Kiki-ing (w/ Oscar Montoya)

Why Won't You Date Me? with Nicole Byer

Headgum & Nicole Byer

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

4.8 • 15.6K Ratings

🗓️ 7 November 2025

⏱️ 66 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

Comedian and friend Oscar Montoya (Dropout TV, Drag Her) is back for another kiki. They talk about the best slutty Halloween costumes, the casual racism in early-2000s fashion, recounts stories of wild audience members, dating someone as a "bit", and Nicole shares the time she officiated a wedding proposal while soaked in toilet water. It's a nice fun time.

See the Bad Drag Race finale in LA Nov 15th, co-hosted by Nicole, Oscar, and Mano. Get tickets here.

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

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

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

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Transcript

Click on a timestamp to play from that location

0:00.0	Want to watch this episode?
0:01.3	Catch the full video on YouTube.
0:03.3	Just hit the link in the episode description.
0:07.1	This is a Headgum podcast.
0:10.4	Extra value meals are back.
0:12.3	For just $5, get a savory and sweet sausage egg and cheese McGrittles.
0:16.6	Plus hash browns and a coffee.
0:19.0	Only at McDonald's.
0:20.5	For limited time only, prices and participation may vary. Prices may be higher in Hawaii, Alaska, and California, and for delivery. It's easier to remain the same than change. Imagine growing and changing. Baby. Imagine going to therapy and figuring out why you think the way you think. Imagine waking up when you've been asleep this whole time. Wake me up this I can't wake up. Oh my God. That evidence is on. It's woke. It's woke. No, she's trying to be woke. And he's saying, no, I can't wake up. And it's a man holding a woman back. I don't know any other lyrics.
0:59.7	All I remember is a music video and I think she's falling off a building and he's holding her, saving her.
1:01.4	But what he's really doing is preventing her from jumping off the cliff of being comfortable
1:06.2	and into a sea of people of color.
1:09.8	Which are there to lift her up.
1:11.4	They're trying to lift her up.
1:12.7	They're saying, come here, baby.
1:14.6	Come here.
1:15.4	Wake me up inside.
1:16.7	Okay, wake up.
1:20.4	Why won't you date me?
1:22.7	Why won't you date me?
1:24.5	Why won't you date me?
1:26.4	Please tell me why. Oh, baby, welcome to another episode of Why Won't
	...

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