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
Being 'In Like' vs Being 'In Love' (w/ Gabrielle Dennis) 17.03.2023 56:01
Comedian and actress Gabrielle Dennis ( A Black Lady Sketch Show, Luke Cage ) chats with Nicole her philosophy as to why falling "in like" with your partner is more important than being in love, opens up about her experience dating a pedophile, and her love for writing Yelp reviews. Plus, the story of the murdering Disney dad. See a live recording of Why Won't You Date Me?! April 5th in Los Ang...
Mormon and Closeted (w/ Bridger Winegar) 10.03.2023 53:56
Writer Bridger Winegar (host of I Said No Gifts! ) joins Nicole to discuss his experience being closeted to himself until the age of 26, being raised Mormon, and the thrill of setting people up on dates. Nicole reads some nasty messages she's received from the Bahamas. Write to Nicole! Submit your dirty pick-up lines, dating stories, or questions to whywontyoudatemepodcast@gmail.com for a chanc...
Marrying Your High School Sweetheart (w/ Adam Pally) 03.03.2023 54:55
Comedian Adam Pally ( 101 Places to Party Before You Die, Who Invited Charlie? ) chats with Nicole about why an easy relationship is a often sign of a good one, marrying his high school sweetheart, and how the both of them broke Steve Harvey on the set of Celebrity Family Feud . Plus, what's it like filming with Sonic the Hedgehog? Nicole is dying to know. Write to Nicole! Submit your dirty pic...
Being The Only One Left (w/ Michael Cruz Kayne) 24.02.2023 57:17
Comedian Michael Cruz Kayne 's dating strategy involves being the only guy left available. He joins Nicole to explain the approach and the success that's come with it. They also discuss how race affects relationships, moving on from them, and his experience getting hit on by the rich kids and moms he was private tutoring. Nicole wishes she was a ~woman~. Season 2 of A Good Cry returns March 9th....
Dating a Groupie (w/ Steph Tolev) 17.02.2023 55:22
Comedian Steph Tolev joins Nicole to discuss what it's like to date a groupie, getting matching tattoos with her partners, her experience dating a 60 year old, and shares SOOO many crazy awful dating stories. Plus, is it weird if your parent keeps in touch with your ex? The answer is YES. Write to Nicole! Submit your dirty pick-up lines, dating stories, or questions to whywontyoudatemepodcast@gm...
Having Sex On-Camera (w/ Jordan Firstman) 10.02.2023 58:44
Comedian Jordan Firstman ( Big Mouth, Ms. Marvel ) joins Nicole to talk about his experience being involved in a threesome where everyone had COVID, having real sex on-camera for a movie, and finding love in Berlin after a drug-fueled bender. Plus, Nicole shares why sucking dick is so joyful. Disclaimer: This episode contains discussion of homophobia, including some strong language, such as the...
Celibate for 18 Years (w/ Debra DiGiovanni) 03.02.2023 57:30
Comedian Debra DiGiovanni joins Nicole to discuss her experience being single and celibate for 18 years, importing her current boyfriend, and shares what it was like to date a feeder. Write to Nicole! Submit your dirty pick-up lines, dating stories, or questions to whywontyoudatemepodcast@gmail.com for a chance to have it read on-air. Black Lives Matter. Click here for an updated list of ove...
Nicole's Boyfriend Speaks His Truth (w/ Dan Black) 27.01.2023 1:06:02
In January, Nicole shocked the world with an Instagram post announcing her relationship with comedian Dan Black . On this episode, Dan joins Nicole to respond to some of the comments they've received about their relationship, discuss their kinks, and reflect on their decision to hard launch the relationship. Write to Nicole! Submit your dirty pick-up lines, dating stories, or questions to whyw...
The Sex Lives of Artists (w/ Ilia Isorelýs Paulino) 20.01.2023 1:07:32
Actress Ilia Isorelýs Paulino ( The Sex Lives of College Girls ) joins Nicole to chat about her sex life at Yale, being 6′2, growing up brainwashed by her pastor dad, and Curvy Wife Guy's new rap career. Write to Nicole! Submit your dirty pick-up lines, dating stories, or questions to whywontyoudatemepodcast@gmail.com for a chance to have it read on-air. Black Lives Matter. Click here for a...
Pandemic Divorce (w/ Punkie Johnson) 13.01.2023 57:34
Comedian Punkie Johnson ( SNL ) joins Nicole to discuss how the pandemic lead to her divorce, learning to love her partner's ugly feet, and tiddy pain. Nicole reports on the unhappy couples she witnessed while in the Bahamas. Write to Nicole! Submit your dirty pick-up lines, dating stories, or questions to whywontyoudatemepodcast@gmail.com for a chance to have it read on-air. Black Lives Mat...
Stories from Nicole's Road Dog (w/ Christi Chiello) 06.01.2023 1:03:43
Comedian and Nicole's opener Christi Chiello joins the podcast to discuss having 5 of her ex-boyfriends come out as gay, why theatre kids are so horny, and crazy stories from touring together. Nicole reminisces about the time she fell down a man's staircase. Write to Nicole! Submit your dirty pick-up lines, dating stories, or questions to whywontyoudatemepodcast@gmail.com for a chance to have it...
Living Your Hoe Phase (w/ Atsuko Okatsuka) 30.12.2022 58:24
Comedian Atsuko Okatsuka returns! She chats with Nicole about dating her community college teacher for 7 years, exploring the world of swing parties, and discusses whether hoe phases are overrated. Write to Nicole! Submit your dirty pick-up lines, dating stories, or questions to whywontyoudatemepodcast@gmail.com for a chance to have it read on-air. Black Lives Matter. Click here for an upda...
