The Torture of Working with an Ex (w/ Nicholas Scheppard)

Comedian and drag queen Nicholas Scheppard ( Very Gay Paint , Art to Me ) is fresh out of a breakup. He joins Nicole for a chat about the uphill climb out of it, why working with an ex-boyfriend is absolute torture, and the haunting theory that your partner will tell you exactly how they'll break your heart in the first week. Nicole shares the messy story about a situationship who didn't believe in monogamy, and her obsession with her Ninja Creami. Watch this episode on our YouTube channel at Check out Nicole's episode of ART TO ME . Follow Trudy Tective 's journey to catch her sister's murderer at @ trudy.tective . Support this podcast and get discounts by checking out our sponsors: » MeUndies : Right now as a listener of my show, you can get to get 20% off your first order, plus free shipping at MeUndies.com/DATEME , promo code DATEME. » Squarespace : Head to squarespace.com/DATEME to save 10% off your first purchase of a website or domain using code DATEME. » IQBAR : Text DATE to 64000 to get 20% off all IQBAR products, plus FREE shipping. Message and data rates may apply. » Wayfair : Get organized, refreshed, and back on track this new year for WAY less. Head to Wayfair.com right now to shop all things home. » Equip : Learn more about Equip’s virtual eating disorder treatment at equip.health/dateme » Planned Parenthood : Donate to support Planned Parenthood now at plannedparenthood.org/defend . Follow: All Links: linktr.ee/whywontyoudateme Tour Dates: linktr.ee/nicolebyerwastaken YouTube: @WhyWontYouDateMePodcast TikTok: @whywontyoudatemepod Instagram: @nicolebyer X: @nicolebyer Nicole's book, : indiebound.org/book/9781524850746 This is a Headgum podcast. Follow Headgum on Twitter , Instagram , and Tiktok . Advertise on Why Won't You Date Me? via Gumball.fm . See Privacy Policy at and California Privacy Notice at .

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The Torture of Working with an Ex (w/ Nicholas Scheppard) is an episode from Why Won't You Date Me? with Nicole Byer by Headgum.

This episode is 00:49:35 long.

This episode was published on Feb 20, 2026.

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