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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

00:59:41

Proposing is So Weird! (w/ Mo Welch)

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

2025/02/21

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 She dives into LA’s tight-knit lesbian scene, questions why society clings to outdated proposal traditions, and pitches her take on improving Love Is Blind.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:

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01:04:39

How Your Attachment Style Predicts Your Dating...

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

2025/02/14

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,

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01:08:35

THE LOST EPISODE (w/ Bobby Moynihan)

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

2025/02/07

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

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00:50:02

Dating as a Child Star, Proposing Naked (w/ Josh Peck)

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

2025/01/31

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

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01:01:38

Hygiene Horror Stories: Mud Butt Mishaps (w/ Siobhan...

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

2025/01/24

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

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01:00:21

Matching Your Silly (w/ Eugene Cordero)

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

2025/01/17

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 subject line "Dirty Message" and Nicole may read it in a future

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00:59:12

Left by my Fiancé, Relationship OCDs (w/ Allison Raskin)

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

2025/01/10

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

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01:08:16

A Naked Proposal (w/ Jimmy Kimmel)

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

2025/01/03

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

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00:45:18

Loving Your Pregnancy (w/ Lennon Parham)

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

2024/12/27

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 whywontyoudatemepodcast@gmail.com with the subject line "Dirty Message" and Nicole may read it in a future

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01:22:34

Ho Ho Ho, Sonic is Here! A Sonic The Hedgehog Holiday...

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

2024/12/20

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, genuine 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

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00:57:11

How to Cover Up Stinky Shits From Your Partner (w/...

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

2024/12/13

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

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01:08:21

Saying 'I Love You' Too Soon (w/ Sam Sanders)

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

2024/12/06

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 of Joker: Folie à Deux.Watch this episode on YouTube at youtube.com/watch?v=HeF1X9XIj6M This

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00:45:12

Cheesy Anniversaries (w/ Alex Moffat)

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

2024/11/29

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 comedy show, being an acrodunker for the Chicago Bulls, and shares some of the worst dating advice

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01:08:05

NickKroll Byer (w/ Nick Kroll)

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

2024/11/22

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-e7w. See Red One, in theatres today! Write to Nicole! Send your dirty messages to

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00:54:46

Validate Bisexuality (w/ Sherry Cola)

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

2024/11/15

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 Nicole may read it in a future episode. Sponsors: Uncommon Goods: To get 15% off your next gift, go to

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00:58:39

We Met Playing Call of Duty (w/ Sarah Silverman)

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

2024/11/08

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.

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00:56:24

Men Who Lie About Their Height (w/ Lauren Lapkus)

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

2024/11/01

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 Nicole! Send your dirty messages to whywontyoudatemepodcast@gmail.com with the subject line "Dirty

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00:45:21

BEST OF: How to Hack Into Your Partner's Phone (w/...

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

2024/10/25

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, exactly how to do it. We're starting a YouTube channel! Subscribe at youtube.com/@WhyWontYouDateMePodcast for upcoming full

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00:58:35

BEST OF: Being a Single Mom of 3 (w/ Francesca Amber)

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

2024/10/18

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 counts down the days until her dick appointment.Originally aired on July 16, 2021. We’re launching a YouTube channel

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01:25:51

BEST OF: Top or Bottom? (w/ Jon Gabrus, Nick Wiger,...

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

2024/10/11

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.We now have a YouTube! Subscribe here for upcoming full length video podcast episodes. Listen to the

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