Tag Archive for: dating IRL

Party Of One & Longtime Crush

Going it alone and noticing the world seems to expect a whole lot from you?

“When are you settling down?” “Have you tried online dating?” – these questions are everywhere, but are we putting too much pressure on ourselves to couple up?

We all know how important it is to find love, but maybe we’re too quick to see singlehood as a problem to be solved. Then again, with shows like Love Is Blind and the Golden Bachelorette constantly bombarding us, can we catch a break?

NPR’s Life Kit founder Meghan Keane to the rescue! Meghan joins Damona this week to unpack the layers of our complicated feelings about being single and to dissect the ways that singlism could be dealt with in your own life. Plus, she shares why embracing your single life is just as important as finding a partner.

And don’t forget to stay tuned for our Dear Damona question: “I recently reconnected with a casual long-term friend. How do I figure out if he likes me without making a fool of myself?”

(2:01)  Meghan Keane

Meghan Keane is the mastermind behind NPR’s Life Kit, your go-to source for real-world wisdom on everything from budgeting to heartbreak. Fun fact: our very own Damona has appeared on several episodes of this fabulous NPR show as a host and guest. !

But wait, there’s more! Before she was dishing out life hacks, Meghan was busy making radio magic. She’s got producer cred on the mind-bending “Invisibilia” and was there from day one for the wildly popular “Ted Radio Hour.”

Now, Meghan’s taking on the ultimate solo adventure with her brand-new book, “Party of One: Be Your Own Best Partner.” It’s hot off the press and ready to revolutionize your single life!

Singlism Showdown (05:13)

“You’re too picky.” “Why aren’t you married yet?” Sound familiar? Suddenly, everyone’s an expert on your love life (or lack thereof). 

Ready for a reality check? Meghan Keane drops this truth bomb: “Singlism is basically just that, having a view of singles as being less than, marginalizing them, discriminating against them.”

Time to rethink how we’re treating our single friends – and ourselves! Because newsflash: being single doesn’t mean you’re broken, it means you’re whole all on your own.

Friendship: The Secret Sauce of Single Life (25:40) 

Think your social circle shrinks when you’re flying solo? Think again! Meghan talks about building a thriving community as a party of one.

Forget the TV drama – real-life connections are often built on the simplest of actions. Get ready for some surprising insights on how to expand your friendship circle and why it’s crucial for your happiness.

Trust that inner social butterfly! You might just discover a whole new world of connections waiting for you.

 

The ‘Party of One’ Revolution (29:39) 

Rushing to find “the one”? Hit the brakes!

Meghan’s new book, “Party of One: Be Your Own Best Partner,” is here to shake up everything you thought you knew about being single. It’s not about waiting for your life to start – it’s about living it to the fullest right now!

Discover why treating your single life like its own fabulous party could be the key to happiness, whether Prince Charming shows up or not.

 

Mind Over Dating Matter (32:33) 

Got a case of the “why am I still single” blues? You’re not alone!

Meghan shares a powerful perspective: “When you focus more on what values you’re trying to express in your life… it’s a lot kinder and healthier than being like, ‘Did I get this thing? Did I check this box?'”

Time to sort through those emotional souvenirs and decide what’s worth keeping. Meghan’s got the tools to help you rewrite your single story from tragedy to triumph.

Connect with Meghan:

Pick up “Party of One: Be Your Own Best Partner”

Website: https://meghanvkeane.com/

Instagram: @DameKeane

(44:88) Dear Damona

Email from Anonymous:

I’ve been casual friends with a guy for years, until the other day I hadn’t seen him in about five years, and we’ve exchanged texts maybe once every six months, briefly. I’ve always had a crush on him, but he was married. 

He got divorced about two years ago, and I know he’s looking to be in a relationship again. My friend saw his profile on a dating app. I reached out to him and said it had been too long, we should get dinner at, etc. it took a while to set this up, but we finally had dinner two nights ago, and everything I felt about him was reinforced.

 He’s kind, sweet, funny. We have so much in common, but I can’t tell if he’s more interested in me than usual or just being himself. He definitely wasn’t overtly flirting. 

My feeling after leaving dinner was that he is not interested in me romantically, but I’m a terrible flirt and horrible at reading signals. As we were leaving, I tried to give him an opening by saying we had to do this again soon and not to let so much time pass. And he agreed. But that was it. 

Under normal circumstances, I would just assume he wasn’t interested in me and let this go. But I so rarely meet guys I connect with and we’re both in our late 40s, so that makes it even more rare. I don’t want to just give up and walk away if there could be a chance. But I also don’t want to make a fool out of myself or embarrass this really sweet guy. Is there any advice you can give me?

Do you have questions? Damona has the answers!Don’t forget you can submit your dating and relationship questions for our Dear Damona segment on Instagram, X, TikTok, or Facebook, or leave us a voicemail or text to 424-246-6255, and hear Damona’s answers live in a future episode!

Dear Damona: Friends with Exes & Chemistry Cooler

Summer flings are fading like falling leaves, and cuffing season is right around the corner. What better time for an all-out Dear Damona extravaganza?

