Celibate for 18 Years (w/ Debra DiGiovanni)

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

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

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

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

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

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

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

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 Jul 202533s