Tag Archive for: not settling

Dear Damona: Have Match, Won’t Travel & Disappearing Profiles

Fall is in full swing, cuffing season is here, and Thanksgiving is just around the corner. Whether you’re navigating long-distance connections, staying safe while online dating, or figuring out how to take your dating game to the next level, this week’s Dear Damona episode has you covered.

We’re dedicating the whole show to your most pressing dating dilemmas and relationship questions as we head into the holiday season. From timing intimacy to challenging gender roles, we’re diving deep into the questions that matter most to you.

(00:25) Dear Damona 

Do you have questions? Damona has the answers! Submit your dating and relationship questions on Instagram, TikTok, or Facebook, or leave a voicemail or text to 424-246-6255, and hear Damona’s answers in a future episode!

Love Beyond Borders (1:43)

Adrian’s dating app experience has been surprisingly wonderful – except for one geographic challenge that keeps getting in the way. 

“Dating sites in the last two years have been wonderful – I’ve made friends, had exciting dates, and even a relationship for a couple of years. The dilemma for me has been my location and the willingness of men to travel. I’m willing to travel to meet them, but of course, that can be tricky. Is there a specific dating site that I should use for this situation?”

When Digital Footprints Fade (10:55)

Sue’s dating detective work uncovered something fishy – between mysteriously disappearing profiles and stories that don’t quite add up, she’s stumbled into a digital dating mystery that’ll make you think twice about your next match. 

She asks: “Dear Damona, recently it seems that a few of the men I’ve met online dating on Bumble have removed their online profiles as soon as we share phone numbers. Do you have any data or insights about this behavior?” Sue shares concerning details about mismatched accents and overlapping life stories between matches that raised red flags.

The Perfect Moment (18:47)

When it comes to intimacy, timing is everything. But who decides when the clock strikes “right”?

This listener’s bedroom boundaries bring up the age-old question of when to take things to the next level.

Our anonymous listener asked, “Do you have a recommendation for when two people who have started dating can sleep together? Or what to say if my date proposes we sleep together and I feel it’s too soon?”

Rewriting the Dating Rulebook (24:39)

Ladies first? More like ladies waiting! 

Why are women still sitting around waiting for men to make the first move? Time to shake up those dusty dating rulebooks! 

Erin writes: “Do you know of any couples or of any relationships in which the woman asked the man out, or the woman was the initiator? It’s a follow-up to the point where you have encouraged women to ask men out. Some people like to think that the world is slowly changing; however, at the same time, a part of me doubts it, as in I just see it as men always being stuck with that gender role.”

 

The Knot’s News & Gift Glitch

What Singles REALLY Want in 2024!

Ever wonder what your potential dates are really looking for? Or if your relationship expectations match up with everyone else’s?

The Knot just released their 2024 Relationship and Intimacy study, revealing fascinating insights about how singles find love, what they’re actually looking for, and those persistent deal breakers that shape our dating decisions.

Get ready to decode modern romance with Esther Lee, deputy editor of The Knot. She’s breaking down the numbers on everything from meet-cutes to marriage, and some of these findings might surprise you!

Plus, don’t miss our Dear Damona segment, where we tackle an awkward gift-giving situation. When is it too soon for intimate presents? 

(1:34) Meet Esther Lee

Esther Lee is the deputy editor of The Knot, leading content on The Knot Wellness with a focus on financial, relationship, and mental well-being. 

She oversees The Knot’s travel vertical, including honeymoons, destination weddings, and bachelorette parties, along with overarching features and trends.

The Knot Esther Lee 2024 Relationship study with Damona Hoffman on Date & Mates podcast discussing relationship and dating trends

The Comfort Connection (05:13)

The Knot’s 2024 study challenges everything you thought you knew about attraction and chemistry. What tops the list of desirable qualities might surprise you – and it’s not what most dating coaches are teaching!

As Esther notes, “There has to be this openness and this lightness, almost like you’re showing up as yourself and being comfortable with who you are.” Find out why authenticity might be your best dating strategy.

Love Offline (17:52)

Dating apps aren’t the only path to partnership. 

The study reveals unexpected ways couples are meeting in 2024, including some surprising new trends in the gaming world.

Plus, discover why traditional meet-cutes might be making a comeback and how Gen Z is revolutionizing the dating scene.

Married Life Myths & Reality (21:20)

Think you know how marriage changes relationships? The study’s findings about intimacy patterns before and after marriage might change your mind.

Esther shares insights from a recently married team member who discovered unexpected shifts in their relationship dynamics post-wedding. 

Learn why “putting a ring on it” might transform more than just your legal status.

