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?

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!

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

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:

• Book: Big Dating Energy by Jeff Guenther, LPC & Kate Happ
• Podcast: Big Dating Energy
• Instagram @TherapyJeff
• Website www.therapyjeff.com

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

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!

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? 

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?