targets dating apps, but the real issue may lie in the behavior of the people using them—rude, dismissive, and sometimes abusive actions are on the rise. This shift is affecting our ability to connect and leaving many of us worried about our dating prospects.

How do we tackle this issue? Damona shares that it starts with rethinking our approach and focuses on creating meaningful connections.

9:44 Mat Boggs

Mat Boggs is a YouTube dating coach and Brave Thinking Institute’s Love and Relationship division founder.

He has appeared on numerous national media outlets, including The Today Show, CNN Headline News, The Style Network, Oprah and Friends, ABC, and more. He’s also the best-selling author of Project Everlasting.

11:16 A Blurry First Date

First-date norms are evolving, leading to confusion about red flags. Damona asked, “How do I know if I need to run away from this person?” 

Mat agrees, suggesting that blurry first dates often stem from unrealistic expectations. He warns against expecting an instant spark or magical connection, which can lead to disappointment.

Instead, Mat recommends approaching first dates with an open mind and realistic expectations. By reframing our mindset, we can better assess compatibility without the pressure of finding “the one” immediately.

14:45 It’s Really Hard to Screw Up the Right Thing

“So often, people go into a first date with the primary goal of getting the other person to like them,” says Mat. 

This pressure to be perfect and seek approval can overshadow our own feelings. Instead, he emphasizes, “It’s really hard to screw up the right thing.” By being yourself and focusing on whether you enjoyed the date enough to want a second one, you shift the dynamic to a more genuine connection.

Mat shares the one simple question that needs to be answered on a first date. 

29:52 Keeping Secrets

What secrets do you not want to share on a first date? Mat emphasizes the importance of leaving a positive impression. 

Focus on stories that reflect personal growth and positivity, carefully avoiding oversharing unresolved issues. Mat says, “It’s about aligning what you share with the outcome you want, suggesting that sensitive topics should be saved for later, once trust is established.

He also suggests setting boundaries early on, recommending a gentle deferral for deeper topics: “If the topic comes up early, it’s okay to say, ‘That’s a great topic, and let’s save it for when we’ve been on a few more dates.'” 

Follow Mat on YouTube @MatBoggs and learn more about his MANifest Your Man Program.


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 Tracy:

Hi, Damona. This is Tracy. I have a question for you. I’m trying to figure out the best way to decline a male friend’s 50th birthday party invite to Cabo San Lucas. I’ve known him since middle school, and we recently reconnected. He was my date for our 30th high school reunion last year. However, in the past few months, he’s been sending mixed signals.

He’ll be really consistent for a while and then nothing. We do live in two different states. However, when we started communicating, he said he was ready to retire and moved to my state to be closer to family. We’ve only seen each other twice over the past year, and although he’s mentioned coming to see me or me coming to visit him, he’s never followed through with those plans. And when I mention my intentions regarding dating and being in a committed relationship, it seems to really push him away. He shared that he just wasn’t ready, and just gave him some time to heal. He said he doesn’t feel like it’s fair for me to have a broken man. He’s been married twice and engaged three times. One wife passed away after they were apart for a few years, but she is the mother of his daughters, and one wife cheated on him. I know he’s been through a lot, and I respect him for his honesty and backed away. However, I still have feelings for him, and I feel like going on this trip will serve feelings that may not be reciprocated.

His daughter did send me the invite. However, we’ve only talked about the trip briefly, and my family has encouraged me to go. My sister and brother-in-law will be going as well. They’re really good friends with him, and they’ve been trying to hook us up for years. It is a family trip, and I know a few of his friends will be there, but I’m not sure if he’ll have a date there. Would it be a wise decision for me to decline? Thanks, Damona!


Learn more about bringing your best self when using dating apps. Listen to Damona’s episode with Dr. Alexandra Solomon: 365 Love Practices & AI Dating Concierge

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!


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”


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.

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?


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*.

Kara Loewentheil joins Damona Hoffman on Dates & Mates podcast

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.”


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.

damona hoffman interviews sara jane ho host of netflix mind your manners

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.


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!

damona hoffman interviews sara jane ho host of netflix mind your manners

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?

  • Use effective pauses – using lulls in conversation.
  • There is an optimal amount of time to speak – how long should you talk?
  • Mirroring – show you are paying attention and are “into” your date

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”


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? 

Dr Scott Lyons on the Dates & Mates podcast with dating and relationship expert damona hoffman talking about the addiction to drama and how to overcome it

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!


