U Up? — "Would You Date Someone With 2 Boyfriends?" ft. Bob The Drag Queen

Podcast by Betches Media
Originally aired: March 4, 2026
Hosts: Jared Freid, Jordana Abraham (out), guest host Bob the Drag Queen

Episode Overview

This episode features comedian and drag icon Bob the Drag Queen as a guest host alongside Jared Freid. They explore the complexities of dating, identity, and personal quirks—digging into non-traditional relationships, navigating changing identities, parasocial relationships, and what red flags to look for in a partner. True to the U Up? spirit, the conversation is sharp-witted, unfiltered, and deeply empathetic, weaving Bob’s unique experiences with broader themes about modern love, labels, and embracing our quirks.

Table of Contents

• Opening Banter & Bob’s Background
• Polyamory: Bob’s Two Boyfriends
• Key Email: My Boyfriend Wants to Do Drag—What Now?
• Parasocial Relationships & The Reality TV “Ick”
• Dating Games: Red Flag or Dealbreaker
• Notable Quotes & Memorable Moments
• Episode Timestamps

Opening Banter & Bob’s Background

[00:52–15:54]

• Comedy & Drag Careers:
  • Bob and Jared connect over their stand-up comedy backgrounds and compare experiences as "niche-but-mainstream" performers.
  • Bob shares how being a drag queen affects audience perceptions—some see drag as a limiting label, while others are surprised to find him “actually funny.”
  • “I think that people who know me like me, but I’m still kind of niche. Some people hear ‘drag queen’ and are immediately turned off, but if they see me on a show they like… they’re like, ‘Oh, Bob’s actually pretty funny.’” – Bob [02:04]
  • Bob recounts early days at New York comedy clubs—sometimes being banned or thrown out for showing up “in full drag” and being seen as “distracting.”
• Family & Roots:
  • Bob and Jared talk about their siblings and families; Bob’s brother is a chef at a children’s hospital, his younger brother wants to be a therapist [15:33].
  • Bob admits to being an annoying, emotional child, seeking attention and crying, with a memorable story about his mom breaking his crying habit [17:15].

Polyamory: Bob’s Two Boyfriends

[20:56–23:32]

• Jared asks: "You have a—you’re in a relationship?" Bob replies coolly: “Yeah, I got two boyfriends.” [20:58]

• How Does It Work?

  • “They’re friends, which is nice… We live separately—me and Jacob live together, and me and Tao live together elsewhere.” [21:41]
  • Both boyfriends were met on Grindr. “I pay [the rent]. They’re broke!” – Bob [21:54]
  • “We started non-monogamous—we were never, like, locking it down… every relationship has ebbs and flows. At one moment, it’s more sexual, then more friendly—just like anyone else.” [23:08]

• Polyamory, explained:

  • Polyamory is described matter-of-factly, “That’s polyamory. Everyone in polyamory is doing it for the tax break.” [22:16, joking]

Key Email: My Boyfriend Wants to Do Drag—What Now?

[34:53–47:17]

• The Letter:

  • A woman writes in: her boyfriend, a straight man in a band, starts performing in drag and is interested in expanding this part of himself. She says she’s “pro-LGBTQ+” but feels insecure about her role, desire, and the future of their relationship.

• Bob’s Deep Dive:

  • “You learn a lot about yourself playing with gender. Once you undo it, you can never put it back together. The toothpaste is out of the tube.” – Bob [37:34]
  • “If you’re going to be on this journey… you have an opportunity to be there for him and grow together. But it sounds like she needs her celebration to come from a man, and someone who feels like a man.” [38:24]
  • Bob brings up how gender is a construct and labels are confining: “There aren't any straight people… it's a myth. Everyone’s a little gay, everyone’s a little straight, a little nonbinary.” [42:39]

• Jared’s Take:

  • “If all else is the same, what’s the issue?… This is your partner.” [39:17]
  • They agree—if her attraction changes, she’s not ‘hateful,’ but maybe not as ‘open-minded’ as she claims.