Eloping on Christmas (w/ Manila Luzon) 23.12.2022 1:01:42
Drag queen legend Manila Luzon ( Drag Race S3, All-Stars 1 & 4, Drag Den ) joins Nicole to discuss her Christmas Eve eloping in Las Vegas, dating after mourning the loss of her boyfriend Sahara Davenport, and some of the most iconic moments from her seasons of Drag Race. For more drag queen interviews, check out our episode playlist on Spotify: bit.ly/wwydmdrag Write to Nicole! Submit yo...
Let's Talk About The Bag Dress (w/ LaLa Ri) 16.12.2022 57:39
On Drag Race , Nicole guest judged one of the most iconic outfits in franchise history - LaLa Ri's gift bag dress . Today, Nicole finally sits down with the queen to express her thoughts that never made it to air. LaLa introduces Nicole to BLK, a Black version of Tinder, and shares the crazy sexual requests she gets from fans on Grindr. Nicole goes to the LA Auto Show for some dick. Write to N...
The First Black Chippendale Dancer (w/ Quentin Plair) 09.12.2022 59:04
Actor Quentin Plair ( Welcome to Chippendales ) chats with Nicole about the fetishization faced with being the first Black Chippendales dancer, the empowering nature of stripping, and whether playing football or dancing attracts more women. Want to write to Nicole? Submit your dirty pick-up lines, dating stories, or questions to whywontyoudatemepodcast@gmail.com for a chance to have it read on-...
How to Hack Into Your Partner's Phone (w/ Keke Palmer) 02.12.2022 43:59
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 us, in great detail, exactly how to do it. Crazy dating story? Looki...
Building Your Date's File (w/ Larry Owens) 25.11.2022 1:02:33
Multi-award winning actor and comedian Larry Owens ( A Strange Loop, Abbott Elementary ) chats with Nicole about his experience attending a bear festival, being the fixer-upper in a relationship, and the dangers of Googling someone after a first date. Plus, Larry teaches Nicole some complex new vocabulary. Crazy dating story? Looking for advice? Let Nicole and her guest help you out. Submit your...
Open Relationships (w/ Cole Escola) 18.11.2022 52:41
Comedian Cole Escola (Difficult People, Tuca & Bertie) helps Nicole craft the perfect answer for dating app small talk, shares the secret to their successful 3 year open relationship, and the terrible time they had taking a Tinder date to Paris. Plus, Nicole learns about the new dating app "The League", which costs $99 a WEEK! Black Lives Matter. Click here for an updated list of over 100...
Nicole's Kicked off Hinge (w/ Julie Klausner) 11.11.2022 59:19
Comedian Julie Klausner ( Billy on the Street, Difficult People ) chats with Nicole about the corny messages she gotten from dating apps, why Nicole was kicked off Hinge, and whether or not Nicole would've met the love of her life at Heidi Klum's Halloween party. Plus, they discuss their favorite New York restaurants. Black Lives Matter. Click here for an updated list of over 100 different th...
Set Up (w/ Aimee Carrero) 04.11.2022 1:09:08
Actress Aimee Carrero ( She-Ra, Elena of Avalor ) joins Nicole to discuss hookup hygiene standards, marrying the man she was set up with, and running into her ex on his honeymoon. Also, Nicole snatches a baby. We're nominated for a People's Choice Award! Cast your vote for Why Won't You Date Me everyday until Nov 7th. Vote at bit.ly/PCAVOTE2022. Black Lives Matter. Click here for an updated l...
Self-Sabotaging your Relationships (w/ Caleb Hearon) 28.10.2022 51:45
Comedian Caleb Hearon ( Human Resources ) joins Nicole to discuss self-sabotaging relationships, dating while still in the closet, and an awful date he went on at a Chipotle. Meanwhile, Nicole plans to fly to Houston for some dick. We're nominated for a People's Choice Award! Cast your vote for Why Won't You Date Me everyday until Nov 7th. Vote at votepca.com/pop-culture/the-pop-podcast-of-2022....
Playing an Extra in a Porno (w/ Rose Dommu) 21.10.2022 57:27
Writer Rose Dommu (Out Magazine, Like a Virgin podcast) joins Nicole to chat about the story behind her transition, the dangers of dating a trans chaser, writing fan fiction, and her experience appearing as an extra on the set of a Cock Destroyers porno. Plus, they answer a listener's question about how to respond to someone when they say call themselves fat. Got a dirty message, question, or co...
Rewriting the Tinder Bio (w/ John Stamos) 14.10.2022 52:38
Actor and heartthrob John Stamos ( Full House, You, Big Shot ) is here to figure out the core of Nicole's dating issues. Stamos tells the story of how he met his wife while acting together on Law & Order: SVU, shares his favorite memories of Bob Saget, and rewrites Nicole's dating app bio. Plus, Nicole continues to match with some wackos on Tinder. Black Lives Matter. Click here for an upd...
Praise Kink (w/ Jujubee) 07.10.2022 1:02:52
Iconic drag queen Jujubee ( Drag Race S2, All-Stars 1 and 5 ) joins Nicole to reminisces over her many seasons of drag competitions, her sobriety, playing a matchmaker, and having a praise kink. For more drag queen interviews, check out our episode playlist on Spotify: bit.ly/wwydmdrag Black Lives Matter. Click here for an updated list of over 100 different things you can do to support racial...
Sex Contracts (w/ Guy Branum) 30.09.2022 1:03:30
Comedian Guy Branum ( Billy On The Street, Bros ) chats with Nicole about establishing sex contracts before a hookup, being a dom/sub in the bedroom, and the perfect sized bed for sleeping with your partner. Black Lives Matter. Click here for an updated list of over 100 different things you can do to support racial justice. Follow Nicole Byer: Twitter: @nicolebyer Instagram: @nicolebyer Me...
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