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PODCAST

Why Won"t You Date Me? with Nicole Byer

Headgum & Nicole Byer

Love and dating can be messy—so let’s talk about it! On this multi-award-winning podcast, comedian Nicole Byer explores romantic highs, lows, and all the juicy stuff in between, alongside comedians, experts, and sometimes an ex or two. New episodes every Friday!

society & culture relationships

All Episodes

00:56:35

Nicole Eats a Banana from a Sex Worker's Pussy (w/...

Why Won"t You Date Me? with Nicole Byer ·

2023/08/25

Broadway star Naomi Rodgers (Tina: The Tina Turner Musical) opens up about secretly dating her co-star while on tour, and offers advice how to grieve and get over a breakup. Nicole shares her latest European dating mishaps, including an unforgettable visit to the Red Light District. Follow Nicole Byer: See Nicole on tour! Get tickets at linktr.ee/nicolebyerwastakenTwitter: @nicolebyerInstagram: @nicolebyerMerch: podswag.com/datemeNicole's book: indiebound.org/book/9781524850746

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01:08:25

300 Episodes of Why Won't You Date Me (w/ Sasheer...

Why Won"t You Date Me? with Nicole Byer ·

2023/08/18

It's episode 300! But how is Nicole STILL SINGLE? On this milestone occasion, she's joined by her best friend Sasheer Zamata (co-host of Best Friends) to get to the bottom of it. In this special retrospective, they explore:How Nicole's dating life has evolved with the podcastThe highs and lows of her love lifeTheir favorite dates they've been onThe best dating advice they've receivedTheir new favorite sex toys they've been usingAnd they answer your questions about whether you should call out

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01:03:55

Romancing Overseas (w/ Zurin Villanueva)

Why Won"t You Date Me? with Nicole Byer ·

2023/08/11

Broadway superstar Zurin Villanueva (Tina: The Tina Turner Musical) joins Nicole for a discussion about the awkwardness of working together with a past hookup, safety precautions when dating abroad, and the best grocery store to find a good man. Plus, don't miss Zurin's recounting of a date gone awry when her phone rang, and on the other end? Her date's ex. Nicole wants to hear from you! Need some dating or relationship advice from Nicole and her guest? Submit your question to

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01:09:59

Gay Orgies (w/ Jay Jurden)

Why Won"t You Date Me? with Nicole Byer ·

2023/08/04

The hilarious comedian Jay Jurden joins Nicole to talk about his secret relationship with a frat boy, working at Abercrombie & Fitch during its peak era, the best app for threeways, and what goes on at a gay orgy. Plus, Nicole gets hit on by a 911 responder. Nicole wants to hear from you! Need some dating or relationship advice from Nicole and her guest? Submit your question to whywontyoudatemepodcast@gmail.com for a chance to have it answered on an upcoming special mailbag episode. Follow Nicole

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01:47:09

Dating an Asexual (w/ Gigi Goode)

Why Won"t You Date Me? with Nicole Byer ·

2023/07/28

Drag queen Gigi Goode (Drag Race S12) joins Nicole for a supersized live episode of the podcast! They talk about her trans journey during the pandemic, how the type of people who are attracted to her has changed since transitioning, making friends through Tinder, and shares her experience being in a long term relationship with a partner who's asexual. She also tells just so many, bad, no awful, date stories. Plus, an audience Q&A: Do queens get cozy on the set of Drag Race? Is it possible to date

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01:04:42

Mutual Ghosting (w/ Robin Fierce)

Why Won"t You Date Me? with Nicole Byer ·

2023/07/21

Drag queen Robin Fierce (Drag Race S15) LIP-SYNCS TO THIS VERY PODCAST! She talks about remixing Nicole's comedy in her drag performance, opens up about her relationship with Drag Race contestant Amethyst, shares the new subtle way to look for a sugar daddy on dating apps, and speaks out on how people are using Grindr for their own personal meet & greets. Robin gives us a exclusive look at her Snatch Game audition as Nicole Byer (and why it didn't help her book the show). Plus, the haunting tale

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00:54:27

Catfishing Men on Craigslist (w/ Bosco)

