Hosting a Sex Party (w/ Big Dipper)
Rapper and friend Big Dipper (host of Sloppy Seconds) returns to the pod! He and Nicole dive into how he became a bear, the many “gaybels” that shape queer dating culture, and the highs and lows of Be...
12 Sep 20251h 11min
I'm Bi Now (w/ Jenson Titus)
Comedian, clown, and artist Jenson Titus (of @VeryGayPaint) tells Nicole what it was like to date someone who's in the process of transitioning. The experience made him realize he’s bi, and left him f...
5 Sep 202549min
Stealing Condoms at the Olympics (w/ Adam Rippon)
Olympic figure skater Adam Rippon (Winner of Dancing with the Stars) joins Nicole to share the dating life of a Olympian. He shares what it was like being one of the first openly gay U.S. Olympians, w...
29 Aug 202556min
Slipping a Note to the Couple Fighting in the Next Room (w/ Dan Gregor & Doug Mand)
Co-writers Dan Gregor and Doug Mand (The Naked Gun) have been writing partners for twenty years - which is basically a marriage at this point. They tell Nicole about the time they were "dumped" by Ada...
22 Aug 20251h 4min
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
