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U Up?

Would You Date Someone With 2 Boyfriends? ft Bob The Drag Queen

U Up?

Betches

Relationships, Sexuality, Comedy, Society & Culture, Health & Fitness

4.714.8K Ratings

🗓️ 4 March 2026

⏱️ 73 minutes

🧾️ Download transcript

Summary

Bob the Drag Queen and Jared kick off today’s episode bonding over their favorite WWF wrestlers and swapping stories from their early stand-up comedy days. Then they dive into modern dating drama, including a straight boyfriend who wants to explore drag, but his girlfriend is feeling insecure and unsure how to navigate it. They red flags, deal breakers, and quirky relationship moments, from mannequins at the front door to reality TV obsession. Bob talks about having two boyfriends and advises an emailer that dating an ENM man is a definite dealbreaker if you’re monogamous at heart! Along the way, Bob shares stories from Eddie Izzard, Harry Styles, Moulin Rouge, and life on stage.  It’s a fun episode you don’t want to miss, and be sure not to miss Bob on Broadway until March 22! 👉: https://www.bobthedragqueen.com/appearances Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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0:00.0

Even if it's not something gross, I honestly don't know how much you have to pay me to eat a spoonful of mustard. Spoonful of mustard? Like a spoonful of like yellow mustard. What would it take? I give you $5. No, Jesus. You wouldn't do it for $5? No, no, no, no. I would do it for free. I love mustard. I hate yellow mustard. You hate? I don't, we can't do the podcast.

0:24.2

Hello and welcome to the U.L. podcast. I am Jared Freed and I am so excited to be here with our

0:30.5

special guest, Bob the drag queen. Thank you for being on the show. Generate Dgeneration X.

0:35.1

Suck it. Are you Xbox? Are you, uh, oh, I, Triple H. No, Sean Michaels. Sean Michaels to me was like... Sweet chain music was your vibe? That's more the, the attitude I would like to bring to the table. This will not shock you, but I was for the nation of domination. Uh-huh. Obviously. Of course. Um, but outside of that, my favorite wrestler was Mick Foley. Really? Always will be. Mick Foley is like... Mrs. Foley's baby boy. Wow. Will always be my favorite. I mean, this, for our audience, this is all Chinese. Yeah, they don't listen to any of this. Even this hat, I'll get a few people that are like whoa generation x hat i love that and then how old are you

1:12.9

i'm 40 40 yeah yeah i've been hearing about you for years um you're you're beloved oh my god really

1:20.5

yeah i would say you're beloved i would say your name comes up people light up do you feel that do you think that

1:27.1

do you know that well i do you know that you do for people?

1:30.8

I think that people who know me like me, but I'm still kind of niche.

1:35.8

Nech fine, but like when they know you love. Because I'm from, I'm not, from the world of like reality TV and cabaret and stand-up comedy, but I'm not like, you know,

1:45.1

Andrew Shultz. There are some of really big names out there who are like someone who I would say

1:49.4

is still kind of niche, but is actually a kind of like mainstream niche, would be like

1:53.4

Caleb Heron, maybe Britney Brookesky. They have like millions and millions of followers.

2:00.7

But I think the drag, some people just kind of hear the name of the drag queen. They're like immediately turned off so that I want to give it a chance. But the people who do, because I ended up on a show they like, like the traitors. Right. So because I'm on a show they like, they have to watch me. They're like, oh, Bob is actually pretty, you know, funny or interesting. It's funny to say that you look at it in the terms of followers. Like, because I think you have a cachet. Like, I think, like, there's a, you know, I heard this quote once. I'm sure it's been said a million times. Difference between a following and an audience. Anyone can get an audience.

2:34.9

You know,

2:35.0

a following is different.

2:49.9

You know, like... Yeah, that's true. Yeah. So I think you have a following. You know, the drag queen thing, I... I think anyone who's hyphenated with what they do feels that a little bit. Like, you know, I do a podcast. I do stand-up. I do, you know.

2:50.7

How many of them stand up?

2:53.2

I've been doing it almost 16 years.

2:54.7

We have almost the exact same.

4:00.9

Is I? You know, I do a podcast, I do stand-up, I do, you know. How many of the stand-up? I've been doing it almost 16 years. We have almost the exact same everything. That's crazy. We've been just two ships in the night. I've been doing comedy for 17 years now. Really? Yeah. Where did you start? What was the first thing? The first club I was passed that was Carolin's Comedy Club. I was passed at the New York Comedy Club, uh, Comics Comedy Club, which I was two of those clubs don't even exist anymore. I've been, um, thrown out of Gotham Comedy Club. How'd you get thrown out? I got thrown out because there was a confusion. I went to the like the young new artist, Bibbop Boop Boop Showdown, bit, but whatever it was. Yeah, I did the bitbop boop show. Yeah. And there was some confusion about what, because I got past to like the second round, but not the third round, but not the third round, which was the showcase. And they were like, oh, you got to come back here and, but then my name was on the list and I was on the list, but I was in full drag and they thought I was distracting. I was got thrown out of Carolines once. I got banned from Caroline's actually. Are you, when you're in full drag and doing standup, is that like, do you think people just don't know how to handle that? Is that like a, because standups, listen, I know this from walking into standup clubs. It's like there is a version of person that's doing stand-up that's like a little just like this sad, you know, like looking at the floor guy with a notebook who's, you know,

4:06.0

not dressed really well is like kind of like.

4:08.6

That's still me.

...

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