Dear Damona: Dating Groove & Twin Flame’s Twin

It’s February, and love is in the air! But before you start stress-scrolling past all those heart-shaped decorations and candy displays, take a deep breath. Around here, we celebrate love in all its beautiful forms, whether that’s self-love, family bonds, friendship, or yes, even romance.

This week’s Dear Damona episode covers everything from finding love after a 30-year marriage (hello, hot Tinder date in Vienna!) to navigating workplace crushes when there are two potential connections. 

We’re tackling real questions about handling singles mixer dynamics, balancing dating with single parenthood, and even exploring what happens when twin bonds impact romantic relationships. 

So grab your favorite chocolate (because let’s face it, it’s way better than those chalky candy hearts), and settle in for some authentic conversation about finding connection in today’s dating landscape.

(00:25) Dear Damona

Got dating dilemmas? Relationship riddles? 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!

Finding Your Groove After Thirty Years of “I Do” (02:18) 

After three decades of marriage, one listener is rediscovering herself through dating apps – and finding unexpected joy in a Viennese romance. 

As she puts it, “I’m not sure who or what was on my side, but I met a smoking hot 40-year-old guy on Tinder and two days with him made up for everything.” But now she’s wondering: how can she date authentically when she’s not even sure what she’s looking for?

When Two Workplace Connections Make Your Heart Race (09:40)

One listener’s dating groove hit an unexpected twist with two potential connections at work: one her age, one ten years younger.

After a playful arcade date with the younger colleague, she’s questioning if she should explore either connection. As Damona notes, “Dating people at work can be messy. If this is not a career job for you, I say go for it.”

When “Hi” Gets You Goodbye (16:28)

After relocating to a new city, one singles mixer attendee discovers that real-life dating might be taking cues from dating apps – and not in a good way. 

“It’s like people are swiping in real life now,” he shares. “No one takes the time to get to know me before judging what they see.” Is there still hope for those seeking deeper connections in our snap-judgment world?

Making Space for Love While Juggling Life (23:55)

When well-meaning friends suggest putting dating on hold during a busy season of life, one listener pushes back: “That advice makes me cry. I don’t want to stop trying. I’m ready to not be alone.” 

Can you pursue partnership while balancing the demands of single parenthood and family caregiving?

When Twin Bonds Test Relationship Boundaries (34:08)

After investing four years in her relationship, one woman faces a difficult reality about her twin partner. 

Despite owning a house with his brother and living together for decades, he kept promising “if it was the right woman” things would change. “It was one of the most heartbreaking situations I’ve been in,” she shares, discovering that some bonds – especially between twins – might be unbreakable.

How To Be Dateable & Rarely Into Anyone

Dating can be tough these days, even for our regular Dates & Mates listeners who are putting in the work to date with intention. 

Many of us grew up in the Disney Prince and Princess era, absorbing these fairy tales about love at first sight and happily ever after. But as adults, we have had to unlearn those stories and redefine what love looks like in the real world. 

The good news? Today’s singles are stepping onto a new path, one of authenticity and intentionality in dating.

This week, we’re talking with Julie Krafchick and Yue Xu about their brand new book “How to Be Dateable: The Essential Guide to Finding Your Person and Falling in Love.” They share practical strategies that help us date smarter and connect deeper.

(2:03) From First Date Horror Stories to Dating’s Dynamic Duo

When Julie Krafchick and Yue Xu met in San Francisco, neither had figured dating out. 

Together, Yue, a former dating coach who specialized in helping clients “trick” people into liking them, and Julie, with her background in human-centered design, realized none of the old rules worked anymore.

Now, after a decade of hosting the Dateable podcast and launching their dating experiment show Exit Interview, they’ve interviewed thousands of daters and uncovered the truth about modern love. 

In their new book “How to Be Dateable: The Essential Guide to Finding Your Person and Falling in Love,” they share what really works (and what definitely doesn’t) in today’s dating landscape.

The Hidden Reason Modern Dating Feels Impossible (4:05) 

“Back in the day, people dated within their network. They formed organic connections. 

They didn’t have to win people over because they saw these people over and over again,” Yue revealed, highlighting why today’s expanded dating pools create unique challenges.

