Vault: The cast asks each other uncomfortable questions

Summary

The Bert Show – Episode Summary

Episode: Vault: The cast asks each other uncomfortable questions
Date: June 18, 2026

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Episode Overview

In this lively and unfiltered episode, the Bert Show cast dives into a round of “uncomfortable questions” submitted anonymously by the hosts themselves. With rules that ban explanations until the following day, the conversation is full of genuine reactions, awkward admissions, and plenty of laughs. The episode showcases the group's camaraderie and willingness to put each other (and themselves) on the spot, offering a candid glimpse into their personalities and relationships both inside and outside the studio.

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Key Discussion Points & Insights

1. Game Setup & Rules

• Anonymous, Unfiltered Questions: Each cast member submitted awkward or personal questions, not knowing who would answer.
• No Explanations Allowed: Unlike previous rounds, this time answers must be given with no elaboration until 24 hours later.
  • Bert: “We're going to change things a little bit this time in that you're not allowed to give an explanation today on your Answer—that comes in 24 hours.” (02:00)
• Final “Super Squirm” Round: The last question must be answered by everyone, regardless of discomfort.

2. Rapid-Fire Awkward Questions

• Are You the Smartest Member?
  • Wendy: “No.” (03:12)
• Sent a Graphic Text or Photo in the Last 3 Months?
  • Wendy: “No.” (04:06)
• Most Embarrassing Kid Moment?
  • Jen shares a vulnerable childhood story about being called “prude” by a crush and not knowing what it meant, leading to tears and embarrassment at school.
    • “I was so embarrassed... I remember going to the bathroom and crying. Cause I knew it was bad, but I didn't know what it meant.” (05:17)
    • Jeff’s support: “Well, you've shown him as a grown up, haven't you?”
• Come Close to Cheating on Current Partner?
  • Jeff: “No.” (06:14)
• Friend You’re Most Jealous Of and Why?
  • Bert envies his friend Dolvett's charisma and looks:
    • “When that dude... he's so good looking, he walks into the room, the whole damn room stops. He's an attention grabber, just from his looks.” (06:24)
• Ever Slept with a Married Person?
  • Wendy: “No.” (07:13)
• Place & Time of Last Outdoor Sex?
  • Wendy, with comical team prompting, can’t quite recall: “Oh God, I don't remember. Isn't that terrible?...I mean it would have to be Walmart parking lot, it would have to be in the car somewhere.” (08:02)

3. Annoyance & Honesty at Work

• How Many Shows Out of 10 Are You Annoyed by a Coworker?
  • Jen: “Out of 10, I'd probably go with five.”
  • Bert: “So, half of the shows we do, you're annoyed by at least one person...” (09:03)
• Telling a Significant Other They Look Good in Something When They Don’t?
  • Jeff: “No, I have not.” (09:20)

4. The “Single” Question

• Why Do You Think Wendy and Jen Are Still Single?
  • (Joking tone)
  • Jeff: “Prudes.” (09:35)
  • Bert: “I just don't think the right guys come along yet.” (09:47)
  • Wendy jokes that perhaps she wrote the question herself.

5. The “Super Squirm” Round: Therapy Edition

Each cast member is forced to answer:
If you stepped into a therapist's office today, what would be the first issue you’d try to fix about yourself?

• Wendy: Issues about parenthood and confidence. (11:04)
• Jen: “The struggle between decisions to be made—between having a life of career focus or family focus. That Little Orphan Annie tug of war.” (11:32)
• Jeff: “I would like to know why I always feel like I have to be working.” (12:15)
• Bert: “Mine would be intimacy issues...I don't let anybody get too close. Like, I sort of keep people at arm’s length.” (12:29)

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Notable Quotes & Memorable Moments

• “We stop each other in mid-sentence and we say on the air. Save it for on the air.” — Bert (03:40), on keeping stories authentic for the show.
• “I love you, but I like you the least.” — Jen to Jeff (02:43)
• “The squirmy round was fun, but I could answer that question. I'm in trouble when I get home.” — Wendy, on the aftermath of sharing live (12:47)
• Crowd goes wild section as everyone tries to talk at once in protest or excitement. (07:01)
• The crew’s banter about “the squirmy round” vs. “super squirm”—a running joke as they up the stakes. (10:03–10:07)

