Worst Hookup EVER (w/ Jasmine Masters)

Why Won't You Date Me? with Nicole Byer

Headgum & Nicole Byer

Love, Single, Couples, Sexuality, Raya, Advice, Comedy Interviews, Dating, Stories, Hookups, Interviews, Comedy, Therapy, Hookup, Relationships, Sex, Relationship, Dating Apps, Nicole Byer, Society & Culture, Tinder, Encounters, Romance, Bumble, Podcast, Health & Fitness, Date, Interview

4.9 • 16K Ratings

🗓️ 27 February 2026

⏱️ 58 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

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

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Transcript

Click on a timestamp to play from that location

0:00.0	Want to watch this episode? Catch the full video on YouTube. Just hit the link in the episode description.
0:07.0	This is a headgum podcast.
0:10.0	Have you ever been on a date with a perfectly nice person and suddenly your brain starts screaming?
0:14.0	But is he the one? And then you start spiraling? And you're comparing him to your ex or that random hot person you saw
0:21.9	and hinge and he can't stop the loop, we all have unwanted thoughts.
0:25.6	But if you're constantly questioning if you love your partner the right way or if you
0:30.0	should break up with them for no reason, you might be dealing with relationship OCD.
0:34.2	OCD is not just about color coding your closet.
0:36.8	Okay, it can latch on to your love life and
0:38.8	create this never-ending cycle of anxiety and reassurance seeking where you never feel secure.
0:45.0	But the good news is that it is highly treatable with no CD. They are the leading provider of
0:50.4	OCD treatment and they use ERP therapy, which is the gold standard for this.
0:55.5	You get live face-to-face virtual sessions with a specialist who teaches you how to take the power
1:00.3	back from those intrusive thoughts. So you can actually enjoy your relationship. It's covered by
1:04.9	insurance for over 155 million Americans, which is amazing. So if you think you might be
1:10.5	struggling with relationship OCD, do not wait. So if you think you might be struggling with relationship
1:11.5	OCD, do not wait. Visit nocd.com to book a free call with their team. That's NOCD.com.
1:21.0	This episode is supported by Planned Parenthood Federation of America. I am currently in a
1:25.4	relationship, and I'm learning that relationships take work.
1:29.3	But you know what? Shouldn't take work? Getting access to basic health care. It should not be a full-time
1:34.7	job just to get the sexual and reproductive care you need to survive. It's just like wild to me.
1:39.2	Planned Parenthood believes we should have the freedom to make decisions about our own bodies and our futures without
	...

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