Holidays can be heartwarming—gathered around the table, enjoying laughs, and sharing stories. But for singles, they can also bring relentless questioning.
“Why are you still single?” or “Are you dating anyone?” suddenly become the headliners of family conversations. If this sounds familiar, you’re not alone in dreading that annual pressure.
Let’s unpack how to navigate these moments with grace, humor, and confidence.
Understanding Family Dynamics
Whether it’s your chatty aunt or a curious cousin, families love updates. Often, this stems from a genuine concern or love for you.
However, the constant focus on your relationship status can feel isolating if you’re single. Families tend to project their views about milestones—relationships, marriage, kids—onto younger generations.
It’s less about personal attacks and more about their expectations of “what’s next” for you. But that doesn’t make it any easier to sit through.
Common Questions You Might Hear
Here’s a sneak peek at the greatest hits you might hear this holiday season:
- “Why are you still single?”: Often said as though your relationship status is a puzzle to solve.
- “Have you tried dating apps?”: As if they’ve cracked modern romance.
- “Don’t you want kids?”: A question that could not feel more personal.
- “I know someone perfect for you!”: Cue the awkward blind-date matchmaking.
No matter the intent, these phrases can feel invasive.
The Pressure of Expectations
Family dynamics create moments where expectations rise like an invisible fog.
For singles, there’s often the unspoken assumption that the ultimate life goal is finding a partner. If you’re content in your singlehood, it might feel invalidated by repeated questioning.
The result? Stress, self-doubt, or frustration by the time dessert is served. Understanding this dynamic can help you take a compassionate approach—even as you find strategies to manage the discomfort.
Coping Strategies for Singles
Here are ways to shield your peace when conversations about your singlehood arise.
Prepare Your Responses
Having a response ready makes unexpected questions much less awkward. Use humor, honesty, or even deflection, depending on the mood:
Humor: “I figured I’d save room at the table for extra pie instead of a partner.”
Honest but firm: “I’m happy where I am right now—thanks for asking.”
Playful: “Still single! Any takers here know Prince Harry’s backup cousin?”
Practice these responses ahead of time to deliver them calmly and with a smile.
Shift the Focus
When conversations veer into uncomfortable territory, subtly change the topic. Ask about their hobbies, interests, or holiday plans. It’s easier to dodge questions when you steer the conversation elsewhere. For example:
“Enough about me! How’s your new project going?”
“Speaking of relationships, how did you and Uncle Bob first meet?”
Redirecting the spotlight can take the pressure off you.
Practice Self-Care
Family gatherings can be draining, so prioritize checking in with yourself.
Whether it’s stepping outside for fresh air or finding a quiet corner for a moment to breathe, don’t underestimate the power of small breaks.
If staying overnight, bring comforting items like a book or playlist to unwind.
Self-care also means knowing when to say no—don’t overextend yourself for anyone’s expectations.
Finding Joy in Being Single
The holidays are an excellent time to celebrate where you are in life—single, dating, or otherwise.
Celebrating Independence
Being single means ultimate flexibility. You control your decisions, your time, and how you enjoy the season.
Want to binge a feel-good movie marathon? Go for it. Interested in splurging on a gift for yourself? You deserve it.
Embrace your freedom during the holidays rather than feeling pressured by societal norms.
Creating Your Own Traditions
Instead of focusing on what you don’t have, create traditions that celebrate you.
Cook your favorite festive meal, decorate your space exactly how you want, or host a “Friendsmas” with other singles.
These personalized traditions can make the holiday season feel refreshing and rewarding.
When to Seek Support
If holiday stress feels overwhelming, seeking support can help.
Building a Support Network
Friends and like-minded communities can offer a buffer. Some friends may also struggle with similar family conversations, so lean on each other.
Plan outings or virtual catch-ups between holiday gatherings to decompress and share laughs.
Professional Help
If the pressure and comments about your singlehood feel too heavy, consider speaking with a therapist. They can provide tools to manage stress, set boundaries, or respond to tough conversations.