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.

Dr. Scott Lyons joins Damona Hoffman, relationship and dating expert to talk about the addiction to drama

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?

Damona Hoffman relationship and dating expert dates & Mates podcast

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

Psychic Matchmaker & Digital Body Language

You’ve heard Damona talk about dating intuition – that inner voice that says, something feels off about this person or my gut is telling me this person may be my person or somebody I want to spend more time with. That’s your internal compass, the metaphorical steering wheel of your heart and it talks to you if you’re willing to listen. 

Today psychic matchmaker Deborah Graham, who’s been tuned into her intuition since she was a child, uses her abilities to pair singles with a match that will last a lifetime. 

And here are a couple of fun parts: Deborah joins us to share how she teaches her clients to dial into their intuition. And as a special bonus, our fabulous podcast producer, Lindsey, volunteers to be read live on air by The Psychic Matchmaker. 

But first, we have a steamy hot dating dish to serve up for you and it’s all about digital body language in online dating. 


In a recent article, Online Dating, Beware of Digital Body Language, Grazia Magazine talks to friend, former guest, and behavioral scientist for Hinge, Logan Ury, about how to read digital body language, which is defined as as emojis, punctuation, message length, and response time. 

A recent Hinge survey found that 69% of respondents claimed they could analyze digital body language to determine if they wanted to take the next step and go out with that person. 

Damona’s takeaway? You have to create momentum and a kinetic feeling of being in a conversation with somebody when you’re texting. In the end, it’s about being responsive and not leaving a conversation hanging if you’re searching for love.

Want to get your messages analyzed? Send screenshots to @DamonaHoffman on Instagram and get your text analyzed!



Deborah Graham was born a gifted psychic, having her earliest premonitions when she was only six. Now with more than 30 years of experience as a psychic relationship expert and matchmaker, Deborah’s work is all about matching you with your true love and soulmate. 

You may recognize Deborah from the 2015 TLC show, Psychic Matchmaker, which featured her helping people find true love. 

(14:01) A blessing, a curse and an arranged marriage  

Damona has always been fascinated with the intersection between the metaphysical and the spiritual – the stuff we can’t see but also the very tangible tactical techniques a lot of her listeners know her for. 

Deboarah says, “Oh, I like to say it’s a blessing and a curse because I’m a third generation psychic. As a child, I would communicate with loved ones I’d never met.”

She talks about one of the moments that changed her life – when her mom arranged her marriage. “My mama just kept saying this is the person. Because of course, she’s intuitive. So she knew. And that’s kind of what my life’s work is. It’s kind of like I give everybody the push.”

(24:37) Teaching singles to use intuition

Damona uses her intuition when assisting her clients and encourages them to do the same. She wonders how Deborah instills the idea in her clients.

Deborah says to look out for Energy Vampires. “If you go out on that first date and that person is constantly talking about themselves and how bad their relationship has been, and they’re blaming everybody for it going wrong, that’s usually when I say run, run, run.”

She also says that eye contact is key. “You’re communicating through the person’s soul because the window to your soul is through your eyes. So that is your own psychic abilities, intuition going in and vibrating energetically.”

(29:02) Reframing the Awkward Silence

Damona says to switch the adjective! What if we consider the silence to be informative, energetic, or contemplative rather that awkward? The only last 2-3 seconds after all.

Deborah adds, “Silence is communication. Because it’s not about what you say. It’s about what you feel.”


Follow Psychic Matchmaker Deborah Graham on Instagram @PsychicDeborahGraham and learn more about her work by visiting psychicdeborahgraham.com


DEAR DAMONA  (41:14)
Submit your questions on Instagram, X, TikTok, or Facebook, and hear Damona’s answers live in a future episode!

Email from Christina

Is there anything you suggest to figure out if a person is going to ghost you after a month or so? I met somebody who made it seem like things were going well and attempts to communicate with them didn’t reveal anything was troubling, yet after some time, something was clearly wrong because they slow-faded me. 

Eventually things ended, and while I know that person was the wrong person for me, I’d like to know how to be able to feel if a person is going to do that much better.

If more details are needed for my question like background, here’s a little more to go with.  I met someone on a dating app and we went out for several dates.  Things seemed to go well enough to where they invited me to keep things at their place, introduced me to their friends, and we spent lots of time together for about six weeks.  I did notice they read a certain male controversial Canadian author’s books in their reading, asked them about it as I am a woman who isn’t a fan of that author, and got an answer that was reasonable, but took it as a yellow flag.  They even said it was going well.  

