Headgum & Nicole Byer
Why Won't You Date Me? with 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!
Author
Headgum & Nicole Byer
Category
Podcast website
Latest episode
Jul 10, 2026
Where to listen?
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Episodes
THE LOST EPISODE (w/ Bobby Moynihan) 07.02.2025 1:08:35
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,...
Dating as a Child Star, Proposing Naked (w/ Josh Peck) 31.01.2025 50:02
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 re...
Mud Butt Mishaps (w/ Siobhan Thompson) 24.01.2025 1:01:38
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 di...
Matching Your Silly (w/ Eugene Cordero) 17.01.2025 1:00:21
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 whywontyoudatemepodcast@gmail.com with the sub...
Left by my Fiancé, Relationship OCDs (w/ Allison Raskin) 10.01.2025 59:12
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...
A Naked Proposal (w/ Jimmy Kimmel) 03.01.2025 1:08:16
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...
Loving Your Pregnancy (w/ Lennon Parham) 27.12.2024 45:18
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 whywont...
Ho Ho Ho, Sonic is Here! A Sonic The Hedgehog Holiday Special (w/ Ben Schwartz) 20.12.2024 1:22:34
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...
How to Cover Up Stinky Shits From Your Partner (w/ Randall Park) 13.12.2024 57:11
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 ....
Saying 'I Love You' Too Soon (w/ Sam Sanders) 06.12.2024 1:08:21
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 o...
Cheesy Anniversaries (w/ Alex Moffat) 29.11.2024 45:12
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...
NickKroll Byer (w/ Nick Kroll) 22.11.2024 1:08:05
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-e7...
Validate Bisexuality (w/ Sherry Cola) 15.11.2024 54:46
Comedian Sherry Cola ( Joy Ride , Turning Red ) shares her journey of coming out as bisexual, how she met her girlfriend, navigating dating in the queer community, and monetizing a breastmilk kink. WATCH this episode on YouTube at: https://youtu.be/RH4fK4ksCNs Write to Nicole! Send your dirty messages to whywontyoudatemepodcast@gmail.com with the subject line "Dirty Message," and Nicol...
We Met Playing Call of Duty (w/ Sarah Silverman) 08.11.2024 58:39
Comedian Sarah Silverman sits down with Nicole to discuss meeting her boyfriend over Call of Duty , the challenges of dating as a female comic, and how many health studies are skewed against women. Plus, Nicole shares her experience getting hit on at Comic-Con. See Sarah Silverman live on her POST MORTEM tour at sarahsilverman.com . WATCH this episode on YouTube at: youtu.be/eOdSuFrUl4s Write to N...
Men Who Lie About Their Height (w/ Lauren Lapkus) 01.11.2024 56:26
We're back - and now in video form! Comedian and actress Lauren Lapkus ( Newcomers podcast ) joins Nicole to discuss why men lie about their heights, motherhood, and her recent trip to Victoria's Secret. Plus, they play a special game of F*ck, Marry, Kill: Newcomers Movies Edition . Watch this episode! Check it out on our new YouTube channel at youtube.com/@WhyWontYouDateMePodcast . Write to Nicol...
BEST OF: How to Hack Into Your Partner's Phone (w/ Keke Palmer) 25.10.2024 45:21
In this best of episode, Emmy-award winning actress Keke Palmer (Nope, Lightyear) shares with Nicole how she got her first kiss from MySpace, why she avoids posting relationships on social media, and how she's learning to trust again after her boyfriend slept with her best friend. Plus, is it ever okay to hack into your partner's phone? Keke teaches, in great detail, e...
BEST OF: Being a Single Mom of 3 (w/ Francesca Amber) 18.10.2024 58:35
While we're on hiatus, we're bringing you the best of the podcast – completely ad-free! In this episode, Nicole’s close friend Francesca Amber (host of Law of Attraction Changed my Life ) opens up about the challenges of being a single mother to twins, the rising trend of 'co-parenting', and how she uses the Law of Attraction to manifest her dream partner. Meanwhile, Nicole count...
BEST OF: Top or Bottom? (w/ Jon Gabrus, Nick Wiger, and Mike Mitchell) 11.10.2024 1:25:51
In this iconic episode, Gabrus ( High & Mighty ), Nick Wiger and Mike Mitchell ( Doughboys ) join Nicole fresh off a power-hour to discuss how they would want to die, their favorite sex positions, and if they're into ass play. They also answer audience questions about post-sex snacks, favorite porn genres, and their craziest sex stories. Plus, Nicole helps officiate a live marriage proposal. W...
BEST OF: Proposal Gone Wrong (w/ Paul Scheer) 04.10.2024 1:04:03
While we're on hiatus, we're revisiting one of Nicole's favorite episodes! Comedian and actor Paul Scheer ( The League , Black Monday ) joins Nicole to chat about how his proposal to June Diane Raphael went terribly wrong, how June's wedding ring was stolen from her finger, and why you should never propose in a hot air balloon. June sits nearby, fact-checking Paul's s...
BEST OF: Same Guy Club (w/ Skyler Hurt) 27.09.2024 1:05:29
We’re bringing you the best of Why Won’t You Date Me? —completely ad-free! In this episode, Nicole is joined by Skyler, who she met on Tinder. Things got awkward quickly when they realized they dated the same man. Nicole asks Skyler why she swiped right, why they kept dating despite Nicole's smoking, and whether she would’ve still gone out with her if she didn’t know about her work. And finally, S...
BEST OF: Getting Paid for Sex (w/ Meatball and Big Dipper) 20.09.2024 1:03:39
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...
BEST OF: Booty Call Horror Story (w/ Jameela Jamil) 13.09.2024 1:00:39
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 whywonty...
A lil update from Nicole 12.09.2024 0:36
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...
Dating Michael Jordan, Larry David, and a $6K Dating App Fail (w/ Garcelle Beauvais) 06.09.2024 55:49
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. ...
Dating Scraps (w/ Riki Lindhome) 30.08.2024 54:24
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...
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