Find Your Joy!
The holidays aren’t just about family traditions—they’re a reminder to find joy, regardless of your relationship status.
By preparing responses, shifting the focus, and embracing your independence, you can transform uncomfortable moments into opportunities for self-assurance.
Stay confident, surround yourself with supportive people, and enjoy the season exactly as you are: whole, complete, and thriving.
First Date Debate & Commitment Phobe
That pivotal first date – it’s so much more than just a casual hang or nice dinner (actually, skip the dinner date – we’ll tell you why).
This week, we explore those nerve-wracking moments that could be the portal to the next entire phase of your life. After all, you might be sitting across from someone who’ll one day share your future.
But even when first dates don’t end in sparks, they shape our dating journey and teach us about ourselves. And here’s the good news – with the right preparation, those first-date jitters can transform into pure magic.
Love and relationship expert Lauren Frances joins Damona to reveal when a first date really begins (hint: it’s not when you think) and how to gracefully wrap one up when it’s just not clicking.
Plus, in our Dear Damona segment, we tackle this week’s question: “Everything is going great with my match, but I am still struggling with the idea of commitment.”
(2:31) Meet Lauren Frances
Author of the internationally acclaimed bestseller “Dating, Mating and Manhandling: The Ornithological Guide to Men,” Lauren’s expert advice has graced the screens of Bravo, Extra, VH1, Oxygen, NBC, KTLA, and Fox.
Through her signature “Romance Camps” and Love Magnet Makeovers, she’s helped countless clients transform their dating lives.
Your First Date Starts Before You Meet (5:53)
Think your first date begins when you meet for drinks? Think again!
Lauren reveals why your initial text exchange might be more crucial than you realize, and the surprising reason she insists all her clients make one specific move before meeting in person.
The Enthusiasm Gap: Why You’re Not Getting Second Dates (20:37)
“A man that’s trying to impress you is impressed with you. A man that’s not trying to impress you is not very impressed with you.”
Lauren reveals why playing it too cool might be freezing your dating prospects.
Plus, learn the simple adjustment that helped one of her clients find her future husband on her very next date.
Hotel Lobbies vs. Starbucks: Location Matters (12:18)
Choosing the right venue could make or break your first impression on a date.
Lauren and Damona break down which date spots send the right signals and which ones might be sabotaging your romance before it begins
Ghost-Proofing Your Love Life (28:59)
“You are a romantic lifestyle brand, whether you know it or not.”
Lauren explains why modern dating is like going viral on TikTok – it’s all about creating that “stickiness” factor that makes people want to stay connected.
Her strategies for standing out in the endless options of today’s dating scene will change how you think about making meaningful connections.
Connect with Lauren:
(40:20) Dear Damona, Help Me!
Email from Anonymous:
Hi Damona, I love your podcast and your book. I’ve used your book, F the Fairy Tale, as a framework for my dating process. Thank you so much.
All right, so here’s a question. While the early stages of dating go really well for me when something starts to become a real potential relationship, it gets kind of scary, and I have a mini freak-out. I noticed a lot of the advice you provide centers around the early stages and first dates. Could you please offer some advice for those in the later stages of the process? What if someone meets all of our criteria and we get along well, but we’re feeling overwhelmed with fear and anxiety?
After applying Damona’s framework for a couple of months, I ended up with someone who fits all three of my criteria and does not have my one deal breaker. We get along great, and things are going well. We’ve been seeing each other about twice a week for a couple of months now, but I’m still having trouble with the idea of committing and entering a serious relationship, though that is what I want. Funnily enough, I now feel much more lost without a roadmap now that I’m getting the thing I wanted.
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!
Single for the Holidays? Here’s How to Handle Nosy Family Questions
Holidays can be heartwarming—gathered around the table, enjoying laughs, and sharing stories. But for singles, they can also bring relentless questioning.