This week, we’re answering your burning questions. Whether you’re dealing with a suddenly chilly connection or navigating the crisp air of undefined relationships, we’ve got some cozy advice to warm your heart.

You asked about everything from the challenges of staying friends with exes to decoding mixed signals after seemingly golden dates. We explore the rich tapestry of communication styles and relationship signs that, like fall foliage, aren’t always what they appear at first glance!

Get ready for some real talk that’ll warm you up faster than a pumpkin spice latte! 

(00:25) Dear Damona 

Do you have questions? Damona has the answers! Don’t forget you can submit your dating and relationship questions for our Dear Damona segment on Instagram, TikTok, or Facebook, or leave us a voicemail or text to 424-246-6255, and hear Damona’s answers live in a future episode!

IG DM from Montie (1:29)

Heyyyyy bestie!  Can you speak to expectations and how not to become jaded when your partner doesn’t take initiative like you do?  

For example, my man’s back was hurting so I took my massage gun and fixed him up without him asking.  However, whenever I’m not well, he doesn’t take that same initiative.  

I realize men think differently than women, but dang!  I’m a caretaker by nature and want to be taken care of when I’m not feeling well, too.  Too much to ask???  Thanks, mama.  Big smooches!

Email from a listener named Lydia (6:44)

 I’m having trouble moving past my feelings for emotionally unavailable people or people who moved too fast to get into a relationship as a result of me catching feelings too quickly or saying no, I’m not sure how to maintain a friendship. 

They say they want to stay friends after the fact, but then when I get told by the individuals that they are with someone now after I shared that I wanted to take it slow, it crushes me. 

Ultimately, I feel that me eliminating the friendship is the best thing to do. I know I’m self-sabotaging, but I don’t know how to be friends right now with a person dating another because it hurts so much, or friends with someone who doesn’t see me as a partner as I hoped they would.

IG DM from J (11:10)

I like very few people, but a few I would go out with again.  Unfortunately, they told me they didn’t feel any chemistry after the first date. 

I am often told that I am very attractive, charismatic, and fun. So what am I doing wrong and how does this not impact me?

Email from D (18:45)

Hey Damona, guy listener here. I only started recently and am slowly catching up.

It comes up frequently that a barometer of a man’s interest is whether they ask questions – and it’s a poor reflection when they don’t. (A favorite recent meme said, “ ‘You’re so mysterious’, says a man who has never asked you anything.”)

Reflecting on this, I realized I used to not ask many questions either. An ex-girlfriend shared how that was a “red flag” on our first date. Here’s the catch: I was VERY interested in her. In general, I’m a really inquisitive person, and remembering details about a person is almost my superpower. I just didn’t ask direct questions, more so expecting the details to come naturally in conversation.

I think it has to do with how men and women communicate differently – men don’t need to be asked – or given permission – to give their perspective. They simply jump in with it. Women, on the other hand, might need to be given more space to share, and when it’s not given, it’s taken as a slight.

Don’t get me wrong: I’m really glad this was pointed out to me, and I now actively ask more questions and have noticed the difference. I just worry that this phenomenon gets misattributed. Yes, men should be more mindful and ask more questions. But I also wonder if there’s space for women to know that it’s not always from a self-involved or uninterested place but potentially just from a difference in communication style.

This is all from anecdotes and conjecture, so I could be way off base. What do you think?

Therapy-Speak & Is it The Apps

 

Feeling like you need a psychology degree to navigate the dating scene these days? 

“Narcissist,” “trauma bonded” – these terms are everywhere, but are we going overboard with the therapy talk?

We all know how important it is to recognize the signs of a toxic relationship, but maybe we’re too quick to slap labels on every bad date. Then again, with online dating bringing strangers into our lives, we need to know what to watch out for, right?

Licensed Marriage and Family Therapist Kiaundra Jackson to the rescue! Kiaundra joined Damona this week to unpack the difference between truly toxic relationships and normal dating hiccups. Plus, she shares why understanding healthy relationship dynamics is just as important as spotting the bad ones.

And don’t forget to stay tuned for our Dear Damona question: “I’ve used them all, but none seem to be a good fit. Is it me or the apps?”

(1:39) Kiaundra Jackson 

Kiaundra Jackson is a licensed marriage and family therapist. You may have seen her on OWN’s TV show Love Goals or on Tubiunpacking shocking true crime stories from a psychological point of view. Kiaundra has been featured in Essence Magazine, Women’s Health, Fox, CBS, and in Forbes “Next 1000”.

Dating Dictionary Detox (05:13)

“He was toxic.” “That was triggering.”Suddenly, we’re all armchair therapists, aren’t we? These buzzwords are flying around the dating scene like confetti at a party. 

Ready for a reality check? Not every bad date is “toxic,” and overusing these terms might just be muddying the waters of your love life.

Kiaundra Jackson drops this truth bomb: “Narcissism, toxic, triggers, all of those words are often misused and overused.” Time to rethink how we’re labeling our dating experiences!

Toxic Love Alarm System (25:40) 

Think you might be in a toxic situation? Time for a relationship health check! Kiaundra spills the tea on those sneaky signs that scream, “danger ahead!”