Why Won"t You Date Me? with Nicole Byer ·

2023/07/14

Drag queen Bosco (Drag Race S14) joins Nicole to discuss their long-term relationship with a fan, recounts her most enchanting full-day date, and tells how to spot chasers vs. genuine men. She shares how catfishing on Craigslist for attention ignited her trans journey, plus spills the tea on the severe highs, lows, and trauma shooting Drag Race. For more drag queen interviews, check out our episode playlist on Spotify: bit.ly/wwydmdrag Nicole wants to hear from you! Need some dating or relationship

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00:41:52

Nicole Wins an Orgasm Contest (w/ Matteo Lane)

Why Won"t You Date Me? with Nicole Byer ·

2023/07/07

Comedian and friend Matteo Lane returns to the podcast! They reminisce about his love life since his last episode, getting kicked off Grindr and Tinder for "catfishing" as himself, and why men are intimidated by successful women. Nicole wins the orgasm contest at the Thunder from Down Under Vegas show. Matteo hooks up with a dancer from Magic Mike. Plus, a whole lot more. Watch Matteo Lane's new special, Hair Plugs & Heartache, free on YouTube. Have a question for Nicole? Submit it to

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00:39:57

Tasteful Dick Pics (w/ Jermaine Fowler)

Why Won"t You Date Me? with Nicole Byer ·

2023/06/30

Comedian & actor Jermaine Fowler (The Blackening) joins Nicole to reminisce on their time working on Guy/Girl Code, his joy of being a unexpected father, and discusses what makes a great dick pic. Nicole is now horny for them, but before you go sliding one into her DMs, she shares her criteria on how to take a tasteful pic. See Nicole Byer live on tour! Get tickets at nicolebyerwastaken.com. Follow Nicole Byer: Twitter: @nicolebyerInstagram: @nicolebyerMerch: podswag.com/datemeNicole's book:

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01:02:00

Finding Your Confidence (w/ Jay Pharoah)

Why Won"t You Date Me? with Nicole Byer ·

2023/06/23

Comedian Jay Pharoah (Saturday Night Live) dives into how a messy breakup ended up saving his SNL career, and the bizarre role Donald Trump played in his escape from a toxic relationship. Jay shares the impressions he's been asked to do during sex, and how developing self-confidence saved him from a bad situation. Plus, what's it like to have your photos used by a catfish? See Nicole Byer live on tour! Get tickets at nicolebyerwastaken.com. Follow Nicole Byer: Twitter: @nicolebyerInstagram:

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00:52:44

Fake It Til You Make It (w/ Melvin Gregg)

Why Won"t You Date Me? with Nicole Byer ·

2023/06/16

Comedian and actor Melvin Gregg (Vine, American Vandal, The Blackening) opens up about his unique romantic path, where pretending to be a couple turned into the real deal. He takes us on a trip down memory lane, tracing his roots from being a Vine sensation to earning the badge of an early verified Tinder user. Plus, he shares his pro tips on sealing the deal at the end of any date or encounter. See Nicole Byer live on tour! Get tickets at nicolebyerwastaken.com. Follow Nicole Byer: Twitter:

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01:03:53

Transcending Norms (w/ TS Madison)

Why Won"t You Date Me? with Nicole Byer ·

2023/06/09

Actress and activist TS Madison (judge on RuPaul's Drag Race) is here for a heartfelt chat on her journey from being a viral TikTok sensation to a vocal advocate for trans rights, and all of the unseen struggles she faced in navigating systemic biases. She discusses doing sex work for survival, shares real examples of the transphobic harassment she receives to this day, and her relentless efforts to forge a better future. This episode is a raw exploration into the battles and victories that come

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00:55:46

Live Your Rom-Com Era (w/ Sam Taggart)

Why Won"t You Date Me? with Nicole Byer ·

2023/06/02

Comedian Sam Taggart (host of StraightioLab) is here to spill some juicy insights on gay relationships and why they often swing open. Have you ever thought of Kevin James as a bear icon? Neither did Nicole, but Sam gives us a whole new perspective! He also tells the crazy story of a strange threesome he had with 2 cops from Boston. Plus, a candid chat about all things anal, and why we need to break the silence and start talking about our holes. Write to Nicole! Submit your dirty pick-up lines,