“Why are you still single?” or “Are you dating anyone?” suddenly become the headliners of family conversations. If this sounds familiar, you’re not alone in dreading that annual pressure.
Let’s unpack how to navigate these moments with grace, humor, and confidence.
Understanding Family Dynamics
Whether it’s your chatty aunt or a curious cousin, families love updates. Often, this stems from a genuine concern or love for you.
However, the constant focus on your relationship status can feel isolating if you’re single. Families tend to project their views about milestones—relationships, marriage, kids—onto younger generations.
It’s less about personal attacks and more about their expectations of “what’s next” for you. But that doesn’t make it any easier to sit through.
Common Questions You Might Hear
Here’s a sneak peek at the greatest hits you might hear this holiday season:
No matter the intent, these phrases can feel invasive.
The Pressure of Expectations
Family dynamics create moments where expectations rise like an invisible fog.
For singles, there’s often the unspoken assumption that the ultimate life goal is finding a partner. If you’re content in your singlehood, it might feel invalidated by repeated questioning.
The result? Stress, self-doubt, or frustration by the time dessert is served. Understanding this dynamic can help you take a compassionate approach—even as you find strategies to manage the discomfort.
Coping Strategies for Singles
Here are ways to shield your peace when conversations about your singlehood arise.
Prepare Your Responses
Having a response ready makes unexpected questions much less awkward. Use humor, honesty, or even deflection, depending on the mood:
Humor: “I figured I’d save room at the table for extra pie instead of a partner.”
Honest but firm: “I’m happy where I am right now—thanks for asking.”
Playful: “Still single! Any takers here know Prince Harry’s backup cousin?”
Practice these responses ahead of time to deliver them calmly and with a smile.
Shift the Focus
When conversations veer into uncomfortable territory, subtly change the topic. Ask about their hobbies, interests, or holiday plans. It’s easier to dodge questions when you steer the conversation elsewhere. For example:
“Enough about me! How’s your new project going?”
“Speaking of relationships, how did you and Uncle Bob first meet?”
Redirecting the spotlight can take the pressure off you.
Practice Self-Care
Family gatherings can be draining, so prioritize checking in with yourself.
Whether it’s stepping outside for fresh air or finding a quiet corner for a moment to breathe, don’t underestimate the power of small breaks.
If staying overnight, bring comforting items like a book or playlist to unwind.
Self-care also means knowing when to say no—don’t overextend yourself for anyone’s expectations.
Finding Joy in Being Single
The holidays are an excellent time to celebrate where you are in life—single, dating, or otherwise.
Celebrating Independence
Being single means ultimate flexibility. You control your decisions, your time, and how you enjoy the season.
Want to binge a feel-good movie marathon? Go for it. Interested in splurging on a gift for yourself? You deserve it.
Embrace your freedom during the holidays rather than feeling pressured by societal norms.
Creating Your Own Traditions
Instead of focusing on what you don’t have, create traditions that celebrate you.
Cook your favorite festive meal, decorate your space exactly how you want, or host a “Friendsmas” with other singles.
These personalized traditions can make the holiday season feel refreshing and rewarding.
When to Seek Support
If holiday stress feels overwhelming, seeking support can help.
Building a Support Network
Friends and like-minded communities can offer a buffer. Some friends may also struggle with similar family conversations, so lean on each other.
Plan outings or virtual catch-ups between holiday gatherings to decompress and share laughs.
Professional Help
If the pressure and comments about your singlehood feel too heavy, consider speaking with a therapist. They can provide tools to manage stress, set boundaries, or respond to tough conversations.
Find Your Joy!
The holidays aren’t just about family traditions—they’re a reminder to find joy, regardless of your relationship status.
By preparing responses, shifting the focus, and embracing your independence, you can transform uncomfortable moments into opportunities for self-assurance.
Stay confident, surround yourself with supportive people, and enjoy the season exactly as you are: whole, complete, and thriving.
Attachment Styles Revisited & Married Too Young
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
Connect with Dr. Alfiee:
(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!
