“Is finding love different at every age?” With shows like The Golden Bachelor and Later Daters dominating our screens, there’s a new interest in seeing the dating lives of older daters explored on TV. 

But as Laura Stassi, host of Dating While Gray, reveals in this week’s episode, many of our dating challenges and solutions remain the same, regardless of age, gender, or sexuality. 

Get ready for an insightful discussion about modern dating that challenges conventional wisdom, plus stay tuned for a special Dear Damona segment where Laura joins Damona to answer listener questions about long-distance dating possibilities and navigating intimacy challenges.

(2:19) From Heartbreak to Dating Superstar: Meet Laura Stassi

You won’t believe how Laura turned her own “gray divorce” into a mission to help thousands find love again. 

After a 30-year marriage ended, she didn’t just bounce back – she revolutionized the conversation about dating after 50. 

Now her podcast Dating While Gray connects with thousands of listeners worldwide, proving it’s never too late for a fresh start in love.

Love Has No Age Limit (6:21) 

Think dating at 25 is totally different from dating at 65? 

Laura and Damona bust this myth wide open, revealing how our core desires for connection stay remarkably constant throughout our lives. 

They explore why being older actually gives you some serious advantages in the dating game and how life experience can make you a better partner than ever before.

The Secret Spots Where Love is Hiding (14:04) 

Forget swiping right – Laura shares her genius strategies for meeting potential partners in places you’d never expect. 

From high school reunions to neighborhood barbecues, she’s got the scoop on where real connections happen naturally. 

You’ll be shocked by her stories of couples who found love in the most surprising places and get actionable tips for expanding your own dating pool beyond the apps.

Dating Rules: Keep ‘Em or Trash ‘Em? (21:53) 

Should men still pay on the first date? Is it okay to text first?

What about waiting three days to call? Laura and Damona dive deep into which dating rules are ready for retirement and which timeless traditions actually help build stronger connections. (Their answers may surprise you!)

Get ready for a fresh take on modern dating etiquette that works for any age.

Connect with Laura:

Podcast: Dating While Gray

Instagram: @datingwhilegray

(30:57) Dear Damona & Laura

Ever wondered about starting a long-distance relationship before moving to a new city? Or how to date confidently when dealing with health issues? 

Question from an Anonymous Listener:

Dear Damona, I just turned 70 years old, and I’m in good health. Still working full-time. 24 years ago, the man I was married to at the time transferred us to California. 

I was originally born and raised in Louisiana, and I’m a Southern girl through and through. 12 years ago, I divorced my husband, and I long to go back to the South. I have a daughter who lives in Tennessee, and my desire is to move there and find a lovely southern gentleman and settle down. 

I did try dating sites for a while here in California, but I would prefer to be in the South. I want to go on a dating site in Tennessee, but I’m not sure how that would work. Long distance or even how to go about that? Frequent commuting, of course, is out of the question, and I’m wondering if you think it’s even a good idea to try to look into relationships long distance until the time that I can move there, perhaps in about a year.

Question from a listener named Jenny: 

I am having an awful dating self-esteem issue, and I know that this particular problem is highly common among women. 

You see, after having three kids who are now 27, 25, and 22, and after being a teacher for 30 years, my bladder has taken a huge turn for the worse. Here I sit at 55 years old, feeling like an elderly person in poise pads. The incontinence has gotten out of hand. I’ve had surgery and physical therapy to fix the problem with no luck. 

I am so sick and tired of people making jokes about others needing adult diapers because it is a real problem that keeps me from doing anything that will prevent me from being near a bathroom, as I have to go every hour. And all of these jokes make me feel like I am unsexy and that no man would ever want me. What am I supposed to do with this problem?

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!

The holidays are arriving, bringing cozy vibes, family gatherings, and those inevitable dating questions. 

Whether you’re bracing for Aunty Sally’s “Why are you still single?” or wondering if you should bring your new fling to the holiday party, this week’s Dear Damona episode is here to help make your season merry, bright, and drama-free.

(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!

When Chemistry Goes Cold (02:01)

After reading “F the Fairy Tale,” Annie challenged her usual dating patterns and found herself in an emotionally fulfilling relationship. But despite having what she calls “the best boyfriend she’s ever had,” something crucial is missing. 

“He is a very good man and probably the best boyfriend I’ve ever had…but after seven months, I should really be feeling something physical, and there is not. We barely ever even kiss.”

The Silent Treatment Strikes at Four Months (07:58) 

When carefully planned Monday meetups suddenly turn into radio silence, one NYC dater finds himself ghosted after building what seemed like a solid connection. 

“We’ve gotten close and we’ve taken a vacation together, spent multiple nights together…I’ve texted and called twice. No response. Clearly, there’s wrongdoing on both sides, but I can’t be wrong in thinking – Ghosting? You ghosted me after four months?”

