Podcast Summary: Why Won't You Date Me? with Nicole Byer

Episode Title: Kiki-ing (w/ Oscar Montoya)
Date: November 7, 2025
Host: Nicole Byer
Guest: Oscar Montoya

Overview

This episode is a hilarious, meandering, and candid conversation between Nicole Byer and Oscar Montoya—both comedians, TV personalities, and drag show hosts in LA. The pair digress gleefully from dating to pop culture, fashion, weird reality TV, and wild personal stories, all wrapped in their signature playful, kiki-ing banter. While traditional relationship advice takes a backseat, the theme of self-acceptance and finding joy (alone or partnered) seeps through. Much of the episode is a celebration of authenticity, laughter, and queer joy.

Key Discussion Points & Insights

1. Opening Banter and T-shirt Discourse (03:10–05:18)

• Nicole compliments Oscar’s T-shirt, leading to a discussion about the real Tasmanian Devil, Looney Tunes character misrepresentations, and “bunny-coded” cartoon animals.
• Funny moment: “That’s not Taz. Is that wild that somebody saw that and then drew that?” (Nicole, 04:04)
• They spiral into a riff about how fashion brands make funny (sometimes problematic) T-shirts.

2. Casual Racism in 2000s Fashion (05:24–09:51)

• Reminiscing about Torrid and Abercrombie shirts, Nicole and Oscar recall problematic/racist T-shirts and commercialized racism in the 2000s.
  • They reference Abercrombie’s “Wong Brothers Laundry Service” and H&M’s “Coolest Monkey in the Jungle" PR disasters.
  • Notable quote: “Casual racism was everywhere. And that's not cool.” (Oscar, 09:01)
  • Discussion about the origins and co-opting of the word “woke.”

3. “Cancel Culture” and Comedy (09:05–11:45)

• They critique how “being canceled” can increase comedians’ income and visibility and question whether social accountability works.
  • Louis CK’s post-cancellation career used as an example.
  • Notable quote: “No one fights harder than bigots.” (Oscar, 10:39)
• They connect the concept of “wake me up inside” from Evanescence to the idea of societal awakening.

4. Nicole's Delivery Disaster and Lean Cuisine Talk (12:28–15:13)

• Nicole shares a story about a $30 salad gone missing due to delivery issues: “Should I simply scream ‘Where's my salad?’ into the night?” (Nicole, 13:25)
• Confessions about eating Lean Cuisine, the struggle with cooking, and the pitfalls of buying chicken in bulk.
  • Hilarious moment: “It never occurred to me [to freeze chicken]...I’m very much like, cook it now, never cook again.” (Nicole, 15:19)

5. Halloween Costumes and Roach Trauma (19:07–22:34)

• Oscar has worn a glamorous, bedazzled cockroach costume for 10 years. Nicole is horrified at the idea of roaches, leading to wild stories about roaches crawling on people in New York.
• Nicole riffs on her gynecologist visit and stoned thoughts about how gynecologists could mess with patients.
• Nicole recounts a child’s one-word joke (“one”) and how it slayed her more than the crowd.

6. Sexy Costumes & Fashion Nova's Wild Offerings (24:09–28:25)

• Nicole and Oscar riff on the most absurd and slutty Halloween costumes they’ve seen (e.g. “Yellow Creature” for Big Bird, “Cookies in the Jar” for Cookie Monster).
• Quote: “I’m truly in awe of what they can slutify.” (Nicole, 26:03)
• Discussion of group costumes like “sexy Oompa Loompas” turning accidentally Amish/colonial, leading to improv about churning butter.

7. Problematic and Bizarre Reality TV (28:40–34:46)

• A deep dive into old reality shows with wild concepts:
  • “Vanilla Ice Goes Amish” (31:12)
  • “Black. White.” (White family in blackface for "empathy") (30:24)
  • Shows using transphobia for shock (“There’s Something About Miriam”), “Joe Millionaire”, “Who’s Your Daddy?”
  • Quote: “The emotional manipulation of that show is crazy.” (Oscar, 33:57)
• Consensus: early 2000s reality TV was a “wild west.”

