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
Having Tandem Sex (w/ Sasheer Zamata) 22.11.2019 1:39:34
"W hen you and your friend fuck at the same time, just in different places ". Best friend Sasheer Zamata ( SNL , Corporate ) shares the time her and Nicole tandem-fucked in Canada and why it was an awful experience for the both of them. Sasheer shares her first kiss story and the time she witnessed a coke bottle dick. Nicole's dog got stoned again. Also, an unfortunate update with Zach. Plus, a sp...
A Nightmare Wedding Experience (w/ Diona Reasonover) 15.11.2019 1:05:28
Diona Reasonover (NCIS, I Love You, America) shares her nightmare wedding experience which included a rear-end accident, a broken wrist, a typhoon, an ASOS wedding dress, and multiple wedding crashers. On top of that, she met her wife's parents for the first time at her wedding! She also shares her experience dating while she was a carnie, why she doesn't wear her engagement ring in the summer, an...
Why Everybody Needs Therapy (w/ Therapist John Kim) 08.11.2019 57:08
Licensed therapist John Kim (aka The Angry Therapist , author of I Used to Be a Miserable F*ck ) discusses the stigma stopping many PoC to join therapy, the challenges of being vulnerable as a therapist, and how long it takes to get over a breakup. Text John Kim at theangrytherapist.com You can play along and see Nicole's dating app profiles and photos on her Facebook at: https://www.faceboo...
Dating as a Virgin in your 30s (w/ Jake Kroeger) 01.11.2019 46:18
Dating in your thirties can be nightmarish. Jake Kroeger (Stand-up, The Comedy Bureau ) shares his experiences navigating the dating scene as a virgin, the cute story behind his first kiss at the age of 31, and his experience working with a professional matchmaker. Plus, Nicole reads an angry DM from a listener. Want Jake to take you on a comedy tour of LA? Book him on Airbnb: https://www.airbnb.c...
100 Episodes of Why Won't You Date Me (w/ Willam Belli) 25.10.2019 1:09:27
Wow, it has been 100 episodes of the podcast and Nicole Byer is still single. In this live anniversary, Willam Belli ( RuPaul's Drag Race, A Star is Born ) joins Nicole to discuss love, his open marriage, cocaine, sleeping in drag, their arrest warrants, among so much more. Willam also shares how he fought to get the cut drag scenes from A Star Is Born back into the film, and gossip about drag cul...
Overcoming Emotional Setbacks (w/ Echo Kellum) 18.10.2019 55:56
" Please acknowledge your pain ." Echo Kellum ( Arrow, Rick & Morty ) discusses overcoming life's pain after emotional trauma, controlling negative feelings, and his experience practicing abstinence as a Jehovah's Witness. They also discuss dream wedding locations, funerals, porn, and Nicole has a breakthrough- she's figured out what she's looking for in a partner. Check out Echo's SoundCloud:...
Managing Anxieties During Intimacy (w/ Dave Ross) 11.10.2019 53:36
" I would eat my ass for flavor, and you can quote me on that. " Dave Ross (stand-up, Suicide Buddies podcast) shares his experience performing at a sex club, the story behind his first handjob attempt, and how to manage anxiety when intimate. Plus, they discuss which body parts would be the tastiest to eat. Check out Dave's new special: The Only Man Who Has Ever Had Sex at http://sex.guns.beer Yo...
Crying Boys (w/ Laci Mosley) 04.10.2019 44:36
" All I want is a dick that is also a coat rack. " Laci Mosley (Florida Girls, Scam Goddess podcast) discusses reckless driving, which dating app has the cutest guys, and how she injured her clit masturbating. Plus, Nicole educates how to schedule a dick appointment. Go see Laci in The Wedding Year film. You can play along and see Nicole's dating app profiles and photos on her Facebook at: h...
Breaking Up (w/ Paul F. Tompkins) 27.09.2019 1:00:27
" I was at a point where I was like... I never sorta played the field and had fun. I'm gonna do that now. " Paul F. Tompkins ( Between Two Ferns: The Movie, Threedom podcast ) discusses how he met his wife, having fun in his thirties, and if you should break up over the phone. Plus, Nicole had sex and is very excited to share all about it. You can play along and see Nicole's dating app profiles an...
Dating Neurodiversity (w/ Sam Pancake) 20.09.2019 59:32
" He said, 'I'd rather be dead than how old YOU are.' " Things get real emotional in this episode. Sam Pancake ( Arrested Development , A Million Little Things ) discusses dating people on the spectrum, losing your partners to HIV, and agism in dating. Plus, Nicole's neighbor's kids are flying drones on her property, and she has a bone to pick with AMDA. Check out Sam Pancake's podcast - Monday Af...
Hooking up on Craigslist (w/ Atsuko Okatsuka) 13.09.2019 50:36
Atsuko Okatsuka (stand-up, Let's Go Atsuko! podcast) discusses living as an undocumented for 7 years, meeting people on Craigslist, and being fetishized for her ethnicity. Plus, Nicole Byer shares her experience sleeping with a Trump supporter who just wouldn't shut up. You can play along and see Nicole's dating app profiles and photos on her Facebook at: https://www.facebook.com/pg/NicoleBy...
Dating Someone with Commitment Issues (w/ Fortune Feimster) 06.09.2019 1:11:18
" You only get to cuddle if there's been penetration. " Fortune Feimster ( The Mindy Project, Chelsea Lately ) shares the cute story how she met her fiancee at Pride, how coming out late in life affected her confidence, and the string of people she's dated with commitment issues. Plus, her and Nicole also discuss their experience working with Steve Harvey, and Nicole shares a bad hookup she had wi...
