Headgum & Nicole Byer

Why Won't You Date Me? with Nicole Byer

Society EN ↓ 457 episodes

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

Society

Podcast website

headgum.com

Latest episode

Jul 10, 2026

Where to listen?

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Episodes

BONUS: The One That Got Away (w/ Blair Socci) 04.06.2019

Blair Socci (stand-up, The Blair & Greta Show) discusses what it's like to date an "influencer", how to have an amicable break up with your ex, and the pro/cons of dating comedians. Plus, Nicole reads your listener submitted stories about the one that got away! This bonus episode is brought to you by Netflix's Always Be My Maybe ! Watch it on Netflix now and in select theaters. Chicago!  ...

Having Sex in Drag (LIVE from DragCon 2019 w/ Vicky Vox) 31.05.2019

Drag queen Vicky Vox (DWV, Magic Mike XX L) joins Nicole to discuss having sex in drag, using AOL messenger to lose your virginity, and where to find the biggest dicks. Nicole had sex with a Canadian that left actual nuts in her pussy. She's also getting photos AirDrop'd to her by audience members. It's a real wild show. They also answer audience questions about fisting, taking a big dick, and the...

Dating in the 3rd Grade (w/ Beth Stelling) 24.05.2019

Beth Stelling ( Crashing , I Love You, America ) discusses the crazy things they learned in school, what it was like to have a 3rd grade boyfriend, how she met her current boyfriend doing stand-up. A fan threatens to sleep with Nicole, but doesn't follow through. Have a story about the one that got away?  Share it for a chance to be read on the podcast! You can email it anonymously to hey@hea...

How to Date Long Distance (w/ Demi Adejuyigbe) 17.05.2019

Demi Adejuyigbe ( The Late Late Show with James Corden , Punch Up The Jam podcast) joins Nicole to discuss how he found love on Twitter, how to successfully date long distance, and at what point you should tell your Tinder match what you're into. Plus, Nicole reads some embarrassing opening Bumble conversations. Be sure to check out Demi's Punch Up The Jam podcast. Venmo $13 to @electrolemon . Hav...

How to get Banned from Tinder (w/ Eleanor Bray) 10.05.2019

Eleanor Bray (Nicole's old assistant!) comes on to discuss what it was like working as Nicole's assistant, how she got banned on Tinder, and the musicals they've performed in. They also share their love for pole-dancing, and Nicole manifests her dream man. Have a story about the one that got away? Share it for a chance to be read on the podcast! You can email it anonymously to hey@headgum.com with...

Heckled Online and Offline (w/ Miel Bredouw) 03.05.2019

"I hope my dad ate ass." Miel Bredouw ( Punch Up The Jam podcast) joins Nicole to discuss online harassment, what it was like to 'date' on Vine and what kind of sex their parents would've been into. Nicole's developed a new technique to handle hecklers on the road, and has a running Twitter beef with John Cleese. She also shares the future of the podcast if she were to ever find a boyfriend. Chica...

Building a Sex Roster (w/ Laura and Rachel) 26.04.2019

" You get a social security number when you're born, you should also get a therapist that you have to see when you turn 13. " Laura and Rachel ( Girls on Porn podcast) teach Nicole how to create a sex roster, shares signs of a good therapist, discuss their favorite type of porn, and if they swipe right on friends. Nicole provides advice to young woman struggling with measuring their sexual expecta...

High School Dating (w/ Cameron Esposito) 19.04.2019

Cameron Esposito ( Put Your Hands Together , Queery podcast) discusses what it's like to host a show with her ex-wife, her past experience working as a circus ring leader, and how it feels to get dumped as a couple. Nicole shares her experience 'coming out' to her parents for liking dicks. Chicago! Come see Why Won't You Date Me at HeadGum Live June 15th. Tickets: https://www.eventbrite.com/e/head...

Getting an STI from Grindr (w/ Matt Rogers) 12.04.2019

" If it got leaked - everyone would know that I'm really good at sucking dick ." Matt Rogers ( What the Tuck? podcast, Las Culturistas podcast) discuss their experiences with Scientology, what it's like being too "intimidating" to date, and shares how he got his first STI from Grindr. Matt also details his last messy relationship, whether he considers himself to be a top or bottom, and his love fo...

Death & Taxes (w/ Punam Patel) 05.04.2019

"Would I rather live a shorter life where I'm happier, than a long one where I have to work so hard to be healthy? More often than not I choose shorter." Things get serious in this episode. Punam Patel (I Feel Bad, Alone Together) joins Nicole to discuss dating as an "aggressive" woman, living as a diabetic, and whether or not they believe in assisted suicide. They also provide plenty of tips for...

BONUS: Bad Birthday Hookup (LIVE w/ Dulcé Sloan) 02.04.2019

" If he had chest hair, I would've had rug burn. That's all I'm saying. " Dulcé Sloan ( The Daily Show with Trevor Noah) discuss their mutual hate for Coffee Meets Bagel , share some of their worst hookup stories, discuss which vibrators they use as massagers, and why Dulcé's superstitious about masturbating. Nicole begs everybody to cum everyday. They also answer questions from the audience in a...

Learning How to Love Yourself (w/ Charla Lauriston) 29.03.2019

"Every black person I know is in therapy. And if they're not, I encourage them to be." Charla Lauriston ( Ghosted, People of Earth ) dissects white privilege, how hard it is to be a black woman in the dating scene, and the uphill battle to learn how to love yourself. Nicole Byer is stating a war with Jeff Bezos, shares her opinion on Taylor Swift (it's not good) and they both discuss their favorit...

