Headgum & Nicole Byer

Why Won't You Date Me? with Nicole Byer

Society EN ↓ 457 episodes

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

Society

Podcast website

headgum.com

Latest episode

Jul 10, 2026

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Episodes

A lil update from Nicole: Best Friends is back! 30.07.2025

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 epis...

We Met on a Podcast (w/ Devon Walker) 25.07.2025

Comedian Devon Walker (SNL) joins Nicole to tell the story of how he met his girlfriend on a live blind date podcast. He figured it was just a bit - until the audience voted for them to win an Applebee’s gift card and that turned into their actual first date. 3 years later, they’re still together! He and Nicole also talk about the woman who went viral  eating 48 oysters on a first date , why...

Flirting, Open Relationships, and Almost Dying (w/ Josh Sharp) 18.07.2025

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-dea...

Nobody Wants to Date a Drag Queen (w/ Meatball) 11.07.2025

Drag queen icon Meatball is back! She and Nicole get into it all - being in her top era, loving the single life, and having weekend boyfriends in different cities. But also... why dating is still so hard when you do drag. Meatball opens up about losing guys the second they find out she’s a queen, and how frustrating it is watching her roster shrink because of it. And of course, the wild date stori...

We Dated?! (w/ Lou Wilson) 04.07.2025

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 with Dimension 20 , being a “silly billy” on dates, and the moment Lou realiz...

A Cruise Ship Romance with a Himbo (w/ Jessica Lowe) 27.06.2025

Actress  Jessica Lowe  ( The Righteous Gemstones, Minx ,  Wrecked ) joins Nicole to share the romantic saga of falling in love on a Second City cruise ship. On the ship, she met a British bassist who became her cruise ship boyfriend - whom she later realized wasn’t as smart as she thought his accent sounded (he tried to dry his pants on a ceiling fan and designed a nightmare de...

I Was a Time Out Magazine Bachelor (w/ Lauren Ashley Smith) 20.06.2025

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 l...

Love Triangle Gone Wrong (w/ Michael Urie) 13.06.2025

Actor Michael Urie ( Shrinking, Ugly Betty ) joins Nicole to discuss the wild hookup culture at Julliard, and the love triangle he had that went sour. Once he got fame from Ugly Betty, he starts going on dates with people who only seem interested in the version of him they saw on TV, until a second shot with actor Ryan Spahn turns into a 17-year partnership. He tells the story of a friend who died...

Skipping Love (w/ Betsy Sodaro) 06.06.2025

Comedian and friend Betsy Sodaro (Ghosts, A Funny Feeling ) joins Nicole to swap crazy Las Vegas stories, their experience getting slammed by puberty, and debate why we shouldn’t have to pay taxes right now (plus what happened when Nicole skipped paying taxes for 5 years). Betsy reveals what life was like spending six months in a hotel, and Nicole confesses she nearly launched an anime-recap podca...

Secretly Dating your Improv Coach (w/ Edi Patterson) 30.05.2025

Actress Edi Patterson ( The Righteous Gemstones ) joins Nicole to talk about falling in love with her improv teacher, hiding their relationship from the world, and mistaking his proposal for a joke. She opens up about being a late bloomer in dating, throwing house parties that felt straight out of a '90s film, and the one dating lesson she learned from a kid that she wishes everyone would follow....

Bizarre Relationships with Animals (w/ Rose McIver) 23.05.2025

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...

Bob Derails the Pod (w/ Bob the Drag Queen) 16.05.2025

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 sca...

The Male Loneliness Epidemic (w/ Drew Afualo) 09.05.2025

TikTok star Drew Afualo joins Nicole to share her enemies‑to‑lovers love story and the worst dates that taught her to trust her gut. She tells the time she dated a man who drank ocean water and ended up getting his stomach pumped, walks through her viral list of red flags in men, and the backlash she received online for sharing it. They dig into the male loneliness epidemic, red‑pill culture,...

Dating Around the World (w/ Colton Dunn) 02.05.2025

Comedian and Nicole's fictional boyfriend Colton Dunn ( Superstore, Grand Crew, Key and Peele ) joins Nicole to talk about dating customs in Europe (and what we can learn from them), getting mad at your partner over what they did in your dream, and what surprised him most about becoming a dad. He reflects on why improv might never be cool- even if you're good at it, and shares behind-the-scenes st...

Too Shy to Talk to People (w/ Owen Burke) 25.04.2025

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. Jo...

DIVORCED!!! (w/ Jackie Johnson) 18.04.2025

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,...

Childbirth Nightmares, Public or Private Proposal? (w/ Melissa Hunter) 11.04.2025

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...

The Funny Guy Trap (w/ Wayne Brady) 04.04.2025

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 st...

Chubby Chasers (w/ Jana Schmieding) 28.03.2025

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...

Oops, All Red Flags! (w/ Mariah Smith) 21.03.2025

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 iP...

Surviving Beergate & Escaping Trans-Chasers (w/ Dylan Mulvaney) 14.03.2025

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...

Coming Out (w/ Sasheer Zamata) 07.03.2025

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 get...

How to Pull Rich Men (w/ Robby Hoffman) 28.02.2025

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 t...

Proposing is So Weird! (w/ Mo Welch) 21.02.2025

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 s...

How Your Attachment Style Predicts Your Dating Disasters (w/ Dating Coach Sabrina Zohar) 14.02.2025

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 rec...

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