Hosting a Sex Party (w/ Big Dipper)

Rapper and friend Big Dipper (host of Sloppy Seconds) returns to the pod! He and Nicole dive into how he became a bear, the many “gaybels” that shape queer dating culture, and the highs and lows of Bear Week and pig events, from the wild parties to the moments that left him questioning everything. Dipper unpacks the twink vs. bear dynamic and explains compersion - the joy of watching your partner get pleasure from someone else.He also shares the wild story of a influencer showing up to his sex party to shoot content, why he won’t let Nicole work his gay orgy, and together they ask the important question: are we having a gay recession?Watch this episode on our YouTube channel at https://www.youtube.com/@WhyWontYouDateMePodcastSupport this podcast and get discounts by checking out our sponsors:» Quince: Keep it classic and cozy this fall —with long-lasting staples from Quince. Go to Quince.com/dateme for free shipping on your order and 365-day returns.» Persona Nutrition: Go to PersonaNutrition.com/Dateme today to take the free assessment and get your personalized daily vitamin packs for an exclusive offer — get 40% off your first order.» Betterhelp: Visit Betterhelp.com/DATEME today to get 10% off your first month.» Swindled Never After: Order Swindled Never After now! http://bit.ly/41dQoqLView 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.

Comedian, clown, and artist Jenson Titus (of @VeryGayPaint) tells Nicole what it was like to date someone who's in the process of transitioning. The experience made him realize he’s bi, and left him feeling “more queer” than ever. He talks about the challenges of having a "Very Gay" brand while dating a woman, launching his mural business, and the surreal job of painting RuPaul’s 1-bedroom, 5-closet mansion. They talk about their dream date ideas, the act of clowning, and Nicole shares her plan to lose her virginity to a gay.Watch this episode on our YouTube channel at https://www.youtube.com/@WhyWontYouDateMePodcastSupport this podcast and get discounts by checking out our sponsors:» NOCD: If you're struggling with OCD or unrelenting intrusive thoughts, NOCD can help. Book a free 15 minute call to get started: https://learn.nocd.com/DATEME» 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.» Nuuly: Nuuly is a great value at $98 a month for any 6 styles, but right now you can get $28 off your first month of Nuuly when you sign up with the code DATEME at Nuuly.com» Persona Nutrition: Go to PersonaNutrition.com/Dateme today to take the free assessment and get your personalized daily vitamin packs for an exclusive offer — get 40% off your first order.» Squarespace: Head to squarespace.com/DATEME to save 10% off your first purchase of a website or domain using 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.Macys.comSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Olympic figure skater Adam Rippon (Winner of Dancing with the Stars) joins Nicole to share the dating life of a Olympian. He shares what it was like being one of the first openly gay U.S. Olympians, why the infamous Olympic condoms left him disappointed, and what the sex life in the Olympic Village is really like. He also breaks down for Nicole exactly what it takes to become an Olympian, and the incestuous nature of figure skaters. Meanwhile, Nicole and her boyfriend take a vacation where he gets to witness her true colors for the very first time.Check out Adam's podcast - Intrusive Thoughts by Adam Rippon.Watch this episode on our YouTube channel at https://www.youtube.com/@WhyWontYouDateMePodcastSupport this podcast and get discounts by checking out our sponsors:» Sorry I Missed This: Search for “Sorry I Missed This” in your favourite podcast app! https://lnk.to/sorryimissedthisPS» OSEA: Get 10% off your first order sitewide with code DATEME at OSEAMalibu.comView 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.

Co-writers Dan Gregor and Doug Mand (The Naked Gun) have been writing partners for twenty years - which is basically a marriage at this point. They tell Nicole about the time they were "dumped" by Adam Pally, how they’ve kept a friendship and business alive without burning each other out, and the rabbi who completely ruined a wedding by trying to do bits. They also shared the best marriage advice they’ve ever gotten, and what it feels like to spiral when you don’t think you’re worthy of love. Plus, while on vacation, Nicole overhears a couple fighting in the next hotel room - and decides to slip a handwritten note under their door.Go see The Naked Gun in theaters! It's very funny!Watch this episode on our YouTube channel at https://www.youtube.com/@WhyWontYouDateMePodcastSupport this podcast and get discounts by checking out our sponsors:» Honeylove: Save 20% Off Honeylove by going to honeylove.com/DATEME ! #honeylovepod» 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.

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.

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.

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.

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.

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.

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.