Ghosting, Gaslighting, and Gay Bars (w/ Roz Hernandez)
For Roz Hernandez, dating as a sober, trans woman comedian is a trifecta of difficulty - and finding love hasn’t been easy. She tells Nicole about going to 4 different Etsy psychics to sketch her futu...
15 Aug 20251h 8min
Dating Life of a Burlesque Superstar (w/ Jessabelle Thunder)
International award-winning burlesque dancer Jessabelle Thunder joins Nicole to talk about why so many partners say they’re cool with burlesque - until they’re not. She shares how she transformed from...
8 Aug 20251h
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 ...
1 Aug 202555min
A lil update from Nicole: Best Friends is back!
Exciting news from Nicole: Best Friends is BACK and 1) now on Headgum, 2) with FULL VIDEO EPISODES! Enter the pantheon of best friendship and check out Nicole and Sasheer's first episode back, availab...
30 Juli 202533s
We Met on a Podcast (w/ Devon Walker)
Comedian Devon Walker (SNL) joins Nicole to tell the story of how he met his girlfriend on a live blind date podcast. He figured it was just a bit - until the audience voted for them to win an Applebe...
25 Juli 202558min
Flirting, Open Relationships, and Almost Dying (w/ Josh Sharp)
Comedian and friend Josh Sharp (Dicks: The Musical) returns to the podcast! Nicole and Josh kick things off by reminiscing about the chaotic live show where Nicole interviewed a man in the audience sh...
18 Juli 202556min
Nobody Wants to Date a Drag Queen (w/ Meatball)
Drag queen icon Meatball is back! She and Nicole get into it all - being in her top era, loving the single life, and having weekend boyfriends in different cities. But also... why dating is still so h...
11 Juli 20251h 3min
We Dated?! (w/ Lou Wilson)
Happy 4th of July!(?) Comedian Lou Wilson (Dimension 20, Jimmy Kimmel Live!) joins Nicole to reflect on the wild state of America. He shares his terrible time living in Boston, where white guys freque...
4 Juli 202551min