The conversation explored how dating has evolved from organic community connections to convincing strangers of our worth. While dating apps have expanded our options, they’ve also created new hurdles in our search for authentic connection – and understanding these dynamics is the first step to mastering them.

The Dating Personality Test That Changes Everything (15:38) 

Julie opened up about her own dating patterns as a Dreamer-Achiever type, sharing how it kept her in a two-year situationship: “I would give people the sixth chance… I would think something was more than it was because I was in a fantasy of what I wanted from someone.”

Their five archetypes – the Achiever, Dreamer, Energizer, Maverick, and Thinker – reveal the hidden patterns in our dating lives. 

Through personal stories and real examples, Julie and Yue demonstrate how understanding your type helps you leverage your strengths while spotting potential pitfalls.

The Sunday Dating Rule That Will Save Your Sanity (30:36) 

Though she is partnered now, Julie’s dating app strategy sparked an “aha” moment in the studio – she only logged in on Sundays, the highest traffic day, with notifications turned off. This simple shift transformed her experience from exhausting to energizing.

The conversation dove into why treating dating apps like a full-time job backfires and how setting clear boundaries around your dating energy creates space for genuine connection. 

The Million Dollar Dating Question No One’s Asking (42:49) 

When Julie and Yue introduced their Dating North Star concept, it completely shifted how we think about dating goals. 

Instead of generic aims like “finding a relationship” or “not being lonely,” they dig deeper into what actually drives our desire for partnership.

Through fascinating examples from their research and podcast interviews, they reveal how getting crystal clear on your true dating motivation changes everything about how you approach finding love.

Connect with Julie & Yue:

(41:04) Dear Damona: When the Spark Feels Lost

A listener struggles to find attraction after breaking free from emotionally unavailable partners. Damona shares insights on rewiring attraction patterns and why taking it slow might be the key to finding lasting chemistry.

💌 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!

When You Get Dumped & Matches on Mute

January may be known as “divorce month,” but let’s be honest – no matter how common breakups are, they never feel common. They’re confusing, painful, and can feel downright debilitating. 

This week’s guests, mother-daughter duo, Suzy Hopkins and Hallie Bateman, take on heartbreak in a refreshing and real way, sharing the insights within their newly published graphic novel “What to Do When You Get Dumped”. Together they share their raw and relatable guide to navigating one of life’s toughest transitions.

Join us for their journey from heartbreak to healing, exploring everything from giving yourself permission to feel your feelings to finally letting go of what’s holding you back. If you’re navigating the end of a relationship (or know someone who is), this episode is your roadmap and reminder that healing is possible – and happiness is waiting on the other side.

Plus, stay tuned for this week’s Dear Damona, where we tackle a common dating app frustration: why do matches like your profile but never write?

(1:06) “My Husband Left Me During Our Book Tour” 

Suzy Hopkins is a former newspaper reporter and magazine publisher and co-author of “What to Do When I’m Gone.” Her daughter, Hallie Bateman, is a writer and illustrator whose work has appeared in The New Yorker, The New York Times Magazine, The Owl, and many others. 

Together, they’ve created “What to Do When You Get Dumped,” a graphic novel guide to navigating one of life’s toughest transitions. The inspiration? Suzy’s own experience of having her husband of 30 years leave her for an old flame just as Suzy and Hallie were about to begin a book tour for their previous work.

When Your Ex Becomes a Stranger (34:07) 

The moment everything changes isn’t just about losing a partner; it’s about losing a language. 

After 30 years of marriage, Suzy found herself unable to speak to her husband as the person she’d known for three decades. “The minute he told me…I could no longer talk to him as my husband. There was a third person in the room at all times, even though she wasn’t physically there.” 

She reveals how this presence transformed their relationship overnight, and shares her unexpected method for maintaining sanity.

Skip the Forgiveness, Find Your Peace (21:03) 

Think you need to forgive to move forward? Think again. 

While wrestling with the end of her marriage, Suzy discovered that the common advice about forgiveness wasn’t serving her healing. Through tears and rewrites, mother and daughter unpack why the pressure to forgive can sometimes do more harm than good. 

They offer a revolutionary perspective on moving forward that doesn’t require you to make peace with what happened – just peace with yourself.