• On the pressure for straight men:

  • “Straight guys reap the benefits of society—but also have the highest pressure. For a gay guy, we’ve already been outcast—so I’m going to wear my heels, my skirt, my lipstick… because I’m already on the outskirts.” – Bob [46:21]

• Memorable Anecdote:

  • Bob tells the story of a couple from his show “We’re Here”—a wife accepting her partner who came out as a trans woman at 68, underscoring how support can transform a relationship [45:45].

Parasocial Relationships & The Reality TV “Ick”

[52:56–61:10]

• Male Listener Writes In:

  • He loves his girlfriend but is turned off by how invested she is in reality TV and celebrity gossip, describing it as “parasocial relationships” and asking: Is this the ick or am I just being picky?

• Bob’s Response:

  • “Parasocial is a strong word. It’s not just ‘I like this person’—that’s like, ‘Kim Kardashian is my friend’… I think she just likes reality TV." [53:19]
  • Jared points out the “ick” isn’t about TV, but how it dominates the relationship and feels ‘childish’ at their age.
  • “Reality TV became big when we were kids, so it seems like a kid thing, but it aged up with us.” — Bob [56:03]

• Jared & Bob’s Consensus:

  • It’s only an ick if the partner expects you to care as much as they do, or constantly references shows without context. Otherwise, sports fans, hobbyists, etc. are all the same: passion is attractive, obsession can be alienating.

Dating Games: Red Flag or Dealbreaker

Highlights: [62:35–72:00]

• Red Flag or Dealbreaker: Previously Poly Person

  • Letter-writer once dated someone non-monogamous, isn’t looking for ENM, asks if this is a red flag. Bob: “Dealbreaker. You’re on different pages. He’s not going to change his thought process—one of you’s hoping the other swings over and it’s not gonna happen.” [63:22]

• Red Flag or Dealbreaker: Mannequin at the Door

  • Listener: “He keeps a mannequin in the front entry of his house.” Bob: “That mannequin will get you every single time… I like quirky people, but not that quirky!” [69:00]

• Bob’s Past Red Flag:

  • Dating someone who wore their teeth as jewelry—“At first, I thought, that’s quirky; but it told me so much more…I should have taken the red flag for what it was.” [71:15]

Notable Quotes & Memorable Moments

• “Everyone can remember three things… It’s the John Madden rule.” – Jared [05:50]
• “You, you have to be that good or that gay.” – Bob, about fashion risks for men [49:17]
• “There are some thieving-ass, conniving-ass drag queens in these streets.” – Bob [12:51]
• “It’s crazy, people don’t know I have four comedy specials!” – Bob [14:06]
• “Straightness is a myth.” – Bob [42:44]
• “You gotta just come to grips with the fact that you don't want to date no gay guy…which is crazy because, on the surface, people act like they're into it.” – Bob [40:23]
• “If you love someone, you should be interested in their passions, but you don’t have to become obsessed with them.” – Bob [60:03]

Episode Timestamps: Key Segments

| Timestamp | Segment/Topic | |------------|-------------------------------------------| | 00:52–04:54 | Bob’s intro & journey in standup and drag | | 15:33–18:00 | Family background and childhood stories | | 20:56–23:32 | Bob’s polyamorous relationships | | 34:53–47:17 | The ‘drag boyfriend’ email & gender talk | | 52:56–61:10 | Reality TV, parasocial relationships, & “ick” vs. “picky” | | 62:35–64:44 | Red flag/dealbreaker: Past poly partners | | 66:27–72:00 | Red flag/dealbreaker: Mannequin at the door | | 74:00–76:38 | Book talk, wrapping up |

Final Thoughts

The episode is a riotous, insightful, and emotionally intelligent tour through what it means to date with openness, self-awareness, and a sense of humor. Bob’s candor about polyamory, gender identity, and the realities of queer dating are especially rich for listeners seeking honest perspectives outside the mainstream. The advice throughout is both practical and compassionate—reminding listeners (and each other) that you can only be yourself, and that genuine connection will require evolving past old scripts, societal constraints, and sometimes, mannequins with cocktails at the front door.

Listen if:
You want a laugh-out-loud, boundary-pushing discussion of modern romance, with both sage advice and plenty of friendly shade thrown around.

Remember:
“You have to be that good—or that gay.” [49:17]