As we continue our hiatus, we're bringing back one of Nicole's all-time favorite episodes! And oh boy, buckle up, because this one is WILD. Nicole is joined by her pals, drag queen Meatball and rapper Big Dipper. They share a wild hookup story involving a dirty diaper, talk about how they like to be choked in bed, and swap stories about the times they were paid for sex. By the end, Nicole is convinced to hire a male escort for her next birthday.

Originally aired 05/25/2018.

For more drag queens on Why Won't You Date Me, check out our episode playlist on Spotify: https://spoti.fi/3fg8Epu

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Actress Jameela Jamil (The Good Place) joins Nicole to share her most horrifying booty call story. They dive into the wild pressure women face to be sexy, why so many play it small for men, and how the relentless pursuit of the 'bad boy' often leads to heartbreak—and HPV.

Originally aired 09/06/2018.

Write to Nicole! Submit your dirty pick-up lines, dating stories, or questions to whywontyoudatemepodcast@gmail.com for a chance to have it read on-air.

Follow Nicole Byer:

Twitter: @nicolebyer

Instagram: @nicolebyer

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

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

We’re taking a short hiatus, but don’t worry—we’ll be back soon with brand new episodes, including more video podcasts! In the meantime, I’m re-releasing some of my all-time favorite episodes of the podcast, completely ad-free.

Stay tuned for updates and all the latest news by following me on Instagram @nicolebyer. We can’t wait to share what’s coming up next with you!

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

Actress Garcelle Beauvais (The Real Housewives of Beverly Hills) joins Nicole to discuss dating the likes of Michael Jordan, Larry David, and Eddie Murphy. She shares her experience working at a Playboy club under a fake ID, and the time she accidentally spent $6,000 on a dating app, without landing a single date. Nicole and Garcelle fantasize about a world with Yelp-style reviews for dating.

Write to Nicole! Submit your dirty pick-up lines, dating stories, or questions to whywontyoudatemepodcast@gmail.com for a chance to have it read on-air.

Follow Nicole Byer:

Twitter: @nicolebyer

Instagram: @nicolebyer

Merch: podswag.com/dateme

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

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

Comedian Riki Lindhome (Garfunkel and Oates, AfrAId) joins Nicole to discuss her harrowing fertility journey, dating someone new just two weeks before her baby was due, and what it means to "soft-partner" or date a "scrap." Meanwhile, a man tries to move into Nicole's house, leading her to seek relationship advice from WikiHow.

Write to Nicole! Submit your dirty pick-up lines, dating stories, or questions to whywontyoudatemepodcast@gmail.com for a chance to have it read on-air.

Follow Nicole Byer:

Twitter: @nicolebyer

Instagram: @nicolebyer

Merch: podswag.com/dateme

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

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

Comedian and actress Chloe Fineman (SNL) joins Nicole to discuss orgasmic meditation and the strange men behind the practice. She shares stories of attending a “slutty” theater school where her friends ended up in a crazy gangbang, dating a 700-pound man who used meth to lose weight, and dating another guy with "school shooter vibes." Chloe also talks about the most ridiculous arguments that have led to her breakups and offers advice on the best dating app.

Write to Nicole! Submit your dirty pick-up lines, dating stories, or questions to whywontyoudatemepodcast@gmail.com for a chance to have it read on-air.

Follow Nicole Byer:

Twitter: @nicolebyer

Instagram: @nicolebyer

Merch: podswag.com/dateme

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

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

Sophia Stallone (The Family Stallone) shares what it's like to date when your dad is Sylvester Stallone. Sophia recounts cringey dates where the guy was more interested in meeting Rocky than getting to know her, the challenges of navigating her dad’s overprotective nature, and how she’s worked to overcome the anxieties that come with dating in the spotlight. Nicole and Sophia also reminisce about being dummies on the set of Are You Smarter Than a Celebrity.

Write to Nicole! Submit your dirty pick-up lines, dating stories, or questions to whywontyoudatemepodcast@gmail.com for a chance to have it read on-air.

Follow Nicole Byer:

Twitter: @nicolebyer

Instagram: @nicolebyer

Merch: podswag.com/dateme

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

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

Comedian and "ho-fessional" Akeem Woods joins Nicole to share his crazy sexcapades. He tells the story about his first Pride parade where he hooked up with a dozen guys in a single day, his experiences having sex with pornstars, accidentally attending an orgy, and having sex with a stranger in a Staples bathroom. He looks back on the time he was still in the closet and made a MySpace account for his fake girlfriend. Nicole gets fisted.

Write to Nicole! Submit your dirty pick-up lines, dating stories, or questions to whywontyoudatemepodcast@gmail.com for a chance to have it read on-air.

Follow Nicole Byer:

Twitter: @nicolebyer

Instagram: @nicolebyer

Merch: podswag.com/dateme

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

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