Vault: Jeff's Unhooking Bra Race

Summary

The Bert Show (Pionaire Podcasting)

Episode: Vault: Jeff's Unhooking Bra Race
Date: December 10, 2025

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Episode Overview

In this lively and nostalgic episode, the cast of The Bert Show recreates a humorous rite of passage: the challenge men face unhooking a bra, as inspired by scenes from classic 80s teen movies. With plenty of banter, confessions, and competitive spirit, the cast organizes a hands-on race—literally—to see who among them can unhook a bra the fastest, with hilarious results and plenty of playful ribbing. The show leans into awkward adolescent memories, team rivalries, and a behind-the-scenes look at their own brand of humor and camaraderie.

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Key Discussion Points & Highlights

1. Setting Up the Challenge

(01:33 – 04:30)

• Nostalgia Trigger: Jen brings up how 80s movies often dramatize the awkwardness of unhooking a bra, prompting memories of adolescent pressure for guys (“Is there any more pressure for a guy than unhooking a bra?” — Jen, 03:52).
• Team Formation: The cast splits into teams: Bert & Tracy, Crash & Melissa, and Jen & Jeff.
• Anticipation & Anxiety:
  • Crash jokes about the “sexual tension” and “anxiety” of the challenge, setting a light, competitive tone.
  • Tracy and Melissa poke fun at the situation, teasing Crash for his supposed enthusiasm and experience.

2. Rules, Rivalries, and Logistics

(04:31 – 09:00)

• The Rules: The challenge must be completed using only one hand, echoing the constraints of teenage make-out sessions.
  • “I think it should be a one-handed thing, because when you were making out back in the day…” — Crash, 05:33
• Authenticity Concerns: There’s joking about which bra clasps count (“There are some bras… women with smaller breasts have less clasps than women with larger breasts, correct?” — Crash, 07:28).
• Good Sportsmanship: Despite the tease, everyone gets on board and recognizes the whole thing is for bragging rights.

3. The Unhooking Bra Race

(09:00 – 10:45)

• The Countdown: Jen orchestrates the countdown to begin the “race.” The room is thick with silly anticipation (“Is anybody else feeling the seventh-grade tension…?” — Jen, 10:01).
• The Results: Jeff surprises everyone by finishing first, despite earlier nervousness.
  • “Jeff’s done.” — Jen, 10:27
  • “I can’t tell you how awkward that was. I couldn’t get anywhere near it. I wasn’t even close.” — Crash, 10:30
• Debrief: Teammates high-five and share laughs over the outcome, with Crash lamenting his poor performance (“I didn’t even get one unclassed.” — Crash, 10:49).

4. Technique Breakdown and Show Banter

(10:46 – 12:24)

• Technique Talk: Jeff explains his two-finger snap method for unlatching bras, making it sound almost like an urban legend.
  • “You take your thumb and finger, put them in between, you snap your fingers and that moves them both at the same time. That’s exactly the technique I did...” — Jeff, 11:23
• Banter on Awkward Moments:
  • Remembering movies where the guy can’t figure out a front-clasp bra (“…you’re searching, you’re rubbing the back, you’re looking for the clasp, and then the girl, it’s in the front.” — Jen, 12:04)
  • Tracy jokes about letting guys “sweat a little bit” before revealing the trick.

5. Listener Call-In: Expert Tips

(12:24 – 13:32)

• Jeremiah’s Call: A listener, Jeremiah, calls in to walk the crew through proper bra-unhooking technique step by step, playfully coaching the group on air.
  • “Take your left hand and put it around her back and stick your index finger between the bra strap and her back… you snap it right open.” — Jeremiah, 12:45

6. Wrap-Up and Aftermath

(13:32 – 14:06)

• Praise and Laughter: The group congratulates Jeff for his deftness and jokes about rotating positions for another round, staying in typical Bert Show comedic flow.

