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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

00:49:13

I'm Bi Now (w/ Jenson Titus)

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

2025/09/05

Comedian, clown, and artist Jenson Titus (of @VeryGayPaint) tells Nicole what it was like to date someone who's in the process of transitioning. The experience made him realize he’s bi, and left him feeling “more queer” than ever. He talks about the challenges of having a "Very Gay" brand while dating a woman, launching his mural business, and the surreal job of painting RuPaul’s 1-bedroom, 5-closet mansion. They talk about their dream date ideas, the act of clowning, and Nicole shares her plan to

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00:56:18

Stealing Condoms at the Olympics (w/ Adam Rippon)

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

2025/08/29

Olympic figure skater Adam Rippon (Winner of Dancing with the Stars) joins Nicole to share the dating life of a Olympian. He shares what it was like being one of the first openly gay U.S. Olympians, why the infamous Olympic condoms left him disappointed, and what the sex life in the Olympic Village is really like. He also breaks down for Nicole exactly what it takes to become an Olympian, and the incestuous nature of figure skaters. Meanwhile, Nicole and her boyfriend take a vacation where he gets

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01:08:24

Ghosting, Gaslighting, and Gay Bars (w/ Roz Hernandez)

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

2025/08/15

For Roz Hernandez, dating as a sober, trans woman comedian is a trifecta of difficulty - and finding love hasn’t been easy. She tells Nicole about going to 4 different Etsy psychics to sketch her future husband, using Grindr to find dates willing to explore haunted places, and the hookup stories that came from visiting 45 gay bars across the country. She opens up about the surprising ways gay men have treated her, why she’s stopped dating straight men altogether, and the many times she’s been

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01:00:43

Dating Life of a Burlesque Superstar (w/ Jessabelle...

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

2025/08/08

International award-winning burlesque dancer Jessabelle Thunder joins Nicole to talk about why so many partners say they’re cool with burlesque - until they’re not. She shares how she transformed from a shy girl into a commanding headliner, the different styles of burlesque dancing, and the time she broke her ankle on stage mid-show. Jessabelle also relives a London date with an Irish DJ who argued he should be allowed to say the N-word. Plus, Nicole forgets her meds, spirals on the future of AI,

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00:55:49

Dating after a Major Scandal (w/ Monica Lewinsky)

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

2025/08/01

Before she was an activist, Monica Lewinsky was the most publicly shamed woman in America. Now, she's reclaiming her story, and her dating life.For the 400th episode of Why Won’t You Date Me?, Monica joins Nicole to talk about dating after a major scandal, being labeled “unmatchable” on eHarmony, and learning to enjoy life when pop culture won’t stop referencing you. She reflects on hosting the wild early-2000s reality show Mr. Personality, shares the worst dates she’s ever had (including ones she

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00:00:33

A lil update from Nicole: Best Friends is back!

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

2025/07/30

Exciting news from Nicole: Best Friends is BACK and 1) now on Headgum, 2) with FULL VIDEO EPISODES! Enter the pantheon of best friendship and check out Nicole and Sasheer's first episode back, available now on Apple Podcasts, Spotify, or wherever you get your podcasts. New episodes every Wednesday. Subscribe to the Best Friends YouTube channel https://youtube.com/@NicoleandSasheer for video episodes. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at

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00:56:03

Flirting, Open Relationships, and Almost Dying (w/...

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

2025/07/18

Comedian and friend Josh Sharp (Dicks: The Musical) returns to the podcast! Nicole and Josh kick things off by reminiscing about the chaotic live show where Nicole interviewed a man in the audience she had slept with. From there, they get into Josh’s foolproof flirting strategy at the club, Annabelle the haunted doll’s cursed tour across America, attending a Big Dick contest, and Josh’s near-death experience in Puerto Vallarta that left him facedown in the ocean with no memory of his own name.They

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00:51:01

We Dated?! (w/ Lou Wilson)

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

2025/07/04

Happy 4th of July!(?) Comedian Lou Wilson (Dimension 20, Jimmy Kimmel Live!) joins Nicole to reflect on the wild state of America. He shares his terrible time living in Boston, where white guys frequently asked him for the N-word pass. They talk about what it was like to sell out Madison Square Garden in just 10 minutes withDimension 20, being a “silly billy” on dates, and the moment Lou realized bits don’t always land on dates when you’re trying to build intimacy. They also bond over the guilty

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00:59:20

I Was a Time Out Magazine Bachelor (w/ Lauren Ashley...

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

2025/06/20

TV writer Lauren Ashley Smith (A Black Lady Sketch Show, Smith Sisters Live) joins Nicole to talk about how she met her wife the old-fashioned way - through Time Out New York’s Singles issue.Lauren reveals the strange public response to being a “bachelor” in a magazine, how her wife was one of the only white women working at BET, and the complications that came with planning an interracial lesbian wedding. She also recalls a bizarre school Valentine’s Day test that matched students based on

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00:53:49

Bizarre Relationships with Animals (w/ Rose McIver)

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

2025/05/23

Actress Rose McIver (Ghosts, iZombie, voice of Headgum) joins Nicole to explain New Zealand, why she doesn’t post her loved ones on social media, and talk about all the cute, funny other ways people show love. They get into weird animal relationship stories, like the woman in love with a dolphin (who died of heartbreak), the man who tried to live among grizzlies, and Nicole’s dream of becoming queen of the whales. Plus: a simple dinner hosting hack from Meghan Markle.WATCH this episode here:

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01:08:08

Bob Derails the Pod (w/ Bob the Drag Queen)

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

2025/05/16

Bob the Drag Queen (The Traitors, winner of RuPaul's Drag Race S8) returns to the podcast to derail the show. This time, Bob interviews Nicole about her current relationship, run through their plans to prep for tariffs, and discuss LA's newest serial killer. He sniffs out the ulta-rich cast members on The Traitors, shares what he hates about Italy, and Canada’s ex-prime minister's blackface scandal. Plus, Nicole shares her latest showdown with the cops.Buy Bob's new book, Harriet Tubman: Live in

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01:04:33

Too Shy to Talk to People (w/ Owen Burke)

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

2025/04/25

Comedian Owen Burke (Drunk History) joins Nicole for a conversation recorded in the middle of the Los Angeles fires (things were unhinged). They talk about trying to function while the world is burning, the early days of UCB, and how Owen managed to find a wife while being painfully shy and awkward with dating—and how you can too. Plus, Nicole shares the time she gave John Mulaney her number. John, please call back.Write Nicole a dirty message! Send it to whywontyoudatemepodcast@gmail.com with

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01:07:48

DIVORCED!!! (w/ Jackie Johnson)

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

2025/04/18

Comedian and friend Jackie Johnson was terrified to do this podcast… until she got a divorce. She joins Nicole to talk about dating a record number of canceled UCB comedians, surviving a nightmare marriage, and only realizing she was unhappy after it ended (plus how to spot signs of abuse in your own relationship). Jackie shares how therapy—and a witch’s spell—helped her find true love. Plus, they discuss the red flags they missed in past relationships, why getting married on Valentine’s Day was a

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00:50:06

Childbirth Nightmares, Public or Private Proposal?...

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

2025/04/11

Writer Melissa Hunter (Santa Clarita Diet, She-Hulk, Home Economics) joins Nicole to talk through the messy reality of childbirth - including her 32-hour labor, an unexpected unmedicated birth after her epidural failed, and shitting on the table. They also get into whether proposals should be private or public (including Nicole’s dream proposal), the red flags of dating someone who won’t drop the bits, and the time Nicole got scammed by a hot Instagram dating coach.WATCH this episode on

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01:12:57

The Funny Guy Trap (w/ Wayne Brady)

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

2025/04/04

Comedian Wayne Brady (Whose Line Is It Anyway?, What If? podcast) joins Nicole to talk about the struggles of dating when everyone expects you to be the funny guy from TV. He opens up about being an introvert, and how his dates sometimes get disappointed when he's not his 'persona' they know him for. Wayne shares the wild story of dating someone whose parent was openly racist, the struggles he's faced navigating racism in relationships, and what it's like dating as a single father. Plus, the crazy

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01:04:08

Chubby Chasers (w/ Jana Schmieding)

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

2025/03/28

Comedian Jana Schmieding (Reservation Dogs, Rutherford Falls) joins Nicole to discuss chub chasers, the difference between being fetishized and being genuinely wanted, and what it was like to date a man with body shame. She shares what it was like to date a sacred Native man, including a agonising "breakup ceremony" he put her through. Plus, they break down Curvy Wife Guy’s BBW bop, try to understand whatever the hell is happening between Kanye and Bianca Censori, and Jana shares her new daily

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00:58:09

Oops, All Red Flags! (w/ Mariah Smith)

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

2025/03/21

Comedian and writer Mariah Smith (Smith Sisters Live) joins Nicole to share some truly wild dating stories, including a guy who got horny discussing Black Lives Matter, and another who cried about his ex on the first date. She talks about her experience using an Instagram matchmaking service, and dishes out a hot tip for boosting your matches on dating apps. Plus, they try to settle the great iPhone vs. Android green bubble debate, and open up about their experiences losing over 100 lbs with

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00:59:15

Surviving Beergate & Escaping Trans-Chasers (w/ Dylan...

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

2025/03/14

TikTok sensation Dylan Mulvaney joins Nicole to share what it's like dating after transitioning in the public eye, including handling trans-chasers, dating straight men who don't live up to the hype, and her hot affair with Irish royalty. She opens up about navigating the aftermath of the infamous "BeerGate" controversy, and why being ignored on a gay cruise felt surprisingly affirming. Plus, Nicole shares the time she performed sketch comedy for Dolly Parton.Check out Dylan's new book Paper

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00:57:44

Coming Out (w/ Sasheer Zamata)

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

2025/03/07

Comedian and best friend Sasheer Zamata (SNL, Agatha All Along) opens up to Nicole about her journey coming out, discusses whether it’s lesbian to collect chairs, and the bizarre YouTube dating show Pop The Balloon Or Find Love. She also shares how working on SNL impacted her dating life and discusses how to actually make new friends as an adult.Meanwhile, Nicole reflects on how she thought getting a boyfriend would change everything… and why it really hasn’t. Plus, the truly horrifying story of

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00:54:21

How to Pull Rich Men (w/ Robby Hoffman)

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

2025/02/28

Comedian Robby Hoffman (Host of Too Far) joins Nicole to discuss being 'Jewish school slutty,' how growing up poor gave her the skills to pull rich men, and the best time to sneak away to the bathroom on a date. She shares the story of how she ended up dating a Bachelorette star mid-'exploration,' her golden rule for relationships (one hot, one smart—no exceptions), and the time she was invited to a Juneteenth cookout.WATCH this episode on YouTube at youtu.be/kKrxnRu_zGk Write to

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