Forget the tv drama – real-life red flags are often subtle but oh-so-important. Get ready for some truth bombs: it’s not just about obvious abuse. Sometimes, it’s that icky feeling in your gut telling you something’s off. 

Trust that inner voice! Plus, learn why your bestie might spot the toxicity before you do.

The All-Weather Love Test  (29:39) 

Rushing into romance? Hit the brakes!

Ever thought about dating someone through all four seasons before getting serious? It’s not about pumpkin spice vs. beach vibes – it’s seeing how they navigate life’s highs and lows. Talk about relationship due diligence!

Discover why watching your partner handle everything from summer BBQs to winter blues could be the ultimate compatibility test.

Emotional Baggage Bootcamp  (32:33) 

Got baggage from past relationships? Don’t we all! 

Rushing into a new relationship is like traveling with a messy suitcase – it’s gonna slow you down. Consider this your call to emotional spring cleaning. Your future self (and partner) will be doing a happy dance! 

Time to sort through those emotional souvenirs and decide what’s worth keeping. 

The Unpopular Truth About Relationships (39:12) 

Brace yourself for a hot take: relationships aren’t actually hard work. Say what? 

Yep, you heard that right. Buckle up – it’s time to challenge everything you thought you knew about making love last. 

Kiaundra’s serving up a fresh perspective that might just make your relationship feel like a breeze.

Connect with Kiaundra:

Find her on YouTube: https://www.youtube.com/c/kiaundrajackson

Website:https://kiaundrajackson.com/

Instagram: @KiaundraJackson

(41:37) Dear Damona

DM from a listener named Nicole:

What dating apps do you recommend for a woman in her 50s? I’m 53 and have used Bumble, Match, and Hinge, but none felt great. I’m not sure if it’s me or if I’m just using the wrong apps.

Do you have questions? Damona has the answers!Don’t forget you can submit your dating and relationship questions for our Dear Damona segment on Instagram, X, TikTok, or Facebook, or leave us a voicemail or text to 424-246-6255, and hear Damona’s answers live in a future episode!

Coaching Session: Secret Affirmations

 

You’ve heard her dish-out advice on The Drew Barrymore Show and seen her chat with daters on the street, but Damona’s deepest work comes in coaching and helping singles identify the dating loops and myths that are holding them back in love. 

That’s why we’re pulling back the curtain and giving you an inside look at Damona’s coaching magic in action in this week’s episode of Dates & Mates! With over 18 years in the dating game, Damona’s about to show you why her approach is anything but typical.

You’ll get to be a fly on the wall of the Dates & Mates Method today as Damona works one-on-one with listener Staci to tackle real dating challenges.  Plus, she’ll give you quick tips and takeaways that you can apply right away to your own dating dilemmas. 

Now, we don’t have to tell you that it is a very brave thing for someone to be willing to do a coaching session live on the Dates & Mates podcast. So we encourage you to listen with compassion, but also listen for connections. 

Think you know what to expect from dating advice? This episode might just change your mind. It’s time to see how Damona really works her magic!

The Dating App Dilemma (5:10)

Let’s be real – swiping has lost its sparkle, hasn’t it? 

Staci’s been there, trying to jazz up her conversations but still hitting dead ends. 

Here’s the tea: there’s a formula that might change your whole app game. Seriously, this could be the boost your dating life needs.

Showing Up Differently (14:38)

Are you actually connecting or just focused on your phone all day long? It could be time to try dating IRL.

Even in person, Staci shares how she can’t seem to flirt without coming off as just friendly. Sound familiar? 

Get ready for the S.E.T. it up method. It’s about to be your new secret weapon—it’s time to turn those friendly vibes into full-on flirty magic.

The Power of Affirmations (27:24)

Forget settling. It’s time to call in your dream partner. 

Staci’s daily affirmations are reshaping her whole love vibe. It’s not just positive thinking—it’s about putting it out there for the universe to hear.

Damona shares the truth on the matter:  “The clearer you can be about who this person specifically is… the more you are calling that relationship into your life.”

Your Dating Challenge (40:29)

Alright, enough talk. Let’s shake things up! Ready for a challenge? 

Try a week of flirty eye contact. Plus, it’s time to get detailed about your dream relationship. Paint that picture! These aren’t just exercises – they’re your ticket to a love life glow-up.

Remember, comfort zones are cute and all, but the real magic? It’s waiting just outside. Let’s go get it!

Do you have questions? Damona has the answers!

Don’t forget you can submit your dating and relationship questions for our Dear Damona segment on Instagram, X, TikTok, or Facebook, and hear Damona’s answers live in a future episode!

Master Class: Overcoming Dating Burnout

 

If you’ve been feeling exhausted, unmotivated, or just plain over it when it comes to your love life, you’re not alone. In fact, dating burnout is  such a hot topic that Damona is dedicating this entire masterclass episode to tackling this dating dilemma head-on.

In this special episode, we dive deep into why so many daters are feeling burned out in their search for love. From the evolving landscape of dating apps to the challenges of meeting people IRL, we’re covering it all. 

