Episodes

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

    Dating Life of a Burlesque Superstar (w/ Jessabelle Thunder)
    Aug 8 2025
    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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    1 hr and 1 min
  • Dating after a Major Scandal (w/ Monica Lewinsky)

    Dating after a Major Scandal (w/ Monica Lewinsky)
    Aug 1 2025
    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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    56 mins
  • A lil update from Nicole: Best Friends is back!

    A lil update from Nicole: Best Friends is back!
    Jul 30 2025

    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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    1 min
  • We Met on a Podcast (w/ Devon Walker)

    We Met on a Podcast (w/ Devon Walker)
    Jul 25 2025
    Comedian Devon Walker (SNL) joins Nicole to tell the story of how he met his girlfriend on a live blind date podcast. He figured it was just a bit - until the audience voted for them to win an Applebee’s gift card and that turned into their actual first date. 3 years later, they’re still together! He and Nicole also talk about the woman who went viral eating 48 oysters on a first date, why it’s a red flag if your partner suddenly starts doing open mics, and how it feels when people send you unsolicited sex tapes in the DMs. Devon shares the absolute nightmare of trying to break up with someone who flooded his phone with scroll-after-scroll of chaotic texts. Plus: He shares the SNL sketch he’s dying to get on air, and they do a deep dive into the food mascot universe - who’s comforting, who’s cursed, and why the Bubba Gump shrimp must be stopped.Watch this episode on our YouTube channel at https://www.youtube.com/@WhyWontYouDateMePodcastCheck out Devon's podcast, My Favorite Lyrics with Devon Walker.Support this podcast and get discounts by checking out our sponsors:» Squarespace: Build the website of your dreams! Head to squarespace.com/DATEME to save 10% off your first purchase of a website or domain using code DATEME.» Quince: Give your summer closet an upgrade—with Quince! Go to Quince.com/dateme for free shipping on your order and 365-day returns.» 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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    58 mins
  • Flirting, Open Relationships, and Almost Dying (w/ Josh Sharp)

    Flirting, Open Relationships, and Almost Dying (w/ Josh Sharp)
    Jul 18 2025
    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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    56 mins
  • Nobody Wants to Date a Drag Queen (w/ Meatball)

    Nobody Wants to Date a Drag Queen (w/ Meatball)
    Jul 11 2025
    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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    1 hr and 4 mins
  • We Dated?! (w/ Lou Wilson)

    We Dated?! (w/ Lou Wilson)
    Jul 4 2025
    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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    51 mins
  • A Cruise Ship Romance with a Himbo (w/ Jessica Lowe)

    A Cruise Ship Romance with a Himbo (w/ Jessica Lowe)
    Jun 27 2025
    Actress Jessica Lowe (The Righteous Gemstones, Minx, Wrecked) joins Nicole to share the romantic saga of falling in love on a Second City cruise ship. On the ship, she met a British bassist who became her cruise ship boyfriend - whom she later realized wasn’t as smart as she thought his accent sounded (he tried to dry his pants on a ceiling fan and designed a nightmare demon tattoo for himself).Jessica recalls dating a Dutch chef with a penis that was “too much!” and recounts what might be the most romantic first date ever told on the podcast. She reflects on the men who surprised her, disappointed her, and the slow work of building a relationship that actually lasted.Plus, Jessica and Nicole reminisce about the chaos of filming Curse Friends when everyone tested positive for COVID - and Nicole opens up about sobbing in a makeup chair over a man who simply wasn’t worth it.Watch this episode on our YouTube channel at https://www.youtube.com/@WhyWontYouDateMePodcastSupport this podcast and get discounts by checking out our sponsors:» OneSkin: OneSkin is redefining the aging process with their proprietary OS-01 peptide. Get 15% off OneSkin with the code DATEME at https://www.oneskin.co/ #oneskinpod» SquareSpace: Head to squarespace.com/DATEME to save 10% off your first purchase of a website or domain using code DATEME.» Booking.com: Book now at Booking.com!» Smalls: Give your cat the food they deserve. For a limited time only, get 60% off your first order PLUS free shipping when you head to Smalls.com and use code 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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    52 mins