That Restaurant Doesn’t Belong to Your Ex (28:14) 

Your favorite places don’t have to be casualties of your breakup. When Hallie spotted her mom staring up at a meaningful Berkeley hotel, she sparked a conversation about reclaiming spaces from painful memories.

 “That old memory becomes a lot smaller,” Hallie explains, “and I think the story of that place…hopefully becomes the memory that’s in the foreground.” 

Together, they explore why avoiding these places only gives more power to the past and share their creative strategy for transforming old haunts into new havens.

The Two-Hour Healing Plan (38:50) 

Forget about “getting back out there” – sometimes victory is just making it through the next 120 minutes. Through counseling and small acts of survival, Suzy discovered that healing doesn’t happen on Instagram’s timeline. 

She shares how accepting the glacial pace of recovery actually helped her heal faster and why counting the days (all 1,582 of them) became an unexpected source of strength. 

The mother-daughter duo offers a refreshing take on moving forward that doesn’t require you to have it all figured out – just the next tiny step.

Connect with Suzy & Hallie:

(41:04) Dear Damona

“Hi Damona, my question is – how come guys on Hinge like my profile but never send a message? It’s happening more than usual lately and feels like it’s becoming the new Bumble.”

💌 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!

Getting It Right This Time & Paying For Premium

We all want to believe in the magic of love. We’ve seen the romcoms and fairy tales, and we crave our own meet-cute. But beyond those fairytales and meet-cutes lies a deeper understanding of connection that could forever transform anyone’s love life.

Orna and Matthew Walters joined us this week to share the knowledge and insights from their new book “Getting it Right This Time: Break Free from Your Hidden Blocks to Find Lasting Love.”

You’ll learn about your love imprint, your pre-wired programming that might be standing in your way when it comes to love, and what you can do to gain back your power and get yourself back on track.

In our Dear Damona segment we tackle choosing the right dating app premium subscription – because let’s face it, dating apps are just tools, and you need to know how to use them effectively!

(3:13) From Dating Disasters to Love Experts: Meet Orna and Matthew Walters 

The founders of Creating Love on Purpose bring their transformative approach to dating to their new book “Getting It Right This Time.” 

Featured on Bravo’s The Millionaire Matchmaker and celebrating their fifth appearance on Dates & Mates, they’ve helped thousands worldwide break free from toxic patterns and find lasting love.

Why Your Brain Keeps Choosing the Wrong Partners (14:32) 

Get ready for a mind-blowing revelation about attraction that will transform how you date forever. 

Learn why that familiar “spark” might actually be your biggest red flag, and discover how to rewire your love GPS for healthier connections.

Stop Eating Raw Relationship Turkey (19:50) 

Why rushing into commitment before really knowing someone is like serving undercooked poultry – and how to know when a relationship is actually ready for the next level.

This fresh perspective will save you from another half-baked situationship.

Childhood Stories That Shape Your Love Life (31:04) 

Think your “perfect” upbringing means you’re immune to relationship struggles? 

Matthew’s surprising journey from avoidant dater to conscious partner will make you rethink everything you believe about relationship readiness.

The Three-Part Path to Love (45:40)

A revealing look at why rushing to manifest your perfect partner without doing the inner work first is a recipe for disappointment. 

The Walters break down their proven three-step approach: awareness, transformation, and, only then, manifestation. This groundbreaking framework explains why some people stay stuck while others find lasting love.

Connect with Orna and Matthew:

(51:31) Dear Damona: Finding Love in Smaller Cities

A listener from Bozeman, Montana, struggles with limited dating options in her area. 

Damona breaks down which dating apps work best for different locations and shares strategies for expanding your dating pool without compromising on distance preferences.

💌 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!

2025 Love Astrology & Lovebombing Bombshell

In this week’s episode, we’re gazing upward and inward as we explore how the stars and planets can guide your love life through the ancient wisdom of Vedic astrology.

Astrology isn’t just about your daily horoscope – it’s about uncovering patterns, timing, and compatibility that can help you make sense of your love life and plan for the future.

Lucky for us, this week’s episode brings back Vedic astrologer Carol Allen, who returns, as she does every January, to share how this sacred practice can illuminate your path to love. This week, she brings her profound insights on relationship timing, compatibility, and the cosmic forecast for 2025.