Taking the Plunge in the Triathlon Club (16:24)

The endorphins are flowing, and the singles are plentiful, but one athlete wonders if mixing romance with her training group could lead to a winning combination or a workout gone wrong. 

“There are a lot of singles in this club, but no one seems to be asking people out…If there are guys in the group I’m interested in, how can I go about breaking the ice?”

When Gender Roles Crash the Perfect Date (23:55) 

Instant connection…flowing conversation…everything seemed perfect – until a dinner reservation revealed a clash of values that had one dater questioning the whole relationship.

 “She clarified that a man should pay for the dates in the early stages of dating because that’s a man’s job. This bugged me. I like balance in any relationship…That fundamental value difference never left my head.”

Feeling like your emotional baggage is weighing down your love life? 

We’ve all got some baggage weighing us down when it comes to dating – from stylish little clutches to oversized trunks stuffed with past experiences. While some of us try to sneak our baggage through security unnoticed, the truth is: at some point in every relationship, we’ll need to open those bags and sort through what’s inside.

Join us for an eye-opening conversation with renowned psychologist Dr. Alfiee as we unpack the complexities of modern dating and mental health. Dr. Alfiee shares game-changing perspectives that will transform how you think about emotional wellness in dating. (She even had Damona tearing up – but don’t worry, the mascara stayed intact!)

Then, stay tuned for this week’s Dear Damona, where we help a listener navigate the dating scene after a marriage that started too young and lasted too long. Is it ever too late for a fresh start? (Spoiler alert: absolutely not!)

(2:10) Meet Dr. Alfiee

Meet this week’s guest: Dr. Alfiee Breland-Noble, a brilliant psychologist and scientist whose work is transforming mental health care through her nonprofit, the AAKOMA Project.

You might know her voice from The Washington Post, CNN, The New York Times, or her insightful podcast “Couched in Color.”

But what makes her perfect for our conversation? She brings a genuine, clear-eyed perspective to mental health, culture, and relationships that will change how you think about your own emotional wellness journey.

Stop Looking for Your Other Half (5:13)

Dr. Alfiee challenges a common misconception in dating: the idea that two halves make a whole. 

“You don’t want half a partner,” she explains. “You want two whole partners coming together to make a whole relationship.” 

This means showing up as your complete self rather than expecting someone else to complete you.

Are You Really “Avoidant” – or Just Adapting? (17:52)

While attachment styles are trending in dating advice, Dr. Alfiee offers a fresh perspective: our patterns aren’t just shaped by our parents but by our entire community – including extended family, cultural background, and early experiences.

What might look like “avoidant” behavior could actually be a healthy adaptation to specific cultural or family dynamics.

The Mental Health Conversation: When and How? (21:20)

When it comes to dating someone managing their mental health, Dr. Alfiee emphasizes looking at the whole picture.

If someone trusts you enough to share their mental health journey, that’s often a sign of a strong foundation. 

The key isn’t the diagnosis – it’s how they manage it.

Moving Your Trauma to the Top Shelf (34:48)

Dr. Alfiee shares a powerful metaphor for healing: imagine your trauma as a book on a shelf. 

At first, it’s on the bottom shelf, easily within reach. As you heal, that book moves higher and higher. 

While the book never disappears, it becomes less accessible – you’re in control of when you take it down.

Dr. Alfiee’s Real Talk

• Dating isn’t easy, no matter what social media tells you.
• You can’t skip the self-work and expect relationship success.
• Trust your gut – but make sure you’ve done the work to understand what your gut is really telling you.

Connect with Dr. Alfiee:

• Website:DrAlfiee.com, AakomaProject.com
• IG: @dralfiee
• Podcast “Couched In Color”

(41:04) Dear Damona, Help Me!

 An email from a listener named Rebecca:

Dear Damona, 2024 has been the year of me. I want to make a purposeful decision about finding a relationship. I’m about to finish your newest book, so I’m off to a great start.

I want to include dating apps and organic meetings in my plan. However, I really have no idea where a 60-ish guy hangs out. Suggestions? I married too young and stayed too long, so I’m really out of the loop. Bars, cooking classes, the local YMCA? Thanks. Can’t wait to hear back from you.

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!

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 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:

• Website:TheKnot.com
• Report:https://www.theknot.com/content/relationship-and-intimacy-study
• elee@theknotww.com

(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 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!

 

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:

• Let’s Talk Finances Conversation Cards on Amazon: https://tinyurl.com/FBLTF
• Personalized Sessions: https://yourfinancialtherapist.com/contact/
• Website:https://yourfinancialtherapist.com
• Instagram: @YourFinancialTherapist

(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 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!

 

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!