Why Won’t You Date Me? with Nicole Byer
Episode: The Torture of Working with an Ex (w/ Nicholas Scheppard)
Release Date: February 20, 2026

Episode Overview

Nicole Byer welcomes comedian, muralist, and drag queen Nicholas Scheppard (“Trudy Detective”) to discuss the complexity of working with an ex, queer dating journeys, breakups, creative careers, and the joyful, wild messiness of life. The conversation moves freely from heartbreak, self-reflection, and creativity to pop culture, drag, and the little rituals of happiness (like making ice cream). The tone is candid, vulnerable, raunchy at times, and consistently hilarious.

Key Topics & Discussion Points

1. Relationship Status & Breakup Reflections

• Nicholas is freshly single (~2 months out), describing the aftermath as “hurts like hell, I’ll tell you that. Every day is an uphill climb.” (06:50)
• He shares the value of self-awareness: “I want to make sure my oxygen mask is on before I start fiddling with someone in the seat next to me.” (07:07)
• Nicole relates, sharing her own pattern of jumping back into dating after breakups and now choosing to pause:

  “My last breakup, I was like you. I was like, I actually can’t do this, and I’m just simply not gonna force myself to do it.” (07:51)

2. Lessons from Breakups & Recognizing Red Flags

• Both discuss the tendency to ignore early signs that a relationship won’t work.
  • Nicholas relays advice:

    “The person that you're seeing always lets you know right away exactly how they're gonna break your heart.” (09:35)

  • Nicole reflects:

    “Honestly, all of them were like, ‘I don’t really want anything serious.’ And I’m like, but if you get to know me, you will, right?” (10:07)

3. Non-Negotiables & Personal Growth

• Nicholas on relationship desires:

  “I would like to have a really just awesome time together... I would like to have someone who is really open to looking at themselves, taking some time in the mirror...” (13:40)

• A recurring metaphor: balancing time in the "emotional mirror" and the "physical mirror”.

  “My advice to me, Nick, when you’re watching yourself later… take one step to the left and look in the physical mirror and leave the house.” (14:20)

4. Early Life, Coming Out, and Queer Adolescence

• Nicholas grew up in Las Vegas and attended a performing arts school close to the Strip.
  • Discusses the “Broadway-level” spectacle of Vegas megachurch events, like Santas on jetpacks and Grinches singing “Old Town Road.” (26:13)
• He came out as gay between high school and college, with dating delayed compared to straight peers.

  “Queer people… there’s such a delayed, like, dating growth thing. So I did, I think, probably what everyone is doing at like thirteen, fourteen, fifteen, in like eighteen, nineteen, twenty.” (33:53)

• Nicole relates her delayed dating due to body image and skin issues.

5. Theater Kid Life, Audition Stories, and Musical Theater

• Nick’s formative trauma: not getting into his high school’s lavish Vegas-themed production of Cats—after being cast in Sweeney Todd as a freshman (30:03).
• Both joke about their limitations as singers and the peculiarity of straight men in musical theater:

  “Some of the nastiest freak bitches I ever met are straight guys that do musical theater.” (33:27)

6. From Theater to Queer Artistry: Mural Career & Drag

• The birth of “Very Gay Paint”:
  • Nicholas and ex-boyfriend Jensen started painting murals during lockdown, which snowballed into a creative business for clients, including RuPaul (35:49).
  • Nicholas describes the process (client inspiration, varied drafts, celebrities often have more specific requests) (36:43).
• On drag persona “Trudy Detective”:
  • Created for the show Bad Drag Race; backstory: "A year ago, her sister was murdered. She’s really, really, really close to finding out who did it… she's so close." (42:43)
• Drag brunches and the magic of performing themes people recognize (“the name of the game is familiarity”—19:10)

7. On Working With an Ex (The Main Theme)

• Nicole asks about maintaining a business after a breakup:

  "Was that hard?" (51:34)

• Nicholas:

  “Excruciating. Every moment of it was torture. Until it wasn’t.” (51:45)
  “It also happened during the height of the most successful we ever were… We were both like, neither of us are in a mental headspace… interacting with each other is the top of the mountain of labor we can do. So do not bring RuPaul here. And then it just got easier. We processed… had different heartbreaks and hard times that we then were able to lean on each other for.” (52:05)

• Nicole praises his boundaries and self-awareness for declining high-profile career opportunities when mental health couldn't support them.