Plus, stick around for our Dear Damona segment, where we tackle love bombing on dating apps.

(3:13) The Stargazer Who’s Read Over 30,000 Love Charts

Since she started practicing Vedic astrology 34 years ago, Carol Allen has become the go-to love forecast expert for celebrities and everyday romantics alike. 

Featured everywhere from E! to Doctor Drew’s Life Changers, she’s helped thousands understand their cosmic love blueprint through her bestselling book “Love is in the Stars: The Wise Woman’s Astrological Guide to Men.” Now she’s back with an exclusive peek at what the stars have in store for your love life in 2025.

The Golden Windows for Love in 2025 (11:23) 

Circle these dates in your calendar immediately! 

Venus, the planet of love and romance, is serving up some seriously magical moments in 2025. “During these times, Venus is really beautiful and happy,” Carol reveals. “For all of us, we’re going to feel the good mojo in some way.” 

From February’s cosmic love fest to November’s partnership potential, these are the periods when the stars are practically pushing you toward romance.

Why Your Ex Might Come Knocking (And Why That Could Be a Good Thing)  (21:20) 

Remember that almost-relationship that fizzled out? There might be a cosmic reason to give it another shot.

“Venus retrograde is amazing for revisiting unfinished connections or people from the past,” Carol shares. This rare planetary dance from March 3rd to April 13th could reignite old flames or deepen current bonds in ways you never expected.

The Hidden Opportunities in Mercury Retrograde (28:40) 

Think Mercury retrograde is just about communication chaos? Think again. 

Carol reveals how to transform these typically turbulent times into opportunities for deeper connection. With three retrogrades in 2025, her practical wisdom will help you navigate the cosmic weather with confidence.

The Celebrity Love-Match Secret You Need to Know (35:07)

Ever wonder why Taylor Swift and Travis Kelce clicked so quickly? Or how is it that Beyoncé and Jay-Z’s power couple status seems to be written in the stars? 

Using her genius technique for reading cosmic compatibility,  Carol shows how understanding your own celestial blueprint could be the key to finding your perfect match.

Connect with Carol:

(00:47:59) Dear Damona: When Love Bombing Strikes

A listener asks about handling love bombing on dating apps – when someone showers you with attention and affection, only to suddenly disappear. 

Damona breaks down this modern dating phenomenon and shares strategies for protecting yourself while staying open to genuine connection.

💌 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!

New Year Love Meditation & Cultivate Grace

Ready for a different kind of dating reset? While most shows are taking a holiday break, we’re closing out 2024 with something special – a guided visualization journey designed to help you release this year’s dating baggage and open your heart to new possibilities in 2025.

Let’s be real – between the dating app fatigue, situationships that went nowhere, and those “what are we?” conversations that left you spinning, your heart could probably use a moment to just breathe. We explore Tinder’s Year in Swipe report together!

This week’s episode offers exactly that: a peaceful pause to reflect, reset, and reimagine what love could look like in the year ahead.

(2:17) A Fresh Take on Your Dating Reset

Instead of our usual dating strategy session, we’re introducing a meditation experience that feels less like a self-help exercise and more like giving your heart a cozy place to rest and dream. Think of it as a spa day for your dating mindset.

(4:09) Beyond the Vision Board

This isn’t just another “manifest your soulmate” exercise. 

We’re diving into a powerful visualization practice that helps you release those “almost relationships” and create space for real connection. Spoiler alert: it involves a magical forest (trust us on this one).

(9:11) The Game-Changing Dating Mindset Everyone’s Sleeping On

Meet your new dating superpower: GRACE. 

Not the “say your prayers before dinner” kind, but the type that lets you date authentically without the pressure to be perfect. It’s like having a best friend who both calls you out on your stuff and holds space for you to figure it out.

(11:53) Mapping Your 2025 Love Story

Forget generic New Year’s resolutions. We’re teaching you how to create a dating snapshot that actually works – because “find the one” is not the vibe we’re bringing into 2025. 

Learn how to set tangible love goals that align with who you really are.

Ready to transform your approach to love?

Our full Meditation Collection is waiting for you!  And don’t forget to follow us on Instagram @DamonaHoffman for daily doses of dating wisdom that keeps it real.

