Dates & Mates with Damona Hoffman

Latest Episodes:

The Best Friend Fantasy & Safest Situation Oct 07, 2025

Show notes

Help Dates & Mates win a Signal Award! Vote by October 9th at damonahoffman.com/award

Loving someone who can't love you back the same way is one of the most tender, complicated situations in relationships. Sometimes the safest relationship in your life becomes the hardest one to navigate, and the person who knows you best is also the one you want most.

This week, a listener shares:

"I'm in love with my best friend. I'm a queer woman in my thirties and she's straight in her mid to late twenties. We've gotten progressively closer to the point where people think we are dating. My therapist told me my friend is the safest relationship that I have in my life. So sometimes I do wonder if what I'm perceiving as romantic love is just a really healthy friendship. Do I tell my best friend I'm in love with her? If I don't, how do I protect my heart and continue to have this incredible friendship that I never want to give up?"

In this episode, Damona explores what happens when deep friendship intersects with romantic feelings. You'll hear about the difference between emotional safety and romantic compatibility, why fantasy relationships feel easier than real ones, and how to navigate truth-telling without causing collateral damage to the relationship that matters most.

What You'll Hear In This Episode:

Why feeling safe with someone doesn't automatically make them your romantic match
How staying in the fantasy can keep you emotionally unavailable to real possibilities
The critical questions to ask yourself before revealing feelings to a friend
What it costs you to stay silent when romantic feelings are involved
Why creating distance might be the most clarifying move you can make right now
How to baby step into gauging openness without risking everything at once
What it means to proceed with compassion for both yourself and your friend

Resources & Links:

Got a relationship question? DM @DamonaHoffman on Instagram, TikTok, or Facebook

Leave a voicemail or text: 424-246-6255

Dates & Mates is a finalist for a Signal Award! We need your support to ensure Love Wins! Vote for Dates & Mates at ⁠damonahoffman.com/award⁠

Learn more about your ad choices. Visit megaphone.fm/adchoices

The Efficiency Trap & The Loneliness Gap Sep 30, 2025

Show notes

Do you believe that Love Wins? Dates & Mates is a finalist for our first-ever Signal Award, and we need every single listener to make their voice heard. We are the ONLY relationship-focused and independently produced podcast nominated in the How To & Advice category.

If you have ever been helped, inspired, or changed by listening to this podcast, this is the moment to let me know.

It takes 30 seconds or less to VOTE at damonahoffman.com/award.

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You've mastered the logistics of life together, but somewhere along the way, you stopped actually living it together.

This week, a listener shares:

"I'm lonely in my own marriage. We've been together 12 years and we're like this well-oiled machine. Kids get to practice, bills are paid, house doesn't fall apart, but that's it. We don't actually talk anymore, just coordinate. Last week I realized we hadn't had a real conversation in probably two months. When I brought it up, he was like, 'what's wrong? We're good. We don't fight.' But I'm dying here. I miss my husband."

In this episode, Damona explores what happens when couples perfect the art of co-managing but lose the skills of co-connecting. You'll hear why functional doesn't have to mean emotionally empty, and how to bridge the gap when one person doesn't even see the problem.

What You'll Hear In This Episode:

Why becoming a "well-oiled machine" can actually work against your relationship
How to practice intimacy skills the same way you schedule soccer practice
The difference between absence of conflict and presence of connection
Why two months without real conversation signals an emotional drought
How to get from logistics to feelings without blindsiding your partner
What "relationship amnesia" looks like and how to recover those lost skills
Why missing someone who's sitting right next to you hits so differently

Resources & Links:

Got a relationship question? DM @DamonaHoffman on Instagram, TikTok, or Facebook

Leave a voicemail or text: 424-246-6255

Dates & Mates is a finalist for a Signal Award! We need your support to ensure Love Wins! Vote for Dates & Mates at damonahoffman.com/award

Learn more about your ad choices. Visit megaphone.fm/adchoices

Good on Paper & Sixth Sense of Humor Sep 23, 2025

Show notes

What happens if you get to the third date and it still feels awkward? Grin and bear it? Or keep waiting for chemistry? And how can you trust that your gut is telling you the right thing?

This week, a listener shares: "I met a man who checks every box on paper. He’s kind, reliable, matches my values… but I feel absolutely nothing. No spark. No butterflies. Is something wrong with me?"

In this episode, Damona shares the truth about emotional resonance, why the three-date rule isn’t a trap, and how to tell the difference between being too picky and being truly honest with yourself.

You’ll hear how to identify the signals your body sends you, why humor matters more than you think, and why being “decent” should never be the bar.