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01:07:59

Sugar Daddies (w/ Sugar & Spice)

Why Won"t You Date Me? with Nicole Byer ·

2023/05/26

Twin drag queen icons Sugar & Spice (RuPaul's Drag Race S15) join Nicole for a conversation about why you can't skirt around the law of attraction, to spilling the tea on the sugar baby lifestyle and how to shine as a high-value woman in today's dating scene. And if you've ever wondered what it's like for twins to audition for Drag Race, Sugar & Spice pull back the curtain on their journey, talking about their impressions of Snatch game, including the unforgettable meltdown Spice had on-set after

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01:00:56

Hot Porn Seaches (w/ Bridget Everett)

Why Won"t You Date Me? with Nicole Byer ·

2023/05/19

The hilarious Bridget Everett (Somebody, Somewhere) joins Nicole to discuss the hot porn searches they've been into, the need for increased privacy on dating apps, Bridget's experience hooking up with a go-go dancer at a gay bar, and her stand-up routine where she has audience members motorboat her huge titties. Plus, the story about the woman whose breast implants started to grow mold. Write something dirty to Nicole! Submit your dirty pick-up lines, dating stories, or questions to

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01:00:47

Monogamously Challenged (w/ Holly Robinson Peete)

Why Won"t You Date Me? with Nicole Byer ·

2023/05/12

Actress Holly Robinson Peete (21 Jump Street, Queen's Court) opens up about her experience being in a relationship with someone who is "monogamously challenged", dating around Paris in order to learn to speak French, and being very publicly proposed to on the set of Hangin' with Mr. Cooper by NFL quarterback Rodney Peete. Plus, the challenges single people now face in today's social media-driven world, and how it affects relationships in ways both big and small. Write something dirty to Nicole

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00:48:04

Secrets To a Long, Loving Marriage (w/ John Leguizamo)

Why Won"t You Date Me? with Nicole Byer ·

2023/05/05

Actor John Leguizamo (Encanto, Moulin Rouge!, Ice Age) chats with Nicole about his secrets to a long, loving marriage, how he balances work and relationships, and his efforts to boost Latin representation in media. Write something dirty 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: @nicolebyerInstagram: @nicolebyerMerch: podswag.com/datemeNicole's book:

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00:59:00

Lesbian Sex (w/ Ashley Gavin)

Why Won"t You Date Me? with Nicole Byer ·

2023/04/28

Comedian Ashley Gavin (host of We're Having Gay Sex) teaches Nicole all about lesbian sex and relationships. They cover scissoring and tribbing, having secret girlfriends in high school, and the details of her open relationship. Ashley also shares her experience being the first openly gay comedian on Carnival Cruise Line, and the homophobia she encountered on the job. Nicole witnesses a bouncer get stabbed at a lesbian bar. Watch Ashley's new comedy special at:

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01:04:26

"Don't Ask, Don't Tell" Poly Relationships (w/ Zoe...

Why Won"t You Date Me? with Nicole Byer ·

2023/04/21

Actress/writer/director Zoe Lister-Jones (Slip) shares her experience opening and closing her "don't ask don't tell" poly relationship, what she's learned after exiting a 17-year marriage, and delves into the empowering nature of "dating to fuck". Nicole really wants to crash the cool teen party down her block. 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:

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01:14:31

Staying Friends with your Ex (w/ James Marsden)

Why Won"t You Date Me? with Nicole Byer ·

2023/04/14

Actor James Marsden (Sonic The Hedgehog, Hairspray, Jury Duty) joins Nicole to talk about his new singledom, remaining friends with all of his exes, his romantic side, and reviews Nicole's latest Tinder profile. Nicole teaches Marsden about bussies and scat porn. This episode was specially recorded in-person at Team Coco's studios. Thank you engineer Rich and the whole team for putting this together! Write to Nicole! Submit your dirty pick-up lines, dating stories, or questions to

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