Because remember – you’re not just looking for love in 2025. You are love. Let’s make this your year to shine.

Dear Damona will be back in 2025!!

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!

2025 Love Predictions & Year in Swipe

Looking for a crystal ball to peek into the future of dating? 

As we wrap up another year of swipes, situationships, and searching for “the one,” this week’s episode offers something special – a deep dive into what actually happened in dating in 2024, plus some expert predictions that might just revolutionize your approach to love in 2025.

We’re breaking down the fascinating data from dating apps Tinder and Bumble, revealing how modern singles are completely shifting their approach to finding love. If you’ve been feeling the dating landscape changing beneath your feet, you’re not alone – and these trends explain exactly why.

(2:15) The Dating Revolution Hiding in Your Bio

Think your dating profile is just another face in the crowd? Think again. 

This year’s most-used profile phrase reveals a massive shift in how singles are approaching their search for love. 

We unpack why being upfront about what you want isn’t just trending – it’s transforming how we connect.

(4:44) Why Your Next Great Love Story Might Start at Pickleball

Forget endlessly scrolling through profiles. 

The latest data shows a surprising new way people are finding their perfect match. That new hobby you’ve been considering? It just might be your ticket to romance.

(13:20) The New Green Flag That’s Making Everyone Swipe Right

Move over, “good vibes only.” There’s a new quality topping everyone’s must-have list in 2024, and it’s changing the game when it comes to choosing potential partners. 

Learn why emotional stability is the new sexy and how it’s reshaping what we look for in relationships.

(20:57) The Return of Old-School Dating (With a Modern Twist)

Sometimes the best path forward means taking a step back. 

Your friends might be your secret weapon in finding love, and dating apps are finally catching up to this timeless truth. 

The surprising role male friends are playing in modern dating? It might make you rethink your approach to finding “the one.”

(22:20) Why 2025 Could Change Everything

Get ready for a major shift in the dating landscape. 

From the rise of micro-communities to a whole new approach to safety and authenticity, we share predictions for what’s coming next in the world of modern love. 

After 17 years of coaching singles, we’ve got a track record of being right – and these predictions might just change how you date in the year ahead.

Stay tuned for next week’s special New Year’s visualization and meditation episode, designed to help you align your heart and mind for love in 2025.

Read more of Tinder’s Year in Swipe: 2024 Tinder’s Dating Trends of 2024 and what’s ahead for 2025

Dear Damona will be back in 2025!!

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!

10 Ways to Ease the Pressure of “Finding Someone” Before the Holidays

The holidays can bring joy, family gatherings, and… pressure. 

Many of us feel the weight of expectations to show up with a partner during this festive season. But why do we feel this way, and how do we shift our perspective? 

Let’s break down some truths to help ease the pressure.

1. Holiday Expectations Aren’t the Rule

Society often paints the holidays as the ultimate “couple” season. Movies, ads, and even social media push this narrative. 

But relationships aren’t seasonal objectives. Let’s remind ourselves that these expectations are external and optional. We don’t need to meet someone else’s timeline.

2. Family Comments Are Not Personal

Aunt Susan asking about your love life at the dinner table isn’t unusual—but it’s not about you. 

Families tend to recycle the same questions, especially when they don’t know what else to say. Their comments don’t define your worth or timeline for finding a partner. 

Change the subject or laugh it off

3. Self-Worth Isn’t Tied to Relationship Status

The holidays can amplify feelings of loneliness, but being single doesn’t mean there’s something “missing.” 

Our value isn’t determined by whether we have a plus-one at the holiday party. It’s determined by how we care for and love ourselves—partner or not.

4. Rushing Into a Relationship Won’t Feel Genuine

Feeling pressured to find someone can lead to forcing connections that might not be right. A meaningful relationship takes time, care, and compatibility. 

Trying to meet artificial deadlines won’t create the foundation for something real. Let’s focus on quality over speed.

5. The Holidays Can Be Fun Without a Partner

The season offers so many opportunities to create joy and connection outside of romance. We can spend time with friends, travel, or start new traditions. 

Being single gives us the freedom to focus on our own needs and celebrate in ways that feel authentic to us.

6. Social Media Isn’t Real Life

Scrolling through perfect couple photos can add to the holiday pressure. But these curated moments don’t capture the full picture.