What You'll Hear In This Episode:

What the three-date rule really means (and what it doesn’t)
Why “good on paper” doesn’t always translate to connection
How to tell if you're genuinely curious or just people-pleasing
The surprising role of humor in long-term compatibility
How to do an energy check after every date
What your nervous system is trying to tell you
The difference between settling and staying open

Connect With Us:

Get your copy of "F the Fairy Tale: Rewrite the Dating Myths and Live Your Own Love Story"
Unlock the Secret to Successful Dating with our ⁠⁠Date Tracker⁠⁠
Call or text your question to: 424-246-6255
Follow @damonahoffman on ⁠⁠Instagram⁠⁠, ⁠⁠TikTok⁠⁠, and ⁠⁠Facebook⁠⁠, and submit questions via DM or voice memo anytime.

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The 12 Date Rule & Matchmaker Maria Sep 16, 2025

Show notes

This week, Damona is joined by her longtime friend, TV and TikTok superstarMatchmaker Maria, a fourth-generation matchmaker with no time for fairy tale fluff.

They get real about why dating feels so lonely now,, the truth about relationship timelines, and why your deep texting doesn’t count as actual connection.

Whether you're stuck on the apps or spiraling in dating burnout, Maria shares practical tools from her new book Ask a Matchmaker that will help you reset your mindset, clarify your compatibility, and finally stop waiting for someone to “just get it.”

What You’ll Hear In This Episode

Why dating has become a solo sport and what to do about it

The truth about the male loneliness epidemic and community loss
How siloization is killing our dating lives
Maria’s 5 pillars of compatibility and why they actually work
How the 12-Date Rule leads to real connection (and yes, sex can wait)
The sneaky trap of texting-as-dating
Why bangs and Alicia Keys might be holding you back

Resources and Links

Connect with Maria on Instagram. Facebook, and TikTok Get the book ⁠Ask a Matchmaker⁠

Unlock the Secret to Successful Dating with our ⁠Date Tracker⁠

Call or text your question to: 424-246-6255

Follow @damonahoffman on ⁠Instagram⁠, ⁠TikTok⁠, and ⁠Facebook⁠, and submit questions via DM or voice memo anytime.

Learn more about your ad choices. Visit megaphone.fm/adchoices

I Miss You Taboo & The Bro Barrier Sep 09, 2025

Show notes

We often talk about romance, but this week, we’re taking a closer look at the quiet epidemic affecting millions: the erosion of deep friendships and emotional openness, especially among men.

What happens when someone says “I miss you”... and it feels too risky to say it back? How do cultural norms shape our ability to express care, and how can we start to rebuild emotional intimacy, not just in partnerships, but in friendships too?

This week’s episode was inspired by a friend of the show, Douglas, whose candid moment with his wife sparked a much bigger conversation about vulnerability, gender norms, and the loneliness many are too afraid to name.

This week, a listener shares:

“Last night my wife told me she was getting lunch with a friend after getting a text that said ‘I miss you.’ I told her it’s nice women can say that — but guys can’t. She insisted we could. I’m not convinced. What do you think?”

What You’ll Hear In This Episode:

Why men’s close friendships have declined dramatically in the last 30 years
How emotional repression becomes loneliness, rage, and disconnection
Why “guys don’t say I miss you” is a cultural myth we need to break
The generational shift that teaches boys to shut down emotional expression
Three step-by-step scripts to help you reconnect or form new friendships
How to create low-pressure connection points that foster deeper bonds
Why you don’t need permission to reach out, just a little courage

Resources & Links: Unlock the Secret to Successful Dating with our Date Tracker

Call or text your question to: 424-246-6255

Follow @damonahoffman on Instagram, TikTok, and Facebook, and submit questions via DM or voice memo anytime.

Learn more about your ad choices. Visit megaphone.fm/adchoices

The Big Confession & Texting Gremlins Sep 02, 2025

Show notes

We’ve all had that one date…the one that felt like lightning. Everything clicks, and before you know it, you're imagining forever. But when you act on that high too quickly, reality can come crashing down hard.

This week, a listener shares: “Late at night, I had to get these thoughts off my mind. I told her I felt like I think I'd found my wife. She expressed that she was disappointed that I would say this after what she told me about moving too fast and that it was best we not see each other.”

In this episode, Damona breaks down what really happens when you come on too strong — and why even the most intense connection can’t be rushed. You’ll hear how fantasy thinking can override our better judgment, why texting late at night can sabotage a budding connection, and how to make amends when you've crossed a line. Most importantly, Damona offers real steps for recovery, both emotional and relational.