Dear Damona: Have Match, Won’t Travel & Disappearing Profiles
Fall is in full swing, cuffing season is here, and Thanksgiving is just around the corner. Whether you’re navigating long-distance connections, staying safe while online dating, or figuring out how to take your dating game to the next level, this week’s Dear Damona episode has you covered.
We’re dedicating the whole show to your most pressing dating dilemmas and relationship questions as we head into the holiday season. From timing intimacy to challenging gender roles, we’re diving deep into the questions that matter most to you.
(00:25) Dear Damona
Do you have questions? Damona has the answers! Submit your dating and relationship questions on Instagram, TikTok, or Facebook, or leave a voicemail or text to 424-246-6255, and hear Damona’s answers in a future episode!
Love Beyond Borders (1:43)
Adrian’s dating app experience has been surprisingly wonderful – except for one geographic challenge that keeps getting in the way.
“Dating sites in the last two years have been wonderful – I’ve made friends, had exciting dates, and even a relationship for a couple of years. The dilemma for me has been my location and the willingness of men to travel. I’m willing to travel to meet them, but of course, that can be tricky. Is there a specific dating site that I should use for this situation?”
When Digital Footprints Fade (10:55)
Sue’s dating detective work uncovered something fishy – between mysteriously disappearing profiles and stories that don’t quite add up, she’s stumbled into a digital dating mystery that’ll make you think twice about your next match.
She asks: “Dear Damona, recently it seems that a few of the men I’ve met online dating on Bumble have removed their online profiles as soon as we share phone numbers. Do you have any data or insights about this behavior?” Sue shares concerning details about mismatched accents and overlapping life stories between matches that raised red flags.
The Perfect Moment (18:47)
When it comes to intimacy, timing is everything. But who decides when the clock strikes “right”?
This listener’s bedroom boundaries bring up the age-old question of when to take things to the next level.
Our anonymous listener asked, “Do you have a recommendation for when two people who have started dating can sleep together? Or what to say if my date proposes we sleep together and I feel it’s too soon?”
Rewriting the Dating Rulebook (24:39)
Ladies first? More like ladies waiting!
Why are women still sitting around waiting for men to make the first move? Time to shake up those dusty dating rulebooks!
Erin writes: “Do you know of any couples or of any relationships in which the woman asked the man out, or the woman was the initiator? It’s a follow-up to the point where you have encouraged women to ask men out. Some people like to think that the world is slowly changing; however, at the same time, a part of me doubts it, as in I just see it as men always being stuck with that gender role.”
The Knot’s News & Gift Glitch
What Singles REALLY Want in 2024!
Ever wonder what your potential dates are really looking for? Or if your relationship expectations match up with everyone else’s?
The Knot just released their 2024 Relationship and Intimacy study, revealing fascinating insights about how singles find love, what they’re actually looking for, and those persistent deal breakers that shape our dating decisions.
Get ready to decode modern romance with Esther Lee, deputy editor of The Knot. She’s breaking down the numbers on everything from meet-cutes to marriage, and some of these findings might surprise you!
Plus, don’t miss our Dear Damona segment, where we tackle an awkward gift-giving situation. When is it too soon for intimate presents?
(1:34) Meet Esther Lee
Esther Lee is the deputy editor of The Knot, leading content on The Knot Wellness with a focus on financial, relationship, and mental well-being.
She oversees The Knot’s travel vertical, including honeymoons, destination weddings, and bachelorette parties, along with overarching features and trends.
The Comfort Connection (05:13)
The Knot’s 2024 study challenges everything you thought you knew about attraction and chemistry. What tops the list of desirable qualities might surprise you – and it’s not what most dating coaches are teaching!
As Esther notes, “There has to be this openness and this lightness, almost like you’re showing up as yourself and being comfortable with who you are.” Find out why authenticity might be your best dating strategy.
Love Offline (17:52)
Dating apps aren’t the only path to partnership.
The study reveals unexpected ways couples are meeting in 2024, including some surprising new trends in the gaming world.