Everyone has their challenges, whether they’re single or partnered. Let’s avoid comparisons and focus on what truly makes us happy.

7. Setting Personal Goals Feels Empowering

Instead of focusing on relationship timelines, why not use this season to reflect on personal growth? 

From hobbies to career goals, there’s power in working toward our own aspirations. We can welcome the new year feeling accomplished and confident.

8. It’s Okay to Say No to Holiday Gatherings

If the pressure from family or social events feels overwhelming, it’s okay to skip them. We have the right to protect our mental health and create boundaries. 

Staying home with a holiday movie marathon can be just as fulfilling.

9. Relationships Don’t Have an Expiration Date

Let’s remember there’s no “too late” when it comes to love. Finding someone isn’t restricted to a season or age. 

The idea that we need to rush before the holidays—or any other time—is outdated. Love comes in its own season.

10. Kindness Toward Yourself Matters

We often focus on giving to others during the holidays but forget about ourselves.

 Let’s practice self-compassion. Taking time for rest, reflection, and self-care can shift our mindset, helping us feel grounded no matter our relationship status.

Remember This:

The holidays don’t have to be a deadline for finding a partner. Let’s focus on what truly matters—our own happiness and well-being. Whether single, dating or in a relationship, we deserve to enjoy this season on our terms. 

The only timeline that matters is the one we set for ourselves.

Dating While Gray & The Later Daters

“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.

Dating while gray host laura stassi joins damona hoffman on the Dates & Mates podcast to discuss love and dating at every age

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

12 Unique Holiday Date Ideas That’ll Spark Connection

The holidays are a magical time to connect, share laughs, and create memories. Whether it’s a first date or rekindling old flames, finding unique date ideas can make all the difference. We’ve put together creative, meaningful, and fun holiday experiences to impress and build a genuine bond.

1. Holiday Lights Walk

Bundle up, grab some hot cocoa, and take a stroll through a holiday lights display. Many neighborhoods or city parks transform into winter wonderlands this time of year. Walking side-by-side gives you time to talk, while the festive lights create the perfect atmosphere.

2. Gingerbread House Building

Get hands-on with a little friendly competition. Buy a gingerbread house kit or make your own components if you’re feeling ambitious. Decorating together sparks creativity and allows for plenty of laughs when things don’t go as planned. Bonus: you can enjoy some sweet treats along the way.

3. Holiday Market Stroll

Wander through a local holiday market or craft fair. The cozy booths, festive music, and hot drinks create a cheerful vibe. You can shop for small gifts or trinkets while sharing stories about favorite holiday traditions.

4. Ice Skating Adventure

Whether you’re a seasoned skater or a total beginner, an ice-skating outing is charming and fun. Holding hands while gliding—or wobbling—across the ice naturally builds a connection. Follow it up with warm drinks at a nearby café.

5. Home Movie Night with Holiday Classics

Transform your living room into a holiday theater. Pick classic holiday movies, gather soft blankets, and enjoy popcorn or seasonal snacks. This cozy option lets you relax without the distractions of a crowded theater.

6. Charity Volunteering Together

Spread holiday cheer by giving back. Sign up to serve meals at a shelter, host a toy drive, or pack care packages together. You’ll connect on a deeper level through shared purpose and compassion. Plus, it feels great to help others during the season.

7. Holiday-Themed Escape Room

If you both enjoy puzzles, this is a fun way to test your teamwork. Many escape rooms offer holiday-themed challenges this time of year. Working side-by-side to “escape” gives you insight into how the other person communicates and thinks.

8. Wine Tasting with Seasonal Pairings

Visit a local winery or wine bar offering seasonal tasting menus. Savoring wines paired with holiday snacks or desserts sets the mood. You can chat about your preferences and learn something new together in a relaxed, cozy setting.

9. Christmas Tree Farm Outing

Head to a local Christmas tree farm to pick out a tree (if they need one) or just enjoy the atmosphere. Roam under the evergreens together, sip apple cider, and maybe even snap a photo or two. It’s an easy way to enjoy classic holiday charm.

10. Cooking a Festive Meal Together

Skip the crowded restaurants and plan a holiday cooking night at home. Choose fun, festive recipes—like roasted veggies, spiced cookies, or mulled wine. Cooking together is an intimate way to bond, share laughs over mishaps, and enjoy a homemade meal.

