Author and mental health advocate Allison Raskin joins Nicole to talk about being left by her fiancé, dating with OCD, and how it affects relationships and intimacy. They learn how to make a guy laugh (according to WikiHow), discuss the most heartbreaking celebrity breakups, and explore the collective trauma we’ve experienced post-pandemic. Plus, Nicole gets hit on at Comic-Con.

WATCH this episode on YouTube at https://youtu.be/Di9fzkjxMDc.

Check out Allison Raskin's books at allisonraskin.com/books.

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.

Follow:

YouTube: @WhyWontYouDateMePodcast

TikTok: @whywontyoudatemepod

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.

TV icon Jimmy Kimmel (Jimmy Kimmel Live!) joins Nicole to share the story of his naked proposal in Africa, the chaotic early days of his late-night show, and why he once prayed for it to be canceled. Kimmel talks about the best (and worst) New Year's resolutions, his tips for picking the perfect slot machines, and the surprising lessons he learned as a wedding DJ. Plus, he offers some unexpected advice on masturbation—and how taking a break might just change your life.

WATCH this episode on YouTube at https://youtu.be/c7gl649E2WQ

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.

Follow:

YouTube: @WhyWontYouDateMePodcast

TikTok: @whywontyoudatemepod

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 and friend Lennon Parham (Veep, Somebody Somewhere) joins Nicole to discuss teaching and flirting between teachers, how she knew she was in love, and what she cherished about being pregnant. Nicole recounts the time her grandpa got caught smuggling razors in his shoes past TSA.

Watch this episode on YouTube at youtu.be/mWWnVL-_2jg

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.

Follow:

YouTube: @WhyWontYouDateMePodcast

TikTok: @whywontyoudatemepod

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.

It’s an extra special holiday treat! Nicole Byer is joined by her friend, comedian, and actor Ben Schwartz to talk about the true love of her life — Sonic the Hedgehog. Nicole opens up to Ben about her deep, emotional connection to Sonic and why it’s not just a bit. Ben shares the unexpected journey of landing the role, the fan backlash to the original 'Ugly Sonic' design, and debunks some of the internet’s wildest Sonic fan theories. Nicole makes her formal pitch for how she’d like to join the Sonic universe herself. Plus, special guest call-in appearances with the voice of Tails, Colleen O'Shaughnessey, and Sonic artist and co-producer, Tyson Hesse. You don't want to miss this!

WATCH this episode on YouTube at https://youtu.be/vveFneSDN4k

See Sonic The Hedgehog 3 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.

Follow:

YouTube: @WhyWontYouDateMePodcast

TikTok: @whywontyoudatemepod

Instagram: @nicolebyer

X: @nicolebyer

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

Sponsor:

» Essie: Shop essie nail polish at Target.

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 and actor Randall Park (Fresh Off The Boat, WandaVision) joins Nicole Byer to talk about the best ways to hide your stinky shits from your partner, how comparing himself to his partner’s ex took an unhealthy turn, and the time he created a jazz club to impress a girlfriend. Meanwhile, Nicole hatches a plan to ride a garbage truck.

Watch this episode on YouTube at youtu.be/4UQS8vtUYZ8. Subscribe so you don't miss an episode!

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.

Follow:

TikTok: @whywontyoudatemepod

YouTube: @WhyWontYouDateMePodcast

Instagram: @nicolebyer

X: @nicolebyer

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

Sponsors:

» Quince: Gift luxury this holiday season without the luxury price tag. Go to Quince.com/dateme for 365-day returns, plus free shipping on your order.

» Essie: Shop essie nail polish at Target.

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.

Journalist Sam Sanders (NPR, Vibe Check) joins Nicole to discuss saying "I love you" during random hookups, the best way to handle breakups when someone has to move out, and how a hookup turned into a relationship. Sam shares the story of his secret gay age-gap romance and the time he dated a drug dealer. Meanwhile, Nicole recounts the time she whacked a man with her tiddy and gives her review of Joker: Folie à Deux.

Watch this episode on YouTube at youtube.com/watch?v=HeF1X9XIj6M

This episode is brought to you by:

» Quince: Gift luxury this holiday season without the luxury price tag. Go to Quince.com/dateme for 365-day returns, plus free shipping on your order.

» Essie: Shop essie nail polish at Target.

Follow:

Our New TikTok: @whywontyoudatemepod

YouTube: @WhyWontYouDateMePodcast

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 Alex Moffat (SNL) joins Nicole to discuss how his relationship is thanks to Velveeta cheese. This episode isn’t sponsored by Velveeta—but we really wish it was. Alex shares how he met his wife at a Velveeta commercial, how the cheese played an essential part in his proposal, and why it’s now a staple of their anniversary. He also discusses his pole dancing skills, bombing at a Nicole Byer comedy show, being an acrodunker for the Chicago Bulls, and shares some of the worst dating advice we've heard on the show.

WATCH this episode on YouTube at: https://youtu.be/Nb4jAt6NvfY

See Alex Off-Broadway in The Big Gay Jamboree!

This episode is brought to you by -

» Uncommon Goods: For thousands of unique gifts & 15% off your first order, visit 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.

» Essie: Shop essie nail polish at Target.

Follow:

Our New TikTok: @whywontyoudatemepod

YouTube: @WhyWontYouDateMePodcast

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 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.