Then in November, things started to get strange for the remaining couple weeks that I considered us dating.  They didn’t include me in their plans, particularly Thanksgiving, they texted me less (and when they did, it may as well have been with an acquaintance), were less affectionate when we did spend time together, and generally their overall behavior was strange.  I know they had family far away and work stress, but wanted to understand things better.  I tried to communicate this with them in a way that was calm and even tried to make it with some humor so they wouldn’t feel put on the spot, yet they offered nothing.  

Finally after a weekend with no plans and no communication, I told them directly what I have been noticing and told them that you have to communicate to show respect and so the other person isn’t left wondering what they don’t know about.  He sent me a very generic text saying we weren’t communicating or on the same page and it wasn’t working out.  Clearly it was over, but it wasn’t a “we” problem, this person slow-faded me when I tried to communicate after things seemed to go so well.  

I am hoping to learn what to observe in the future so this doesn’t happen again as ghosting is already bad enough early in the process and worse as you spend more time together.  Dating a commitment-phobe is something I want to avoid again and Damona’s advice would be invaluable.

Codependent Patterns & Are We Dating The Same Guy

In her book, F The Fairy Tale Damona says choosing a life partner is one of the most important decisions you’ll ever make. Goals, values, communication, and trust are key to a successful relationship and that begins before you’ve even met your match, because it begins with you.

One of our guests today says, “Real choice comes when we don’t need the other person to be okay.” We couldn’t have said it better ourselves and that’s why we invited friends, co-authors, podcasters, and spouses, Mark Groves and Kyle McBeth, to share their stories. 

But first, we have a dangerously hot dating dish to serve up. According to Axios, Facebook groups like, Are We Dating the Same Guy, are stirring up controversy and we’re going to unmask the dark side.  


Several articles were published this week detailing legal action being taken against members of a private group called, Are We Dating The Same Guy. These groups originally served as a kind of background check to keep women safe, were a great idea, but critics say they’ve become an arena for public persecution. 

But there are real-world consequences  – like being sued for defamation.  A lot of these claims are subjective. Damona warns us, “if you say somebody is clingy or psycho, and that means that they don’t get a job because of it, or that they lose clients because of it, you actually could be liable for damages.”

Damona unpacks the story further saying that daters seem to think that talking to these groups will give them closure or give a sense of power back. She suggests we talk to our match about our concerns to create real change.

We know this was a dating dish of a different color, but with all of the headlines, we felt like it had to be said. 

(8:30) Mark Groves & Kylie McBeath

Second-time guest Mark Groves is a Human Connection Specialist, founder of Create the Love and host of the Mark Groves Podcast. Mark’s work bridges the academic and the human, inviting people to explore the good, the bad, the downright ugly, and the beautiful sides of connection.

Kylie McBeath, also known as @beingisbeautiful to her 130K Instagram followers, shares daily guidance and teachings on relationships, spirituality, and embodied liberation. She is also a Certified Health Coach and the host of The Journey Home podcast.

(9:54) Tell us about liberated love

Kylie explains liberated love is about coming from a place of grounded centeredness where you’re not needing somebody for a source of safety, security, validation, or to soothe aloneness. Liberated love is about actively, fully choosing a relationship.

Mark agrees that liberated love is about being dedicated to telling the truth. He says so many people are afraid to fully express themselves in a relationship because we’re afraid we’ll lose someone, we’ll push them away.

Liberated love is all about freedom. 

(18:34) Is it codependency or co-creating?

Codependency, Kylie shares, is any relational dynamic where we source safety outside of ourselves at the expense of our own needs and well-being. “But it’s when it becomes at the expense of your wholeness, at the expense of your core needs, at the expense of your total well-being, that we begin to have a problem.”

We all have emotional, sexual and safety needs, Damona says, but it’s sometimes difficult to discern if we are co-creating or being codependent. 


(25:27) Your body, your compass

Daters need to get in touch with their bodies. Kylie says,,  “I think this is probably one of the most important pathways we are being invited to walk on the planet at this time is returning back to the body and returning back to trusting our intuition and our instincts and our somatic experience. 

Kylie explains that for her it meant accessing her anger so that she could listen to and honor her emotional input impulses as a compass.