8. Pop Culture, Drag, and Humor

• Joking about Natasha Bedingfield, The Rock’s “Do you smell what The Rock is cooking?” (20:16), and how audiences lose their minds when they recognize something familiar.
• Extended riffing on “bukkake” and food, and pondering the shelf life of cum (“Not designed to last. The shelf life could not be shorter. That’s why they don't sell it at grocery stores.” —Nick, 48:05).

9. Tiny Joys: Ice Cream & Affirmation Rituals

• Nicole’s joy in acquiring a Ninja Creami ice cream machine from Facebook Marketplace and the ritual of making treats with her “nice man.” (54:00–56:38)
• Nicholas describes making it through heartbreak by talking “like a little baby” to himself:

  “I’ve been doing the out loud, ‘I love you, so, you’re gonna be okay.’” (16:53)

10. Advice & Affirmations

• Nicholas’s advice for singles:

  “Decide percentage-wise between the two mirrors—one which looks inward and one that helps you check your hair and your teeth. Make a goal for what percentage you want to spend in each mirror…” (58:59)

11. “Would you date me?”

• Nicole: “Would you date me?”
• Nicholas: “Yeah. I think we’d have so much fun. Especially now that I know you have a Creami.” (59:36)

Notable Quotes & Memorable Moments

• "I want to make sure my oxygen mask is on before I start fiddling with someone in the seat next to me." – Nicholas (07:07)
• "The person that you're seeing always lets you know right away exactly how they're gonna break your heart." – Nicholas quoting Kim Pierce (09:35)
• “Some of the nastiest freak bitches I ever met are straight guys that do musical theater.” – Nicholas (33:27)
• “Excruciating. Every moment of it was torture. Until it wasn’t.” – Nicholas on working with an ex (51:45)
• “I've been doing the out loud, ‘I love you, so you're gonna be okay.’” – Nicholas, on self-soothing after a breakup (16:53)
• “It’s not designed to last. The shelf life could not be shorter. That's why they don’t sell it at grocery stores.” – Nicholas, on the shelf life of certain bodily fluids (48:05)
• "Especially now that I know you have a Creami. I would cream so much for you." – Nicholas and Nicole, on hypothetical dating (59:41)

Timestamps for Significant Segments

• 04:39 – Nicholas introduced; community and relationship status
• 06:41–09:03 – Breakup honesty, grieving, advice from Sundance, ignoring relationship red flags
• 13:40 – Nicholas’s relationship “non-negotiables” and mirror metaphor
• 26:06 – Vegas childhood, school, megachurches, and performing arts experiences
• 33:16–34:24 – Queer adolescence, coming out, delayed dating, theater kids
• 35:49 – How “Very Gay Paint” was born; going from theater to artist/creative business owner
• 42:08 – Drag story: birth and backstory of “Trudy Detective”
• 51:45–52:53 – The difficulty and eventual resilience of keeping a business with an ex
• 54:00–56:38 – Ninja Creami ice cream stories, joy, and relationship rituals
• 58:59–59:28 – Final advice for singles (“two mirrors”)
• 59:32 – “Would you date me?” exchange

Final Takeaways

The episode is heartfelt and howlingly funny, grounding big topics—breakups, business and exes, self-esteem, creative accidents, queer community—in a loose, honest, and playful rapport. Nicholas’s story models self-reflection, resilience, and humor throughout life’s transitions. Nicole’s boisterous warmth guides the conversation, resulting in an episode packed with real talk, raunchy bits, and wisdom for anyone navigating love, creativity, or just trying to survive heartbreak (and maybe get some ice cream along the way).

Promotion/Plugs:
Nicole appeared as the first guest on the new season of Nicholas’s podcast, Art to Me (Thursdays). Nicholas performs as “Trudy Detective” in Southern California. Affirmations, encouragement, and offers from tall funky weirdos are welcome.

This summary omits advertisements and sponsorship breaks to focus on core content and heart of the episode.