Worst Hookup EVER (w/ Jasmine Masters)

Worst Hookup EVER (w/ Jasmine Masters)

From Why Won't You Date Me? with Nicole Byer by Headgum & Nicole Byer

February 27, 2026 · 47 min · Episode 430

About this episode

Jasmine Masters joins Nicole Byer to discuss her experiences on Drag Race and her worst hookup story.

Legendary drag and meme queen Jasmine Masters (Drag Race S7, All-Stars 4) joins Nicole for a chat about being high for most of Drag Race season 7 and exactly how she snuck weed into the show. Jasmine spills on the origins of her viral "And I Oop-" video and recounts her absolute WORST hookup ever. Plus, we hear about the time her friends accidentally threw her a sold-out meet-and-greet at an Olive Garden on her birthday, and her strict rules for taking care of bad feet. Watch this episode on our YouTube channel at  https://www.youtube.com/@WhyWontYouDateMePodcast Support this podcast and get discounts by checking out our sponsors: »  Cozy Earth : Share a little extra love this February and wrap yourself—or someone you care about—in comfort that truly feels special. Head to cozyearth.com and use my code DATEME for up to 20% off. And if you get a Post-Purchase Survey, be sure to mention you heard about Cozy Earth right here! »   Jones : Ready to quit for good? Go to quitwithjones.com/DATEME to start your personalized quitting journey and get 15% off with code DATEME. »  Equip : Learn more about Equip’s virtual eating disorder treatment at&nbsp…

People in this episode

Host: Nicole Byer

Guest: Jasmine Masters

Topics covered

  • drag culture
  • relationships
  • comedy
  • hookup stories
  • viral moments

Keywords

  • Jasmine Masters
  • Drag Race
  • worst hookup
  • viral video
  • comedy podcast

Sponsors

Cozy Earth, Jones, Equip, Planned Parenthood, NOCD, Cash App

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