Conan O'Brien is here to help solve the root problems behind Nicole's singledom. They also discuss his sexually repressed Catholic upbringing, what it's like to have Big Dick Energy, and his plans for his 20th wedding anniversary.  Nicole demands to marry into the O'Brien family, explains to Conan how some of her vibrators work, and describes how she's now using a Theragun to masturbate.

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Big Dick Energy (w/ Conan O'Brien)

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

Actor Jesse Tyler Ferguson (Modern Family) joins Nicole to share his proposal story and how it was hilariously overshadowed by Sofía Vergara. They chat about food as a love language, their shared love for musical theatre, and the aftermath of the "Take Me Out" Broadway show nude leak. Jesse reflects on the challenges of working on Modern Family during a time when there were no gay writers. Plus, the wild story of getting hit by an accidental squirting.

Love in Theater (w/ Jesse Tyler Ferguson)

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.

Big Dick Energy (w/ Conan O'Brien)

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