The Distance Dance (34:48)

When it comes to deal breakers, distance tops many singles’ lists. 

But what exactly counts as “long-distance”? For some New Yorkers, it’s crossing boroughs; for others, it’s crossing oceans.

Plus, discover the other relationship red flags that made the list and why they might matter more than you think.

Connect with Esther and The Knot:

(39:19) Dear Damona, Help Me!

Email from a listener named Cathy:

This is a little off the beaten path, but my 17-year-old grandson is dating a lovely young woman, and she recently had a birthday for a birthday gift. 

He bought her a Victoria’s Secret bra. She interpreted this as him wanting much more out of the relationship, and she promptly slapped him in his face and stormed off.

I gotta say, I love the gal’s chutzpah since there was certainly no ambiguity in her reaction. Any ideas on how he might navigate this precarious situation? 

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 InstagramTikTok, or Facebook, or leave us a voicemail or text to 424-246-6255, and hear Damona’s answers live in a future episode!

 

Dating Horror Stories & The Flirt Coach

This Halloween, we’re embracing the ghosting, the ghouls, and the downright ridiculous tales of love gone wrong.

On Dates & Mates this week, we’re diving into our annual Halloween tradition with a collection of dating horror stories that will make you laugh, gasp, and hopefully help you to avoid your own awkward dates.

We’ve got five cringy  listener stories that prove sometimes the scariest part of dating isn’t the ghosting – it’s what happens when you actually meet! Plus, my guest  and I share our expert tips on how to avoid becoming the star of your own dating horror story! 

To help dissect these strange and unusual encounters and offer some love advice, we have Benjamin Camras, The Flirt Coach, joining us. 

So dim the lights (but skip the candy corn – we’ll die on this hill), and get ready for some haunting tales of dating gone wrong.

(1:54) Benjamin Camras, The Flirt Coach 

From self-described introvert to social media sensation, Benjamin Camras (who introduces himself proudly as “the gay Libra”) is spreading “BFE” (Big Flirt Energy) across the digital world. 

He hosts the Flirtations Flirtcast podcast and specializes in helping fellow introverts and the socially anxious find their flirting groove with more confidence, clarity, and fun.

Your Dating Horror Stories  (05:13) 

Join Damona and Benjamin as they dissect these strange tales:

  • Blindsided by a Blind Date (7:08) 

When Amanda finally decided to dive back into dating, she thought a simple movie date with Steve – an ex-military geek – would be a safe bet. 

  • The Vegetarian Variation (15:28)

When a late-night Tim Hortons run in Canada revealed an unexpected plot twist about dietary preferences, our listener learned that sometimes what you see isn’t exactly what you get. 

  • The Creepy Car Concert (19:48)

 What happens when you take a chance on an older, handsome suitor? Our listener found out the hard way that age doesn’t always equal maturity.

  • The Deskside Date (30:10) 

When Covid forced dating to go virtual, our listener dolled up with wine in hand for what she hoped would be a romantic Zoom connection. Instead, she found herself starring in an impromptu episode of “The Office.” 

  • The Freudian Movie Man (40:07) 

When a second date to see “Inside Out” turned inside-out, our listener found herself beside a man who came prepared with everything. 

Connect with Benjamin:

Dear Damona, Help 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 InstagramTikTok, or Facebook, or leave us a voicemail or text to 424-246-6255, and hear Damona’s answers live in a future episode!

 

Dating Anxiety & Financial Therapy

Money matters can make or break relationships, but they don’t have to be a source of stress.

Financial issues often top the list of relationship stressors, creating tension and misunderstandings between couples. But what if money could actually strengthen your bond instead of straining it?

This week on Dates & Mates, we’re flipping the script on financial conversations and exploring how they can build trust and improve communication with your partner.

Joining us is Erika Wasserman, known as “Your Financial Therapist” and one of only 70 certified financial therapists in the US. She’s here to help destigmatize money talk in relationships and offer insights for both couples and singles navigating the financial aspects of dating.

Plus, don’t miss our Dear Damona segment, where we tackle this tricky question: “I have social anxiety. Do I need to focus on making more friends before pursuing a romantic relationship?” Stick around for some surprising advice on balancing social and romantic pursuits.

(1:54) Erika Wasserman 

Erica Wasserman is the CEO of Your Financial Therapist. She’s the creator of the Let’s Talk Finances Financial Wellness Conversation Cards, which allows people to explore the topic of money with thought-provoking questions. 

She earned a Bachelor of Business Administration degree from the University of Florida and a graduate certificate in financial therapy from Kansas State University, making her one of only 70 certified financial therapists here in the country.

