The Nice Guy 9 & The Materialists Myth
Is Your Dating Checklist Secretly Sabotaging You?
This week’s Dates & Mates episode kicks off with a listener question that struck a chord and sparked a full-on love-life unpacking session.
After watching Materialists, a film about a matchmaker who builds relationships by check-box and statistics, one listener wrote in with a plea:
“How do we stop dating by checklist and start choosing real connection? We dive into the assumptions, patterns, and emotional blind spots that keep us stuck. I’m always the friend, never the boyfriend, just because I don’t hit the right numbers on their list.”
That question leads us into one of the realest conversations we’ve had about dating patterns, fantasy thinking, and what it really means to be “the nice one.”
(2:00) The Listener Question That Unlocked Everything
What happens when rom-com tropes meet real-life frustration?
Our listener reflected on the movie: Materialists, and suddenly, it’s not just a movie. It’s his dating life on screen. He’s the nice guy. The friend. The emotional crutch. And the reason? He doesn’t meet the “list.”
There is a deeper cultural script we’ve all been fed: that you’re either the fantasy or the fallback. And in this episode, we begin to ask a better question: what are these lists really protecting us from?
(10:40) Matchmakers, Fairytales & the Pay-to-Play Illusion
On the surface, matchmaking sounds dreamy: someone else does the heavy lifting and hands you your perfect match.
But beneath the fantasy is a truth most people don’t realize: matchmaking is expensive, exclusive, and not nearly as magical as it seems.
We talk about the real mechanics of modern matchmaking, the myths that drive people to outsource their love life, and why no one (not even a professional) can save you from the deeper emotional work.
Spoiler: even the best matchmakers can’t make your list love you back.
(15:50) What If the Friend Zone Isn’t About You Being “Too Nice”?
You’re emotionally available, you listen, you care—and yet, the people you date keep choosing the unpredictable, unavailable, emotionally erratic “bad boy” instead.
Sound familiar?
We explore the stories we tell ourselves when things don’t go our way in dating, and the mental leaps we make to protect our egos.
Because sometimes, it’s easier to believe “they always pick the jerk” than to face the possibility that something in your approach might need a shift. It’s not about blaming, it’s about reclaiming your narrative.
(25:25) The Nice Guy Nine: The Moves That Actually Make a Difference
This is your playbook reset.
Forget what you’ve been told about what “nice” means. We lay out the nine habits,what we call “The Nice Guy Nine”, that shift how others see you and how you show up.
These aren’t gimmicks or games. They’re connection skills rooted in presence, confidence, and emotional intelligence.
From giving deep compliments and creating safe physical contact, to the surprisingly powerful move of simply telling someone you like them, this list is a guide for anyone tired of being misunderstood or overlooked.
Bonus: you’ll hear how Damona’s own husband went from perpetual friend zone to forever love using these exact behaviors.
(42:00) When Dating Feels Hopeless, Try This One Reframe
Maybe you’ve been ghosted. Maybe you’re exhausted from trying. Maybe you’re telling yourself that it’s just not in the cards for you.
This closing segment is your emotional reset. It’s about challenging the narratives that leave you powerless—and discovering the small shifts that can lead to big changes.
Maybe it’s not about doing everything differently. Maybe it’s about doing one thing differently and letting the ripple effect unfold
💌Have a communication conundrum? Damona’s got you.
Whether it’s love, conflict, or just figuring out what to text back, no question is too big or too small. Submit your dating, relationship, or communication 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!
And don’t forget — Dates & Mates is now about all your significant relationships, not just romantic ones.