8. Traitors, Drag Race, and Casting Wishes (34:55–37:27)

• Nicole and Oscar gush about “The Traitors” reality show, imagining themselves as contestants and talking about friends/drag queens like Monet and Peppermint.
  • Concerns about how drag queens are treated on such shows.
  • “No, Monet is going to eat them alive. Either Monet will be the first out or she'll win.” (Nicole, 36:41)
• Nicole reveals Monet’s skill as a liar for strategic reality TV.

9. Dating...Briefly (37:30–56:00)

• Nicole tries to pivot to dating. Oscar shares how his first relationship was a joke-turned-real (“We were doing a bit. I thought it was a bit… at the very beginning,” Oscar, 51:15).
• Oscar reveals his current relationship, which began when he suspected a neighbor was following him, only to discover love after confronting him (53:10).
• Both admit to keeping relationships private, and reflect on shifting their self-image from “perpetually single” to “partnered.”
• Discussion of developing one’s own personality and being comfortable with oneself as prerequisites for a healthy relationship.
  • Advice for singles:

    “There is so much joy in being alone that a lot of people are scared of. And I would say, face that fear of being alone and come out the other side stronger… Be happy being single.” (Oscar, 55:16)

  • Nicole concurs: “It took me a very long time to learn how to be happy being Single… if it ended, yes, I would be sad, but I wouldn't, like, immediately jump to another one because I'm like, I'm okay being alone.” (Nicole, 56:40)

10. Drag Race, Stand-up, and The Sordid Tale of the Broken Toilet (57:53–50:53, non-linear)

• Oscar and Nicole promote the live “Bad Drag Race” show and swap stories about their mutual friend Mark Rennie’s iconic drag persona “Queef Counselor.”
• Nicole shares the infamous story of breaking a toilet at a venue by swinging her legs while sitting, sending water everywhere.
  • Quote: “The toilet broke out of the wall. I was propelled forward. Toilet water is shooting out...” (Nicole, 48:45)
• Discussion of being a stand-up comic, dealing with hecklers/main character audience syndrome, and Nicole’s evolution from sketch/improv to stand-up tours post-Girl Code.
  • Notable: Nicole admits she never actually felt she “got it,” but learned to craft jokes and handle disruptive audiences with grace and humor.

Memorable Quotes

• “It's easier to remain the same than change. Imagine going to therapy and figuring out why you think the way you think.” — Nicole and Oscar, multiple times (01:09, 10:48)
• “You’ve got to know when to shut up. If I say shut the fuck up twice, that's good. If I got to say it a third time, you're a fucking nuisance.” — Nicole (44:22)
• “It should be only a boon for the person that you're seeing to be surrounded by your energy.” — Oscar (55:16)
• “She needed a personality on Josh. Now that's a shirt.” — Nicole (55:02)
• “I'm glad that we're in a woke culture where… if I saw a barbed dick, I would go, no!” — Nicole (65:01)

Timestamps for Important Segments

• Tasmanian Devil, 2000s Fashion & Casual Racism: 03:10–09:51
• Cancel Culture & Comedy: 09:05–11:45
• Missing Salad & Lean Cuisine: 12:28–15:13
• Oscar’s Roach Costume & Gynecologist Jokes: 19:07–22:34
• Absurd Halloween Costumes: 24:09–28:25
• Reality TV’s Wild West: 28:40–34:46
• The Traitors / Monet Exchange: 34:55–37:27
• Dating Journeys & Self-acceptance: 37:30–56:00
• Broken Toilet Story: 47:54–50:53
• Advice for Singles: 55:16–56:40

Tone and Language

Throughout the podcast, the language is candid, comedic, playful, self-deprecating, and marked by queer slang and improvisational riffs. Nicole and Oscar bounce off each other with ease, sharing personal stories and messy confessions in a way that’s both vulnerable and uproariously funny. They use humor to approach topics like body image, race, and queerness, while still offering nuggets of real wisdom.

Conclusion & Takeaway

While the episode spends minimal time on “traditional” dating chat, Oscar and Nicole’s honest dialogue about self-acceptance, personality, and living joyfully—single or partnered—provides the most compelling relationship insight. The journey matters more than the destination, and being “happy being single” before partnering up is the ultimate lesson from their backed-up banter.

For those seeking relationship advice, a laugh, or pop culture nostalgia laced with biting wit, this is a classic Why Won’t You Date Me? episode.