Drag king Tenderoni (Winner of The Drag Queen of the Year Pageant 2021) chats with Nicole about why they love older women, the challenges of performing as a drag king on your period, the scandalous story behind how they met their 12-year partner, and shares tips on how to be a flirt. Plus, Nicole reads some cringey dating app pick-up lines she's received.

Granny Chaser (w/ Tenderoni)

Dating can be a hot mess, from being ghosted by your crush to realizing that you've been catfished by a Tinder match. Why Won't You Date Me? is here to help.

Join Nicole Byer, the perpetual singleton, as she invites fellow comedians, friends, and ex-flings to talk romance and share their wildest dating tales, from cringeworthy first dates to jaw-dropping hookup stories. Nothing is off-limits.

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Comedy Interviews

Writer Jessica Gao (She Hulk: Attorney at Law, Rick & Morty) joins Nicole to discuss male friends who are "single for a reason", the pressures of dating in the Chinese culture, people sticking in bad relationships in order to avoid dating again, and how hormones from an IUD can significantly affect your attraction levels. Plus, she shares her experience writing Rick and Morty's iconic 'Pickle Rick' episode, and the targeted backlash she received from fans.

Forever Single Friends (w/ Jessica Gao)

Kamie Crawford (Host of Catfish: The TV Show)  joins Nicole to explore the most bizarre catfishing schemes she's witnessed, and reveals the tricks catfish use to deceive you. She shares how being crowned Miss Teen USA immediately affected her dating life in a creepy way, and discusses her frustrating experiences as a plus-size model.

Catfished! (w/ Kamie Crawford)

Comedian Craig Conant joins Nicole to discuss how sleeping with a chucklefucker led to him to become a baby daddy, his experience winning MTV's hit dating show "Next", and having sex at the movies on a first date. Plus, his many tales of farting on authority.

Winning a TV Dating Show (w/ Craig Conant)

WNBA superstar and Olympic gold medalist A'ja Wilson joins Nicole to discuss how her 6'4" height shapes her dating experiences, what it's like to be single and mingle amongst Olympians, and the special treatment of being a WNBA icon. Meanwhile, Nicole is enjoying her own singledom.

Dating as an Olympian (w/ A'ja Wilson)

Comedian William Stanford Davis (Abbott Elementary) joins Nicole to share how he met his wife in an improv class, the unique dynamic of her managing his career, and the importance of finding a partner who truly invests in you. William also offers a glimpse into his unconventional teenage years DJing in adult clubs and reflects on his experiences with segregation growing up.

Granny Chaser (w/ Tenderoni)

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