Why Won't You Date Me? with Nicole Byer

Episode: Oversharing (w/ Yvie Oddly & Ryan Mitchell)
Release Date: December 5, 2025

Episode Overview

In this vibrant and hilariously candid episode of "Why Won't You Date Me?", Nicole Byer welcomes drag superstar Yvie Oddly (winner of RuPaul's Drag Race Season 11) and media personality Ryan Mitchell. Together, they delve into messy dating stories, polyamory, sexual openness, body image, and sex positivity within queer communities, all while bringing the playful chaos of their own podcast "High Key" to Nicole's signature space for oversharing. The episode is peppered with personal confessions, jokes, and genuine moments of insight about intimacy, identity, and the queer experience.

Key Discussion Points & Insights

1. Meeting, Chemistry, and Co-Hosting ‘High Key’

• How Yvie and Ryan Met: Despite their easy chemistry, the two had only met in person twice before the recording.
  • "It's literally our second time, like, getting to be together in person." — Ryan [02:20]
• Shared their motivation for creating "High Key," aiming for a blend of "The View" and unapologetic Black queer mess.
• Yvie was the drag queen who said yes after several others were unavailable, which Ryan sees as fate.
  • "We need to have, like, a drag queen, like, to really come on and give that vibe." — Ryan [02:43]
  • "They called, like, five drag queens, and they were like, uh, we're all busy, bitch." — Yvie [02:48]

2. Praise from Ariana Grande and Drag Race Reflections

• Yvie shares surprise and joy at Ariana Grande naming her one of her favorite drag queens.
  • "I was honestly pretty shocked because I know she's a weirdo." — Yvie [04:25]
• Discussion about Yvie’s experience and self-image on Drag Race, and being an unapologetic force of honesty.
  • "I didn't even think I was gonna win. I was just so drastically disappointed in everyone that my judgmental bitch came out." — Yvie [06:33]
• Recollections of RuPaul's Drag Race Season 11 drama, specifically with Silky and behind-the-scenes realities.
  • "We spent the whole season being like, oh, God, Silky's gonna win." — Yvie [07:22]

3. Reality TV Fantasies

• All three guests discuss which reality shows they’d want to appear on: Nicole chooses "Traitors," Ryan wants "Big Brother," Yvie is open to being on TV but noncommittal.
  • "I would do Traitors. I love traitors." — Nicole [08:19]
  • "I wanna do Big Brother. I'm so down for living in a house for 90 days." — Ryan [08:28]

4. Dating Stories & Relationship Structures

• Yvie is married and "still fucking," sharing how openness evolved in her relationship, especially during COVID lockdown.
  • "I mean, I feel like I don't like the word rules. Cause I don't like rules. But we do have lots of communication." — Yvie [13:45]
• Ryan reflects on moving for an ex and a history of toxic, monogamous relationships, then learning to embrace sexual openness.
  • "I'm historically known for dating awful men." — Ryan [09:44]
  • "I wish he would've actually been more honest with me." — Ryan [11:06]
• The dynamics of honesty, sexual exploration, and openness are unpacked and celebrated.

5. Sexual Openness & Humor

• The trio goes deep (and explicit) about sexual dynamics, verbal play during sex, labels, and reclaiming stigmatized terms (e.g., "slut," "cum dumpster").
  • "I love slut. I love sexy name. Slut." — Nicole [18:26]
  • "Load it up, load it up, load it up. Barry, put that on my tombstone." — Ryan [19:21]
• Yvie jokes about treating hookups as “boyfriends for a couple of hours.”
  • "All of my fucks are like dates, but my fucking, they are, you know, they're like a boyfriend for a couple of hours." — Yvie [19:53]

6. Navigating Body Image, Vulnerability & Queer Spaces

• Ryan shares about embracing style and self-love despite biases against larger bodies in queer spaces.
  • "It's taken me a long time to be like, okay, this person actually wants me for me." — Ryan [36:31]
• Yvie reflects on learning to see herself as desirable, drawing from her parents' confidence and community history.
  • "It wasn't until I got older...I just have to give myself more credit." — Yvie [34:13], [34:44]
• Discuss the importance of affirming support within queer friendships and hookups.