Blowjob Tips (w/ Jake and Amir) 22.03.2019

Jake Hurwitz and Amir Blumenfeld (Jake and Amir) discuss their favorite porn, whether they like to 69, if they would enjoy sucking their own dick, the best lubes to masturbate with, and give some blowjob advice. Nicole shares the insane things she requests in her final will and funeral. She's also jumping back in the app game and has Jake and Amir rate her new Tinder profile. Check out Jake and Am...

Date Exit Strategy (w/ Grace Helbig and Mamrie Hart) 15.03.2019

"Guys go on Raya just to see how famous of a person they can match with." Grace Helbig and Mamrie Hart ( This Might Get Weird podcast) discuss their go-to lies to get out of bad dates, share their awful dating experiences, and go through Nicole's Raya profile. Nicole's not feeling so horny and is worried there may be something wrong with her. She also shares an insane meet-cute she had with a very...

Putting Faith in your Love Life (w/ Liza Treyger) 08.03.2019

"Go out into the world with confidence, not desperation." Can crystals and candles help with your love life? Liza Treyger (stand-up , Horace and Pete ) joins Nicole to discuss their benefits or lack thereof. They also talk how their religious and spiritual beliefs that help to shape their relationships, in addition to make-up and wardrobe issues, the Fyre Festival documentaries, and how boring peo...

How to Kiss (w/ Matt Ingebretson) 01.03.2019

" A fun thing that I like to do is when kissing someone, is to open my eyes to see what their face looks like ." Matt Ingebretson ( Corporate ) talks all about kissing - the stress of going in for the first kiss, when to use tongue, and whether you should keep your eyes open or closed for the duration of it. They also discuss whether being on TV has helped their dating life, and what a "date night...

Why You Need Couple's Therapy (w/ Naomi Ekperigin) 22.02.2019

" There's nothing I love more than a slutty wedding vibe " Naomi Ekperigin ( Broad City ) shares her experience dating on Craigslist, why every couple should go to couple's therapy. Nicole describes why she loves going to weddings, and her ideal proposal. Also, Nicole gets a crazy text from her sister, and helps her find a husband. Be sure to check out Naomi's podcast, Couple's Therapy ! You can p...

Same Guy Club (w/ Skyler Hurt) 15.02.2019

Nicole met Skyler through Tinder, and they turned out to have dates the same man. Things got weird in their relationship real fast when Nicole began dating her ex-boyfriend's ex-girlfriend - without him knowing. Nicole questions Skyler on why she swiped right on her, why they continued dating despite Nicole's smoking, and asks if she would've still dated her if she hadn't known her work. Skyler gi...

Period Horror Stories (w/ Toni Charline) 08.02.2019

Periods suck. Toni Charline (UCB) joins Nicole to share all their embarrassing period-related stories. From their first tampon applications, to getting a period mid- Doughboys recording, and the times they've worn underwear incorrectly. You can play along and see Nicole's Tinder bio and photos on her Facebook page at:  https://www.facebook.com/pg/NicoleByerComedy Be sure to rate  Why Won...

Dealing with Creeps (w/ Trixie Mattel) 01.02.2019

Trixie Mattel (Winner of  RuPaul's Drag Race: All Stars Season 3 ) discusses getting touched by strangers in public, being in an "I t's Complicated " relationship on Facebook, shares getting catfish'd by a fan, and of course talks all about Drag Race All Stars! Love Drag Race ? Check out Nicole Byer's Drag Race recap podcast What the Tuck? on HeadGum. You can play along and see Nicole's Tinde...

All Things Panties (w/ Eliot Glazer) 25.01.2019

Eliot Glazer ( Broad City, New Girl ) discusses spending money on nice underwear for your partner, the grimiest requests he's received on dates, and how people need to set boundaries in and out of a relationships. Nicole describes her NYE helicopter ride from hell. Be sure to check out Eliot's podcast, You're Making it Worse! You can play along and see Nicole's Tinder bio and photos on her Faceboo...

Role-Playing (w/ Rachel Bloom) 18.01.2019

" Good role-playing is just bad improv " Rachel Bloom ( Crazy Ex-Girlfriend ) has an open discussion about finding therapy and using medication to treat mental health. She also discusses why improvisers should not role-play in the bedroom. As kids, Nicole and Rachel both had imaginary friends they would have sex with. Nicole's given up on dating and considers dating a ghost. She also describes her...

Seeking Professional Advice (w/ Dr. Chris Donaghue) 11.01.2019

Dr. Chris Donaghue (Host of Loveline , sex and relationship therapist) provides Nicole with an honest assessment why she may be single. He provides her relationship advice and a Tinder bio makeover. He also shares how to manage dating multiple people at once, the importance of sharing your needs and kinks with your partner, and the importance in masturbating in this sex-positive episode! Than...

Finding your S/O's Pet Name (w/ Elizabeth Ho) 04.01.2019

Did you know that couples with pet names statistically have longer lasting relationships? In today's episode, Nicole and Elizabeth Ho ( Disjointed ) consider what pet name they would want to have. Elizabeth discusses what it's like being in a competitive relationship with your S/O, and Nicole's providing relationship advice to fans over DMs. You can play along and see Nicole's Tinder bio and photo...

Scheduling Your Booty Calls (w/ Raiza Licea) 28.12.2018

"If you're busy, you need to book a dick appointment" Raiza Licea (UCB) agrees that life is busy and sometimes you just gotta book time for a dicking. Nicole goes on a wild date with her Lyft driver, and reads her latest failed Tinder conversations. Nicole also discusses some crazy kinks and reveals a few of her own. You can play along and see Nicole's Tinder bio and photos on her Facebook page at...

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