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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

00:44:01

The 90 Day Fiancé Interview (w/ Alex Roshon)

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

2024/05/31

Relationship therapist and star of 90 Day Fiancé: Love in Paradise, Alex Roshon, is here to answer all of Nicole's burning relationship questions. What's it like to apply for 90 Day Fiancé? What's her foolproof method for approaching someone for a threesome? Alex shares her terrible dating stories that led her to date overseas, and her experience dating a man who loved to wear women's panties. Nicole tries to find love at the Sonic The Hedgehog-themed cafe.Follow Nicole Byer: Twitter:

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00:51:27

Interview with a MILF from MILF Manor (w/ Crystal)

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

2024/05/24

This season of MILF Manor takes a wild turn as MILFs date young men and their fathers at the same time. Nicole sits down with MILF and celebrity makeup artist Crystal Jennings to discuss how she got cast on MILF Manor, her preference for dating younger men versus their fathers, and to answer all of Nicole's burning questions about the show. Plus, she shares her expert sex tips for giving 'pornstar head.'

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00:58:57

The Hookup Queen (w/ Mistress Isabelle Brooks)

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

2024/05/17

Drag queen Mistress Isabelle Brooks (Finalist of RuPaul's Drag Race S15) joins Nicole to discuss her dating life as 'The Hookup Queen,' their body counts, and what she items she stole from the set of Drag Race. Mistress shares the story of the time she broke her ankle on stage in front of 1000 people. Nicole remains horny. For more drag queen interviews, check out our episode playlist on Spotify: bit.ly/wwydmdragFollow Nicole Byer: Twitter: @nicolebyerInstagram: @nicolebyerMerch:

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00:55:01

Love in Theater (w/ Jesse Tyler Ferguson)

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

2024/05/10

Actor Jesse Tyler Ferguson (Modern Family) joins Nicole to share his proposal story and how it was hilariously overshadowed by Sofía Vergara. They chat about food as a love language, their shared love for musical theatre, and the aftermath of the "Take Me Out" Broadway show nude leak. Jesse reflects on the challenges of working on Modern Family during a time when there were no gay writers. Plus, the wild story of getting hit by an accidental squirting.Watch this episode here:

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00:55:27

Forever Single Friends (w/ Jessica Gao)

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

2024/05/03

Writer Jessica Gao (She Hulk: Attorney at Law, Rick & Morty) joins Nicole to discuss male friends who are "single for a reason", the pressures of dating in the Chinese culture, people sticking in bad relationships in order to avoid dating again, and how hormones from an IUD can significantly affect your attraction levels. Plus, she shares her experience writing Rick and Morty's iconic 'Pickle Rick' episode, and the targeted backlash she received from fans. Follow Nicole Byer: Twitter:

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00:54:15

Catfished! (w/ Kamie Crawford)

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

2024/04/26

Kamie Crawford (Host of Catfish: The TV Show) joins Nicole to explore the most bizarre catfishing schemes she's witnessed, and reveals the tricks catfish use to deceive you. She shares how being crowned Miss Teen USA immediately affected her dating life in a creepy way, and discusses her frustrating experiences as a plus-size model. Follow Nicole Byer: Twitter: @nicolebyerInstagram: @nicolebyerMerch: podswag.com/datemeNicole's book: indiebound.org/book/9781524850746

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00:51:56

Winning a TV Dating Show (w/ Craig Conant)

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

2024/04/19

Comedian Craig Conant joins Nicole to discuss how sleeping with a chucklefucker led to him to become a baby daddy, his experience winning MTV's hit dating show "Next", and having sex at the movies on a first date. Plus, his many tales of farting on authority.Check out Craig's tour dates here: www.craigconant.com/#tour

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00:53:09

Dating as an Olympian (w/ A'ja Wilson)

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

2024/04/12

WNBA superstar and Olympic gold medalist A'ja Wilson joins Nicole to discuss how her 6'4" height shapes her dating experiences, what it's like to be single and mingle amongst Olympians, and the special treatment of being a WNBA icon. Meanwhile, Nicole is enjoying her own singledom. Check out A'ja's new book, Dear Black Girls, wherever books are sold. Follow Nicole Byer: Twitter: @nicolebyerInstagram: @nicolebyerMerch: podswag.com/datemeNicole's book: indiebound.org/book/9781524850746

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00:52:51

A Partner to Invest In (w/ William Stanford Davis)

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

2024/04/05

Comedian William Stanford Davis (Abbott Elementary) joins Nicole to share how he met his wife in an improv class, the unique dynamic of her managing his career, and the importance of finding a partner who truly invests in you. William also offers a glimpse into his unconventional teenage years DJing in adult clubs and reflects on his experiences with segregation growing up. Follow Nicole Byer: Twitter: @nicolebyerInstagram: @nicolebyerMerch: podswag.com/datemeNicole's book:

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00:48:33

Addicted to Love (w/ Moshe Kasher)

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

2024/03/29

Comedian and writer Moshe Kasher chats with Nicole about being a ho, going to a 12-step program for sex addicts, and his experience going through therapy 8 days a week. Plus lots of dating horror stories, including the tale of the biting blowjob.Follow Nicole Byer: Twitter: @nicolebyerInstagram: @nicolebyerMerch: podswag.com/datemeNicole's book: indiebound.org/book/9781524850746

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00:54:08

Meeting Singles in the Wild (w/ Franchesca Ramsey)

