Why Won’t You Date Me? with Nicole Byer

Episode: Coming Out (w/ Sasheer Zamata) – March 7, 2025
Guest: Sasheer Zamata (comedian, actress, Nicole’s best friend, co-host of “Best Friends” podcast)

Episode Overview

In this heartfelt and hilarious episode, Nicole Byer welcomes her best friend and frequent collaborator Sasheer Zamata for an intimate and open conversation about dating, boundaries, community, coming out, and all the delightful messiness of modern relationships. Sasheer discusses her recent experience of coming out, navigating the complexities of labels and identity, and how her own dating journey informs her sense of self. The duo also touches on the need for community, managing work-life balance in relationships, and the importance of just being yourself—even if that means loving sturdy shoes, chairs, or visiting random cars in your neighborhood.

Key Discussion Points & Insights

1. Setting Boundaries & Learning from Experience

• Nicole applauds Sasheer for her clarity in knowing what she does and doesn’t want in relationships.
  • Sasheer: “Time and experience… you kiss enough frogs and you start to learn what you don’t like.” (05:15)
  • As you get older, it becomes easier to communicate needs and recognize incompatibilities.
• Nicole reflects on struggling with boundaries in dating, often tolerating too much out of a desire to be liked.
  • Nicole: “I tolerated a lot. I’ve been like, ‘okay, whatever, just please like me.’ And then I learned that doesn’t work either.” (06:12)

2. Petty 'Icks' vs. Actual Dealbreakers

• The hosts discuss the trending culture of “ick” lists (petty turn-offs) and challenge the idea that minor annoyances are valid reasons to end something.
  • Sasheer: “If someone’s a misogynist, says hurtful things—those are real icks. It’s okay to not like your person sometimes.” (08:10)
• The conversation pokes fun at dating app shows (like “Pop the Balloon”) and how swiping mimics instant rejection culture.
  • Nicole: “We’re all popping the balloon right in each other’s faces.” (11:18)

3. Longing for Community

• Both lament the loss of organic, in-person community, especially as adults.
  • Nicole: “There is no community!” (13:35)
  • Sasheer: Points out new attempts to create it, such as curated dinner parties for strangers.

4. Coming Out & Navigating Identity

• Sasheer openly discusses coming out as queer and the motivations behind it.
  • Sasheer: “I don’t want to feel like I’m hiding that part of me...I just didn’t want that piece of me to feel secret.” (21:30)
• The duo talks about the nuances of coming out to friends versus public figures, and how often friends might “already know.”
  • Nicole: “When we discovered you loved sturdy shoes, I was like, that’s pretty gay.” (24:50)
• Labels like bisexual and pansexual are debated for their personal fit and meaning.
  • Sasheer: “Pan feels like the last level of a video game...I just got here.” (29:12)
  • Memorable Quote: “I’m a lesbian who likes to get railed sometimes.” (31:20)

5. Relationship Status & Validation

• Nicole reflects humorously on the anti-climax of finally having a boyfriend.
  • Nicole: “I was on set, I was like, yeah, my boyfriend... and nobody’s eyes lit up. Nobody smiled.” (39:21)
  • Both express how personal milestones sometimes matter more to us than those around us.

6. Balancing Work and Partnership

• Sasheer shares experiences balancing acting gigs and being partnered, especially when travel is required.
  • Sasheer: “I was very upfront. I won’t see you. Sorry, but I’m on call. I’m a comedy doctor.” (50:15)
• They stress the importance of clear communication during busy times.
  • Sasheer: “You can’t say the wrong thing to the right person.” (54:04)
• Nicole learns the value of asking partners how they’d like to communicate amid busy schedules.

7. The Importance of Authenticity in Dating

• Advice for singles: authenticity and specificity are attractive.
  • Sasheer: “Maybe don’t be afraid to say something unique about you, instead of what you think will attract somebody.” (65:10)
  • Nicole: “You can only pretend for so long...three months is the longest someone can pretend.” (68:32)
• It’s celebrated when partners (and friends) take interest in each other’s odd fascinations—be it the moon or cherry-red Volkswagens.

8. Pop Culture Tangents and Community Joy

• Delight in connecting over movies, especially “Joker 2: The Squeakquel” and “Madame Web.”
  • Nicole: “Everything is better on a bigger screen. We need community—go to the movies as a gang!” (58:54)
• Group recitation of Nicole Kidman’s pre-movie speech is longed-for.

9. Behind the Scenes of “Agatha All Along”

• Sasheer recounts adventures filming the Disney series, including wild stunts, community with cast, and being submerged in mud.
  • Sasheer: “They truly lowered me until I was submerged in mud… and then hosed me off.” (82:40)

Notable Quotes & Memorable Moments

• On boundaries:

  “Being older and being better at communicating… These are the things I like, these are things I don’t like. If you don’t like that, then we’re not compatible.”
  — Sasheer Zamata, 05:45

• On labels:

  “Pan feels like the last level of a video game. I beat everybody to get pansexual.”
  — Sasheer Zamata, 29:12

• On relationships:

  “You can’t say the wrong thing to the right person.”
  — Sasheer Zamata, 54:04
  “I thought everything in my life was gonna change when I got a boyfriend, and my life’s pretty much the same.”
  — Nicole Byer, 39:56

• On community:

  “There is no community!”
  — Nicole Byer, 13:35

• On unique dating bio strategies:

  “I like the moon. And she was like, hey, I like the moon too. I was like, I’m in love.”
  — Sasheer Zamata, 65:13

Timestamps for Important Segments

• 05:15 — Sasheer talks about learning boundaries in dating
• 11:18 — Popping the balloon/popular dating app analogy
• 13:35 — Rant on the lack of community
• 21:30 — Sasheer on coming out and keeping her personal life private
• 24:50 — "Sturdy shoes" lesbian joke and recognizing signs
• 29:12 — Debating labels (bi, pan, latent-life lesbian)
• 39:21 — Nicole on the anti-climax of having a boyfriend
• 50:15 — Balancing work and relationships, "comedy doctor" bit
• 54:04 — “You can’t say the wrong thing to the right person”
• 58:54 — Moviegoing as community
• 65:10 — Advice for singles: authenticity
• 68:32 — How long you can “pretend” in a new relationship
• 82:40 — Wildest moment on “Agatha All Along”: being submerged in mud

Final Advice

Be yourself, lean into your weirdness, and trust that the right people for you will love you for it. Don’t overthink your label or how you’ll be received—just do you.

For more: Stream Sasheer’s Disney show “Agatha All Along” and standup special “The First Woman,” both on Hulu.