Be sure to grab a copy of Mark and Kylie’s new book, “Liberated Love: Release Codependent Patterns and Create the Love You Desire” and follow them on Instagram @CreateTheLove and @BeingIsBeautiful


(41:02) DEAR DAMONA 
Submit your questions on Instagram, X, TikTok, or Facebook, and hear Damona’s answers live in a future episode!

Question from Spotify listener, Brent.

Question about navigating fake profiles on dating websites. I’ve learned some cues that seem to be linked to the fakes, but any advice on not getting exhausted weeding through the nonsense?

Speed Dating Do’s and Don’ts & Heartbreak Coach

Spring is here! We love new beginnings, the hope, and the possibility of a blank slate.

However, most new relationships form after another one has ended. So this week, we are looking at the other side of the dating equation – breakups.

And, our guest is flipping the script on heartache. Keishorne Scott, author and heartbreak coach, will share his strategies for healing after a breakup and setting boundaries. Plus he’ll also tell us which matches to avoid and to whom to give your precious heart.

But first, we have a steamy hot dating dish to serve up for you. Damona was recently interviewed by USA Today for a piece called,  “Speed dating is making a comeback as Gen Z ditches dating apps…and we shouldn’t be surprised.”


Is speed dating making a resurgence? Is the rhetoric around Gen Z ditching dating apps true? 

Damona says dating apps are all Gen Z has ever known, and while they’re frustrated with them, they often end up redownloading the apps after a short hiatus.

You CAN make dating apps work for you while and dip your toe into the IRL waters. Damona tells her clients to create a balanced portfolio for their dating life.

(06 51: ) Ready to give speed dating a try?

In speed dating, you only have 5-7 minutes to be memorable. It’s not about getting matches from everyone, it’s about getting matches with the right people.  

In her Dating Accelerator course, Damona talks about demonstrating your goals and values and having preloaded topics to talk about. Ask someone for their opinion on something benign like do they like the scent of grapefruit, are they a morning person or a night owl? 

Skip the, “Where do you work” and “Where are you from?” questions. They’re boring and won’t make you memorable.

(14:00) Planting the seeds of hope and possibility

If you don’t have your copy of “F The Fairy Tale” yet, you can grab a copy right now on Amazon on sale for a limited time! 


Keishorne Scott is an author, speaker, media personality, and relationship and heartbreak coach. 

His best-selling books include, “The Mouse, The Bird, The Dog and The Lion: 3 Men To Avoid and 1 to Marry” and “The Heartbreak Workbook: 10 Proven Strategies for Healing, Renewing and Recovering.” 

Keishorne has also been featured by Forbes, Good Morning America, BBC Radio, ABC News, MSN.com, and Marriage.com. 

(16:22) From heartbreak to happiness

Keishorne says, it’s possible to go from disappointment, frustration and heartbreak to a healthy relationship, though it takes time. He says that he had totake a step back, start to love myself, care about myself, invest in myself and then I started the healing process.”

Damona says he flipped the script. While most people might think that they are not good enough, Keishorne decided that someone wasn’t  good enough for him.

(20:51) What do a mouse, a bird, a dog and a lion have to do with love?

Keishorne breaks it down in his book, but shared:

  1. The Mouse is sneaky.
  2. The Bird doesn’t deal with conflict.
  3. The Dog will run out the gate if it’s left open and he’s also jealous.
  4. But the Lion is the king. He’ll be accountable. 

Damona appreciates the metaphors but wonders if we sometimes expect too much from our partners. She emphasizes the importance of balance in a relationship.

(30:49) How do you know you’re ready to move on?

Keishorne says everyone wants an exact answer for how long the process of healing after heartbreak will take. 

Healing is a non-negotiable and you have to do the work. Keishorne says, “there’s no timeline for it. Everybody heals and falls in love at their own pace.” 

Damona encourages people to push through the pain to seek healing. She quotes a line from her book, “F The Fairy Tale”, “discomfort is the feeling of change happening.”


Find Keishorne Scott on Instagram @keishornescott or learn more about his work by visiting Keishornescott.com.



Submit your questions on Instagram, X, TikTok, or Facebook, and hear Damona’s answers live in a future episode!

Text from Alexandra. 

Dear Damona,

I’m approaching 30 in 2 months, and I’ve been single for the past seven and a half years and recently been giving a shot at the dating world. I’ve had a very busy work life, so real dating was off the table. 