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Notable Quotes & Memorable Moments

• Jen (on the pressure of the moment):
  “Is there any more pressure for a guy than unhooking a bra?” (03:52)

• Crash (on competitive nerves):
  “I just now got all sorts of anxiety.” (03:57)

• Tracy (on Crash’s supposed experience):
  “Office mates in Crash have been trying to get my bra off for years, so he’s gonna be speedy on this.” (04:33)

• Crash (post-race, humbled):
  “I couldn’t get anywhere near it. I wasn’t even close.” (10:30)

• Melissa (evaluating Jeff’s skills):
  “He was actually really good at it, you guys.” (10:47)

• Jeff (explaining his method):
  “You take your thumb and finger… you snap your fingers and that moves them both at the same time.” (11:23)

• Jen (on the classic movie blunders):
  “You’re searching, you’re rubbing the back, you’re looking for the clasp, and then the girl, it’s in the front.” (12:04)

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Timestamps for Main Segments

• 01:33-04:30: Setup and nostalgia—how the challenge idea came up
• 04:31-09:00: Teams, rules, and competitive banter
• 09:00-10:45: The live unhooking bra race and outcomes
• 10:46-12:24: Technique talk and pop culture recollections
• 12:24-13:32: Listener (Jeremiah) calls with expert tips
• 13:32-14:06: Aftermath and closing laughter

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Tone & Style

The episode is infused with the Bert Show’s signature mix of authenticity, playful teasing, and frank reminiscence, punctuated by moments of absurdity and warmth. The cast keeps the tone light and inclusive, poking fun at themselves and their own adolescent awkwardness. The topic, while slightly risqué, is handled with humor and camaraderie, making it a memorable (and replay-worthy) bit for fans.

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For listeners who missed it:
This episode is a throwback to hilarious teenage mishaps, packed with competitive antics and offbeat wisdom about that classic movie trope—the struggle of unhooking “the bra.” Through their candid conversation and in-studio race, The Bert Show cast delivers both laughs and a reminder of life’s most human, awkward, and universal moments.

Transcript

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[Jen]

Purch the first show, we were talking, you know, just a minute ago about the, you know, going back to. What's that? Probably elementary school and even a little middle school.

And I was watching on TV one of those, like 80s, you know, fast times at Ridgemont High movies or whatever.

[Jeff]

Classics.

[Jen]

Tracy, you can go stand here.

[Melissa]

Burt.

[Crash]

Ooh, bring it.

[Tracy]

Oh, we have places.

[Melissa]

So I thought places, people, places.

[Crash]

People exit stage lefty.

[Jeff]

Then I thought.

[Jen]

Thought of a contest, you know, kind of like a bet that we could do. And I'll need Crash and Melissa to share a microphone. And then Jen, if you could come over here.

[Melissa]

Okay.

[Jen]

Because this is a team.

[Crash]

Oh, no, this is.

[Jeff]

We have to share a microphone or can we close?

[Crash]

This is Jeff's party pocket bit.

[Melissa]

Hey, I hope that this has nothing to do with naming as many people as you can think of from high school, because I graduated with 19 shows. We're good.

[Tracy]

All right, Crash, hands on the table, Hun.

[Jen]

Hands on the table. Oh, for the guys. Women, you can do whatever you want with this.

[Jeff]

Touch me where I pe.

[Jen]

Now, here's.

[Melissa]

No, he didn't. Oh, my God.

[Tracy]

You are that uncle.

[Crash]

What is the matter?

[Tracy]

You are the uncle that kids are scared to go see.

[Crash]

What the matter with you?

[Jen]

Melissa, do you want filterana?

[Melissa]

And I was about to say.

[Tracy]

No, I can handle Crash.

[Paige Desorbo]

I can handle.

[Jeff]

Sorry.

[Jen]

So I'm watching this 80s movie and I know the guys. This is going to be relatable to all of us, to Jen and Melissa and Tracy. Just so the listeners know, Burt is partnered with our producer, Tracy. Crash and Melissa are on one team, and then Jen and I are on another team.

[Crash]

Okay, is this going to be a competition? Because if so, I feel sad for you, because Jen is as competitive as it gets, and Carter over here also.

[Jen]

It's a competition, Chase. And I think it's more. I mean, it's more for bragging rights. Like, the guys are going to be the ones to leave with the bragging rights. But the girls are on our team.

[Tracy]

I'm afraid of them.

[Jen]

Well, let me explain it. You guys always knew the amount of pressure that would come when you were out on a date and you were kind of fooling around and it came time to unhook the bra.

[Crash]

Oh, boy.

[Jen]

Right?

[Jeff]

Okay.

[Jen]

Like, is there any more pressure for a guy than unhooking a bra?

[Crash]

I just now got all sorts of anxiety.

[Tracy]

I am so glad. I am so glad the Crash is on my team.

[Jeff]

Hey, just Jeff, her bra's already off.

[Jen]

Crash has her bra in his pocket.

[Jeff]

I hear the Clint Eastwood music already.

[Melissa]

No, it's cause Melissa burned hers years ago.