Plus, discover why traditional meet-cutes might be making a comeback and how Gen Z is revolutionizing the dating scene.
Married Life Myths & Reality (21:20)
Think you know how marriage changes relationships? The study’s findings about intimacy patterns before and after marriage might change your mind.
Esther shares insights from a recently married team member who discovered unexpected shifts in their relationship dynamics post-wedding.
Learn why “putting a ring on it” might transform more than just your legal status.
The Distance Dance (34:48)
When it comes to deal breakers, distance tops many singles’ lists.
But what exactly counts as “long-distance”? For some New Yorkers, it’s crossing boroughs; for others, it’s crossing oceans.
Plus, discover the other relationship red flags that made the list and why they might matter more than you think.
Connect with Esther and The Knot:
(39:19) Dear Damona, Help Me!
Email from a listener named Cathy:
This is a little off the beaten path, but my 17-year-old grandson is dating a lovely young woman, and she recently had a birthday for a birthday gift.
He bought her a Victoria’s Secret bra. She interpreted this as him wanting much more out of the relationship, and she promptly slapped him in his face and stormed off.
I gotta say, I love the gal’s chutzpah since there was certainly no ambiguity in her reaction. Any ideas on how he might navigate this precarious situation?
Do you have questions? Damona has the answers! Don’t forget you can submit your dating and relationship questions for our Dear Damona segment on 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!
Dating Horror Stories & The Flirt Coach
This Halloween, we’re embracing the ghosting, the ghouls, and the downright ridiculous tales of love gone wrong.
On Dates & Mates this week, we’re diving into our annual Halloween tradition with a collection of dating horror stories that will make you laugh, gasp, and hopefully help you to avoid your own awkward dates.
We’ve got five cringy listener stories that prove sometimes the scariest part of dating isn’t the ghosting – it’s what happens when you actually meet! Plus, my guest and I share our expert tips on how to avoid becoming the star of your own dating horror story!
To help dissect these strange and unusual encounters and offer some love advice, we have Benjamin Camras, The Flirt Coach, joining us.
So dim the lights (but skip the candy corn – we’ll die on this hill), and get ready for some haunting tales of dating gone wrong.
(1:54) Benjamin Camras, The Flirt Coach
From self-described introvert to social media sensation, Benjamin Camras (who introduces himself proudly as “the gay Libra”) is spreading “BFE” (Big Flirt Energy) across the digital world.
He hosts the Flirtations Flirtcast podcast and specializes in helping fellow introverts and the socially anxious find their flirting groove with more confidence, clarity, and fun.
Your Dating Horror Stories (05:13)
Join Damona and Benjamin as they dissect these strange tales:
Blindsided by a Blind Date (7:08)
When Amanda finally decided to dive back into dating, she thought a simple movie date with Steve – an ex-military geek – would be a safe bet.
The Vegetarian Variation (15:28)
When a late-night Tim Hortons run in Canada revealed an unexpected plot twist about dietary preferences, our listener learned that sometimes what you see isn’t exactly what you get.
The Creepy Car Concert (19:48)
What happens when you take a chance on an older, handsome suitor? Our listener found out the hard way that age doesn’t always equal maturity.
The Deskside Date (30:10)
When Covid forced dating to go virtual, our listener dolled up with wine in hand for what she hoped would be a romantic Zoom connection. Instead, she found herself starring in an impromptu episode of “The Office.”
The Freudian Movie Man (40:07)
When a second date to see “Inside Out” turned inside-out, our listener found herself beside a man who came prepared with everything.
Connect with Benjamin:
Dear Damona, Help Me!
Do you have questions? Damona has the answers! Don’t forget you can submit your dating and relationship questions for our Dear Damona segment on 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 Perfect Pitch
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Dating Anxiety & Financial Therapy
Money matters can make or break relationships, but they don’t have to be a source of stress.
Financial issues often top the list of relationship stressors, creating tension and misunderstandings between couples. But what if money could actually strengthen your bond instead of straining it?