And in the past, I have invested too much in men who were not available. But I finally met someone who truly seems like he could be the right match for me. I thought we hit it off on our date and we have been intermittently texting throughout the day since. It was a Bumble match, and we met in person before he headed back to his home state. 

I don’t really like to be pushy, but I’m starting to doubt if he enjoyed the date as much as I did. I also do not know his dating intentions. 

Obviously, many more details that apply, but my main question is how frequently do I text? Do I worry about texting first, or reading too much into short messages and not too muchto much deeper conversations? 

It’s been five days. Mostly it’s hard because I really felt it with him and I don’t know where he stands.

Furniture Anniversary & Next Gen Dating

Did you know that the traditional gift for a 17th wedding anniversary is furniture? Damona says it’s perfect timing because she and her wonderful husband Seth are celebrating 17 years of marriage this week and they desperately need a new couch.

Why furniture you might ask? Well, some say it represents the security, comfort and familiarity of a marriage that has lasted almost 20 years. 

Funny enough, Damona compares a successful relationship to a table in her book, F The Fairy Tale. She says, “Think of a relationship like a table. If it’s built with a solid foundation, it can stand for years…You can build a table with only three legs, but it probably won’t last as long as one with four. And what will happen when you put something heavy on it?..”

In the end, a foundation built on the 4 pillars – goals, values, communication and trust – creates the space for a successful relationship future and the ability to overcome challenges. Grab a copy of Damona’s book F The Fairy Tale: Rewrite the Dating Myths and Live Your Own Love Story to learn more.

But enough of the past, let’s look ahead to the future. While she has been doing this work for over a decade, Damona still finds herself consumed by curiosity about where dating and relationships are headed. Recently, it dawned on her that the future of dating is sitting in her home, her daughter Addie.

And so, this week, we’re welcoming Damona’s teenage daughter, Addie Hoffman to Dates & Mates. She will be giving a , to give the Gen Z perspective on dating – and it’s surprisingly relatable to daters of all ages. 


But first we have the Dating Dish.


A New York Times article about tells the stories of five couples who married, divorced and then married their ex-spouses again. 

We thought this would be rare, but a study published in the Journal of Divorce and Remarriage estimated the number of people who remarry their ex spouse is actually about 10%.

Damona highlights some of her favorite stories of remarriage and shares some of her top takeaways.


Addie Hoffman is Damona’s 13-year-old daughter. This is Addie’s very first podcast appearance, but you can see her TV debut on America’s Funniest Videos on April 14th, and you’ll probably see her on stage at a comedy show in 10 years!

Addie identifies as cis-het and attends an all girls school.

(13:53) The Dating Life of a Young Gen Z 

At age 13, she is still a little young for dating, but Addie shares that she has some interest and wonders where she might meet future dates. 

Damona asks Addie where her friends have met their dates. “Most people find them in their extracurricular classes, but it’s hard because what if you don’t like anyone that does the sport you do?” 

(15:36) What Addie’s Learned From Damona & Seth

Damona asks Addie what she has learned from her parent’s relationship, so Addie shares a story about the family preparing for an event. It seems laughter is key!

When asked for another lesson, Addie jokes about mutual care. “If I have a partner who can rub my feet, or Theragun my back, we set!”

(18:07) Designing your dating destiny 

Damona says that when she was Addie’s age, she had already been sold the fairy. She recounts how she would write her name next to her crush’s last name. 

Damona asks Addie if she has considered marriage and kids saying that today’s daters don’t have to toe that line. 

Addie replies, “I think I would like to have kids and marriage. That sounds really weird coming out of my mouth. I’ve thought about it, but I’ve never said it.”



Submit your questions on Instagram, X, TikTok, or Facebook, and hear Damona’s answers live in a future episode!

In this unique take on Dear Damona, Damona answers questions from Addie and her teenage friends about dating: 

  • If you don’t think a person is a good match for your friend, is it okay to tell them they should break up?
  • How can you tell if someone is attracted to you?
  • How do you break up with someone if you know that you don’t have feelings for them anymore?

Dating With Intention & Taking A Break

Look, we all want to be dateable, but here’s the real question – would you date yourself? 

Before you start your dating journey, ask yourself, do I embody the type of person I am looking for? Because it’s not enough to be an expert dater, the search for your match goes deeper, within. We have to love and know ourselves first, and that takes time. In a fast-paced digital world with DMs and endless swiping, the texting trap and A.I. dating profiles, it can be hard to be intentional about how you’re dating.