11. Winter Hike with Scenic Views

Not all holiday dates need to be indoors. If you both enjoy nature, bundle up for a winter hike. Many trails are quieter this time of year, and snow-dusted landscapes can feel almost magical. Pack a thermos with warm drinks to share at the summit.

12. Festive DIY Ornament Crafting

Bring out your creative sides by making holiday ornaments together. Whether simple or elaborate, it’s an activity that encourages laughter and teamwork. You’ll leave with mementos you can both cherish, no matter where the relationship leads.

Conclusion

Holiday dates don’t need to be complicated or expensive to be special. By focusing on shared activities, creativity, and the season’s warmth, you’ll leave a lasting impression. Whether skating under twinkling lights or crafting ornaments, these unique holiday ideas go beyond the ordinary and help build genuine connections. Get out there, have fun, and let the holiday magic work its charm.

Matchmaker, Matchmaker & Signs of Interest

“When will I know they’re the one?” It’s the question that’s launched a thousand rom-coms and kept countless singles tossing and turning at night. Along with its equally anxiety-inducing cousins: “What if I’m missing the red flags?” and “Is it too soon to get physical?”

Lucky for us, this week’s episode brings back a true love expert who’s helped thousands find their perfect match. Celebrity matchmaker Aleeza Ben Shalom steps away from her starring role on Netflix’s Jewish Matchmaking to share some serious advice about modern dating – including some unconventional wisdom from her new book “Matchmaker, Matchmaker: Find Me a Love That Lasts.”

Ready to challenge everything you think you know about finding lasting love? Aleeza’s got some surprising insights that might just revolutionize your dating game. Plus, stick around for our Dear Damona segment where we decode the signs that someone’s truly interested in you and talk about dating a co-worker.

(2:14) Meet Aleeza Ben Shalom

Since her last appearance on Dates & Mates, Aleeza Ben Shalom has taken the matchmaking world by storm. 

As the star of Netflix’s Jewish Matchmaking and author of “Matchmaker, Matchmaker: Find Me a Love That Lasts,” she’s connected with over 20,000 people worldwide, from Australia to Argentina, sharing her unique approach to finding lasting love.

Why You Should Date Them Till You Hate Them  (4:02) 

Don’t let first impressions fool you! Aleeza’s famous dating philosophy challenges our quick-judgment culture. 

That little thing bothering you on date one might be meaningless compared to the amazing connection you could discover by date five. 

Aleeza explains when to keep going and when it’s truly time to say goodbye.

The Love-Building Power of Keeping Your Hands to Yourself  (14:42) 

Get ready for Aleeza’s most controversial rule: the “Five Date Challenge” of no physical contact. 

This isn’t just about restraint – it’s about building magnetic attraction and genuine connection. 

She reveals why breaking the touch barrier too soon might be sabotaging your chances at lasting love.

The Secret Mathematical Formula for Relationship Success (21:06) 

Love isn’t all mystery and magic – sometimes it’s about doing the math. 

Aleeza breaks down why shared Netflix preferences matter less than shared values, and explains her fascinating formula for calculating true compatibility. 

Spoiler alert: you need at least 70% alignment in the areas that really count.

 

Dating By Numbers: The 5-5-5 Rule That Changes Everything (31:04) 

Time to revolutionize your dating strategy with Aleeza’s game-changing framework: five dates, five hours max per date, and never more than five days between meetings. 

This isn’t about playing games – it’s about building unstoppable momentum toward real connection.

Connect with Aleeza:

(40:20)  Dear Damona: Dating at Work & Reading the Signs of True Interest

Instagram DM from Mor:

I work at a high tech company and there’s a colleague I’m interested in, but I’m not sure if he feels the same way. I’d like to explore how to approach this in a way that would help me understand if he’s interested, and possibly suggest meeting up if it feels right. 

Second, there’s a guy I see sometimes at the office gym. He seems much younger than me, around 27 or 28, and he used to glance my way quite often, but lately not as much. I’m wondering if I should do something to see if there’s potential there, or if I’m just imagining things. How could I better understand if someone is interested in me?

 I’d really appreciate your guidance on both situations.