Don’t worry, this isn’t just another doom-and-gloom conversation about modern dating. Damona is here to light a fire under your love life and help you rise from the ashes of dating burnout. By the end of this episode, you’ll be ready to jump back into the dating pool with renewed energy and a fresh perspective.

What the heck is dating burnout? (0:57)

Why does swiping left and right feel more exhausting than exhilarating these days? 

Dating burnout is more than just feeling tired of the dating scene – it’s a real phenomenon affecting singles everywhere. You’re not alone if you’ve been feeling less than enthusiastic about your dating app notifications lately!

What exactly is dating burnout, and why does it matter? Understanding this could be a game-changer for your love life.

(1:29) Why NOW?

We live in a time of unprecedented connectivity, yet paradoxically, forming meaningful connections has never been more challenging. 

From the constant ping of dating apps to the recent shifts in how these platforms operate, the landscape of love is evolving faster than ever.

But what’s really behind this wave of dating fatigue? Is it just about too many options, or is there something deeper at play? 

What are the real reasons behind the current dating burnout crisis? Hint: it’s not what you might expect.

(4:17) Dating is like a muscle – use it or lose it!

After spending so much time in isolation, many singles are finding their dating skills a bit rusty. It’s not just about getting back out there; it’s about relearning how to connect in meaningful ways, both online and in person.

But is all this effort worth it? Absolutely. Staying “comfortably single” often means we’re actually in tremendous discomfort.

The person you choose to partner with can impact every aspect of your life. Despite the challenges and potential for burnout, rediscovering the joy in dating is a journey worth taking. It’s time to flex those dating muscles agai

(7:35) Let’s talk facts…

Dating app usage is down across the board. But here’s the surprising part – people aren’t actually leaving the apps. Instead, they’re falling into what we call “zombie dating.” It’s a state of mindless swiping and endless, go-nowhere conversations.

But don’t delete those apps just yet! The solution isn’t to abandon ship, it’s to practice better “dating hygiene.” 

What’s that, you ask? It’s all about using these tools more mindfully and effectively.

(10:44) How do we actually fix dating burnout?

It turns out the solution might be counterintuitive.

Instead of pulling back, it’s about getting strategic and connecting more deeply. We’re talking about tracking your progress, forming a “connector circle,” and even creating a comprehensive dating plan.

But here’s the real kicker – the antidote to dating apathy might just be empathy.

 

Do you have questions? Damona has the answers!

Don’t forget you can submit your dating and relationship questions for our Dear Damona segment on Instagram, X, TikTok, or Facebook, and hear Damona’s answers live in a future episode!

Dear Damona: Soberish & First Date Rut

 

This week’s all Dear Damona special is tackling your SOS dating situations.

How do you juggle family importance while prioritizing relationships? What’s the best way to find a more laid-back match in a buzzing drinking culture? And the classic problem: you’ve done the work but can’t seem to attract someone who’s done the same. From family dynamics to social scene struggles, we’re answering it all.

Get ready for some real talk on breaking dating patterns and attracting the right energy. This isn’t just an advice column come to life; it’s your roadmap through the wild world of modern love. 

Let’s turn those dating distress signals into smooth sailing!

Dear Damona (2:56)

Submit your questions for our Dear Damona segment on Instagram, X, TikTok, or Facebook, and hear Damona answer YOUR question live in a future episode!

 

(3:01) Email from a listener named Briana:

Hi Damona,I love your podcast and book and appreciate your dating advice! 

I wanted to write in since I recently have been going out on good first dates where the men seem interested (I am, too), we have a connection, talk about seeing each other again, and then I get ghosted. Is this a new trend, or just plain bad luck? 

It has me anxious going on first dates where I worry even if it’s great I’ll never hear from them again. I feel stuck in a rut with endless first dates and want to break this unfortunate trend. 

Should I text them the next day? Any advice is appreciated! 

(9:14) Text message from a listener named Michelle

Damona, help me! My name is Michelle, and I’m in my late fifties. I have two grown daughters and children of their own. However, I’m also hoping to find someone who can make a relationship a priority. 

Here’s my question: How and when do I communicate that while I am very pro-family, I am also looking to find someone who can prioritize a romantic relationship and whose life does not revolve entirely around children and family? Is there language I can use in my profile, or how do I bring this up delicately in the early stages of dating?

(14:28) Email from a listener named L.K.

Hi Damona! I’ve been listening to your show for a year or two now, and I don’t recall hearing you address substance use. I’m in my mid to late 30s and not as interested in dating men who use a lot of recreational substances or who get drunk intentionally/frequently. I love a drink or two with great food or out with friends, but I am well past where I find heavy intoxication fun. 

I’ve found it hard to talk about this, though, as the cities I’ve lived in have big drinking cultures, and I’ve been teased about my preferences before. I’m just not really interested in that lifestyle and am not sure how to communicate about it. 

Do you have any tips on how to kindly communicate this preference or find more people with similar lifestyles? Thanks!

 

(20:40) Instagram DM from a listener named Colleen:

After my divorce, I worked on myself until I became the type of person I would swipe right on before dating.  I find myself really disappointed in the people who “like” me on apps for many reasons besides not being physically attracted to them.  