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

2024/03/22

Comedian Franchesca Ramsey (iCarly) joins Nicole to discuss what she's learned after going through an expensive divorce, finding singles in the wild, queer speed dating, and how dogs can sense when the end of a relationship is coming. Nicole tries to flirt with an older man on a bike.Check out Franchesca's new podcast, Black History, For Real.Follow Nicole Byer: Twitter: @nicolebyerInstagram: @nicolebyerMerch: podswag.com/datemeNicole's book: indiebound.org/book/9781524850746

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00:55:56

Love is In the Air (w/ Zach Woods)

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

2024/03/15

Comedian Zach Woods (Silicon Valley, The Office, In The Know) joins Nicole to discuss shooting your shot with your crush, having vulnerably romantic encounters on airplanes, and the time he professed his love to a recording of Moonlight Sonata. Plus, Nicole receives a very special "dirty message" to the podcast. Stream In The Know, on Peacock. See Nicole's in episode 3!Follow Nicole Byer: Twitter: @nicolebyerInstagram: @nicolebyerMerch: podswag.com/datemeNicole's book:

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00:50:53

Roommate Sex Drama (w/ Asha Ward)

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

2024/03/08

Comedian and writer Asha Ward (SNL) joins Nicole to share her wild roommate sex drama, reflects on being raised by a gay dad, having her first kiss after karate lessons, and discusses the dynamics of having 'fuckboy' energy. Follow Nicole Byer: Twitter: @nicolebyerInstagram: @nicolebyerMerch: podswag.com/datemeNicole's book: indiebound.org/book/9781524850746

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00:58:48

The Art of Kissing (w/ LU KALA)

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

2024/03/01

Musician LU KALA joins Nicole to discuss why the dating world feels so broken after COVID, the skill behind a good kiss, planning what should happen to your sex toys when you die, the stigma around dating a plus sized woman, and roleplay flirting with each other. Plus, Nicole receives an unexpected large black dildo to her door. Check out LU KALA's new single, Looking for Love. Nicole has a new crowd working special! Watch it on YouTube. Follow Nicole Byer: Twitter: @nicolebyerInstagram:

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00:46:48

Proposals (w/ Rory Scovel)

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

2024/02/23

Comedian Rory Scovel joins Nicole for a chat about their Valentine's Day experiences, dealing with horny audience members, his cute proposal story, and the ways parenthood has transformed his relationship dynamic. Nicole shares her fun time smoking weed before performing. Check out his special, Rory Scovel: Religion, Sex and a Few Things In Between, on Max. Nicole has a new crowd working special! Watch it at youtu.be/OMrZshGJORg?si=5de666DSXrnlKfBU Follow Nicole Byer: Twitter: @nicolebyerInstagram:

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01:04:14

Dating with Anxiety (w/ Lamar Woods)

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

2024/02/16

Comedian Lamar Woods (New Girl, Grand Crew) joins Nicole to discuss their 2024 vision boards, taking yourself on self care dates, the best ways to manage anxiety while dating, and how to be open about your sensitivities to a potential partner. Check out Lamar's new album, Highly Sensitive Person at lamar-woods.com. Write something dirty to Nicole! Submit it to whywontyoudatemepodcast@gmail.com for a chance to have it read on air. Nicole has a new crowd working special! Watch it at

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00:59:26

Valentine's Day (w/ Laurie Kilmartin)

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

2024/02/09

Comedian Laurie Kilmartin (Conan) joins Nicole to discuss all things Valentine's Day - the gifts, their dream dates, and Nicole's regrettable Valentine's Day experience. They open up about their most regretful hookups, the time Laurie's date called her out in a YouTube comment, and Nicole's experience sleeping with a member of her audience.Write something dirty to Nicole! Submit it to whywontyoudatemepodcast@gmail.com for a chance to have it read on air. Follow Nicole Byer: See Nicole live! Tickets

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00:56:04

Singles Mixers (w/ Rashida "SHEEDZ" Olayiwola)

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

2024/02/02

Comedian Rashida "SHEEDZ" Olayiwola (Jury Duty) joins Nicole to discuss the best places to go for singles mixers, the time she learned her date was homeless, and the struggle of finding men who can listen to your basic needs. Plus, Nicole realizes her birth control is making her depressed. Write something dirty to Nicole! Submit it to whywontyoudatemepodcast@gmail.com for a chance to have it read on air. Follow Nicole Byer: Twitter: @nicolebyerInstagram: @nicolebyerMerch: podswag.com/datemeNicole's

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00:59:38

Faking Orgasms (w/ Stavros Halkias)

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

2024/01/26

Comedian Stavros Halkias (Fat Rascal, Stavvy's World) joins Nicole to discuss hooking up with audience members, why he believes he would be perfectly cast for 90 Day Fiancé, and faking an orgasm during a disgusting fling just to be polite. Plus, is the golden age of dating apps over? According to Bustle, it is. Write something dirty to Nicole! Submit it to whywontyoudatemepodcast@gmail.com for a chance to have it read on air. Follow Nicole Byer: Twitter: @nicolebyerInstagram: @nicolebyerMerch:

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01:01:48

Heartbreak at Homecoming (w/ Garrick Bernard)

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

2024/01/19

Comedian and writer Garrick Bernard (Rick & Morty, Solar Opposites) joins Nicole to discuss finding love at BuzzFeed, the awkwardness of audience members hitting on him while on stage, and why homecoming was the worst day of his life. Plus, they explore their mutual obsession for cars. Vroom vroom! Write something dirty to Nicole! Submit it to whywontyoudatemepodcast@gmail.com for a chance to have it read on air. Follow Nicole Byer: Twitter: @nicolebyerInstagram: @nicolebyerMerch:

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