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November 7, 2025 62 mins

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:

Uncommon Goods: To get 15% off your unique gifts this year, go to https://uncommongoods.com/dateme.


Follow:

All Links: linktr.ee/whywontyoudateme

Tour Dates: linktr.ee/nicolebyerwastaken

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

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

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