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Apr 2025
First Date Red Flags with Jeremy Jacobowitz
We have our friend, content creator, and second GGE guest ever Jeremy Jacobowitz back on the show to talk about our favorite topics – food and dating. We kick this fun convo off talking about the most underrated food cities, traveling to Japan, LA vs. NYC food scenes, Jeremy’s be ... Show More
1h 41m
Aug 1
Dating after a Major Scandal (w/ Monica Lewinsky)
Before she was an activist, Monica Lewinsky was the most publicly shamed woman in America. Now, she's reclaiming her story, and her dating life.For the 400th episode of Why Won’t You Date Me?, Monica joins Nicole to talk about dating after a major scandal, being labeled “unmatcha ... Show More
55m 49s
Jun 13
Love Triangle Gone Wrong (w/ Michael Urie)
Actor Michael Urie (Shrinking, Ugly Betty) joins Nicole to discuss the wild hookup culture at Julliard, and the love triangle he had that went sour. Once he got fame from Ugly Betty, he starts going on dates with people who only seem interested in the version of him they saw on T ... Show More
58m 51s
Jul 2024
F*ck the Fairytale, Find What’s Real with Damona Hoffman
Are the stories you’re telling yourself hurting your love life? We are so excited to have dating coach and author Damona Hoffman tell us why we should say F*CK THE FAIRYTALE and find what’s real. We talk about why romanticizing pop culture fantasies, chemistry, and soulmates coul ... Show More
1h 38m
May 10
Confessions From The Dating Apocalypse
Modern dating… is it a total disaster or just a sexy little mess we secretly love to hate? 😏 This episode, I spill all the tea while reacting to a spicy convo from Diary of a CEO about the downfall of dating apps, “short king” struggles, and why everyone's ghosting. I get real a ... Show More
51m 52s
May 30
Secretly Dating your Improv Coach (w/ Edi Patterson)
Actress Edi Patterson (The Righteous Gemstones) joins Nicole to talk about falling in love with her improv teacher, hiding their relationship from the world, and mistaking his proposal for a joke. She opens up about being a late bloomer in dating, throwing house parties that felt ... Show More
50m 23s
Jun 25
Bryce & Crystal – Hot Sauce to the Eye and a Murdery Vibe?
Bryce thought his date with Crystal was going great—wings, darts, laughs, and even a kiss. But when he accidentally got hot sauce in her eye and followed it up with a dark joke, Crystal went ghost. Now she's back to explain why she got major true crime red flags. Was it just a sp ... Show More
11m 25s
Mar 2025
A Wild Journey Through Sex, Divorce, and Glowing Up with Comedian Jiaoying Summers
Strap in for an unfiltered (and inspirational) journey with the hilarious Jiaoying Summers. She takes us through growing up in China with an overprotective mother, to then coming to the US and finding love with someone whose family didn’t approve of her, breaking up, and then mar ... Show More
1h 34m
Nov 2024
Are You the Crazy Ex? with Nick Viall
We’ve all done some crazy ex things, or at least thought about it, but does that make it ok? We’re joined by our friend, fellow podcaster, and new dad Nick Viall to discuss crazy ex behavior, the things we do (from the minor to the major leagues), and how to hold back from those ... Show More
1h 30m