[Crash]

Shouldn't there be, like a horse race almost where you and I should be handicapped? Cause is obviously the favorite.

[Jen]

I envision Crash doing something like this.

[Jeff]

And it's off.

[Jen]

Bam. Right through the chair.

[Tracy]

Office mates in Crash have been trying to get my bra off for years, so he's gonna be speedy on this.

[Jen]

Am I safe to assume that all women here have a bra that clasped in the back this morning?

[Melissa]

Yes.

[Crash]

Oh, no.

[Melissa]

Uh.

[Tracy]

Oh.

[Crash]

You don't have a bra.

[Melissa]

Who's in the front?

[Crash]

Ursa winner.

[Jen]

Well, guess what? The new intern's getting broken in. Oh, hers is in the front too.

[Tracy]

Hers is in the front too.

[Jeff]

Well, let's get Leslie Fram.

[Crash]

I'm not going.

[Jen]

Yeah, we need somebody in the building with a back clasping bra.

[Tracy]

Unless Mandy.

[Melissa]

How about Phil intern Mandy might have one.

[Jen]

Mandy.

[Jeff]

She's got one here.

[Melissa]

She's got one. Here she comes.

[Crash]

Oh, this would be fun.

[Jen]

Mandy, you're on birds team. Sorry.

[Jeff]

Oh, that's a hell of a switch between Tracy and Wow.

[Tracy]

Jeff has come up with. This is a race to unhook our bras.

[Crash]

Yeah. You're stunned by this.

[Jen]

Yeah. So I think what we'll do is we'll. We'll do a countdown and then we will all attempt to unhook the rebound.

[Melissa]

Now, do we have two hands?

[Jeremiah]

One hand?

[Crash]

One hand or both? Yeah, two hands.

[Jen]

What do you guys want to do?

[Tracy]

I think it should be a one handed.

[Crash]

One handed thing because when you were making out back in the day.

[Melissa]

Okay, now do we have to be facing you guys or back?

[Jeff]

How are we doing this?

[Jen]

No, I think we.

[Tracy]

I think. Right.

[Jen]

So then we.

[Crash]

I mean, it should be as authentic as possible.

[Melissa]

Yeah.

[Tracy]

Jeff, it's your game. How do you.

[Jeff]

Well, if it's all fishing this.

[Melissa]

I feel like I'm in seventh grade. I'm getting sweaty palms.

[Tracy]

And I'm sitting here going, how do I tell him I'm gay? I tell him I'm gay.

[Jeff]

There is absolutely no reason that I'm not gonna be here till Jeff Miles comes on. I'm taking my time.

I finally get to go up Melissa's shirt. I'm not getting out fast.

[Jen]

So are we all in agreement that Crash probably will win this?

[Crash]

Oh, yeah, he'd be that hands on favorite. I don't know. Oh, yeah, for sure. I didn't have to do this in a long time.

[Melissa]

No.

[Jeff]

Well, you don't understand.

[Crash]

You probably did this just two weeks ago.

[Jeff]

My Neanderthal brain knows not foreplay.

Gunga wants.

[Crash]

Oh, boy.

We both have children. You understand this is just all about business, right? And I know the sexual tension that's been going on between you and I At this point, let's try to put that aside.

[Jen]

Okay, so this is now. Here are people.

[Melissa]

Oh, wait, where's Phil?

And Phil, he used to be in on this.

[Crash]

He doesn't have anybody's.

[Jen]

He doesn't wear a bra, Jen. They'll stand up like that on their own.

[Melissa]

Yeah.

That'S.

[Tracy]

Me and Jeff should be talking.

[Melissa]

What?

[Jen]

All right, so are we all. If we're going to put money in, are we betting on Crash?

[Crash]

Oh, I Would bet on Crash.

[Melissa]

I wouldn't.

[Jeff]

I'm telling you.

[Tracy]

This is so bizarre.

[Melissa]

Do we face like a moment on the Bird show? This is weird. This is worse than the football kissing game.

[Crash]

You make the rules. I don't care.

[Tracy]

Weird.

[Jen]

I think we just. I think. I think we get in position so, like, Jen would stand right in front of me.

[Crash]

See, I don't think this is a real fair competition, and I, I. I hope I'm not being insensitive.

[Jen]

I mean, if you wanted to do it really fair, we technically should be in the backseat of my 1986 Mercury Marquis.

[Melissa]

Help. Fecal.