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Timestamps for Important Segments

• 03:04 – The rules and setup for the uncomfortable questions
• 04:26–05:49 – Jen recounts her most embarrassing childhood moment
• 06:24 – Bert discusses jealousy toward a friend’s charisma
• 09:00–09:08 – Jen admits to being annoyed at coworkers half the time
• 10:04–12:47 – The Super Squirm/Therapy round, with each cast member’s honest self-assessment

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Episode Tone & Language

This episode is playful yet revealing, with the Bert Show's signature blend of humor, honesty, and the occasional jab. The hosts’ realness comes through as much in their laughter over awkward questions as in their willingness to be vulnerable with each other—and their audience. Regular inside jokes and group camaraderie make even tough or embarrassing admissions feel safe and entertaining.

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Summary Use Case:
For listeners who missed the episode, this summary provides a full picture of the discussion’s depth and fun, highlights where to find the juiciest confessions, and captures the humor, warmth, and candor that define The Bert Show’s “uncomfortable questions” tradition.

Transcript

[Narrator/Host]

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[Bert]

Spinquest is a free to play social casino void where prohibited. Visit spinquest.com for more details. The first show okay, so here I have all of our questions. We have submitted them anonymously and it's tricky writing these kind of squirmy kind of questions because you don't want to write one that you might have to answer yourself on the air.

[Wendy]

Right. So you want to make everybody else uncomfortable but knowing you have to answer it. Yeah, there's a balance there.

[Bert]

We haven't seen each other's questions.

[Jen]

Don't know what's coming. We just are going around the room, right?

[Bert]

We're going around the room and we're going to change things a little bit this time in that you're not allowed to give an explanation today on your Answer that comes in 24 hours.

[Wendy]

Okay.

[Jen]

Right.

[Bert]

So, for instance, like Jen, the last time we did this, got the question,

[Jen]

which it was, who on the show do you like the least? And I had to answer that honestly and I gave an explanation for what my answer was.

[Bert]

Right. She said Jeff. But then she gave an explanation. So today she would have to say Jeff and then wait 24 hours to give her definition of why.

[Jen]

And my explanation was that you just

[Bert]

hate him to the core.

[Jen]

Jeff is my friend that is the most brutally honest with me. So sometimes I don't like that. But it's probably. He's probably the best friend on the show because he's that way. And I love you.

[Jeff]

If you stop being an idiot, I

[Jen]

wouldn't have to be so honest with you. I love you, but I like you the least.

[Bert]

Wendy, we will go around the room and we'll start with you first today.

[Jen]

Awesome.

[Jeff]

And are we doing the thing where we all. The last question we all have to answer no matter what it is.

[Bert]

Oh, yeah, yeah, yeah, yeah.

[Jen]

Great on here, Jack.

[Jeff]

Yeah. Super squirm.

[Jen]

That sounds like a dance or a move.

[Bert]

Wendy, are you the smartest member of the Burt show?

[Wendy]

No.

[Bluff (Ad Presenter)]

Explain that.

[Jen]

I can't.

[Bert]

Yeah. Whoever wrote this should have put are you the smartest member of the Burch show? If not, who is. But I think I wrote that one.

[Wendy]

I was gonna say. Were you looking at me?

[Narrator/Host]

I didn't know.

[Bert]

I would obviously answer that.

[Jeff]

I'm not even.

[Jen]

I mean, I can answer the follow up.

[Bert]

No, no follow up.

[Wendy]

Tomorrow.

[Jeff]

You're not even allowed to talk until 10am on the air.

[Jen]

We are on the air. We have to explain that.

[Bert]

Yeah. Whenever we're. We're sharing stuff on the air that would. That would be good content. We stop each other in mid sentence and we say on the air. Save it for on the air.

[Wendy]

So our reaction is authentic.

[Jen]

We do it in the hallway, in the studio, when the commercials are playing, whatever.

[Bert]

On the phone telling the story. On the air. On the air, Melissa. Yes.

[Bluff (Ad Presenter)]

Or.

[Bert]

So you sent a graphic, sexual text or photo within the past three months?

[Wendy]

No.

[Bert]

You want to explain why not?

[Jeff]

Do you want to think about that?