I’m 44 and I don’t want to date someone who isn’t at an equal point in their emotional maturity/availability, finances, career, etc. I’m beginning to think there’s no one available that’s up to par.  

Should I lower my standards?  Work through my expectations in (more) therapy?  I’d love to hear your advice!

Check out the past podcast episodes Damona mentioned in this episode:

Addiction & Love with Dr. Cali Estes

Minisode: A Dates & Mates Love Story

 

Too Hot to Handle & Inner Intimacy

Intimacy is the foundation of any great relationship, but here’s the thing: true intimacy doesn’t start with someone else, it begins with you. That’s right, we’re talking “intimacy:  into me, see?”

Our guest, Brenden Durell, the intimacy expert  from Netflix’s Too Hot to Handle, is here to guide us on this spiritual dating journey. He’s bringing exercises straight from the show and his retreats, promising a live transformation on our podcast. Don’t worry; we’re keeping it PG while still hitting those deep notes.

And because we love to keep you on your toes, we’ve got a juicy Dear Damona question coming up: “I’m stuck in a cycle of falling for guys who are either all in or MIA. How do I break free?” Stick around for some real talk on changing those pesky patterns.

Brenden Durell (2:05)

Brenden is a former professional athlete and the CEO of Unknown Intimacy.

His work spans various disciplines, including sacred sexuality, intimacy coaching, breathwork, and plant medicine.

You probably recognize him as the intimacy expert on Netflix’s Too Hot to Handle, but today, you will get to know him as a mentor who specializes in mental, emotional, and spiritual health.

(8:07) Mirror Mirror on the Wall

Mirror work isn’t just for checking your hair—it’s a powerful tool for self-love and personal growth.

Brenden suggests starting your day with a little reflection magic while doing your usual morning routine. It’s about looking beyond the surface and giving yourself some genuine love, no pom-poms required!

This practice isn’t just for the “Too Hot to Handle” crowd with their picture-perfect looks. Even those seemingly flawless folks have their insecurities, and Brenden’s mirror work helps peel back those layers.

(11:08) Healing Through Self-Apology

Brenden drops a mind-bending concept: apologizing to yourself for societal expectations you never asked for. 

It’s not about blame, but acknowledging the weight we carry. This isn’t a one-and-done deal—it’s a lifelong practice of shedding those “keep up with the Joneses” pressures.

Brenden challenges us to dial back vanity and reconnect with our deeper selves. It’s about moving past those voices that do not affirm our enoughness and finding a new way to see ourselves.

(16:27) Intimacy in the Jungle

Brenden’s “Intimacy in the Jungle” program takes place in the Amazon rainforest. This city boy turned jungle guide believes Mother Earth is the ultimate relationship counselor.

“For people to make deeper connections with others, with themselves, they have to first make a connection with mother, which is our first parent, Mother Earth,” he explains. It’s not about roughing it Survivor-style but embracing nature’s stillness to reset our connection compass.

This jungle journey isn’t for the faint of heart, but that’s the point. Confronting the raw, untamed wilderness mirrors our own internal landscapes.

(24:42) We Don’t Need Time Until We Do

Ever feel like you’re in a never-ending race against the clock? 

Brenden’s got a mind-bending take on that: “We don’t need time until we do.” It’s a wild concept—we’ve built our entire society around something that doesn’t really exist. But step into nature, and suddenly, that ticking clock loses its power. 

Brenden’s retreats tap into this time warp, resetting everything from your circadian rhythm to your perspective on life.

(38:36) Brenden’s Most Unpopular Opinion about Relationships

Brenden’s on a mission to bust the taboo that equates intimacy with getting down and dirty. For Brenden, sex is more like a spiritual ceremony than a shameful secret.

He suggests you try reframing sex as something beautiful. After all, without it, none of us would be here! He’s not asking you to go from prude to nude overnight. It’s all about baby steps, people. 

Connect with Brenden:

Dear Damona (44:02)

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

An anonymous email sent from a listener: 

I’m recently divorced after a 13-year marriage. I’ll be 38 in May. I’m successful in my career and have an almost 13-year-old son, but I have been on the backburner for years, and I have finally begun to prioritize myself. What I miss most is sharing my life with someone, though.

Unfortunately, some of the men I have come across range from falling hard and fast for me or not giving me the time of day. These are the ones I find myself attracted to. Sick I know. Is it some weird validation I need? I guess help? I’ve never really dated and feel lost. 

TherapyJeff & Down to DM

It’s a new season for Dates & Mates—Season 12, to be exact—and that means it’s time for a state-of-the-date check-in.

To help us do just that, we’ve got Licensed Professional Therapist Jeff Guenther on board—you might know him better as TherapyJeff on Instagram. He’s going to share some gems from his new book, Big Dating Energy, which covers everything from figuring out what you’re really looking for to the ins and outs of the date itself to how to handle commitment and even how to part ways if it comes to that.

It’s going to be a great conversation, and then we’ll get into our Dear Damona question of the week: “What’s the best way to reach out to someone on LinkedIn?” LinkedIn love—just in time for fall!