The neuroscience behind why we overshare when we feel a spark
How to tell if it’s a true connection or a fantasy projection
Why texting your feelings late at night is rarely a good move
What to say if you’ve overwhelmed someone with big emotions
How to show up as your full self without rushing the process
The one mistake people make after hearing someone’s boundary
A script for taking accountability while leaving the door open

Download the Frustration-Free Dating Guide: DamonaHoffman.com

Leave a voicemail or text your question: 424-246-6255

Follow @DamonaHoffman on Instagram, TikTok, and Facebook DM or voice memo your question to be featured in a future Dear Damona segment

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Love After Loss & The Vulnerability Gap Aug 26, 2025

Show notes

Grief changes us, and sometimes, it’s also what brings us together.

This week, a listener shares: “My partner and I both lost our spouses, and we bonded over that. Now, three months in, I’m the only one opening up and being vulnerable. Am I asking too much? Or moving too fast?”

In this episode, Damona explores what it really means to show up emotionally after loss, and why vulnerability often doesn’t look the same from both sides. You’ll hear how to honor your own emotional pace, set gentle boundaries, and recognize the difference between emotional availability and avoidance—even when love is in the room.

What You’ll Hear In This Episode:

Why shared grief doesn’t always mean shared emotional timing
How to spot different expressions of vulnerability (and not miss what’s there)
What to do when language that’s meant to be playful actually feels off
How to speak up about emotional needs without creating conflict
Why “moving in” can’t solve emotional distance

Resources & Links: Download Damona’s Frustration Free Dating Guide at DatesandMates.com

Got a question? Text or leave a voicemail for Damona at 424-246-6255

Follow @damonahoffman on Instagram, TikTok, and Facebook Submit your question via voice memo or DM to have it answered on a future episode.

Learn more about your ad choices. Visit megaphone.fm/adchoices

The Friendship Drift & Support Squads Aug 19, 2025

Show notes

Friendships can be some of our most important relationships, but they don’t always stay the same.

Careers, relationships, moves, and life stages can all shift the way we connect, sometimes leaving us wondering if the closeness we once had is gone for good.

This week, a listener shares:

“My best friend and I used to share everything. Lately, it’s just work updates and weekend plans. When I try to talk about deeper stuff, the subject changes. Are we growing apart, or is there a way back?”

In this episode Damona shares why even the strongest bonds can feel distant and offers practical, low-pressure ways to reignite connection.

You’ll learn how to adapt to friendship changes, bring back emotional depth, and keep your support network thriving without it feeling awkward or forced. Plus you’ll also get vital communication tips that you can apply to dating or to feel more connected to people in your world.

What You’ll Hear In This Episode:

The role of “resistance” in making things feel weird and how to lean into it
Why longevity doesn’t always equal depth in a friendship
Using shared memories and storytelling to re-open emotional doors
The power of intentional questions and the “pause” in deepening connection
Why diversifying your emotional support network is key to resilience
Low-stakes ways to invite deeper conversations without making it awkward
Resources & Links:

Download Damona’s Frustration Free Dating Guide at DatesandMates.com

Got a question? Text or leave a voicemail for Damona at 424-246-6255

Follow @damonahoffman on Instagram, TikTok, and Facebook and submit your question via voice memo or DM to have it answered on a future episode

Learn more about your ad choices. Visit megaphone.fm/adchoices

Boundaries, Moms, & The Post-Date Spiral Aug 12, 2025

Show notes

A long-time listener sent in a heartfelt question:

“My Mom constantly has opinions about who I should date, what kind of guy is right for me, even how I should look or act to attract the right person… one comment from her has me spiraling.”

In this episode, Damona explores how well-meaning love advice can actually sabotage your future relationships and offers step-by-step strategies for gently setting boundaries and building up your own self-confidence.

What You’ll Hear In This Episode:

Why outside opinions (especially from parents) can derail your dating momentum
How to shift from second-guessing to self-trust in your dating decisions
The invisible cost of oversharing—and how to protect your emotional energy
Pre-date and post-date rituals that build confidence and clarity
Damona’s personal rulebook for managing advice overload
When to share... and when to keep your dating life to yourself

Resources & Links:

Get clarity on your dating patterns with Damona’s FREE Date Tracker

Have a question about dating or any relationship that matters to you? Text or leave a voicemail for Damona at 424-246-6255

DM @damonahoffman on Instagram, TikTok, and Facebook

Learn more about your ad choices. Visit megaphone.fm/adchoices

Feminine Energy Fatigue & The Myth of Being Chosen Aug 05, 2025

Show notes

A longtime listener sent in a question that speaks to something many women have wondered:

“How does one become a woman who builds up a man and always makes them more confident and stronger? How do I get into my feminine state and energy around a guy on a date?”

In this episode, Damona shares what it really means to be “in your feminine,” explores the gender polarity debate, and offers a new way to think about strength, softness, and self-worth in modern relationships.

What You’ll Hear In This Episode: