Why Won't You Date Me? with Nicole Byer

Headgum & Nicole Byer
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Aug 29, 2025 • 56min

Stealing Condoms at the Olympics (w/ Adam Rippon)

Olympic figure skater Adam Rippon, a trailblazer as one of the first openly gay U.S. Olympians and host of Intrusive Thoughts, shares his hilarious experiences from the Olympic Village, including a humorous take on the infamous Olympic condoms. He dives into the complexities of becoming an Olympian, the unique dating challenges within the figure skating community, and relationships in the spotlight. With lighthearted insights and personal anecdotes, he captures the chaos and joy of love and competition in the world of athletics.
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Aug 22, 2025 • 1h 4min

Slipping a Note to the Couple Fighting in the Next Room (w/ Dan Gregor & Doug Mand)

Dan Gregor and Doug Mand, comedy writers noted for their work on The Naked Gun and How I Met Your Mother, dive into their 20-year creative partnership, likening it to marriage. They share hilarious stories, including a wedding sabotaged by a comedian rabbi and the time they were 'dumped' by Adam Pally. They reflect on the complexities of friendships in the entertainment industry and dish out valuable marriage advice. Plus, Nicole's eavesdropping on an intense hotel argument leads to a comically bold act of slipping a note to the fighting couple.
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Aug 15, 2025 • 1h 8min

Ghosting, Gaslighting, and Gay Bars (w/ Roz Hernandez)

For Roz Hernandez, dating as a sober, trans woman comedian is a trifecta of difficulty - and finding love hasn’t been easy. She tells Nicole about going to 4 different Etsy psychics to sketch her future husband, using Grindr to find dates willing to explore haunted places, and the hookup stories that came from visiting 45 gay bars across the country. She opens up about the surprising ways gay men have treated her, why she’s stopped dating straight men altogether, and the many times she’s been ghosted - in love and in life. Nicole shares why she loves her boyfriend so much, and the two dive into what might really be behind the male loneliness epidemic.Get tickets to Roz Hernandez's tour at RozHernandezTour.comWatch this episode on our YouTube channel at https://www.youtube.com/@WhyWontYouDateMePodcastSupport this podcast and get discounts by checking out our sponsors:» Betterhelp: Visit Betterhelp.com/DATEME today to get 10% off your first month.» Wayfair: Every Style, Every Home.» Mint Mobile: This year, skip breaking a sweat AND breaking the bank. Get your summer savings and shop premium wireless plans at mintmobile.com/DATEME.View all of our sponsors and discounts codes at wwydm.notion.site/sponsors.Follow:Tour Dates: linktr.ee/nicolebyerwastakenYouTube: @WhyWontYouDateMePodcastTikTok: @whywontyoudatemepod Instagram: @nicolebyerX: @nicolebyerNicole's book, #VERYFAT #VERYBRAVE: indiebound.org/book/9781524850746This is a Headgum podcast. Follow Headgum on Twitter, Instagram, and Tiktok. Advertise on Why Won't You Date Me? via Gumball.fm.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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Aug 8, 2025 • 1h 1min

Dating Life of a Burlesque Superstar (w/ Jessabelle Thunder)

International award-winning burlesque dancer Jessabelle Thunder joins Nicole to talk about why so many partners say they’re cool with burlesque - until they’re not. She shares how she transformed from a shy girl into a commanding headliner, the different styles of burlesque dancing, and the time she broke her ankle on stage mid-show. Jessabelle also relives a London date with an Irish DJ who argued he should be allowed to say the N-word. Plus, Nicole forgets her meds, spirals on the future of AI, and goes to a pet psychic to figure out why Cylde be biting.Watch this episode on our YouTube channel at https://www.youtube.com/@WhyWontYouDateMePodcastSupport this podcast and get discounts by checking out our sponsors:» Quince: Elevate your fall wardrobe essentials with Quince. Go to Quince.com/dateme for free shipping on your order and 365-day returns.» Squarespace: Head to squarespace.com/DATEME to save 10% off your first purchase of a website or domain using code DATEME.» Mint Mobile: This year, skip breaking a sweat AND breaking the bank. Get your summer savings and shop premium wireless plans at mintmobile.com/DATEME.View all of our sponsors and discounts codes at wwydm.notion.site/sponsors.Follow:Tour Dates: linktr.ee/nicolebyerwastakenYouTube: @WhyWontYouDateMePodcastTikTok: @whywontyoudatemepod Instagram: @nicolebyerX: @nicolebyerNicole's book, #VERYFAT #VERYBRAVE: indiebound.org/book/9781524850746This is a Headgum podcast. Follow Headgum on Twitter, Instagram, and Tiktok. Advertise on Why Won't You Date Me? via Gumball.fm.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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Aug 1, 2025 • 56min

Dating after a Major Scandal (w/ Monica Lewinsky)

Before she was an activist, Monica Lewinsky was the most publicly shamed woman in America. Now, she's reclaiming her story, and her dating life.For the 400th episode of Why Won’t You Date Me?, Monica joins Nicole to talk about dating after a major scandal, being labeled “unmatchable” on eHarmony, and learning to enjoy life when pop culture won’t stop referencing you. She reflects on hosting the wild early-2000s reality show Mr. Personality, shares the worst dates she’s ever had (including ones she walked out on), and even offers up the exact scripts she uses when there’s just no spark.Plus, stick around to the very end as Nicole gets a little reflective on what 400 episodes of the show have meant to her.Check out Monica's podcast, Reclaiming with Monica Lewinsky.Watch this episode on our YouTube channel at https://www.youtube.com/@WhyWontYouDateMePodcastSupport this podcast and get discounts by checking out our sponsors:» Green Chef: Make this summer your healthiest yet with Green Chef. Head to Greenchef.com/50DATEME and use code 50DATEME to get 50% off your first month, then 20% off for two months with free shipping.» Smalls: Protein packed cat food! For a limited time only, get 60% off your first order PLUS free shipping when you head to Smalls.com and use code DATEME.» Mint Mobile: This year, skip breaking a sweat AND breaking the bank. Get your summer savings and shop premium wireless plans at mintmobile.com/DATEME.View all of our sponsors and discounts codes at wwydm.notion.site/sponsors.Follow:Tour Dates: linktr.ee/nicolebyerwastakenYouTube: @WhyWontYouDateMePodcastTikTok: @whywontyoudatemepod Instagram: @nicolebyerX: @nicolebyerNicole's book, #VERYFAT #VERYBRAVE: indiebound.org/book/9781524850746This is a Headgum podcast. Follow Headgum on Twitter, Instagram, and Tiktok. Advertise on Why Won't You Date Me? via Gumball.fm.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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Jul 30, 2025 • 33sec

A lil update from Nicole: Best Friends is back!

Exciting news from Nicole: Best Friends is BACK and 1) now on Headgum, 2) with FULL VIDEO EPISODES! Enter the pantheon of best friendship and check out Nicole and Sasheer's first episode back, available now on Apple Podcasts, Spotify, or wherever you get your podcasts. New episodes every Wednesday.Subscribe to the Best Friends YouTube channel https://youtube.com/@NicoleandSasheer for video episodes.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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Jul 25, 2025 • 58min

We Met on a Podcast (w/ Devon Walker)

Comedian Devon Walker, known from SNL and the host of My Favorite Lyrics, shares his delightful love story of meeting his girlfriend during a live blind date podcast, which turned into an unexpected romance. He and Nicole dive into the wild world of dating, from chaotic DM encounters to the hilarity of a viral first date involving 48 oysters. They also explore the unsettling vibes of food mascots, dissect the challenges of breaking up, and share the ultimate SNL sketch Devon dreams of performing. It's a blend of laughter and relatable dating mishaps!
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Jul 18, 2025 • 56min

Flirting, Open Relationships, and Almost Dying (w/ Josh Sharp)

Comedian and friend Josh Sharp (Dicks: The Musical) returns to the podcast! Nicole and Josh kick things off by reminiscing about the chaotic live show where Nicole interviewed a man in the audience she had slept with. From there, they get into Josh’s foolproof flirting strategy at the club, Annabelle the haunted doll’s cursed tour across America, attending a Big Dick contest, and Josh’s near-death experience in Puerto Vallarta that left him facedown in the ocean with no memory of his own name.They also discuss the realities and benefits of open relationships, how to quiet negative self-talk while dating, and the dangers of eating straight men’s ass. Fun times!In New York? Get tickets to Josh Sharp's show, Ta-da! at joshsharptada.com.Watch this episode on our YouTube channel at https://www.youtube.com/@WhyWontYouDateMePodcastSupport this podcast and get discounts by checking out our sponsors:» Betterhelp: Visit Betterhelp.com/DATEME today to get 10% off your first month of therapy.» Wayfair: Wayfair. Every Style, Every Home.» Mint Mobile: This year, skip breaking a sweat AND breaking the bank. Get your summer savings and shop premium wireless plans at mintmobile.com/DATEME.View all of our sponsors and discounts codes at wwydm.notion.site/sponsors.Follow:Tour Dates: linktr.ee/nicolebyerwastakenYouTube: @WhyWontYouDateMePodcastTikTok: @whywontyoudatemepod Instagram: @nicolebyerX: @nicolebyerNicole's book, #VERYFAT #VERYBRAVE: indiebound.org/book/9781524850746This is a Headgum podcast. Follow Headgum on Twitter, Instagram, and Tiktok. Advertise on Why Won't You Date Me? via Gumball.fm.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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Jul 11, 2025 • 1h 4min

Nobody Wants to Date a Drag Queen (w/ Meatball)

Drag queen icon Meatball is back! She and Nicole get into it all - being in her top era, loving the single life, and having weekend boyfriends in different cities. But also... why dating is still so hard when you do drag. Meatball opens up about losing guys the second they find out she’s a queen, and how frustrating it is watching her roster shrink because of it. And of course, the wild date stories are endless - projectile vomiting in a car on a date, sucking 3 different dicks in one night (one the size of a beer can), a hookup who did stand-up after sex, and turning down a dude mid-date for turning on fart porn. It's a wild one. Tune in!You can buy Meatball's jarred farts at meatland.bigcartel.com (it is currently sold out)Watch this episode on our YouTube channel at https://www.youtube.com/@WhyWontYouDateMePodcastSupport this podcast and get discounts by checking out our sponsors:» Quince: Give your summer closet an upgrade—with Quince. Go to Quince.com/dateme for free shipping on your order and 365-day returns.» OneSkin: Get 15% off OneSkin with the code DATEME at oneskin.co #oneskinpod» SquareSpace: Head to squarespace.com/DATEME to save 10% off your first purchase of a website or domain using code DATEME.» Mint Mobile: This year, skip breaking a sweat AND breaking the bank. Get your summer savings and shop premium wireless plans at mintmobile.com/DATEME. View all of our sponsors and discounts codes at wwydm.notion.site/sponsors.Follow:Tour Dates: linktr.ee/nicolebyerwastakenYouTube: @WhyWontYouDateMePodcastTikTok: @whywontyoudatemepod Instagram: @nicolebyerX: @nicolebyerNicole's book, #VERYFAT #VERYBRAVE: indiebound.org/book/9781524850746This is a Headgum podcast. Follow Headgum on Twitter, Instagram, and Tiktok. Advertise on Why Won't You Date Me? via Gumball.fm.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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Jul 4, 2025 • 51min

We Dated?! (w/ Lou Wilson)

Happy 4th of July!(?) Comedian Lou Wilson (Dimension 20, Jimmy Kimmel Live!) joins Nicole to reflect on the wild state of America. He shares his terrible time living in Boston, where white guys frequently asked him for the N-word pass. They talk about what it was like to sell out Madison Square Garden in just 10 minutes withDimension 20, being a “silly billy” on dates, and the moment Lou realized bits don’t always land on dates when you’re trying to build intimacy. They also bond over the guilty thrill of watching other couples on visibly bad dates, and the drama they've witnessed unfold one table over. Plus, Lou reminds Nicole that they once dated. Nicole completely forgot. He gives an honest review of what it was like to date her, and why there was never a second date. Y'all, it's a wild one.Check out Lou Wilson's podcast, Worlds Beyond Number.Watch this episode on our YouTube channel at https://www.youtube.com/@WhyWontYouDateMePodcastSupport this podcast and get discounts by checking out our sponsors:» CashApp: Download Cash App Today: https://capl.onelink.me/vFut/3v6r90n6 #CashAppPod *Referral Reward Disclaimer: As a Cash App partner, I may earn a commission when you sign up for a Cash App account.View all of our sponsors and discounts codes at wwydm.notion.site/sponsors.Follow:Tour Dates: linktr.ee/nicolebyerwastakenYouTube: @WhyWontYouDateMePodcastTikTok: @whywontyoudatemepod Instagram: @nicolebyerX: @nicolebyerNicole's book, #VERYFAT #VERYBRAVE: indiebound.org/book/9781524850746This is a Headgum podcast. Follow Headgum on Twitter, Instagram, and Tiktok. Advertise on Why Won't You Date Me? via Gumball.fm.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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