Why Won't You Date Me? with Nicole Byer

Drag icon Mistress Isabelle Brooks (Drag Race S15, All Stars 10) returns, and she isn’t afraid to cause a little mayhem. She sits down with Nicole to talk about how she broke the rules of her All Stars season, and how her Drag Race sisters almost blew her cover. Mistress comes out as bisexual, explains her twink rebirth at 28, and shares how losing nearly 200 pounds in a year cost her a few relationships. Plus, the new legal name she’s picking out, organizing a Last Supper before her surgery, and why straight audiences can’t get enough of her cheerleader alter ego, Eleanor Charles. Nicole reveals which Drag Race queens she’d sleep with.

Listen to her last appearance on Why Won't You Date Me? here: https://www.art19.com/shows/why-wont-you-date-me/episodes/fb5190fe-3438-4c25-b380-96e9ddb9954d

Check out Mistress's YouTube channel at: https://www.youtube.com/@MistressisabelleBrooks

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

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If you caught your partner sexting an AI, would you break up with them? 1 in 7 people in committed relationships have a secret AI partner on the side. Tech journalist Bridget Todd (host of There Are No Girls on the Internet) shares her reporting on why so many people are falling in love with chatbots. She breaks down why AI chatbots are built to pull you into an intimate place, how dating apps are already using AI on you without you knowing, and why tech companies are betting on you being lonely and horny. Plus: the wildest AI love story she's come across, how to actually use AI to improve your dating life without crossing a line, and an optimistic look on AI and human connection.
For more insight on our relationships with AI, listen to Bridget's audiobook, Love at First Prompt: AI and the Future of Intimacy. Get it at https://www.simonandschuster.com/books/Love-at-First-Prompt/Bridget-Todd/9781668179826
Check out Bridget's podcast, THERE ARE NO GIRLS ON THE INTERNET.

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

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Three weeks after ending a 15-year relationship, comedian Adam Conover (Adam Ruins Everything, Factually!) went on a date with a 6'3" dominatrix whose first question was how he wanted to be dominated. He joins Nicole to share his side of the breakup with Lisa Hanawalt and dive into his newly single life, including exploring his sexuality, rediscovering himself, and experimenting with power dynamics in the bedroom. Plus, he shares stories from the messy dates he’s been on along the way, explains why he thinks straight men are the most sexually repressed people in America, and reveals how he’s learned to turn a bad date into a great night.

Adam's new special, BIG DIVORCE ENERGY, is out today on YouTube! Watch at https://www.youtube.com/watch?v=9jHAggpB4ak
See Adam Conover on tour: https://www.adamconover.net/tourdates/

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

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Follow:
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This is a Headgum podcast. 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.

Illustrator and friend Lisa Hanawalt (Bojack Horseman, Tuca & Bertie) returns to the podcast to chat about starting fresh in the dating scene after a 15-year relationship with Adam Conover, and what happened when they tried opening things up before they parted ways. Lisa explains wanting to be a slut while still needing to feel safe, her dates with a pathological liar who claimed he’d survived three train crashes, and what it’s like explaining PMDD mood swings to a new partner.
Next week, Adam Conover joins Nicole to share his side of things.

Lisa Hanawalt's new book, I Can’t Stop Thinking About Horses and Sex, is out October 20.
https://www.penguinrandomhouse.com/books/837946/i-cant-stop-thinking-about-horses-and-sex-by-lisa-hanawalt/

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

Support this podcast by checking out our sponsors:
» Squarespace: Head to https://www.squarespace.com/DATEME to save 10% off your first purchase of a website or domain using code DATEME.
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This is a Headgum podcast. 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.

Drag queen Darlene Mitchell (Drag Race S18) joins Nicole for a chat about finding love in the Instagram DMs, pulling off a tear-jerking surprise proposal, and coming out to her conservative family via a massive group text right before leaving to film reality TV. Darlene spills on a disastrous first date with an aspiring news anchor who was stuck in his persona, and dumping a college crush after finding out he was making out with someone ugly. Plus, they discuss why weaponized therapy speak on social media is ruining modern dating, and why you actually might need to change who you are for a partner if your habits are the problem. Finally, Nicole brings in her tooth to show off the instrument left in it by TruGlo Modern Dental. Avoid them at all cost!

Get tickets to A Drag Queen Christmas at https://www.dragfans.com/

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

Support this podcast by checking out our sponsors:
» Hers: Visit https://forhers.com/dateme to get a personalized, affordable plan that gets you.
» Bask and Lather Co: Explore viral bestsellers and products for healthier hair of ALL types at baskandlatherco.com
» Warby Parker: Our listeners can buy one pair of glasses and get 20% off any additional pairs at https://WarbyParker.com/DATEME — and using our link helps support the show. #WarbyParker #ad
» Cash App: Download Cash App Today: https://capl.onelink.me/vFut/3v6r90n6 #CashAppPod Cash App is a financial services platform, not a bank. Banking services provided by Cash App’s bank partner(s). Prepaid debit cards issued by Sutton Bank, Member FDIC. Cash App Visa® Debit Flex Cards issued by Sutton Bank, Member FDIC, and The Bancorp Bank, N.A., pursuant to a license from Visa U.S.A. Inc. See terms and conditions for the Sutton prepaid card, Sutton debit flex card, and Bancorp debit flex card. Discounts and promotions provided by Cash App, a Block, Inc. brand. Visit cash.app/legal/podcast for full disclosures.
» Planned Parenthood: Donate to support Planned Parenthood now at https://plannedparenthood.org/defend
Check out all of our sponsors and discount codes at wwydm.notion.site/sponsors.

Follow:
All Links: linktr.ee/whywontyoudateme
Tour Dates: linktr.ee/nicolebyerwastaken
YouTube: @WhyWontYouDateMePodcast
TikTok: @whywontyoudatemepod
Instagram: @nicolebyer
X: @nicolebyer
This is a Headgum podcast. 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.