Jeff Guenther (4:32)

We’re thrilled to have Licensed Professional Therapist Jeff Guenther joining us—you probably know him better as TherapyJeff from Instagram.

Jeff shares insights from his new book, Big Dating Energy, which dives deep into every stage of authentic dating. With 20 years of experience in private practice therapy, he really knows his stuff.

Beyond his book, Jeff is the host of the Big Dating Energy podcast and co-hosts the This Changes Everything podcast, another must-listen. His expertise has landed him interviews on NPR, Time, CNN, Rolling Stone, Business Insider, and Slate.

(5:17) Big Dating Energy

Jeff just released his highly anticipated book, Big Dating Energy, and he’s here to give and eus the inside scoop. Jeff opens up about the highs and lows of the writing process, from the joy of creating the content with his co-author Kate to the challenges of marketing, design, and endless editing.

But what makes this book even more unique is that Jeff’s co-author is his ex-wife, Kate Happ. Despite their divorce, they managed to maintain a strong friendship, which made the writing process smoother and more collaborative.

(11:45) When is a Deal Breaker NOT a Deal Breaker?

Clear thinking about what truly matters is key to finding a healthy relationship. Jeff suggests making lists, whether it’s fears, defenses, non-negotiables, or deal breakers.

As he wisely says, “A deal breaker has to actually be a deal breaker—if it shows up in the relationship, you’re done, you’re out.” This advice can really help you avoid confusing minor annoyances with true red flags.

But Jeff doesn’t stop there—he also challenges us to look deeper at where these deal breakers are coming from. Are they genuine, or just defenses we’ve built up over time?

(20:45) Dating Apps: A Big Chaotic Evil

If you’ve ever felt stuck in the endless swipe cycle on dating apps, Jeff really gets it. He reminds us that these apps are just one tool in the dating game, and they’re often designed more to keep us hooked than to help us find true love. 

This is a good reminder not to put all your hopes in  the apps and to keep your eyes open to other ways of meeting people.

(30:35)  Long-Term Relationship Survival Guide

Jeff shares some real wisdom for anyone in a long-term relationship. He’s all about making sure your relationship is healthy and that both partners are getting their needs met. 

One key tip? Learn how to handle conflict in a way that brings you closer instead of driving you apart. Jeff believes that every disagreement can be an opportunity for growth, not just a fight to be won. It’s about understanding each other’s feelings and finding common ground.

(32:40) Conversations to Have After Sex

Sex in a relationship doesn’t have to be perfect right from the start, and mismatched desires or awkward first encounters aren’t necessarily red flags.

 As Jeff says, “Sex gets weird.” But with some open, honest communication, most of these challenges can turn into opportunities for growth and connection. He shares some thought-provoking questions to ask after having sex with your partner. 

Jeff also emphasizes the importance of keeping the spark alive over time. 

 

Connect with Jeff:

Dear Damona (44:02)

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 a listener named Chris:

Dear Damona, I enjoyed your Dating Decoded webinar, and I learned a lot. I know you get a ton of DMs, but it’d be great to get your advice. What’s the best way to reach out to someone new on LinkedIn without sounding creepy? Do I use your PS world method?

 It turns out we have a mutual connection, but there’s no profile picture, and I can’t click on it, so I don’t know who it is. I could use the connector circle if I find out our mutual connection. Please help

 

Dating Solutions: The Communication & Trust Pillars

We’re back with the final bite-sized episode of the F the Fairy Tale Summer Series on Dates & Mates, inspired by themes from Damona’s new book F the Fairy Tale.

Last week, we examined the Goals and Values Pillars, which are crucial for laying the foundation of any relationship.

Now, we’re moving forward with the final two pillars: Communication and Trust. These pillars are essential for building strong, lasting connections. To guide you through these final two pillars, we have insights from one of Damona’s favorite segments of our recent F the Fairy Tale forum.

This segment features two of the most respected dating and relationship coaches, Carol Allen and Katherine Woodward Thomas, who help break down the pillars and answer listener questions like, “What do you think are the top three dealbreakers in a relationship?”

Let’s explore how mastering the Communication Pillar and Trust Pillar can transform your love life.

dating and relationship expert damona hoffman's book F the Fairy Tale

(0:53) The Communication Pillar

We all love the idea of chemistry—that instant connection and those fluttering butterflies when meeting someone new. However, the Chemistry Myth often leads to the belief that something magical must happen right away.

But those butterflies might be warning signals that things are moving too fast or that a familiar, unhealthy pattern is being repeated. Instead, slow down, communicate effectively, and focus on the Communication Pillar.

Embracing slow love is key to building a solid foundation and overcoming many dating challenges.

(1:46) The Trust Pillar

As we shift our focus from meeting someone special to building a future together, it’s time to replace the Soulmate Myth with the Trust Pillar.

Your soulmate isn’t found through magic; trust is built in small moments, micro-decisions, and actions. It’s through developing the Trust Pillar that you’ll find the person you choose as your soulmate.

Remember, it’s not destiny or magic that forms lasting love, but the consistent, trust-building actions that create a strong, enduring relationship.