7. Sex Parties & Safety

• Ryan confesses to spontaneous risky encounters (giving "the best head of my life" to a stranger from a sex club parking lot).
  • "I followed him to his hotel and gave him the best head of my life." — Ryan [45:29]
• Yvie muses on the thrill and (sometimes) danger inherent in queer sex and analogizes sex to spider mating habits:
  • "It's the danger that, like, makes you feel alive." — Yvie [46:26]

8. Drag, Celebrity, and Dating “Fans”

• Yvie gets candid about the awkwardness when hookup partners are over-invested as fans.
  • "It's probably not the biggest turn on to be like, yeah, you look up to me in a weird, idealistic way...I'm so hard, I'm gonna wreck that puss." — Yvie [39:53]
  • Describes experiences where fans reveal their true selves AFTER sex.

9. Pop Culture, TV Nostalgia & Representation

• The group bonds over shared pop culture, TV nostalgia (Charmed, Stripperella, Nick at Night, Adult Swim), and the coded Blackness in animated series.
  • "Do you think the Simpsons are black because Marge has a texture?" — Ryan [53:42]
  • "Her name is like Bouvier, which is Creole." — Yvie [53:51]

10. Final Advice for Singles

• Yvie and Ryan offer their tongue-in-cheek (yet half-serious) advice:
  • "Don't take advice from anyone who's not single. They don't know what the fuck is up." — Yvie [58:17]
  • "Also, don't take advice from single people because we all are pretty jaded and it's the ghetto out here." — Ryan [58:23]
  • "Continue to fuck yourself. Use your hands, use the toy. They will never let you down." — Ryan [58:36]

Notable Quotes & Memorable Moments

• Yvie, on open relationships:
  "I just want to appreciate you for, like, whatever I get with you. Like, in these little moments we get to see. And we're just not gonna talk about the other guys." [13:59]

• Yvie, on living authentically:
  "She's so sexually open that it only makes me also want to be like…" — Ryan, referencing Yvie’s influence [12:03]

• On affirming body positivity in hookups:
  "I was just like, you know, I appreciate you for not making me feel weird about…" — Ryan [37:43]

• Yvie, on fan hookups:
  "If we're able to get to the sexual part without you…making some reality TV joke at me, then we're probably gonna be chill." [40:04]

Important Segments (with Timestamps)

• Meeting & "High Key" Origins – [01:50–03:44]
• Ariana Grande’s Compliment & Drag Race Talk – [04:00–07:22]
• Reality TV Dreams – [08:14–09:14]
• Ryan’s Past Relationships & Moving for a Partner – [09:26–11:02]
• Sexual Openness & Relationship Rules – [13:45–15:37]
• Sexual Play & Dirty Talk – [16:35–19:37]
• Wildest Dates & Love Bombing Stories – [19:42–22:56]
• Body Image, Queer Space, and Self-Acceptance – [36:31–38:14]
• Being a Public Figure and Hookup Dynamics – [39:41–41:18]
• Nick at Nite, Adult Swim, and TV Nostalgia – [52:02–54:09]
• Dating Advice (Comic and Real) – [58:17–59:16]

Tone & Style

The episode is riotously funny, irreverently sexual, yet also heartfelt and warm—reflecting the lived realities, humor, and resilience of Black queer community members. Oversharing is celebrated as an act of liberation, and the episode is sprinkled with running jokes, playful ribbing (especially around drag and dating), and pop culture references.

Where to Find More

• High Key Podcast: Mondays, wherever you get podcasts and on YouTube and TikTok.
• Nicole Byer: Subscribe, rate, and review. Send flirty emails to whywontyoudateme[at]podcastmail.com.

Endnote: Skip this episode with the kids in the car—this one, in their own words, is “oversharing” at its wildest.