Comedian Nick Kroll (Big Mouth, Oh, Hello) joins Nicole for an episode of just... absolute chaos. They discuss how Nick asked his girlfriend to go steady, why playing a woman was his most challenging acting role, and using John Mulaney's hypnotist to quit smoking. Plus, Nicole shares the story of the time she hooked up with an audience member.

WATCH this episode on YouTube at youtu.be/PawfFj2-e7w.

See Red One, in theatres today!

Write to Nicole! Send your dirty messages to whywontyoudatemepodcast@gmail.com with the subject line "Dirty Message," and Nicole may read it in a future episode.

Sponsors:

Uncommon Goods: To get 15% off your next gift, go to uncommongoods.com/dateme.

Betterhelp: This episode is sponsored by BetterHelp. Give online therapy a try at betterhelp.com/DATEME and get on your way to being your best self.

Follow Nicole Byer:

Website: nicolebyerwastaken.com

Instagram: @nicolebyer

X: @nicolebyer

Nicole's book: indiebound.org/book/9781524850746

This is a Headgum podcast. Follow Headgum on Twitter, Instagram, and Tiktok. Advertise on Why Won't You Date Me? via Gumball.fm.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Comedian Sherry Cola (Joy Ride, Turning Red) shares her journey of coming out as bisexual, how she met her girlfriend, navigating dating in the queer community, and monetizing a breastmilk kink.

WATCH this episode on YouTube at: https://youtu.be/RH4fK4ksCNs

Write to Nicole! Send your dirty messages to whywontyoudatemepodcast@gmail.com with the subject line "Dirty Message," and Nicole may read it in a future episode.

Sponsors:

Uncommon Goods: To get 15% off your next gift, go to uncommongoods.com/dateme.

Betterhelp: This episode is sponsored by BetterHelp. Give online therapy a try at betterhelp.com/DATEME and get on your way to being your best self.

Follow Nicole Byer:

Website: nicolebyerwastaken.com

Instagram: @nicolebyer

X: @nicolebyer

Nicole's book: indiebound.org/book/9781524850746

This is a Headgum podcast. Follow Headgum on Twitter, Instagram, and Tiktok. Advertise on Why Won't You Date Me? via Gumball.fm.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Comedian Sarah Silverman sits down with Nicole to discuss meeting her boyfriend over Call of Duty, the challenges of dating as a female comic, and how many health studies are skewed against women. Plus, Nicole shares her experience getting hit on at Comic-Con.

See Sarah Silverman live on her POST MORTEM tour at sarahsilverman.com.

WATCH this episode on YouTube at: youtu.be/eOdSuFrUl4s

Write to Nicole! Send your dirty messages to whywontyoudatemepodcast@gmail.com with the subject line "Dirty Message," and Nicole may read it in a future episode.

Sponsors:

Betterhelp: This episode is sponsored by BetterHelp. Give online therapy a try at betterhelp.com/DATEME and get on your way to being your best self.

Follow Nicole Byer:

Website: nicolebyerwastaken.com

Instagram: @nicolebyer

X: @nicolebyer

Nicole's book: indiebound.org/book/9781524850746

This is a Headgum podcast. Follow Headgum on Twitter, Instagram, and Tiktok. Advertise on Why Won't You Date Me? via Gumball.fm.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.