(2:24) Carol Allen

Carol Allen is a Vedic astrologer and relationship coach. Her methods are really a blend of East and West.

She combines her training in astrology in India with cutting-edge, real-world relationship research.

Carol has appeared on E!, Bridezillas, Xtra,, Doctor Drew’s Life Changers, and Chicken Soup for the Soul.

(2:49) Katherine Woodward Thomas

Katherine is a New York Times best-selling author, licensed marriage and family therapist,, and teacher to thousands of people worldwide in her virtual and in-person learning communities.

You may have heard of her book Conscious Uncoupling-Conscious Uncoupling: 5 Steps to Living Happily Even After. She also has an amazing online course: Calling in “The One:” 49 Days to Love.

(3:34) It Starts with a Relationship with Yourself

When asked how to improve communication with a partner or date, Katherine Woodward Thomas emphasizes that “our relationships with others can never really be any better than our relationship with ourselves.”

Communication often becomes distorted when driven by unresolved issues.

(7:52) We All Come with a Divine Design

Is there really such a thing as astrological compatibility?

Carol emphasizes that everyone has a unique divine design, with personality traits that are largely genetic. This innate temperament affects how we connect with others.

It’s important to find those connections where trust and communication flow easily, “You want to look for those people where you don’t have to work so hard.”

Listener Questions:

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

14:04 Anonymous Listener:

Do you find it true that the scarcity mindset really plays out in limiting success in dating? I get so few responses, which leads me to experience scarcity. How do I bring abundance into my dating life?

19:00 Anonymous Listener:

How do you keep your energy up when you’ve been dating for a long time and you’re still waiting to meet your life partner?

25:02 Anonymous Listener:

What do you think are the top three dealbreakers in a relationship?

27:15 Anonymous Listener:

I am struggling to maintain an abundant mindset even while engaging in activities I love, repeating affirmations but not seeing any matches. Help!

 

Dating Solutions: The Goals & Values Pillars

Welcome back to our F the Fairy Tale Summer series, where we’re serving up bite-sized episodes inspired by Damona Hoffman’s new book, “F the Fairy Tale.” 

This week, we shift from busting myths to seeking solutions in dating. We’ve already tackled the four biggest myths that hold singles back: the rules myth, the chemistry myth, and the soulmate myth. If you missed those, be sure to catch up on the last four episodes!

But what good is identifying these myths if we don’t know how to solve them? This week’s mini-episode focuses on the Goals and Values Pillars from Damona’s book. 

We dive deeper into the Goals Pillar and the Values Pillar with three of Damona’s dear longtime friends in the love business: relationship experts Orna and Matthew Walters and Evan MarcKatz. Join us as we revisit one of Damona’s very favorite panels from the F the Fairy Tale Forum last year, and start transforming those myths into actionable steps towards finding true love!

dating and relationship expert damona hoffman's book F the Fairy Tale

The Goals and Values Pillars (1:17) 

The Goals and Values Pillars offer fresh solutions to two of the biggest dating myths. 

The Goals Pillar helps you dodge the list myth by focusing on shared goals rather than superficial qualities. This way, you make sure you’re on the same page with your partner from the get-go, avoiding that dreaded moment when you realize you’re not heading in the same direction.

On the other hand, the Values Pillar is all about breaking free from the rules myth. Those rigid dating rules might feel safe, but they can keep you from truly growing and connecting. 

By letting go of these rules, you can dive into self-inquiry, understand your values on a deeper level, and write your own love story. These pillars guide you toward more fulfilling and authentic relationships, helping you navigate the dating world with confidence.

(3:18) Orna and Matthew Walters

Orna and Matthew Walters  are amazing love coaches, but they do so much more than that. 

They are featured on Bravo’s The Millionaire Matchmaker and have helped transform thousands of singles around the globe. 

They also have a new book coming out in January 2025 through a division of Penguin Random House. It’s called “Getting It Right This Time: Break Free from Your Hidden Blocks to Lasting Love,” it’s available for pre-order now!

(3:44) Evan Marc Katz

Evan Marc Katz is a name well-known in the dating world, especially if you’ve been navigating it for a while. 

He is renowned as the dating coach for smart, successful women. With not one, not two, but four books to his name. Evan has been featured on hundreds of media outlets since 2003. He hosts The Love U podcast and runs a blog launched in 2006, which boasts over 30 million readers today.

Fun fact: Evan is one of Damona’s very first friends in this business. About 13 or 14 years ago, he took a call from Damona when she was considering leaving her TV producing career to become a full-time love coach. 

(5:55) Release the First Date Pressure!

Evan is all about putting values first. Instead of trying to figure out if someone is your soulmate on the first date (because who can do that?), he suggests a more relaxed approach.

Pay attention to your feelings and let people show you who they are over time. You’ll learn a lot about someone in the first month and save yourself from making big mistakes.

Damona points out that it all starts with knowing your own goals and values. So many people come to her saying they’ll “know it when they see it,” but having that clarity from the get-go is super important. It’s all about setting yourself up for success in finding the right partner!

(10:30) What is Your Love Imprint?

