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
Chased by the KKK (w/ Brandon Kyle Goodman) 23.09.2022 1:10:16
Actor and writer Brandon Kyle Goodman (Netflix's Big Mouth, Human Resources ) chats with Nicole about the time he was chased by the KKK, the struggles of doing a long distance relationship, and the adorable first date story with his husband, and saving money by getting married at the courthouse. Black Lives Matter. Click here for an updated list of over 100 different things you can do to support...
Comedy Dominatrix (w/ Nori Reed) 16.09.2022 59:49
Comedian and writer Nori Reed ( Raven's Home ) chats with Nicole about getting her breast augmentation, how she soft-launched her transition process, and what it's like being a comedy dominatrix. Plus, Nicole continues to beef with Magic Mike Live . Black Lives Matter. Click here for an updated list of over 100 different things you can do to support racial justice. Follow Nicole Byer: Twitt...
A Halloween Wedding (w/ Mary Holland) 09.09.2022 1:06:42
Friend and comedian Mary Holland ( Corked podcast) chats with Nicole about having a spooky Halloween themed wedding under a blue moon, managing her codependency in a relationship, and her time working as a wench at Medieval Times. Plus, Nicole shares her first time trip to Disneyland. Black Lives Matter. Click here for an updated list of over 100 different things you can do to support racial...
Relationship Baggage (w/ Justin Cunningham) 02.09.2022 59:31
Actor and co-star Justin Cunningham ( Grand Crew ) chats with Nicole about recognizing toxic relationships, finding a partner who has a mutual respect for your baggage, and how his selective erectile dysfunction has become a indicator of true compatibility with a mate. Black Lives Matter. Click here for an updated list of over 100 different things you can do to support racial justice. Follo...
The Art of Online Stalking (w/ Sona Movsesian) 26.08.2022 1:03:17
Conan's assistant, Sona Movsesian (author: The World’s Worst Assistant ) is here! Sona shares how she met her husband at Comic-Con, the art of online stalking a date, giving your number to your waiter, and dating guys who just wanted to get close with Conan. Plus, Nicole pitches her new business idea: Rent-A-Baby . Black Lives Matter. Click here for an updated list of over 100 different things...
Throupled (w/ Mae Martin) 19.08.2022 59:58
Comedian Mae Martin ( Feel Good ) chats with Nicole about being in a throuple relationship, their experience addicted to drugs, and starting a fresh life in new country. Plus, they share their changing theory on love and relationships, and why they were kicked off Hinge. Black Lives Matter. Click here for an updated list of over 100 different things you can do to support racial justice. Fol...
Dealing with FBoys (w/ Nikki Glaser) 12.08.2022 1:05:00
Comedian Nikki Glaser ( FBoy Island, Good Clean Filth ) chats with Nicole about being in a 9 year on-and-off again relationship, how to deal with an FBoy, why men struggle to express their feelings, and offers tips on how to attract a 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: @...
Hired a Matchmaker (w/ Amy Aniobi) 05.08.2022 1:05:03
Writer/director Amy Aniobi ( Silicon Valley, 2 Dope Queens ) joins Nicole to discuss her experience dating with the help of a professional matchmaker, what it was like being raised by parents of an arranged marriage, and making the mistake of posting your significant other on Instagram. Nicole has injured herself singing karaoke. Black Lives Matter. Click here for an updated list of over 100 di...
Dating a Mom (w/ Lil Rel Howery) 29.07.2022 54:22
Comedian Lil Rel Howery ( Get Out , Keepin' It Rel with Young Wayne podcast) chats with Nicole about dating a single mom of 4, getting thrown off a horse on a date, matching with Lizzo on Raya, and shares his tips on how to hit on women at bars. Black Lives Matter. Click here for an updated list of over 100 different things you can do to support racial justice. Follow Nicole Byer: Tour Da...
Main Character Energy (w/ Willow Pill) 22.07.2022 1:13:20
Reigning drag queen Willow Pill (winner of RuPaul's Drag Race S14 ) is here! She chats with Nicole about selling mushrooms as a pandemic side hustle, her thoughts on the iconic catchphrase RuPaul gave her on the show, and partying with fans while tripping on Molly. Plus they celebrate her iconic win being the first disabled person to win Drag Race, and Willow discusses the toxicity of hustle cultu...
The Story of a Kissless Virgin (w/ Benton Ray) 15.07.2022 50:02
Comedian Benton Ray is a kissless virgin. He chats with Nicole about the circumstances of this choice, they learn new terms for different sexual orientations, and what it means to go "basket shopping" for a partner. Plus, Benton matches with straight guys on Tinder? There's a lot to unpack here. Black Lives Matter. Click here for an updated list of over 100 different things you can do to suppo...
Bringing Down Your Walls (w/ Penn Badgley) 08.07.2022 1:03:03
Oh my god, he's here. Penn Badgley (You, Gossip Girl, host of Podcrushed ) joins Nicole to discuss why people are infatuated by his serial killing character, why love is not depicted accurately in media, bringing down your walls to connect with people, and the existential insecurities he had when dating. Black Lives Matter. Click here for an updated list of over 100 different things you can do t...
Caught Cheating... Twice! (w/ Ketra Long) 01.07.2022 1:00:03
Comedian Ketra Long joins Nicole to tell the story about how she got caught cheating twice in her relationship. She also shares the time she convinced Ne-Yo to come see her stand-up show, which she proceeded to absolutely bomb . Ketra teaches Nicole how she manages to get flown out of the country for expensive dates, plus talks about her first kiss and first fingering. This is a wild episode, fol...
