A short man who is newly returned to the dating world finds his height is disqualifying him from a lot of women. Does this happen in gayland?
A 39 year-old straight man just can't keep an erection when he's wearing a condom? How common is this condom conundrum?
On the Magnum, comedian Matteo Lane DARED to start an advice segment in his comedy routine. Dan d ... Show More
Jun 12
After Action Report #33
Somewhere in Peru, 1,100 feet above the sea, a handsome masseuse in Peru offered our brave, queer woman weed, sensual massage and “yoni massage.” Seems sketchy, but he got lots of good reviews on Google. After this show comes out we expect an uptick of tourism to Peru… Have you t ... Show More
16m 39s
Sep 2025
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 feeling “more queer” than ever. He talks about the challenges of having a "Very G ... Show More
49m 13s
Aug 2025
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 future husband, using Grindr to find dates willing to explore haunted places, and th ... Show More
1h 8m
Jan 2025
Mental Health, Stalkers, and Pussy Popping with Da’Vinchi
It’s estimated that one in five Americans suffer from mental illness—but where does it come from and what can we do about it? Well, today we’ve got our man Da'Vinchi in the building, and he’s dropping some major gems on mental health. From his experience growing up with what he c ... Show More
1h 4m
Aug 2025
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