This week on Dates & Mates, we’re flipping the script on financial conversations and exploring how they can build trust and improve communication with your partner.
Joining us is Erika Wasserman, known as “Your Financial Therapist” and one of only 70 certified financial therapists in the US. She’s here to help destigmatize money talk in relationships and offer insights for both couples and singles navigating the financial aspects of dating.
Plus, don’t miss our Dear Damona segment, where we tackle this tricky question: “I have social anxiety. Do I need to focus on making more friends before pursuing a romantic relationship?” Stick around for some surprising advice on balancing social and romantic pursuits.
(1:54) Erika Wasserman
Erica Wasserman is the CEO of Your Financial Therapist. She’s the creator of the Let’s Talk Finances Financial Wellness Conversation Cards, which allows people to explore the topic of money with thought-provoking questions.
She earned a Bachelor of Business Administration degree from the University of Florida and a graduate certificate in financial therapy from Kansas State University, making her one of only 70 certified financial therapists here in the country.
Show Me the Money Talk (05:13)
Cha-ching! Is that the sound of love or your piggy bank breaking? Financial counselor Erika Wasserman says it could be both – in a good way!
She flips the script on money talks, turning budget battles into bonding sessions. Plus, she’s got the lowdown on navigating those awkward “who pays?” moments in the dating game.
Bling or Bank: The Dating Dilemma (17:52)
Think your date’s designer watch spells ‘jackpot’? Not so fast! Erika reveals there’s more to wealth than meets the eye, and it’s not about flash and cash.
“Wealth is done in secret,” she shares. It’s the behind-the-scenes stuff – property, stocks, and personal growth. So, next time you swipe, ask yourself: Are you after arm candy or someone who’s rich in life’s real treasures?
Family Ties and Money Lies (21:20)
Your money habits didn’t appear out of thin air! Erika breaks down our financial DNA: background, religion, and experiences. It’s a wild mix that shapes our cash attitudes.
Picture this: sneaking shopping bags past Dad as a kid. Sound familiar? These money memories stick around, influencing our adult spending sprees and savings struggles.
But here’s the kicker – we’re often clueless about cash chat, leading to relationship drama.
Playing Your Cards Right (34:48)
Who knew money talk could be a party game?
Erika’s “Let’s Talk Finances” cards turn budget chats into a blast. Forget boring spreadsheets – we’re talking juicy questions like “Splurge on stuff or adventures?” and “What’s your guilty pleasure purchase?”
It’s not just fun and games, though. Erika calls it “financial intimacy” – fancy talk for getting cozy with your partner’s money mindset.
She also has a Divorce Edition for those navigating the financial waters of divorce. As Erika quips, “If you don’t do the couples edition, you’re going to need the divorce edition.”
Connect with Erika:
(42:00) Dear Damona: Help Me!!
Instagram voice memo from Hayden:
So, a question – I’ve got really bad social anxiety.
I’m way better than I used to be, but I still don’t have many friends, and I’m bad with relationships just in general. Plantonic or romantic.
So should I work on friendships and whatnot first, or try something out with romantic relationships?
Do you have questions? Damona has the answers! Don’t forget you can submit your dating and relationship questions for our Dear Damona segment on 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!
Coaching Session: Light Bulb Moment
Are you ready to transform your love life?
As we approach the end of the year, we naturally reflect on what we want for our future. For many of you, that’s a relationship.
But you might be wondering: how does Damona get people like YOU from where you’re at into a committed partnership? How is coaching DIFFERENT from listening to this podcast or following her on social media?
Today’s episode is special because you get a front-row seat inside a real coaching session with Michelle, a prior client who was pregnant and becoming a solo mom by choice when she took Damona’s course two years ago.
You’ll witness firsthand how we go from confusion to clarity, from frustration to dating success. Sit back and get ready for some real, raw, and actionable advice that could change your love life.