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!

The Great Dating Power Shift: Who Really Makes the Rules Now?

Dating today looks different than it did just a few decades ago. Gender roles, once rigid and predictable, are now more fluid and open to interpretation. 

As traditional expectations shift, single women aged 20-45 are navigating these evolving dynamics in their search for love. 

Let’s look at how gender roles play out in modern dating and what it means for women stepping into the dating world in an era that values balance and equality.

Are Traditional Gender Roles Still Relevant?

Some of us wonder if traditional gender roles still hold sway in a world that champions individuality. In past decades, men were typically expected to make the first move, pay for dates, and take on the role of the protector. Meanwhile, women were often seen as the nurturers, the ones to be “wooed.”

Fast forward to today, and we’re seeing more of a mixed approach. Many Gen Z daters are grappling with questions like, “Who should pay on the first date?” While some believe men should always foot the bill, others argue for the importance of sharing financial responsibility.

But here’s the truth, as noted in “F the Fairy Tale”: there’s no one-size-fits-all answer, dating should feel like a dance, not a tug-of-war. Reevaluate outdated scripts and embrace authenticity in relationships.

The First Move: Who Makes It?

A growing number of women feel empowered to take the lead when it comes to asking someone out. For some, it’s a clear rejection of old-school norms. However, others still appreciate when men initiate—the key is understanding and respecting each person’s individual preferences.

We also see this reflected on dating apps. Bumble initially launched as the app where women make the first move and although they have recently rolled that back and allow anyone to initiate a chat after matching, it caused us to reevaluate antiquated rules about who makes the first move. 

In fact, OkCupid data revealed that conversations lasted twice as long when women messaged first so there are tangible benefits behind shaking up gender rules. Ultimately, what we’re striving for is balance—a dynamic where both partners feel equally valued and invested.

Sharing or Splitting Responsibilities?

The topic of finances in dating often sparks debate. Should men continue paying for most dates, or should we share the cost? Surveys suggest opinions are divided. Some women prefer traditional chivalry and view it as a sign of effort, while others see shared expenses as reflective of an egalitarian partnership.

Cultural expectations influence these choices, too. For example, studies highlight how some Australian women still lean toward traditional dating scripts. Their preference often aligns with broader societal values they grew up with.

In contrast, many women today are financially independent and don’t feel comfortable allowing someone else to always pay. Splitting helps them maintain autonomy and signals respect for mutual effort.

We also hear confusion from LGBTQ daters around bill-splitting. Overall, for daters of all genders, it seems that the fairest thing is for the person who asked to offer to pay or to “go dutch.”

Shifting Expectations Around Masculinity

One of the most intriguing currentdating trends focuses on reimagining masculinity. Articles discuss “open-hearted masculinity,” which redefines male roles in relationships. The focus shifts from dominance to emotional vulnerability, recognizing that closeness and trust build lasting connections.

Women are seeking men who listen, communicate openly, and show emotional awareness. These modern “masculine traits” challenge outdated gender stereotypes, helping couples create healthier dynamics.

Are We Doing Things “Right”?

It’s easy to feel unsure about where we stand when navigating updated relationship dynamics. One partner might prefer traditional gestures, while the other sees them as outdated. This clash of expectations can lead to misunderstandings.

So, how do we navigate these issues? Simple—communication. Talk openly about what makes each of you comfortable. Are thoughtful actions, like opening doors, appreciated or unnecessary? Is it important that one person leads, or does balance feel better? When both partners listen, they’re more likely to find common ground.

The Bottom Line on Gender Roles in Dating

The days of strict gender roles in dating are fading, but that doesn’t mean they’re gone entirely. Instead, modern dating sees a fusion of old and new. Some people still hold on to classic ideas, while others embrace flexibility.

Ultimately, finding love requires authenticity. Be upfront about what feels natural to you. Whether you enjoy chivalry or prefer splitting the check, there’s no wrong way—just what works best in your relationship.

Stop striving for what’s ‘normal.’ Start building the love story that works for you.

Dating is less about conforming to rules and more about creating mutual happiness. Instead of worrying whether you’re doing it “right,” focus on what feels genuine. With communication, respect, and balance, modern relationships can surpass outdated molds—and lead us to meaningful connections.