Dating after divorce and dating in your 40s can be a wild, emotional, and often hilarious ride—and that’s exactly what co-hosts Autumn Calabrese and Donald Stamper unpack in this laugh-out-loud, painfully relatable episode of Everything’s Perfect. Yes, we’re saying it twice for the ones in the back: dating after divorce and dating in your 40s is the main dish on today’s plate, and this is a feast you don’t want to miss.
From cringe-worthy first dates and uncomfortable dating app encounters to shocking “ick” moments and unexpected dealbreakers, this episode delivers an honest deep-dive into modern dating culture for grown-ups. Autumn opens up about what it's like navigating romantic relationships as a divorced mom raising a son, while Donald recounts colorful stories from gay dating apps and memorable LA date nights—including one particularly unforgettable encounter involving a “Christmas Room” in July and a surprise Lady Gaga ticket saga.
Listeners will laugh, gasp, and maybe even wince along with the hosts as they reflect on red flags like angry drunks and ghosters, and share their thoughts on toxic green flags (you know—the kinds that seem attractive but spell future trouble). They also explore what it means to date with intention, how to set boundaries, and why respecting your own happiness is key to any lasting relationship.
This episode doesn’t shy away from the messy parts—there’s poop talk (yes, that kind), stories of unfortunate wardrobe choices, and even a horrifying motel memory featuring a dead cat. But it’s all wrapped in humor and heart, with the hosts emphasizing the importance of loving yourself first before expecting someone else to love you well.
Autumn offers insight into what it's like dating with kids and managing expectations around family introductions, while Donald reveals how his own empathy sometimes leads to “savior dating”—the desire to fix or rescue a partner. The duo also delve into the psychological effects of dating apps, swiping culture, and the dopamine highs that can interfere with forming real connections.
Whether you're single and swiping, back on the scene after a breakup, or in a committed relationship trying to figure out what your past patterns meant, this conversation is loaded with laughs and wisdom. Autumn and Donald remind us that while everything might not be perfect, embracing your imperfections (and your ridiculous dating stories) makes the journey all the more worth it.
Plus, they want to hear from you! Got your own dating disaster or dilemma? Email the show at everythingsperfectpodcast@gmail.com or find them on social at @EverythingsPerfectOfficial.
If you’ve ever muttered, “What the hell am I doing on this date?”—this one’s for you.
0:37 - Podcast Kickoff + Listener Review
2:28 - Why Dating in Your 40s Is a Whole New Game
3:07 - Donald’s “Christmas Room” Date Story
9:22 - Autumn’s Disaster Date via Dating Agency
14:36 - Donald’s Dead Cat Motel Experience
20:01 - Dating With Kids & Family Dynamics
23:10 - Red Flags & Toxic Green Flags
32:41 - “The Ick” Moments
36:21 - Staying Too Long + “Mr. Surprise”
52:05 - Dating App Culture & Final Advice
Autumn and Donald recently announce a new three-month challenge centered around the 21 Day Fix program. With community workouts, playlists, live Zooms, and giveaways, this challenge is designed for those who want consistency and fun—not perfection—this summer. It will be $50/month and you can sign up here: https://everythings-perfect.mn.co/plans/1539731?bundle_token=e48e7dcc3758a4fd50f93372323b04de