A Stalking Ex-Boyfriend, a Gang Member, and a Gun (w/ Aaron Jennings) 24.06.2022 1:01:18
Co-star Aaron Jennings ( Grand Crew ) and Nicole discuss grade school romances, talking finances with your partner, the benefits of dating an older man, and that iconic Oscar #slap. Aaron shares a wild date story involving a stalking ex-boyfriend, a gang member, and a gun. Plus, Nicole's crazy neighbor pays her a visit at 3:00AM. For more Aaron Jennings, stream Grand Crew on Peacock, and the upc...
Having a Drama-Free Divorce (w/ Grasie Mercedes) 17.06.2022 1:02:18
Co-star Grasie Mercedes ( Grand Crew, Access Hollywood ) reflects on her 14-year relationship and the breakthrough she had in therapy which led to her divorce. They also discuss getting back into the dating scene at a later age, why white men love drinking milk, and what it means to Afro-Latina. Plus, Nicole shares her rave review for a Broadway show which featured many exposed dicks. Black Li...
Setting Yourself on Fire (w/ Vanity Jay) 10.06.2022 46:58
Stripper and exotic entertainer Vanity Jay chats with Nicole about all things stripping and sex work. She shares the complicated nature of dating both customers and strippers from clubs, the time she accidentally burned herself lighting her pussy on fire, and the challenges of dating a jealous partner. Plus, they help give advice to a listener seeking sex position recommendations for their partner...
Farting in Bed with your Lover (w/ Sudi Green) 03.06.2022 1:05:08
Comedian and writer Sudi Green ( SNL, I Love That For You ) joins Nicole to discuss their awkward encounters with celebrities, having baby fever, and farting in bed with your lover. Sudi shares a horrible hookup story where her partner was into "intense sex", but failed to preform. Nicole realizes she's horny for magic. Black Lives Matter. Click here for an updated list of over 100 different th...
Quit your Job (w/ Kornbread "The Snack" Jeté) 27.05.2022 1:08:47
Drag queen and reigning Miss Congeniality Kornbread "The Snack" Jeté ( RuPaul's Drag Race S14 ) joins Nicole for a live episode, where they discuss her favorite kind of dick, the bad jobs she had before drag, and the men in prison who are contacting Nicole. Then, they answer audience questions about their favorite sex toys, the weirdest compliment they've gotten on a date, and blowjob tips. For...
Keeping Relationships Off Social Media (w/ Raja Gemini) 20.05.2022 1:01:07
Drag queen icon Raja Gemini (winner of Drag Race S3) joins Nicole to discuss the stress of competing in the first all-winners season of RuPaul's Drag Race All Stars , why she keep her relationship off social media, and shares all of her firsts - first kiss, handjob, and relationship. Plus, the story of why they got fired from MAC cosmetics, and how meeting RuPaul lead them to a job working on Ame...
Coping With Anxiety (w/ Taylor Tomlinson) 13.05.2022 55:47
Comedian Taylor Tomlinson chats with Nicole about using Instagram to document her panic attacks, coping with anxiety, and the time she was accused for being a catfish. Meanwhile, Nicole slept with a man who thought Black people were aliens. Black Lives Matter. Click here for an updated list of over 100 different things you can do to support racial justice. Follow Nicole Byer: Tour Dates: li...
Married, but Living Apart (w/ Judy Gold) 06.05.2022 1:08:41
The hilarious Judy Gold joins Nicole to chat about the challenges of dating a therapist, her experience being selected as one of Time Out New York's Most Eligible Singles , the ethics of writing jokes about your partner, and the benefits of being married but living apart. Black Lives Matter. Click here for an updated list of over 100 different things you can do to support racial justice. F...
Do Men Not Like Funny Women? (w/ Drew Lynch) 29.04.2022 1:15:29
Comedian and friend Drew Lynch ( America's Got Talent S10 ) chats with Nicole about a harrowing bee incident they had together on tour, managing high levels of anxiety, and why female comics have such a hard time attracting men. Plus, Nicole's horny for emo Batman, and explains why she loves giving blowjobs so much. Black Lives Matter. Click here for an updated list of over 100 different things...
Left for my Best Friend (w/ Tika Sumpter) 22.04.2022 1:02:21
Actress Tika Sumpter ( Sonic The Hedgehog 1 & 2 ) recounts the times that boys have left her for her best friend, losing her expensive engagement ring, and meeting her partner on a Tyler Perry set. Nicole realizes she has abandonment issues, and campaigns to be cast in Sonic the Hedgehog 3. We're running low on dirty messages! Write Nicole something nasty and send it to whywontyoudatemepod...
Bisexual Erasure (w/ Stephanie Beatriz) 15.04.2022 1:07:35
Actress Stephanie Beatriz ( Encanto, Brooklyn Nine-Nine ) chats with Nicole about leaving a 9 year relationship, dealing with bisexual erasure, and explains the scam behind the cult-like Twin Flames dating platform. Nicole recounts her wild experience hosting the Critics' Choice awards. Crazy dating story? Looking for advice? Want to leave Nicole a dirty message? Submit it all to whywontyoudatem...
How to have a WAP (w/ Donnell Rawlings) 08.04.2022 1:04:28
Comedian Donnell Rawlings ( Chappelle's Show, Winning Time: The Rise of the Lakers Dynasty ) chats with Nicole about the powers of having a WAP, why successful Black women have the hardest time in relationships, being a throat goat, and hottest locations to meet new people. Meanwhile, Nicole gets her tiddy caught in a car window. Crazy dating story? Looking for advice? Want to leave Nicole a dirt...
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