Problematic Issues of Porn (w/ Erika Lust) 30.08.2019 1:06:55
"I would like to see films where women's pleasure is also in focus. Where it's important to the story that she is also having a good time." Erotic film director, screenwriter, and producer Erika Lust discusses the science behind what arouses us, the problematic issue behind "teen porn", porn's worst stereotypes, and her favorite porn bloopers. Plus, Nicole shares her ultimate porn fantasy. Why Won...
Married at 20 (w/ Ron Funches) 23.08.2019 55:16
" We stayed married for 7 years - and we should've never gotten married. " From the age of 20, Ron Funches ( Trolls, Giggle Fit, The Eric Andre Show ) was married with a son. He shares his struggles being in a committed relationship from a young age, and what it's like now re-entering the dating world with a son. He also shares the cute story how he mistook his current girlfriend for a robot on Bu...
Dating Dogs and Werewolfs (w/ Justin Simien) 16.08.2019 1:08:23
"When he came, did he go AWOOO?" Justin Simien (Creator of Dear White People ) joins Nicole to talk about the kinkiest thing he's ever done, teach her about gay "puppy-pack" arrangements, and Nicole shares a story about dating a werewolf. Plus, Nicole's dogs are eating her weed, and she expresses her thoughts on Logan Paul. Be sure to check out the new season of Dear White People on Netflix! You c...
The Joy of Being Alone (w/ Ashley Nicole Black) 09.08.2019 1:00:53
"I would love for Guy Fieri to narrate my sex" Ashley Nicole Black ( Full Frontal with Samantha Bee , A Black Lady Sketch Show ) joins Nicole to share her love of being alone, whether they like to play music during sex, and Nicole's dream anniversary date. Also, Ashley exclusively dated gay guys in high school, meanwhile Nicole's was asking her gay friend to help lose her virginity. Be sure to che...
Power-Bottom (w/ Monique Heart) 02.08.2019 1:08:09
" I thought I had contracted an STD where I was rotting from the inside " Drag queen Monique Heart ( RuPaul's Drag Race Season 10, All Stars Season 4) has never been in a real relationship. He shares his experiences with growing up in a religious upbringing, the girl he once wanted to marry, and his fear of the new wave of STDs. Also, they dive into their kinks and all the crazy public places they...
Making a Polyamorous Relationship Work (w/ DeRay Davis) 26.07.2019 50:33
DeRay Davis ( Snowfall , 21 Jump Street ) has lived a polyamorous relationship with 2 women for most of his life. He explains how he introduces it to his partners, how to show respect to the parents, and how they make their atypical relationship work. DeRay breaks the stigma on polyamorous relationships and shares how him and his partners live together, vacation together, and sleep together. Plus,...
A Boyfriend for Every Stage of your Life (w/ Jessica McKenna) 19.07.2019 1:04:55
Jessica McKenna ( Off Book podcast) has had a boyfriend in every stage of her life. She details the drama behind her middle school romance, to meeting boys in high school mock trial, and charming her current man with her Disneyland bathroom knowledge. Nicole shares a moment she had with a homeless man, and shares her story of sexual assault in public. You can play along and see Nicole's Tinder bio...
Microdosing (w/ Johnny Pemberton) 12.07.2019 54:01
" I thought I was going to die. I was actually laughing at the idea of living. " Johnny Pemberton ( 22 Jump Street, Superstore ) discusses taking LSD at Disneyland, and accidentally overdosing while trying to microdose. Meanwhile, Nicole's candy-flipping and wants to start microdosing shrooms. Plus, Nicole goes over some of her latest awkward dating app conversations, and Johnny suggests some new...
Nicole's Choice of Porn (w/ Ronnie Adrian) 05.07.2019 59:18
" I'm crazier than you. I'll fuck you up with these dildos " Ronnie Adrian ( Comedy Bang Bang , White Women ) joins Nicole to discuss their mutual struggle with flirting, and the best way to end a bad date with courtesy. Nicole shares her favorite porn videos to masturbate to, and calls out a woman for peeing on her toilet seat. You can play along and see Nicole's Tinder bio and photos on her Face...
The Opposite of a Meet-Cute (w/ Alice Wetterlund) 28.06.2019 1:00:03
Alice Wetterlund (Girl Code, Treks and the City podcast) joins Nicole to discuss their Girl Code tour horror stories, talk about men who claim to have dated celebrities (we're talking about YOU, Moby) and Alice's newfound interest in butt stuff. Plus, Nicole shares details on her new book deal! You can email Nicole at baconcansave@gmail.com. Nicole might respond if she's drunk. You can play along...
Top or Bottom? (LIVE w/ Jon Gabrus, Nick Wiger, and Mike Mitchell) 21.06.2019 1:25:01
Freshly drunk from a power-hour, Gabrus ( High & Mighty ), Nick Wiger and Mike Mitchell ( Doughboys ) join Nicole to discuss how they would want to die, their favorite sex positions, and if they like 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. Listen to the High...
How to Share Secrets on Drag Race (w/ Shangela) 14.06.2019 59:32
D.J. 'Shangela' Pierce ( RuPaul's Drag Race, A Star is Born ) discusses his struggles with dating, getting picked up by fans, and describes his perfect partner. Plus, Shangela shares how drag queen share secrets on the set of Drag Race, and who he's rooting to be cast on the next season. Be sure to check out Shangela's podcast, Shangela . For more drag queens on Why Won't You Date Me, check out ou...
Sleeping with DJs (w/ Greta Titelman) 07.06.2019 59:33
"What happens in Vegas, stays in Vegas... But not this ." Greta Titelman ( The Worst podcast) breaks the double-standard behind having sex on a first date, talks about their first masturbation stories, and what it's like to date and sleep with DJs. Nicole enlists Twitter to help her find a man she met in a shoe. You can play along and see Nicole's Tinder bio and photos on her Facebook page at:&nbs...
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