Show Me the Money Talk (05:13)

Cha-ching! Is that the sound of love or your piggy bank breaking? Financial counselor Erika Wasserman says it could be both – in a good way!

She flips the script on money talks, turning budget battles into bonding sessions. Plus, she’s got the lowdown on navigating those awkward “who pays?” moments in the dating game.

Bling or Bank: The Dating Dilemma (17:52)

Think your date’s designer watch spells ‘jackpot’? Not so fast! Erika reveals there’s more to wealth than meets the eye, and it’s not about flash and cash.

“Wealth is done in secret,” she shares. It’s the behind-the-scenes stuff – property, stocks, and personal growth. So, next time you swipe, ask yourself: Are you after arm candy or someone who’s rich in life’s real treasures?

Family Ties and Money Lies (21:20)

Your money habits didn’t appear out of thin air! Erika breaks down our financial DNA: background, religion, and experiences. It’s a wild mix that shapes our cash attitudes.

Picture this: sneaking shopping bags past Dad as a kid. Sound familiar? These money memories stick around, influencing our adult spending sprees and savings struggles.

But here’s the kicker – we’re often clueless about cash chat, leading to relationship drama. 

Playing Your Cards Right (34:48)

Who knew money talk could be a party game? 

Erika’s “Let’s Talk Finances” cards turn budget chats into a blast. Forget boring spreadsheets – we’re talking juicy questions like “Splurge on stuff or adventures?” and “What’s your guilty pleasure purchase?”

It’s not just fun and games, though. Erika calls it “financial intimacy” – fancy talk for getting cozy with your partner’s money mindset. 

She also has a Divorce Edition for those navigating the financial waters of divorce. As Erika quips, “If you don’t do the couples edition, you’re going to need the divorce edition.” 

 

Connect with Erika:

(42:00) Dear Damona: Help Me!!

Instagram voice memo from Hayden:

So, a question –  I’ve got really bad social anxiety. 

I’m way better than I used to be, but I still don’t have many friends, and I’m bad with relationships just in general. Plantonic or romantic. 

So should I work on friendships and whatnot first, or try something out with romantic relationships?

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 InstagramTikTok, 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: Light Bulb Moment

Are you ready to transform your love life? 

As we approach the end of the year, we naturally reflect on what we want for our future. For many of you, that’s a relationship. 

But you might be wondering: how does Damona get people like YOU from where you’re at into a committed partnership? How is coaching DIFFERENT from listening to this podcast or following her on social media?

Today’s episode is special because you get a front-row seat inside a real coaching session with Michelle, a prior client who was pregnant and becoming a solo mom by choice when she took Damona’s course two years ago. 

You’ll witness firsthand how we go from confusion to clarity, from frustration to dating success. Sit back and get ready for some real, raw, and actionable advice that could change your love life.

Single Mom to Dating Pro (05:13)

Talk about a plot twist! Michelle dove into dating coaching while navigating early pregnancy. Who knew impending motherhood could spark such a dating revolution?

There’s no “perfect” time to seek love – sometimes, the most unexpected moments lead to the greatest growth.

As she balances the excitement of a new chapter with the search for a partner, we see how self-discovery and dating can go hand in hand.

Navigating the Dating Pool (14:11)

“I’m getting more matches because I’m more curious about people, but I’d say the people who I’m swiping on, who I’m both curious and excited about, that number is much less,” Michelle reflects on her dating experiences.

It’s all about casting a wider net and trusting your instincts! Sometimes, the perfect match might come from an unexpected place. 

There is a delicate balance between quantity and quality in the digital dating world

The Unavailable vs. The Nice Guy (21:20)

In her coaching session, Michelle found herself caught between two types of men: those who weren’t fully available and those who were almost too available. Is there a happy medium?

Damona breaks it down: “You can’t judge yourself into attraction… The attraction should build. And if it’s not building or if it’s actually decreasing, then that is your answer.” This dilemma sheds light on a common dating struggle – the quest for that elusive spark. 

Michelle’s experience prompts us to question: Are we sometimes drawn to unavailability? Do we overlook potential partners who are ready and willing?

Trusting Your Instincts (37:46)

As the session wraps up, Michelle realizes she needs to trust herself more in the dating process. But how do you silence that inner critic that says you’re doing it all wrong?

Damona encourages a mindset shift: “You have all the answers already, trust in yourself that you do. You do know what you’re doing in dating.” 

We often know more than we give ourselves credit for. The challenge lies in quieting the doubts and tuning into our inner wisdom. 

Dear Damona: Help 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 InstagramTikTok, or Facebook, or leave us a voicemail or text to 424-246-6255, and hear Damona’s answers live in a future episode!

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.