[Jen]

Melissa, there's no photo on the air Thursday.

[Bert]

On the air.

[Jen]

In the air.

[Bert]

Jen, What is your most embarrassing moment as a kid?

[Jen]

As a kid. This embarrassing moment on the air.

[Bert]

We are.

[Jen]

This is one of those you have to have time to prepare for.

[Bert]

Well, that's why you're part of a live morning show. Talent.

[Wendy]

Who's the most condescending on the show.

[Jeff]

Yeah. Who's turned into an a hole since

[Bert]

the beginning of this band.

[Jen]

I remember one. I mean, I can say this was in like the eighth grade. And there was a boy that I liked. His name was Brian. I can't remember his last name right now, but I can remember exactly what the kid looked like. And I remember like wanting to go to a dance with him, but he told all of his friends he wouldn't take me to the dance because I was prude and was like making fun of me about it. And I had no idea what that meant.

[Jeff]

Well, you've shown him as a grown up, haven't you?

[Jen]

I had no idea what that meant. And I was so embarrassed. I remember going to the bathroom and crying. Cause I knew it was bad, but I didn't know what it meant. And I was so embarrassed that he was calling me that. And I had to go home and I asked my mom, I was like, what does that mean?

[Wendy]

And she's like, thank God.

[Jeff]

I'll tell you what it means. It means you're a very good girl.

[Jen]

It's really, really embarrassing though, because I'm an ugly crier. And I cried so hard at school that day that like my face was all blotchy and red and, you know, eyes were bloodshot or whatever because I had no idea what that meant. And then I didn't like him anymore.

[Bert]

Of course you didn't.

[Jeff]

Why would you?

[Jen]

But I liked him for a couple of months. He was like the check.

[Wendy]

Yes.

[Jen]

And the do you like me or not? Box.

[Bert]

And now looking back, you realize how wrong he was. Obviously.

[Jen]

Don't call me prude.

[Wendy]

Say that.

[Bert]

Jeff, have you ever come close to cheating on the person you're with now?

[Wendy]

Damn.

[Jen]

Oh, ouch.

[Jeff]

No.

[Jen]

You want to explain that?

[Bert]

Which friend of yours has qualities that you're most jealous of? And what are they? I think I talked about these a couple of days ago. Dolvett. I mean, when that dude, he's just. He's so good looking, he walks into the room, the whole damn room stops. Stops. He's attention grabber, just from his looks. And he's just got sort of this big personality that everybody's drawn towards. I'm jealous of that bastard. Wendy, you want to explain?

[Wendy]

But you explained it. Yeah, wait a second.

[Jen]

There was an explanation.

[Bert]

It asked me, it said why?

[Jen]

Okay, everybody talk at once.

[Jeff]

We're all gonna talk right now. At the same time. Every one of us is just gonna say something right now.

[Bert]

Why would it be any different than any other day? Wendy, have you ever slept with a married person?

[Wendy]

No.

[Jeff]

Has a married person ever slept with you?

[Jen]

No follow ups, no explanations.

[Bert]

Melissa, where and when is the last time you had sex? Outdoors.

[Jen]

That's a funny one.

[Wendy]

You said sex.

[Bluff (Ad Presenter)]

What?

[Wendy]

Hmm, let me think. Katie's probably screaming at the phone, at the radio right now.

[Jen]

Was it her on the air?

[Wendy]

The only person I've had sex with is Katie.

[Jeff]

That's the right answer.

[Jen]

There's no explanations.

[Wendy]

Last time we were outside

[Jeff]

your mom's backyard maybe.

[Wendy]

Oh God, I don't remember. Isn't that terrible? I don't mean to be taking so long.

[Jen]

I know.

[Jeff]

Is there like a parking lot somewhere?

[Wendy]

Well, I was trying to think if we were outside. I mean, it's like if we were outside, it would have to be parking

[Bert]

lot of a dumpster.

[Wendy]

Maybe that's it. Yeah, that's right. I mean it would have to be Walmart parking lot. It would have to be in the car somewhere. But I thought like us like out in the park or something.

[Bert]

I don't know. You can't remember.

[Wendy]

You know what, follow up with me tomorrow and it'll make sure it happens this afternoon.

