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
Doing Your Own Hair (w/ Tawny Newsome) 08.05.2020 1:03:57
Comedian Tawny Newsome (Space Force) chats with Nicole about learning how to do your own hair in quarantine, their crazy fashion phases, and the current state of "Zoom dating" along with the crazy logistics behind it. For more Nicole Byer, check out her new podcast - Newcomers ! Her and Lauren Lapkus are watching and reviewing Star Wars films for the very first time. Subscribe today so...
Quarantine Breakup (w/ Jamie Loftus) 01.05.2020 38:04
"On what date do you reveal you're a merperson?" Comedian and TV writer Jamie Loftus ( Robot Chicken , host of The Bechdel Cast ) theorizes what it must be like being broken up but quarantined together, shares her fascination with balloon fetishists, and how 'Zoom-dating' has been working for people. Plus, Nicole's so dang horny, she's asking her roommate to sleep with her. For more Nicole Byer, c...
Instagram DM Sex (w/ Ira Madison III) 24.04.2020 52:56
Ira Madison III (TV writer, host of Keep It ) chats about how he's staying sane while quarantine alone, his guest appearance on You , and how he's having sex over Instagram. For more Nicole Byer, check out her new podcast - Newcomers ! Her and Lauren Lapkus are watching and reviewing Star Wars films for the very first time. Subscribe today so you don't miss an episode . Rate Why...
Third Wheel in a Quarantine (w/ Tommy Lenk) 17.04.2020 55:03
"Marriage should be a lease with an option to renew" Tommy Lenk ( Buffy the Vampire Slayer , host of Trashcast ) shares his ideas to modernize marriage, points out the archaic rules of straight dating, and talks about his experience living in quarantine with his ex-bf's new bf. We've hit peak horny!! Nicole is having a full blown meltdown. Stay inside and stay safe everyone! For more Nicole Byer,...
Saying Yes to the Dress (w/ Megan Gailey) 10.04.2020 51:24
Comedian Megan Gailey ( Conan , Tonight Show Starring Jimmy Fallon ) chats with Nicole about life as a newlywed in quarantine, the horrors of wedding dress shopping, and the freaks using dating apps right now. Plus, how early is it acceptable to start drinking? Quarantine is causing crazies. For more Nicole Byer, check out her new podcast - Newcomers ! Her and Lauren Lapkus are watching and...
Loving Your Boobs (w/ Amy Miller) 03.04.2020 49:31
Stand-up comedian & Nicole's opener Amy Miller (host of Who's Your God ) teaches us how to spot a chucklefucker, shares her experience going through Steve Harvey's 90 day sex rule, and how to feel powerful giving a blowjob. Plus, a motivational chat about loving your girls, and a check-in from quarantine. For more Nicole Byer, check out her new podcast - Newcomers ! Her and Lauren Lapkus...
Dating During Coronavirus (w/ Jacquis Neal) 27.03.2020 52:17
"We're all just on Zoom trying to date people?" Jacquis Neal (host of Culture Kings ) joins us remotely while in quarantine to discuss what it's like being cooped up with your S/O in isolation, how people are dating during the COVID-19 pandemic, and if you can stay friends with an ex. Plus, he shares the cute story behind his Disney World proposal. Meanwhile, Nicole has started taking therapy sess...
Love (w/ Paul Rust) 20.03.2020 1:02:28
Paul Rust ( Love, Comedy Bang! Bang!, Arrested Development ) has been married for 5 years. He discusses what it's like to date and work with his partner, the differences between his show ' Love' and his real love life, and bare boner rules. Plus, they share public pranks gone wrong, and Nicole's dream marriage proposal. This was our last studio recording, prior to social isolation. We'll do our be...
Recognizing your Self-Worth (w/ Nicolette Mason) 13.03.2020 57:49
" Everyone that I thought was 'the one', was a piece of trash. " Nicolette Mason (plus-size fashion blogger) joins Nicole to discuss the latest dating buzzwords of 2020, reflecting on your self-worth, whether they've dated fans, and so much more. For more Nicole Byer, check out her new podcast - Newcomers ! Her and Lauren Lapkus are watching and reviewing Star Wars films for the very first t...
Open Relationships (w/ Kelly Hudson) 06.03.2020 1:01:01
" My life's work was dating people ." Kelly Hudson ( Search Party, Sunnyside, CollegeHumor ) left her open-relationship to be with the man she's married to today. She shares her tricky experience dating 4 people at once, her first rules for dating in an open relationship, and what it's like to be on dating apps while married. Plus, Nicole shares her hard stance on feet, and period sex. Need more N...
BONUS: The Struggles of your Twenties (w/ Rae Sanni) 03.03.2020 1:04:16
Writer/stand-up Rae Sanni ( The Good Place , A Black Lady Sketch Show) joins Nicole to discuss all the struggles of their twenties, and how it has defined them. From the string of bad sex, hustling for money, dealing with colorism in the black community, and more. This bonus episode is brought to you by BET's new Twenties . See it March 4th. Search and post on social with hashtag #TwentiesonB...
Seeking Single Men at Target (w/ Janelle James) 28.02.2020 49:51
Janelle James (stand-up, writer for Black Mondays ) joins Nicole to discuss the difference between East coast and West coast men, when to let a guy see you without makeup, and the best time to find single men at Target. Plus, Nicole shares her experience co-hosting the gay porn awards. Need more Nicole Byer? Check out her new podcast - Newcomers ! Her and Lauren Lapkus will be watching and r...
Unpacking Nicole's Fear of Relationships (w/ Jess Rona) 21.02.2020 59:18
"Once both people like each other, the games are over." Close friend and dog groomer Jess Rona (Author of Groomed ) has a heart-to-heart with Nicole to unpack her fears of being in a relationship. They also read some crazy dating app messages from men, discuss the benefits of couple's therapy, and how to talk to kids. Plus, Nicole's trying to match with Channing Tatum on Raya. Need more Nicole Bye...
Finding Love at DragCon (w/ Taylor Orear) 14.02.2020 55:45
Friend and fashion stylist Taylor Orear joins Nicole to shares the most adorable story behind meeting his boyfriend at RuPaul's Drag Con. They also discuss the importance of leaving baggage behind when starting new relationships, their crazy trip to Italy together, and their love for Obama's juicy butt. Need more Nicole Byer? Check out her new podcast - Newcomers ! Her and Lauren Lapkus will...
Drugs & Dogs (w/ Eric Edelstein) 07.02.2020 1:17:11
'She saved me in her phone as ' Eric Weirdo" . Eric Edelstein ( Jurassic World, American Dad ) shares the story behind meeting Jess, his lovely dog grooming wife. Him and Nicole also discusses how to smuggle a dog into the country and their drugs of choice, including the time Nicole accidentally did meth. Plus, a round of audience questions about: how to get out of bad dates, finding motivation to...
Setting 2020 Resolutions (w/ Kevin T. Porter) 31.01.2020 56:26
Podcast pro Kevin Porter (Host of Inside Voices , Good Christian Fun , and Gilmore Guys podcast) helps Nicole set some 2020 dating goals - starting with deleting her Raya app. They also identify her negative loops to break, and have an education rundown on managing the iPhone's hidden app subscriptions. Plus, Nicole realizes she has no straight guy friends. Want to learn more about Nicole's podcas...
Hiring a Professional Matchmaker (w/ Grace Edwards) 24.01.2020 56:11
Nicole's old roommate Grace Edwards (writer - Unbreakable Kimmy Schmidt, Loosely Exactly Nicole ) answers Nicole's questions about professional matchmaking and shares the challenges of dating 3 men at once. Nicole has witnessed a stabbing, and wonders if she can die from horniness. She also has cancelled her dating subscriptions! New year, new Nicole. Need more Nicole Byer? Check out her new podca...
Prison Dating (w/ Ann Pyne) 17.01.2020 1:01:23
" He had committed arson when he tried to kill himself in his mother's basement " Ann Pyne (Drag queen booker) is the queen for drag queens. She discusses being a daily drinker since she was 13 years old, dating multiple guys who were in prison, and being a mistress in relationships. Support the show! Rate Why Won't You Date Me 5-stars on Apple Podcasts with a dirty comment for a chanc...
Dead Mom Club (w/ Kate Spencer) 10.01.2020 1:01:13
Kate Spencer ( Forever 35 podcast, author of Dead Mom's Club ) discusses Nicole Byer's mention in The Masked Singer, explains to Nicole what a "VSCO Girl" is, and discusses life after losing a parent. Nicole shares the advice she's got from Anthony Atamanuik that changed her life. Support the show! Rate Why Won't You Date Me 5-stars on Apple Podcasts with a dirty comment for a chance to have...
Running into Past Flings (Live w/ Josh Sharp) 03.01.2020 1:23:19
Josh Sharp ( The Opposition with Jordan Klepper, The Chris Gethard Show ) joins Nicole to discuss their previous liveshow where Nicole ran into a guy who she's slept with. They also discuss Josh's open relationship, Craigslist missed connections ads, and Nicole shares details about her 3-way with a friend. Nicole also surveys the 1 single male audience member to see if they would have sex with her...
Vehicular Assault (w/ Akilah Hughes) 27.12.2019 55:52
Akilah Hughes (host of What a Day podcast) discusses why she doesn't believe in long term relationships, shares her worst date stories, and the time she cut all her toes during sex. Nicole fears for her future as a motorcyclist. She also talks about the multiple times she's been hit by cars, and that she is now so horny she's committing vehicular assault. Support the show! Rate Why Won't You...
Moving On After a Nasty Breakup (w/ Marty Michael) 20.12.2019 57:10
Nicole starts the episode with a DM from her doppelgänger who's been taking advantage of her likeness. Marty Michael (Co-Founder of Headgum) shares a wild first date he had with a girl who's life was spiraling out of control, how him and Amir Blumenfeld bonded over breakups, and why he started counseling after a bad relationship. They also discuss camping, Nicole's new motorcycle, and Nicole share...
Emojis are a Red Flag (w/ Whitney Cummings) 13.12.2019 1:11:01
"We're taught to laugh at guys' jokes that aren't funny so they don't feel insecure." Whitney Cummings (stand-up, creator of Two Broke Girls ) explains why she likes to be the beta in her relationship, what's it like living with a sex doll of herself, and why emojis are a red flag for her. She also gives Nicole tips how to manage rowdy audience members at live shows and discuss why we shouldn't en...
Living with Nicole Byer (w/ John Milhiser) 06.12.2019 45:29
Nicole's roommate John Milhiser ( SNL, CollegeHumor ) discuss how Nicole serves as a third in his relationship, if they've ever heard each other have sex, and their dog's drug problem. Plus, he shares what's life like living with Nicole Byer. Also, Nicole describes her experience crashing a motorcycle. Check out John's baguette Instagram page at @baguettemenots and watch his new movie Greener Gras...
What's it Like to Finally Date a Good Guy (w/ Michaela Watkins) 29.11.2019 44:42
Michaela Watkins ( SNL , The Unicorn, Big Mouth ) has been boy crazy her whole life. She discusses the hot kids they were into, shares why her husband proposed with a t-shirt, and her mom's "orgies" with students. Plus, Nicole admits she's never said "I Love You" to anyone. You can play along and see Nicole's dating app profiles and photos on her Facebook at: https://www.facebook.com/pg/Nico...
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