[Crash]

Fecal finder. I'm just saying that there are some bras. Women with smaller breasts have less clasps than women with larger breasts. Correct?

[Jen]

That's right.

[Jeff]

You could be here all day with hers.

[Crash]

And Mandy here. Yeah, she's got huge boobs. So this. I've got more obstacles to go around than y' all do.

[Jen]

It's the luck of the draw.

[Melissa]

I mean, Jeff, you really have very few obstacles.

[Jeff]

All Jeff has to do is sneeze, and the Jen's gonna come off.

[Crash]

How do you get off a training bra?

[Tracy]

Now, that's insens.

[Melissa]

It's like a sports bra. You have to take it over my head.

[Jeff]

You got to get over the romper room tag first.

[Crash]

My little bra.

[Melissa]

It's not even an A. It's almost an A.

[Tracy]

Is the size.

[Melissa]

Come on. No, it's not really.

[Jeff]

It's like teaspoons with material on them.

[Tracy]

But I'm sure she. Yeah, whatever.

[Paige Desorbo]

Go ahead.

[Crash]

All right.

[Jen]

Hey, Melissa, when's the last time a man removed your bra?

[Tracy]

Yeah, I can't remember. If ever.

[Jen]

Here's what we'll do is we'll do a countdown, and then it'll be on your market. Set, go. And then we. I'll do. It'll be 1, 2, 3, go. We all go on go.

[Crash]

Okay.

[Jen]

And then it's the wait.

[Tracy]

We raise our hand.

[Melissa]

Phil has to officiate. Phil, you gotta be the referee.

[Tracy]

I'm not lifting my shirt to show anybody anything. I think that we can just go. By the way, raise your hand when we feel that the bra has been eye class.

[Jeff]

How about when the bra is off, we pull it out from the shirt and swing it around.

[Melissa]

I can't believe we're doing this.

[Tracy]

I can't either.

[Crash]

I can't believe you guys didn't even fight. It instantly got up, came right over to us. Jeff said what the rules were, and you guys were like, all right.

[Tracy]

Based on the vibe of the room and the past conversations. If we said anything against this.

[Melissa]

Ah, you bit killer. You women. You get fatty bitty bit.

[Tracy]

So here's the deal.

[Crash]

We do it the way we do it.

[Melissa]

Wouldn't he?

[Jen]

We do it. Oh, God. We do an anti woman bit, and then it's one man gets to have sex with Melissa. And she'll do it. Just not be a bit killer.

[Tracy]

Right?

[Jen]

All right, we ready?

[Crash]

You ready to do this? You can't have your hands like that. I can't get.

[Jeff]

I gotta go up your shirt there, hot stuff.

[Jen]

So I'm gonna do wine glue.

[Melissa]

His idea.

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You were the only man in.

[Jen]

Ryan's asleep. Right.

[Hers Advertiser]

Who has touched my bra besides my husband?

[Crash]

Well, you're the only woman in 10 years that. That I.

[Paige Desorbo]

You know.

[Jen]

So I'm going to do 1, 2, 3, go, and then we all. So it'll be 1, 2, 3.

[Melissa]

This is really awkward.

[Jeff]

Melissa's already got her hand on my shoulder.

[Crash]

She's like, take me, big boy.

[Tracy]

I'm competitive. We're going to win this thing.

[Jeff]

Now we're using two hand. As many as we want, right?

[Crash]

Just one hand.

[Jeff]

Oh, it's one hand.

[Jen]

Okay, one hand. Side.

[Jeff]

Does it matter that I have a boo boo on my finger?

[Jen]

I'm going right.

[Jeff]

You're going like that.

[Melissa]

Okay.

[Crash]

All right, you ready? I'm going on this way. You ready?

[Melissa]

I'm really nervous about this.

[Jen]

Okay, you ready?

[Melissa]

Yeah.

[Jen]

Is anybody else feeling the seventh grade tension or ninth, tenth grade tension?

[Tracy]

Totally.

[Jen]

Where you're like, okay, ready? We sure already.

[Jeff]

I'm taking my time.

[Jen]

Hey, Mandy, was this in the intern description?

[Crash]

If it wasn't, write it in.

[Tracy]

Okay, go.

[Crash]

All right, ready?

[Melissa]

Ready?

[Jen]

1, 2, 3, go.

[Jeff]

I don't want to, like.

[Jen]

I can't.

[Melissa]

Oh, Jeff's done.

[Jen]

Jeff's done.

[Jeff]

I couldn't get you.

