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
Sex and Love Addict (w/ Maria Bamford) 08.09.2023 59:36
Ever wondered what it's like getting intimate with a clown? Deep dive as comedian Maria Bamford (Arrested Development, Big Mouth) unravels her experiences as sex and love addict, the relationship tools she's learned in her 12 step programs, and her mental illnesses. Plus, for those seeking lasting love, Maria shares the 4 behaviors to avoid divorce. Follow Nicole Byer: See Nicole on tour! Get ti...
Feeling Safe in a Relationship (w/ Uzo Aduba) 01.09.2023 57:41
The Emmy-winning Uzo Aduba (Orange Is The New Black) chats with Nicole about how her dating app DMs changed after booking Crazy Eyes, finding love at a mixer, the deep connection between her personal grief and art, and the importance of honesty in relationships. Plus, Nicole fails to hit on a cashier. Recorded July 13th 2023. For more information on the SAG-AFTRA strike, see sagaftrastrike.org....
Nicole Eats a Banana from a Sex Worker's Pussy (w/ Naomi Rodgers) 25.08.2023 56:35
Broadway star Naomi Rodgers (Tina: The Tina Turner Musical) opens up about secretly dating her co-star while on tour, and offers advice how to grieve and get over a breakup. Nicole shares her latest European dating mishaps, including an unforgettable visit to the Red Light District. Follow Nicole Byer: See Nicole on tour! Get tickets at linktr.ee/nicolebyerwastaken Twitter: @nicolebyer Instagra...
300 Episodes of Why Won't You Date Me (w/ Sasheer Zamata) 18.08.2023 1:08:25
It's episode 300! But how is Nicole STILL SINGLE ? On this milestone occasion, she's joined by her best friend Sasheer Zamata (co-host of Best Friends) to get to the bottom of it. In this special retrospective, they explore: How Nicole's dating life has evolved with the podcast The highs and lows of her love life Their favorite dates they've been on The best dating advice they've received Their n...
Romancing Overseas (w/ Zurin Villanueva) 11.08.2023 1:03:55
Broadway superstar Zurin Villanueva (Tina: The Tina Turner Musical) joins Nicole for a discussion about the awkwardness of working together with a past hookup, safety precautions when dating abroad, and the best grocery store to find a good man. Plus, don't miss Zurin's recounting of a date gone awry when her phone rang, and on the other end? Her date's ex . Nicole wants to hear from you! Need...
Gay Orgies (w/ Jay Jurden) 04.08.2023 1:09:59
The hilarious comedian Jay Jurden joins Nicole to talk about his secret relationship with a frat boy, working at Abercrombie & Fitch during its peak era, the best app for threeways, and what goes on at a gay orgy. Plus, Nicole gets hit on by a 911 responder. Nicole wants to hear from you! Need some dating or relationship advice from Nicole and her guest? Submit your question to whywontyoudat...
Dating an Asexual (w/ Gigi Goode) 28.07.2023 1:47:09
Drag queen Gigi Goode ( Drag Race S12 ) joins Nicole for a supersized live episode of the podcast! They talk about her trans journey during the pandemic, how the type of people who are attracted to her has changed since transitioning, making friends through Tinder, and shares her experience being in a long term relationship with a partner who's asexual. She also tells just so many, bad, no awful,...
Mutual Ghosting (w/ Robin Fierce) 21.07.2023 1:04:42
Drag queen Robin Fierce ( Drag Race S15 ) LIP-SYNCS TO THIS VERY PODCAST! She talks about remixing Nicole's comedy in her drag performance, opens up about her relationship with Drag Race contestant Amethyst, shares the new subtle way to look for a sugar daddy on dating apps, and speaks out on how people are using Grindr for their own personal meet & greets. Robin gives us a exclusive look at...
Catfishing Men on Craigslist (w/ Bosco) 14.07.2023 54:27
Drag queen Bosco ( Drag Race S14 ) joins Nicole to discuss their long-term relationship with a fan, recounts her most enchanting full-day date, and tells how to spot chasers vs. genuine men. She shares how catfishing on Craigslist for attention ignited her trans journey, plus spills the tea on the severe highs, lows, and trauma shooting Drag Race . For more drag queen interviews, check out our...
Nicole Wins an Orgasm Contest (w/ Matteo Lane) 07.07.2023 41:52
Comedian and friend Matteo Lane returns to the podcast! They reminisce about his love life since his last episode, getting kicked off Grindr and Tinder for "catfishing" as himself, and why men are intimidated by successful women. Nicole wins the orgasm contest at the Thunder from Down Under Vegas show. Matteo hooks up with a dancer from Magic Mike. Plus, a whole lot more. Watch Matteo Lane's ne...
Tasteful Dick Pics (w/ Jermaine Fowler) 30.06.2023 39:57
Comedian & actor Jermaine Fowler (The Blackening) joins Nicole to reminisce on their time working on Guy/Girl Code, his joy of being a unexpected father, and discusses what makes a great dick pic. Nicole is now horny for them, but before you go sliding one into her DMs, she shares her criteria on how to take a tasteful pic. See Nicole Byer live on tour! Get tickets at nicolebyerwastaken.com....
Finding Your Confidence (w/ Jay Pharoah) 23.06.2023 1:02:00
Comedian Jay Pharoah ( Saturday Night Live ) dives into how a messy breakup ended up saving his SNL career, and the bizarre role Donald Trump played in his escape from a toxic relationship. Jay shares the impressions he's been asked to do during sex, and how developing self-confidence saved him from a bad situation. Plus, what's it like to have your photos used by a catfish? See Nicole Byer live...