Single Mom to Dating Pro (05:13)
Talk about a plot twist! Michelle dove into dating coaching while navigating early pregnancy. Who knew impending motherhood could spark such a dating revolution?
There’s no “perfect” time to seek love – sometimes, the most unexpected moments lead to the greatest growth.
As she balances the excitement of a new chapter with the search for a partner, we see how self-discovery and dating can go hand in hand.
Navigating the Dating Pool (14:11)
“I’m getting more matches because I’m more curious about people, but I’d say the people who I’m swiping on, who I’m both curious and excited about, that number is much less,” Michelle reflects on her dating experiences.
It’s all about casting a wider net and trusting your instincts! Sometimes, the perfect match might come from an unexpected place.
There is a delicate balance between quantity and quality in the digital dating world
The Unavailable vs. The Nice Guy (21:20)
In her coaching session, Michelle found herself caught between two types of men: those who weren’t fully available and those who were almost too available. Is there a happy medium?
Damona breaks it down: “You can’t judge yourself into attraction… The attraction should build. And if it’s not building or if it’s actually decreasing, then that is your answer.” This dilemma sheds light on a common dating struggle – the quest for that elusive spark.
Michelle’s experience prompts us to question: Are we sometimes drawn to unavailability? Do we overlook potential partners who are ready and willing?
Trusting Your Instincts (37:46)
As the session wraps up, Michelle realizes she needs to trust herself more in the dating process. But how do you silence that inner critic that says you’re doing it all wrong?
Damona encourages a mindset shift: “You have all the answers already, trust in yourself that you do. You do know what you’re doing in dating.”
We often know more than we give ourselves credit for. The challenge lies in quieting the doubts and tuning into our inner wisdom.
Dear Damona: Help Me!!
Do you have questions? Damona has the answers! Don’t forget you can submit your dating and relationship questions for our Dear Damona segment on 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!
Party Of One & Longtime Crush
Going it alone and noticing the world seems to expect a whole lot from you?
“When are you settling down?” “Have you tried online dating?” – these questions are everywhere, but are we putting too much pressure on ourselves to couple up?
We all know how important it is to find love, but maybe we’re too quick to see singlehood as a problem to be solved. Then again, with shows like Love Is Blind and the Golden Bachelorette constantly bombarding us, can we catch a break?
NPR’s Life Kit founder Meghan Keane to the rescue! Meghan joins Damona this week to unpack the layers of our complicated feelings about being single and to dissect the ways that singlism could be dealt with in your own life. Plus, she shares why embracing your single life is just as important as finding a partner.
And don’t forget to stay tuned for our Dear Damona question: “I recently reconnected with a casual long-term friend. How do I figure out if he likes me without making a fool of myself?”
(2:01) Meghan Keane
Meghan Keane is the mastermind behind NPR’s Life Kit, your go-to source for real-world wisdom on everything from budgeting to heartbreak. Fun fact: our very own Damona has appeared on several episodes of this fabulous NPR show as a host and guest. !
But wait, there’s more! Before she was dishing out life hacks, Meghan was busy making radio magic. She’s got producer cred on the mind-bending “Invisibilia” and was there from day one for the wildly popular “Ted Radio Hour.”
Now, Meghan’s taking on the ultimate solo adventure with her brand-new book, “Party of One: Be Your Own Best Partner.” It’s hot off the press and ready to revolutionize your single life!
Singlism Showdown (05:13)
“You’re too picky.” “Why aren’t you married yet?” Sound familiar? Suddenly, everyone’s an expert on your love life (or lack thereof).
Ready for a reality check? Meghan Keane drops this truth bomb: “Singlism is basically just that, having a view of singles as being less than, marginalizing them, discriminating against them.”
Time to rethink how we’re treating our single friends – and ourselves! Because newsflash: being single doesn’t mean you’re broken, it means you’re whole all on your own.
Friendship: The Secret Sauce of Single Life (25:40)
Think your social circle shrinks when you’re flying solo? Think again! Meghan talks about building a thriving community as a party of one.