But slow love is key to success in long-term relationships and even short-term relationships. And as our guests today say, it’s not about getting to a bunch of second and third dates, but going on dates that make you feel connected or curious, Damona often says.  

Those guests are none other than Julie Krafchick & Yue Xu, the hosts of Dateable! They will be discussing the true meaning of dating intentionally and how some daters may need to reframe their approach.


So you’ve probably heard Damona talk about dating burnout and a recent survey proves the point – statistically speaking.  The Survery Center on American Life released an article titled, “From Swiping To Sexting: The Enduring Gender Divide In American Dating And Relationships,” summarizing it’s recent American Perspectives Survey. 

According to the survey, 42% of participants said they are not currently dating anyone, but they’re open to the possibility. 41% said that they are not interested in dating anyone at the moment at all, and 11% of single Americans said that they are currently dating one person. Only 2% are dating more than one person. 

In the end, Damona suggests intentionality in dating as a solution. She says that by carefully selecting which matches we spend time with and limiting how and when we interact with the apps, can save us a lot of frustration. 

Damona says, “time is your most valuable resource. We’re not getting any more of it and the way you spend it – whether it’s swiping Tinder and being frustrated or showing up to a speed dating event or asking friends for setups, the way you spend your time does matter.”

(13:56) Hosts of the Dateable podcast, Julie Krafchick  & Yue 

This week we’re welcoming app designer and researcher, Julie Krafchick, & former dating coach, Yue Xu. They are active daters turned dating sociologists. Together they help daters challenge the way they think about modern dating so they can design the love life they’ve always wanted.  

They are the creators of Dateable, a podcast, community, and knowledge source for finding love in today’s world. Their work has been featured on CNN, NBC News, MSNBC, BET, and New York Public Radio, amongst others. 

 (15:48) Why is dating so hard today?

Julie and Yue shared their thoughts that dating might seem hard because of the expectations we put on the whole process, such as

  • Wanting our partners to be our best friend, therapist, life partner and fellow yogi.
  • Expecting our partners to always be available.
  • Expecting someone to prove they can before our forever person before we’ve decided we like them

 (18:18) It’s like we’re snacking and we’re full, but we keep on snacking! 

Damona compares today’s constant communication to snacking and the desire to have just a little more. 

Yue says, “Yes! The more we snack, the hungrier we get because we feel like there’s more for us to snack on. We also live in one big echo chamber with social media and the Internet. Everyone’s always echoing each other’s misery when it comes to dating. And misery loves company.”  

(25:14) Is my racket even hitting the ball here? 

Damona asks Yue to share her tennis analogy. After beginning tennis lessons recently, her coach told her one of the biggest mistakes beginners make is taking their eye off the ball. Yue mimics her coach, “Watch it make contact with your racquet before you see where it lands.”

Yue says, “ it’s such a great analogy for how we date today. Before we even assess if there’s a connection, if we truly even like this person, we’re already looking five years ahead.”

Find and follow Yue and Julie on Instagram @DateablePodcast And be sure to check out Dateable the podcast wherever you listen to Dates & Mates!


Submit your questions on Instagram, X, TikTok, or Facebook, and hear Damona’s answers live in a future episode!

Text from Anonymous

Hi Damona, do I need to take a break from dating to get my personal life in order?

She says, coming into 2023, I quit a very stressful and draining but decent paying job for two part-time jobs that I later found would each burn me out and set me back financially. Now, in 2024, I, like many educated and capable millennials, am struggling to jump back into the corporate and or otherwise known as safer and more financially secure jobs I’ve been dating.

 And despite my struggle to reposition myself back to a place of financial stability. I recently hit my opinion of a rock bottom. My financial life is a mess, and I’m currently living paycheck-to-paycheck, living at home with my parents, with increasing credit card debt merely to get by. I’m very educated and driven, so I know that this isn’t forever, even though it feels like I’m stuck. I’ve put off love and dating in the past many times to focus on my financial life, and admittedly, it’s never been this low. I desire healthy love and companionship now more than ever in my life. Plus, I’m approaching 30, so I don’t want to get stuck in a loop of not dating at all, which will put me completely out of the game of finding my person.

I know money isn’t everything, but I can’t help feeling like I may have to sit out dating again for a while to make improvements. The last two guys I dated were a bit of a reflection of this type of financial turmoil I’ve been experiencing, and I’m quite  

Should I sacrifice the next six months to a year to become a better me financially, for the type of man I want to attract?