[Melissa]

Damn it.

[Crash]

Oh, I can't tell you how awkward that was. I couldn't get anywhere near it. I wasn't even close. Oh, I got one.

[Jeff]

I got one.

[Melissa]

You got one?

[Jeff]

I got one.

[Crash]

I didn't even get one.

[Jeff]

I got one.

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Damn.

[Melissa]

Oh, I can't. I can't.

[Jen]

High five, Jen. Cause she's getting dressed.

[Tracy]

Jeff, let me just ask a question.

[Melissa]

He was actually really good at it, you guys.

[Crash]

Yeah, I didn't even get one. Unclassed.

[Tracy]

What was the motivate? What?

[Melissa]

Sparks?

[Tracy]

I'm just curious how you came up with this contest.

[Jen]

I was watching some stupid, you know, movie that was running, like, in one of those marathon things on cable, and one of the scenes in the movie was a guy just trying to unhook the girl's bra. And it was just very funny because he kept doing it and kept doing it, and I'm like, oh, my God. I remember. I used to be pretty good at that.

[Crash]

I'll tell you what this is all about. This is Jeff getting, like, the sexual harassment handbook two weeks ago and trying to figure out how to get around.

[Jen]

How can I still touch boob and say it's a bit.

[Jeff]

Well, you know what? You know what they. They say the old urban legend myth or whatever is when you have a bra that's just your basic two clasper. You take your thumb and your finger and you put them in between. You snap your fingers, and that moves them both at the same time. That's exactly the technique I did to Melissa, but the tag got in the way. But basically, that's what you do.

[Crash]

I never could get it wrong. I never could get it wrong. I was always stumbling and bumbling and finally had to use both hands.

[Jeff]

Yeah, you just kind of give it the old side to side.

[Crash]

Then there's that awkward moment where you realize you can't get it done, and she realizes you can't get it done, and she starts to take it off for.

[Tracy]

That totally reminds me one movie that came to mind. Like the Animal House, when he was like. Remember when he was just pulling and tugging and on the toilet, he tried.

[Jeff]

To cut it with the scissors.

[Jen]

Yeah. And I'll tell you what. Is there anything worse? And you know what? I shouldn't have asked the question, but is there anything worse than you going for the back and having to be a front? And you find you're searching, you're rubbing the back, you're looking for the clasp, and then the girl, it's in the front.

[Crash]

Right.

[Tracy]

And of course, she has to wait to tell you because she always loves for the guy to have to do a little search and sweat a little bit.

[Melissa]

Good morning.

[Crash]

All the hits. Q100.

[Jeremiah]

Hey, bud.

[Crash]

How's it going?

[Jeremiah]

This is Jeremiah.

[Crash]

Hey, Jeremiah.

[Jeremiah]

I wanted to give you a lesson on how to unhook a bra from the back.

[Crash]

Okay.

[Jeremiah]

Is there. Pick somebody, I guess, and get in front of them.

[Melissa]

Oh, I was gonna coach. You know what? Step by step.

[Jen]

Here we go again.

[Melissa]

Go ahead. Enter Mandy.

[Tracy]

Oh, my God.

[Crash]

Okay, you ready? Yeah.

[Jeremiah]

Okay, take your left hand and put it around her back and stick your index finger between the bra strap and her back. Right Underneath where it. Right behind where it clips.

[Crash]

Got it.

[Jeff]

I'm there.

[Jeremiah]

Take your middle finger and Your thumb and squeeze around your index finger to kind of make a little bow in the bra where the clasp is.

[Melissa]

Yep. Not working.

[Jeremiah]

And then you take your finger out and it. And it, you know, it's like a little bit of slack and it just pops it right open.

[Crash]

Yeah, it's not working.

[Tracy]

Oh, I see what you're saying.

[Crash]

See what you got.

[Melissa]

Now?

[Jeff]

Do you have. Now maybe do you have the one or two clasps where you have like the four shotter?

[Crash]

It's just two.

[Melissa]

Just two?

[Crash]

Yeah.

[Jen]

What was yours, Carter? One or two minus two.

[Melissa]

But Jeff did Snap. Snap.

[Crash]

Very nicely done. Very well done.

[Jeff]

Very good, Jeff.

[Jen]

Okay, everybody, let's rotate.

[Crash]

The bird show.

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[Jen]

So good, so good, so good.

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[Melissa]

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[Melissa]

My holiday shopping hack, join the Nordiclobe.

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