Orna and Matthew start by helping clients understand their love imprint—a concept that explores how early childhood experiences shape our attraction patterns.

It is common to be attracted to people who emulate our families because it feels comfortable, normal or safe, but it can lead to repeating unhealthy relationship patterns. 

Orna and Matthew help clients identify and break these subconscious habits. By first understanding themselves, clients can form healthier, more fulfilling relationships.

Listener Questions:

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

21:00 Jeannie asks:

 What’s the best site for women over 65?

22:53 Anonymous Listener:

 For women, I feel like the message is often to lower your standards. Meanwhile, men are not improving themselves like we have. And in my area, it feels like a dating dessert. I have likes on my profile, but not anyone I’ve been curious about lately, and I don’t know if it’s connected to the next question. Does that mean that my standards are too high? 

 

The Soulmate Myth & Growth Mindset

You might be surprised to learn that Damona does NOT believe in soulmates. In fact, neither does Mr. Hoffman. They believe that there are many possible matches out there for you, but you choose to make someone your soulmate every day. You choose to keep learning and growing into your relationship.

As we continue our F The Fairy Tale Summer Series, this week’s Dates & Mates minisode will focus on the Soulmate Myth.You’ll hear an excerpt from the book, get answers to a listener question, dive into some dating dish-esque stats, and receive the best relationship advice you’ll hear all week. 

The Soulmate Myth (1:40) 

What’s the soulmate myth? It’s the idea that there’s one perfect person out there for you, and finding them will make you happy forever. If there were a soulmate finder app, it would make millions! 

But here’s the thing—it’s just a myth. Chasing the idea of one perfect match prevents you from committing to a fulfilling relationship and sticking with someone when times get tough.

(2:14) Straight from F the Fairy Tale

Damona shares an excerpt from her book, F the Fairy Tale, on the myth of soulmates: “Pursuing that ideal keeps you constantly in a scarcity mindset.”.

She explains that believing there’s only one perfect match limits your choices and can make you question a great relationship. Instead she urges daters to embrace a growth mindset which will allow them to overcome issues and build strong relationships.

(7:03) It Takes a Mindset Shift 

Damona shares some surprising data about the soulmate myth. Former NASA engineer Randall Munroe found that the probability of meeting your perfect soulmate is once in 10,000 lifetimes. 

“So, if the odds aren’t in our favor, it’s imperative that singles shift from the soulmate myth mindset.” Instead, focus on long-term compatibility. 

Based on years of coaching, Damona emphasizes that common goals and shared values are the true markers of a successful relationship.

Listener Questions

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

(4:24) I feel like my ex was my soulmate. I’ve been dating on the app since we broke up, and I’m starting to worry that I’ll never feel that way again.

(8:28 ) Do soulmates exist? I used to believe in Twin Flames, but now, 20 years in with a family, mine is no longer interested in me and I’m trying to separate.

 

The Chemistry Myth & Sleeping Together

What if chemistry is just a myth? Damona is here to challenge everything you thought you knew about those initial sparks.

In this solo minisode, we dive into The Chemistry Myth. We start with an excerpt from Damona’s book, F the Fairy Tale, and follow up with top tips and takeaways on understanding chemistry in relationships. 

Plus she answers this sizzling Dear Damona question: “How fast is too fast to have sex with a new person?” 

So, grab your favorite beverage, get comfy, and join us for an episode filled with insights and revelations.

The Chemistry Myth (0:58) 

The Chemistry Myth is the belief that you need to feel immediate, romantic sparks for a long-term relationship to develop. 

True relationship success starts with slow love. When we try to shortcut the road to a relationship by steering around red flags, we miss the true markers of relationship success and then we second guess our dating and relationship choices. 

(1:33)  When are the Flutters Not Butterflies?

The Chemistry Myth touches a lot of lives! RomComs and romance novels spread the myth of chasing butterflies! But what if you don’t really understand what they mean? 

Damona shares an excerpt from the book about how the Chemistry Myth has affected her own dating life.

(3:51) Butterflies May Be a Window to the Past

You may think that the “chemistry” you feel points to the future, but it often reflects our past. 

True connection and compatibility develop over time, which is why Damona advocates for slow love in her book F the Fairy Tale, and pretty much everywhere!

By ditching the List Myth and the Rules Myth, you can truly see who someone is and how they align with your deeper goals and values. 

Dear Damona (6:02)

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 Miss. M:

Dear Damona, if slow love’s the only way to go, which for me, I definitely don’t want first, second, or even third date sex, then what’s considered too fast or too slow? I’m happy to report I’m dating a guy who has aligned values, is a good open communicator, and makes me feel amazing and heard. Here’s our timeline. Met for a 1.5-hour coffee a week after app chatting. After the second-date dinner, he asked for consent to kiss me good night. Third date dinner, kissed a little more good night in the car.

Fourth date hung out at his place, and he politely asked how far I would like to go making out, we kept it PG. Date number five: dinner again, invited him to my place, and had sex. I realized this morning it’s only been three weeks since we matched, both feeling excited about each other and have date six planned for tomorrow. Do you think sex within three weeks is considered slow love?