Fake It Til You Make It (w/ Melvin Gregg) 16.06.2023 52:44
Comedian and actor Melvin Gregg ( Vine , American Vandal, The Blackening ) opens up about his unique romantic path, where pretending to be a couple turned into the real deal. He takes us on a trip down memory lane, tracing his roots from being a Vine sensation to earning the badge of an early verified Tinder user. Plus, he shares his pro tips on sealing the deal at the end of any date or encounter...
Transcending Norms (w/ TS Madison) 09.06.2023 1:03:53
Actress and activist TS Madison (judge on RuPaul's Drag Race ) is here for a heartfelt chat on her journey from being a viral TikTok sensation to a vocal advocate for trans rights, and all of the unseen struggles she faced in navigating systemic biases. She discusses doing sex work for survival, shares real examples of the transphobic harassment she receives to this day, and her relentless efforts...
Live Your Rom-Com Era (w/ Sam Taggart) 02.06.2023 55:46
Comedian Sam Taggart ( host of StraightioLab ) is here to spill some juicy insights on gay relationships and why they often swing open. Have you ever thought of Kevin James as a bear icon? Neither did Nicole, but Sam gives us a whole new perspective! He also tells the crazy story of a strange threesome he had with 2 cops from Boston. Plus, a candid chat about all things anal, and why we need to br...
Sugar Daddies (w/ Sugar & Spice) 26.05.2023 1:07:59
Twin drag queen icons Sugar & Spice ( RuPaul's Drag Race S15 ) join Nicole for a conversation about why you can't skirt around the law of attraction, to spilling the tea on the sugar baby lifestyle and how to shine as a high-value woman in today's dating scene. And if you've ever wondered what it's like for twins to audition for Drag Race, Sugar & Spice pull back the curtain on their journ...
Hot Porn Seaches (w/ Bridget Everett) 19.05.2023 1:00:56
The hilarious Bridget Everett ( Somebody, Somewhere ) joins Nicole to discuss the hot porn searches they've been into, the need for increased privacy on dating apps, Bridget's experience hooking up with a go-go dancer at a gay bar, and her stand-up routine where she has audience members motorboat her huge titties. Plus, the story about the woman whose breast implants started to grow mold. Write...
Monogamously Challenged (w/ Holly Robinson Peete) 12.05.2023 1:00:47
Actress Holly Robinson Peete ( 21 Jump Street , Queen's Court ) opens up about her experience being in a relationship with someone who is "monogamously challenged", dating around Paris in order to learn to speak French, and being very publicly proposed to on the set of Hangin' with Mr. Cooper by NFL quarterback Rodney Peete. Plus, the challenges single people now face in today's social media-drive...
Secrets To a Long, Loving Marriage (w/ John Leguizamo) 05.05.2023 48:04
Actor John Leguizamo ( Encanto, Moulin Rouge!, Ice Age ) chats with Nicole about his secrets to a long, loving marriage, how he balances work and relationships, and his efforts to boost Latin representation in media. Write something dirty 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. Follow Ni...
Lesbian Sex (w/ Ashley Gavin) 28.04.2023 59:00
Comedian Ashley Gavin (host of We're Having Gay Sex ) teaches Nicole all about lesbian sex and relationships. They cover scissoring and tribbing, having secret girlfriends in high school, and the details of her open relationship. Ashley also shares her experience being the first openly gay comedian on Carnival Cruise Line, and the homophobia she encountered on the job. Nicole witnesses a bouncer g...
"Don't Ask, Don't Tell" Poly Relationships (w/ Zoe Lister-Jones) 21.04.2023 1:04:26
Actress/writer/director Zoe Lister-Jones ( Slip ) shares her experience opening and closing her "don't ask don't tell" poly relationship, what she's learned after exiting a 17-year marriage, and delves into the empowering nature of "dating to fuck". Nicole really wants to crash the cool teen party down her block. Write to Nicole! Submit your dirty pick-up lines, dating stories, or questions to...
Staying Friends with your Ex (w/ James Marsden) 14.04.2023 1:14:31
Actor James Marsden ( Sonic The Hedgehog, Hairspray, Jury Duty ) joins Nicole to talk about his new singledom, remaining friends with all of his exes, his romantic side, and reviews Nicole's latest Tinder profile. Nicole teaches Marsden about bussies and scat porn. This episode was specially recorded in-person at Team Coco's studios. Thank you engineer Rich and the whole team for putting this t...
A Love Queen (w/ Sasha Velour) 07.04.2023 59:43
Drag queen icon Sasha Velour (winner of Drag Race S9 ) chats with Nicole about coming out to their dad at a TGI Fridays, the challenges of working with their boyfriend, and speaks out on the current backlash against drag. We just recorded a fabulous LIVE episode of Why Won't You Date Me with Gigi Goode! It's available on video on demand until April 19th. Stream it now at moment.co/dateme. Wri...
Why Won't You Go Get a Transvaginal Ultrasound? (w/ X Mayo) 31.03.2023 1:06:47
Comedian and writer X Mayo ( The Daily Show, American Auto, Swarm ) chats with Nicole about her success making friend connections on Raya, how she positively re-framed her outlook on dating, and her life changing experience shooting a nude scene in Swarm . Plus, a PSA on pussy health and why you should go get a transvaginal ultrasound. Write to Nicole! Submit your dirty pick-up lines, dating sto...
Marrying for Tax Purposes (w/ Jeff Hiller) 24.03.2023 59:46
Comedian and actor Jeff Hiller ( Somebody Somewhere ) reunites with Nicole to share how he met his husband on Chemistry.com, his experience acting on a reality TV dating show, and how a fight on Fire Island saved his marriage. Plus, Nicole reads the DM that lead her to deactivate a dating app. We're live streaming a new episode April 5th! See a live video recording of Why Won't You Date Me? w...
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