[Jeff]

You know, I bet we could follow up with you in about three and

[Bert]

a half minutes and you'll know the end right now.

[Wendy]

I'm sorry. Yeah, exactly.

[Bert]

Jen, out of 10, how many shows are you annoyed by a coworker?

[Jen]

Out of 10?

[Jeff]

That is a good question.

[Jen]

Out of 10 shows. I'm trying to be honest

[Bert]

and there's no explanation. You just got to throw the number out there.

[Jen]

Out of 10, I'd probably go with five.

[Bert]

So half of the shows we do, you're annoyed by at least one person

[Jen]

on the show at some point during the show?

[Bert]

Yeah.

[Wendy]

Such a prude.

[Bert]

Make it six. Jeff, have you ever told your significant other that they looked good in something when they didn't and went out anyways?

[Jeff]

No, I have not.

[Jen]

No explanation on the air.

[Jeff]

That wasn't an explanation.

[Jen]

I know.

[Bert]

Why do you think Wendy and Jen are still single?

[Jeff]

Prudes.

[Bert]

Yeah, right. I just haven't found the right dude yet.

[Jeff]

Or maybe the right dude hasn't found them.

[Bert]

Yeah, I just think that's it. Are they looking for anything like. Yeah, I just don't think the right guys come along yet. I don't want to end on that note. It's too easy.

[Jeff]

That was probably Wendy who submitted that question going, God, I really would love to answer.

[Wendy]

Should this next one be one that we all answer to end it?

[Bert]

What'd you say it was called?

[Jeff]

The squirmy round.

[Bert]

Squirmy round.

[Jeff]

Super squirm.

[Wendy]

Super squirm.

[Jeff]

Time for the super squirm.

[Bluff (Ad Presenter)]

Oh, good one.

[Bert]

For the last one. Wendy, if you were going to step into a therapist's office today, what would the first issue be you try to fix about yourself?

[Jen]

Oh, this is a good question. Good question.

[Bert]

This one's gonna be easier for me to answer. Cause I was just there yesterday.

[Jeff]

Hmm.

[Jen]

I would fix about myself.

[Bert]

Well written. Whoever wrote this?

[Bluff (Ad Presenter)]

Oh, it was me.

[Jen]

Good question.

[Wendy]

Oh, my God. Are you kidding me? No, dude.

[Jen]

Bertz would be his ear, right?

[Jeff]

Really? Because mine would be Bert's ego also.

[Bert]

Wow. For you, coming from you, I would

[Jen]

say my lack of confidence.

[Bert]

She said confidently, Melissa, I probably would

[Wendy]

try to wrestle with the issues of parenthood, like, because I really am still not confident that I'll be.

[Jen]

No explanation. God, Melissa, explain it tomorrow.

[Jeff]

Maybe you should talk to your therapist about talking too much on the air.

[Wendy]

10 out of 10.

[Bert]

No, Jen, Jen, the last time you were in your therapist's office, what was last? What issue were you working on?

[Jen]

That's not the question, Bert. The question is what would it be? Today, Right?

[Bert]

Yes.

[Jen]

Or next Monday when I go in.

[Bert]

What would the first issue be you try to fix about yourself?

[Jen]

The first issue today, I think it would be. I'm trying to figure out how to. I know what it is. I'm trying to figure out how to define it clearly. The struggle between. Decisions to be made, between having a life of career focus or family focus. That Little Orphan Annie tug of war that goes on in my head.

[Jeff]

Okay, Jeff, I would like to find out.

[Bert]

This is such a far fetched idea for you that you would need help. Help in any area of your real stretch.

[Jeff]

For you, I really was struggling, but then I came to one because I thought Jen was gonna steal mine. So I had to think of another one. But my other one's better. I would like to know why I always feel like I have to be working.

[Bert]

Why you always have to be working?

[Jeff]

Yep.

[Jen]

Okay.

[Bert]

And mine would be intimacy issues. That's what I'm going for now. It's like I don't let anybody get too close. Like, I sort of keep people at arm's length. And I'll talk about that again next Tuesday with my therapist. The squirmy round was fun, but I

[Wendy]

could answer that question. I'm in trouble when I get home.

[Bert]

Yeah, you better have an explanation tomorrow.

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[Bert]

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