Comedian Mo Welch joins Nicole to share how she met her wife at a lesbian bowling event, the unique “proposal order” they planned for their engagement, and whether height really matters in lesbian relationships. She dives into LA’s tight-knit lesbian scene, questions why society clings to outdated proposal traditions, and pitches her take on improving Love Is Blind. Plus: the story of how she lost her virginity at circus school—with a clown.

WATCH this episode on YouTube at: youtu.be/iIE1Acf-y_0

Check out Mo Welch's new special, DAD JOKES, on Hulu.

Write to Nicole! Send your dirty messages to [email protected] with the subject line "Dirty Message" and Nicole may read it in a future episode.

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Nicole's book, #VERYFAT #VERYBRAVE: indiebound.org/book/9781524850746

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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.

Happy Valentine's Day! Dating coach Sabrina Zohar joins Nicole for a deep dive into attachment styles and how they shape our love lives. Are you anxiously attached, always seeking reassurance and fearing abandonment? Or are you more avoidant, pulling away when things get too close? Sabrina breaks down the key differences, explaining how both styles stem from a common fear of rejection- and how recognizing your patterns can help you build healthier relationships.

They discuss how to stop spiraling, set boundaries, manage emotional dysregulation, and choose self-love over external validation. Plus, Sabrina shares her personal experiences and expert strategies to help you rewire your attachment style and create connections that feel safe, stable, and fulfilling.

WATCH this episode at youtu.be/WgrjHKyk57o

Learn more about Sabrina Zohar at sabrinazohar.com.

Write to Nicole! Send your dirty messages to [email protected] with the subject line "Dirty Message" and Nicole may read it in a future episode.

Follow:

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

To support this podcast, check out our sponsors & get discounts:

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

Equip: To learn more about Equip's virtual eating disorder treatment, visit Equip.Health/dateme.

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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.

Rescued from a broken time machine, we travel from the past with an unhinged LOST episode of the podcast. Comedian and friend Bobby Moynihan (SNL) joins Nicole to discuss dating on SNL, how he met his wife while teaching improv, and why the TV show LOST played a weirdly huge role in their relationship. He talks about loving being a dad, and what he planned for his dream wedding.

Also, we may have gotten way too drunk. Questionable decisions were made. We don't know who the president is yet. Minds were lost. Chaos ensued. A must-listen.

Heads up: This episode contains MAJOR LOST spoilers.

WATCH this episode on YouTube at: https://youtu.be/KmuyBNbd7nI

Write to Nicole! Send your dirty messages to [email protected] with the subject line "Dirty Message" and Nicole may read it in a future episode.

Follow:

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TikTok: @whywontyoudatemepod 

Instagram: @nicolebyer

X: @nicolebyer

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

To support this podcast, check out our sponsors & get discounts:

Arya: Visit arya.fyi and use code DATEME for 15% off today!

Quince: Upgrade your closet this year without the upgraded price tag. Go to quince.com/dateme for 365-day returns, plus free shipping on your order.

Squarespace: Head to squarespace.com/DATEME to save 10% off your first purchase of a website or domain using code DATEME.

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Audience Survey: ​​Go to GUM.FM/DATEME to fill out our audience survey.

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 Josh Peck (Drake and Josh, Good Guys podcast) joins Nicole to talk about meeting his wife at a Halloween party, proposing to her while naked, and what it was like to date as a child star. They share their experiences of being fat, how losing weight changed their dating lives, and why the right person just gets you. Plus, Nicole reflects on past relationships… and admits she really misses her fat ass.

WATCH this episode on YouTube: https://youtu.be/zTe1yl5Nr-E

Write to Nicole! Send your dirty messages to [email protected] with the subject line "Dirty Message" and Nicole may read it in a future episode.

Follow:

YouTube: @WhyWontYouDateMePodcast

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Instagram: @nicolebyer

X: @nicolebyer

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

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Arya: Visit arya.fyi and use code DATEME for 15% off today!

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.

Writer and comedian Siobhan Thompson (Dimension 20, Rick & Morty) joins Nicole to dive into the messy realities of hookup culture—from men leaving skid marks in bed to requesting ass-eating with a muddy butt. They debate whether it’s okay to ghost someone after a one-night stand. Siobhan shares why she had to turn off DM requests from D&D fans, her biggest dating 'icks,' and the differences between dating in London and Los Angeles. Plus, a PSA on why you should NEVER DATE YOUR IMPROV TEACHER. 

WATCH this episode on YouTube: youtu.be/asu1JrsFkxc.

Write to Nicole! Send your dirty messages to [email protected] with the subject line "Dirty Message" and Nicole may read it in a future episode.

Follow:

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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 actor Eugene Cordero (Loki, The Mandalorian) joins Nicole to discuss having a UCB-involved proposal, his most awkward date, and finding someone that matches your silly. Plus, Nicole shares her attempt to get into anime - for a man.

WATCH this episode on YouTube at youtu.be/ffIFVa7Ba0o.

Write to Nicole! Send your dirty messages to [email protected] 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.

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 [email protected] with the subject line "Dirty Message" and Nicole may read it in a future episode.

Follow:

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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 [email protected] 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 [email protected] 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 [email protected] with the subject line "Dirty Message" and Nicole may read it in a future episode.

Follow:

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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 [email protected] 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.