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Headgum & 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!

Why Won't You Date Me? with Nicole Byer

Drag queen, singer, and actress Adore Delano (RuPaul's Drag Race S6, All Stars 2, American Idol) joins Nicole to share stories about hooking up with go-go dancers, filming a sex tape she regrets, and her path to sobriety. She opens up about transitioning twice, the facial feminization surgery she underwent, and her current relationship with a trans man Nicole and Adore swap dating lessons, talk about why a healthy relationship can feel so strange, and discuss why an amusement park date is the ultimate compatibility test.

Watch this episode on our YouTube channel at https://www.youtube.com/@WhyWontYouDateMePodcast

Support for this episode comes from Bumble. Start your love story on Bumble - bumble.com #bumblepartner

Follow:

Tour Dates: linktr.ee/nicolebyerwastaken

YouTube: @WhyWontYouDateMePodcast

TikTok: @whywontyoudatemepod 

Instagram: @nicolebyer

X: @nicolebyer

Nicole's book, #VERYFAT #VERYBRAVE: indiebound.org/book/9781524850746

This 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.

Hooking Up with Go-Go Dancers (w/ Adore Delano)

Actress Rachel Bilson (The O.C., Broad Ideas) once lost a job over something she said on a podcast. She tells Nicole what that was like, current cancel culture, and why “free speech” doesn’t always apply to everyone. Rachel shares some of her wildest dating stories, from terrible first dates, rejected kisses, and men who love bomb too fast. Also, is it good to call before a first date, or is it unhinged? Rachel discusses what it's like to date in the spotlight, the time she got into a fight with a pig, and teaches Nicole all about Labubus.

Check out Rachel Bilson's podcast, Broad Ideas on Headgum!

Watch this episode on our YouTube channel at https://www.youtube.com/@WhyWontYouDateMePodcast

Support this podcast and get discounts by checking out our sponsors:

» Squarespace: Head to squarespace.com/DATEME to save 10% off your first purchase of a website or domain using code DATEME.

» 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.

» Jones Road Beauty: Use code DATEME at jonesroadbeauty.com to get a Free Cool Gloss with your first purchase! #JonesRoadBeauty #ad

» 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

» OSEA: Get 10% off your first order sitewide with code DATEME at OSEAMalibu.com

» Mint Mobile: Quit stalling and start saving when you make the switch. Shop plans at mintmobile.com/dateme.

» Wayfair. Every Style, Every Home.

View all of our sponsors and discounts codes at wwydm.notion.site/sponsors.

Follow:

Tour Dates: linktr.ee/nicolebyerwastaken

YouTube: @WhyWontYouDateMePodcast

TikTok: @whywontyoudatemepod 

Instagram: @nicolebyer

X: @nicolebyer

Nicole's book, #VERYFAT #VERYBRAVE: indiebound.org/book/9781524850746

This 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.

Sex Talk Got Me Fired (w/ Rachel Bilson)

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/@WhyWontYouDateMePodcast

Support 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/41dQoqL

View all of our sponsors and discounts codes at wwydm.notion.site/sponsors.

Follow:

Tour Dates: linktr.ee/nicolebyerwastaken

YouTube: @WhyWontYouDateMePodcast

TikTok: @whywontyoudatemepod 

Instagram: @nicolebyer

X: @nicolebyer

Nicole's book, #VERYFAT #VERYBRAVE: indiebound.org/book/9781524850746

This 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.

Hosting a Sex Party (w/ Big Dipper)

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/@WhyWontYouDateMePodcast

Support 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/nicolebyerwastaken

YouTube: @WhyWontYouDateMePodcast

TikTok: @whywontyoudatemepod 

Instagram: @nicolebyer

X: @nicolebyer

Nicole's book, #VERYFAT #VERYBRAVE: indiebound.org/book/9781524850746

This is a Headgum podcast. Follow Headgum on Twitter, Instagram, and Tiktok. Advertise on Why Won't You Date Me? via Gumball.fm.

Macys.com

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

I'm Bi Now (w/ Jenson Titus)

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/@WhyWontYouDateMePodcast

Support 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.com

View all of our sponsors and discounts codes at wwydm.notion.site/sponsors.

Follow:

Tour Dates: linktr.ee/nicolebyerwastaken

YouTube: @WhyWontYouDateMePodcast

TikTok: @whywontyoudatemepod 

Instagram: @nicolebyer

X: @nicolebyer

Nicole's book, #VERYFAT #VERYBRAVE: indiebound.org/book/9781524850746

This 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.

Stealing Condoms at the Olympics (w/ Adam Rippon)

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/@WhyWontYouDateMePodcast

Support 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/nicolebyerwastaken

YouTube: @WhyWontYouDateMePodcast

TikTok: @whywontyoudatemepod 

Instagram: @nicolebyer

X: @nicolebyer

Nicole's book, #VERYFAT #VERYBRAVE: indiebound.org/book/9781524850746

This 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.

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

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.com

Watch this episode on our YouTube channel at https://www.youtube.com/@WhyWontYouDateMePodcast

Support 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/nicolebyerwastaken

YouTube: @WhyWontYouDateMePodcast

TikTok: @whywontyoudatemepod 

Instagram: @nicolebyer

X: @nicolebyer

Nicole's book, #VERYFAT #VERYBRAVE: indiebound.org/book/9781524850746

This 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.

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

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/@WhyWontYouDateMePodcast

Support 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/nicolebyerwastaken

YouTube: @WhyWontYouDateMePodcast

TikTok: @whywontyoudatemepod 

Instagram: @nicolebyer

X: @nicolebyer

Nicole's book, #VERYFAT #VERYBRAVE: indiebound.org/book/9781524850746

This 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.

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

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/@WhyWontYouDateMePodcast

Support 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/nicolebyerwastaken

YouTube: @WhyWontYouDateMePodcast

TikTok: @whywontyoudatemepod 

Instagram: @nicolebyer

X: @nicolebyer

Nicole's book, #VERYFAT #VERYBRAVE: indiebound.org/book/9781524850746

This 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.

Dating after a Major Scandal (w/ Monica Lewinsky)

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.

Hooking Up with Go-Go Dancers (w/ Adore Delano)

Lyt når som helst, hvor som helst

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