10: Vault: How do "drag relationships" work?

Summary

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The Bert Show – Episode Summary

Episode: 10: Vault: How do "drag relationships" work?
Date: May 14, 2026
Hosts & Cast: Bert (Birch), Melissa, and other commentators

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Episode Overview

In this lively episode, The Bert Show team dives into the unique and thought-provoking dynamics of "drag relationships." Using a real-life example from a friend’s circle, the hosts explore how romantic attraction, gender identity, and sexual orientation intersect in relationships involving drag queens and drag kings. The cast candidly discusses their curiosities, challenges, and the surprising nuances that come with such partnerships, weaving humor, personal perspective, and genuine fascination throughout.

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Key Discussion Points & Insights

1. Understanding the "Drag Relationship" Dynamic

• The storyteller introduces a friend’s friend, a man (pseudonym: "Jacob") who is a drag queen and has always dated men, and his relationship with a woman drag king who has always dated women.
• Both individuals are attracted to each other primarily when presenting in drag—Jacob as a woman, his partner as a man.

Notable Quote (Storyteller, 01:21):

“Jacob is a man who dresses up like a woman and is a drag queen… he found himself very interested in the drag king, which is a woman who likes to dress up like a man.”

2. Exploration of Gender and Sexual Attraction

• The cast tries to untangle the complexities, noting that anatomically, it’s a straight relationship, but with swapped gender presentations.
• They grapple with how presentation affects attraction, especially when the partners are not dressed in drag.

Notable Quote (Commentator 2, 02:12):

"So do they go out together, him dressed as a girl and she dressed up as a guy?"
Storyteller responds: "Yes."

3. Questions and Curiosities about Physical Intimacy

• The group discusses intimacy and the possible confusion when it comes to sexual encounters, especially since neither partner has previous experience with the other's anatomy.
• Discussion highlights how these experiences might challenge or expand their ideas about sexuality.

Notable Quote (Storyteller, 03:03):

“That was some of the questions that he was having for my girlfriend, because he’s never had to handle a vagina before... he didn’t know what to do in some of those situations.”

4. Perceptions from the Cast

• Melissa and others share their perspectives. Melissa, who identifies as a "gold star lesbian," expresses that while she can appreciate drag artistry, she personally can’t imagine intimacy with a man out of drag.
• The group debates whether this is a unique case of bisexuality, or something different.

Memorable Moment (Melissa, 03:57):

"I can understand being in the club and seeing them dressed up… but when they take the clothes off, then it’s completely different. Like a drag queen takes her clothes off and it’s a guy. No. Thank you."

Notable Quote (Commentator 1, 04:17):

"So this is a truly bisexual couple because he has fallen in love with a woman, a woman has fallen in love with a man, even though the clothes, they’re full on. Whoa."

5. The Power of Connection Beyond Labels

• The hosts marvel at how love and attraction can transcend labels and conventional boundaries.
• They express curiosity about what makes the relationship work, emphasizing the importance of identity, performance, and self-expression.

Notable Quote (Storyteller, 04:36):

"I mean, I’ve never heard of anything like it in my life..."

Memorable Moment (Commentator 1, 04:41):

"...ready to happen or an interview on Oprah, because I would sit there glued the whole time."

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Notable Quotes & Moments (with Timestamps)

• On Gender Presentation:

  • (Storyteller, 01:41): “She sees herself really as a man in her life, and he sees himself really as a woman in his life.”

• On Attraction:

  • (Commentator 3/Melissa, 02:26): “They found an attraction when they’re dressed up, that’s who they’re attracted to.”

• On Bisexual Dynamics:

  • (Commentator 1, 04:17): “So this is a truly bisexual couple because he has fallen in love with a woman, a woman has fallen in love with a man, even though the clothes, they’re full on. Whoa.”

• On Personal Discomfort:

  • (Melissa, 03:57): “I cannot... when they take the clothes off, then it’s completely different. Like a drag queen takes her clothes off and it’s a guy. No. Thank you.”
  • (Melissa, 05:31): “I’m a gold star lesbian, baby.”

• On Relationship Depth:

  • (Storyteller, 04:48): “Apparently. Like, head over heels. Attached at the hip, can’t stop talking about each other like so into each other.”

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Timestamps for Important Segments

• [01:21] – Introduction of the drag queen and drag king dynamic
• [02:12] – Discussion about presenting together as drag king and queen
• [03:03] – Challenges around sexual intimacy and anatomical “firsts”
• [03:57] – Melissa’s perspective on attraction and intimacy with drag performers
• [04:17] – Discussion about bisexuality and the uniqueness of the couple
• [04:36] – Reflecting on the uniqueness and depth of the relationship
• [05:31] – Melissa’s self-identification and the humor among the cast

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Summary

This episode is a candid and often humorous exploration into how "drag relationships" work, prompting the hosts to reflect on their own assumptions about gender, attraction, and sexuality. Through the lens of a real-life couple who cross traditional boundaries in both gender presentation and orientation, The Bert Show leaves listeners with intriguing questions about what really draws us to one another—and whether those connections can flourish far beyond labels and appearances.

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Transcript

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[Host (Birch)]

The Birch Show.

[Storyteller]

I have a friend of a friend who is a guy who's a drag queen. So he is a man who in a lot of times in his life is, you know, dressed as a man. You can see that he's a man, but he prefers to dress up like a woman and goes and competes in different drag queen contests and that kind of stuff. I've only met him once, but. But know him. But my friend knows him very well. And the most interesting story she told me the other day about him.

[Commentator 1]

Okay, you're gonna need a scorecard.

[Storyteller]

Follow me here. So he. I need to give him probably a fake name. Give me one. A guy name.

[Host (Birch)]

Aaron.

[Storyteller]

That's a. Both.

[Host (Birch)]

Oh, okay. Chris.

[Storyteller]

Okay.

[Commentator 1]

I could be both, too.

[Commentator 2]

Jacob.

[Storyteller]

Thank you.

[Commentator 1]

I could be both. I know a lot of chicks named Jacob.

[Storyteller]

Okay, let's go.

[Commentator 3 (Melissa)]

So do I, Bert.

[Commentator 1]

So do I.

[Storyteller]

Okay, so Jacob is a man who dresses up like a woman and is a drag queen. Okay. So we entered a contest, won it, and found himself very interested in the Drag king, which is a woman who likes to dress up like a man.

[Commentator 2]

Okay.

[Commentator 1]

Woman that wants to dress up as a man.

[Storyteller]

Right. So she dresses as a man. So she sees herself really as a man in her life, and he sees himself really as a woman in his life. Okay.

[Commentator 2]

Okay.

[Storyteller]

But they both, typically, in their lives have been gay. So he's dated men his whole life. She's dated women her whole life.

[Commentator 1]

Got it.

[Storyteller]

Well, now they have found one another and they are together in an anatomically straight relationship. But flip flop genders.

[Commentator 3 (Melissa)]

So he's attracted to the male part, the drag king part, the drag king. She's attracted to the girl part following this.

[Commentator 2]

Yeah, I think I've got it. So do they go out together, him dressed as a girl and she dressed up as a guy?

[Storyteller]

Yes.

[Commentator 2]

Whoa. Yeah. That's crazy.

[Commentator 1]

So it's a straight gay couple.

[Commentator 2]

Well, if you thought

[Commentator 3 (Melissa)]

they found an attraction when they're dressed up, that's who they're attracted to. Wow.

[Commentator 2]

So what happens when they're not dressed up? Right, but I want to know what happens when they're not dressed up.

[Commentator 1]

You couldn't what?

[Commentator 3 (Melissa)]

I couldn't sleep with them. You know, like if. When drag queens are beautiful and like, there's camp drag and there's drag drag. I'm assuming he's drag drag. Which is like, you couldn't tell the difference unless you knew. And there's some beautiful.

[Storyteller]

He's drag drag. Like, you cannot tell he's a he when he's in drag.

[Commentator 3 (Melissa)]

So there's some. There's some drag queens in Atlanta that are absolutely drop dead gorgeous as women. But the obstacle I would have is knowing that there are a guy underneath. There's no way I could sleep with him.

[Storyteller]

Well, and then that was some of the questions that he was having for my girlfriend, because he's never had to handle a vagina before.

[Commentator 1]

Whoa.

[Storyteller]

So he didn't know what to do in some of those situations when there were some things going on, when, you know, things were getting exciting. What does it mean when this happens and what do I do with this? Whatever. Because he didn't know.

[Commentator 1]

And how old is he?

[Storyteller]

I'm not sure. I don't know.

[Commentator 1]

30.

[Host (Birch)]

So what about her 20s?

[Storyteller]

Probably late 20s.

[Commentator 1]

Late 20s.

[Host (Birch)]

Has she ever had to handle a

[Storyteller]

No, I don't think so.

[Host (Birch)]

Man before?

[Storyteller]

Yeah, but I know that's gonna be a disappointing surprise. My friend knows him, so I know more of that side of the story rather than the woman who's the drag king.

[Commentator 1]

Yeah.

[Storyteller]

But is that the most fascinating. It, like, mind boggles me.

[Commentator 1]

I'm like, melissa's looking at you like it's really not a big deal.

[Storyteller]

Try to figure it out.

[Commentator 3 (Melissa)]

No, no, that's not that. I can understand the attraction. I can't understand them being together. I can understand being in the club and seeing them dressed up. I can understand him being attracted to her when she's dressed up, but I cannot. When they take the clothes off, then it's completely different. Like a drag queen takes her clothes off and it's a guy. No. Thank you.

[Commentator 1]

So you. But you have said before that if you're bisexual, that means you can fall in love with both a man and a woman. So this is a truly bisexual couple because he has fallen in love with a woman, a woman has fallen in love with a man, even though the clothes, they're full on. Whoa.

[Storyteller]

Fascinating, right?

[Commentator 1]

It really is.

[Storyteller]

I mean, I've never heard of anything like it in my life that is

[Commentator 1]

ready to happen or. Yeah. Or an interview on Oprah, because I would sit there glued the whole time.

[Storyteller]

But they are in love.

[Commentator 3 (Melissa)]

Really.

[Storyteller]

Apparently. Like, head over heels. Attached at the hip, can't stop talking about each other like so into each other.

[Commentator 1]

And he's never dated anything except men and she has never dated anybody except women. But now they have this in common and they're attracted to each other but

[Storyteller]

because they dress as the opposite gender.

[Commentator 3 (Melissa)]

Yeah,

[Commentator 1]

that is cool. That's cool.

[Storyteller]

It's crazy.

[Commentator 2]

I would have a lot of questions for them. How do they make that work? Because I want to talk to them and see how that happens.

[Commentator 3 (Melissa)]

What do you mean?

[Commentator 1]

Like it happens? Melissa's not buying it. She's shaking her head no.

[Commentator 3 (Melissa)]

I'm not saying I'm not buying it. I'm just grossed out by again when he takes his clothes off. Hell no.

[Host (Birch)]

Melissa makes that same face when she imagines any man taking clothes off, whether or not it starts with a pair of jeans or a skirt.

[Commentator 3 (Melissa)]

I'm a gold star lesbian, baby.

[Host (Birch)]

The bird show.