Forget the TV drama – real-life connections are often built on the simplest of actions. Get ready for some surprising insights on how to expand your friendship circle and why it’s crucial for your happiness.
Trust that inner social butterfly! You might just discover a whole new world of connections waiting for you.
The ‘Party of One’ Revolution (29:39)
Rushing to find “the one”? Hit the brakes!
Meghan’s new book, “Party of One: Be Your Own Best Partner,” is here to shake up everything you thought you knew about being single. It’s not about waiting for your life to start – it’s about living it to the fullest right now!
Discover why treating your single life like its own fabulous party could be the key to happiness, whether Prince Charming shows up or not.
Mind Over Dating Matter (32:33)
Got a case of the “why am I still single” blues? You’re not alone!
Meghan shares a powerful perspective: “When you focus more on what values you’re trying to express in your life… it’s a lot kinder and healthier than being like, ‘Did I get this thing? Did I check this box?'”
Time to sort through those emotional souvenirs and decide what’s worth keeping. Meghan’s got the tools to help you rewrite your single story from tragedy to triumph.
Connect with Meghan:
Pick up “Party of One: Be Your Own Best Partner”
Website: https://meghanvkeane.com/
Instagram: @DameKeane
(44:88) Dear Damona
Email from Anonymous:
I’ve been casual friends with a guy for years, until the other day I hadn’t seen him in about five years, and we’ve exchanged texts maybe once every six months, briefly. I’ve always had a crush on him, but he was married.
He got divorced about two years ago, and I know he’s looking to be in a relationship again. My friend saw his profile on a dating app. I reached out to him and said it had been too long, we should get dinner at, etc. it took a while to set this up, but we finally had dinner two nights ago, and everything I felt about him was reinforced.
He’s kind, sweet, funny. We have so much in common, but I can’t tell if he’s more interested in me than usual or just being himself. He definitely wasn’t overtly flirting.
My feeling after leaving dinner was that he is not interested in me romantically, but I’m a terrible flirt and horrible at reading signals. As we were leaving, I tried to give him an opening by saying we had to do this again soon and not to let so much time pass. And he agreed. But that was it.
Under normal circumstances, I would just assume he wasn’t interested in me and let this go. But I so rarely meet guys I connect with and we’re both in our late 40s, so that makes it even more rare. I don’t want to just give up and walk away if there could be a chance. But I also don’t want to make a fool out of myself or embarrass this really sweet guy. Is there any advice you can give me?
Do you have questions? Damona has the answers!Don’t forget you can submit your dating and relationship questions for our Dear Damona segment on Instagram, X, TikTok, or Facebook, or leave us a voicemail or text to 424-246-6255, and hear Damona’s answers live in a future episode!
Access Daily: Date Night Fall Fashion
Spotlight on Fall Date Night Fashion with Damona on Access Daily
Damona joined Access Daily to talk about “Date Night Fall Fashion.” Collaborating with fashion guru Lauren Messiah they explored the essential trends for autumn. Damona highlighted how crucial style is for making a memorable first impression and discussed building a capsule wardrobe that allows for seamless transitions between various date scenarios.
Lauren presented stylish looks ideal for museum visits, romantic dinners, and weddings. Each was designed to showcase personal flair while ensuring comfort and confidence. Damona’s insights on blending fashion with dating strategy create a powerful fall date night message!
Access Daily: Dating with Damona
Dating with Damona Celebrates the Joys of Being Single!
In Damona Hoffman’s brand-new segment, Dating with Damona on Access Daily, she celebrates National Singles Day by discussing how to embrace singlehood. She highlights the freedom and personal growth that come with being single and encourages viewers to use this time to focus on themselves and their relationship goals without external pressure.
The segment also covers the hot topics of coffee dates and speed dating efficiency and introduces fun dating terms like “texting” and “dial toning.” Damona’s lively, down-to-earth advice helps singles navigate the modern dating scene with confidence and humor.