Vault: Asking Bert Show members uncomfortable embarrassing questions

Summary

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The Bert Show - "Vault: Asking Bert Show Members Uncomfortable Embarrassing Questions"

Date: June 15, 2026
Cast: Bert, Jeff, Melissa, Jen, Wendy, Tracy, Kiana

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Episode Overview

This episode takes listeners inside The Bert Show’s infamous "uncomfortable question" game, where cast members challenge each other with embarrassing, boundary-pushing questions they've written themselves. The premise: each draws anonymous, tricky questions meant to spark frank, awkward admissions and deeper conversations. The result is a mix of laughs, real vulnerability, and classic Bert Show camaraderie—and yes, a bit of squirming in their seats!

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Key Discussion Points & Insights

1. The Setup: Why Do This To Ourselves?

• Right off the bat, the team jokes about their recurring decision to play this awkward Q/A game.
• Notable exchange:
  • Jeff: “Why do we continue to do these? They always seem like a great idea in the post show meeting, but then it gets time to do them and I'm like, what?” (01:32)
  • Wendy: “I wanted mine to be like the best uncomfortable questions... But then I'm like, why did I just do that?” (01:46)
• Wendy’s goal: to bring the “best worst” questions and secretly win a non-existent competition.

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2. The Uncomfortable Questions Begin

A. Who Would You Call to Bail You Out of Jail?

• Question: “If you had to call one member of the show to bail you out of jail, who would you call and why?” (03:11)
  • Bert: “Tracy. Cause she's the one who would not be drunk.” (03:18)
  • This sparks quick laughter about Tracy bringing her baby to jail.

B. Who Do You Like Least on the Show?

• Question: “Which Bert show member do you like the least and why?” (03:43)
  • Jen hesitates, struggles, dodges, then honestly says:
    • “The first thing that came to my mind was... Jeff. But I like Jeff the least in certain situations because he is the most honest with me, and it makes me squirm the most… it kind of stung for days.” (04:38–05:17)
  • Bert reframes: “I will take any criticism of me and manipulate it into a compliment.” (05:35)

C. Sexual Dreams About Cast Members

• Question to Melissa: “Have you had a sexual dream about another Bert show member, and who?” (06:16)
  • Melissa: “I had a sexual dream about Jen… it didn’t go real far. I woke up before any action.” (06:22–06:35)
  • Jen, mock-offended: “In your dreams, do I have bigger boobs?” (06:53)
  • Melissa: “I don’t have a problem with your boobs.” (06:57)

D. Would You Take Back Your Virginity?

• Question to Wendy: “If you could take back your virginity from your first partner, would you?” (07:23)
  • Wendy: “Yes, I would. It was nothing I think I wanted to do at the time, but it’s something I felt I had to do. So, absolutely would take it back.” (07:32–07:41)

E. Sexual Dreams About Surprising People

• Question: “Who in your personal life have you been surprised you had a sexual dream about?” (08:06)
  • Jeff: “I had a sexual dream about my sister-in-law… for the life of me, even today I can’t figure out why.” (08:46–08:59)

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3. Turning the Table: Questions About the Show & Listeners

A. Top Complaint About Listeners

• Question to Bert: “What’s your top complaint about our listeners?” (09:32)
  • Bert: After playful jokes, shares a real concern:
    • “When people think that between 5:30 and 10, when we’re doing the show, there is, like, access to us… like people just show up in the studio to promote something while we’re on air. I’d like more appreciation for the fact that when we’re working, it really is work.” (10:17–11:05)
  • Jeff shares an analogy:
    • “If Bon Jovi was on stage, would his wife be on the side stage going, ‘hey, don’t forget to bring up some milk’? ... This is his stage.” (11:08–11:29)

B. Ever Paid for Sex?

• Question to Jen: “Have you ever paid for sex or any sexual services?” (11:32)
  • Jen and Kiana: immediate “No.”
  • Jen (playfully): “Why would a woman have to… I mean, I could walk to the 7-11 right now and… you know what I mean?” (11:43–11:53)

C. Any Huge Untold Secrets?

• Question to Melissa: “True or false: I have a huge personal secret I haven’t shared for fear it will be exposed.” (12:05)
  • Melissa: “No, because the biggest skeleton in my closet is that I’m gay. And I think everybody knows that by now… it’s so energy draining to hide something.” (12:14–12:48)

D. Who Would You Kiss on the Show, and Why?

• Question to Wendy: “If you had to pick one person on the show to kiss for two minutes, who and why?” (13:23)
  • Wendy: “I’d have to go with Jen because I don’t want to kiss any of the guys.” (13:53)
  • On why she chose Jen: “You pick the one girl who’s not into girls…” (14:11, Jen)
  • Bert, joking: “With Jen you could go up her shirt and pretend it’s a boy.” (14:16)

E. Who’s the Best Looking on the Show?

• Question to Jeff: “Do you think you are the best looking member of the show?” (14:28)
  • Jeff (without hesitation): “Absolutely. I mean, it’s not even close.” (14:28–14:44)

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Memorable Quotes & Moments

• Jen on Jeff’s tough love:

  • "Sometimes when Jeff is bitingly honest, it gets mean, and it hurts my feelings sometimes... but it's probably the best because it's the most honest." (04:36–05:07)

• Melissa on her sexuality:

  • "The biggest skeleton in my closet is that I'm gay. And I think everybody knows that by now." (12:14)

• Bert on working radio hours:

  • "I’d like a little more appreciation for the fact that when we are working, it really is work." (10:54–11:05)

• Wendy’s instant karma:

  • Wendy draws her own tough question about virginity, admitting “absolutely would take it back.” (07:32–07:41)

• Jen’s deadpan on paying-for-sex question:

  • “I could walk to the 7-11 right now and… you know what I mean? Like, women don’t... That’s a bad question to direct at a woman.” (11:49–12:00)

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Notable Timestamps

• 01:32: The game and its premise are explained.
• 03:18: Bert picks Tracy to bail him out of jail.
• 04:36: Jen gives a vulnerable answer about Jeff making her uncomfortable with honesty.
• 06:22: Melissa admits to having a sex dream about Jen.
• 07:32: Wendy says she would take back her virginity.
• 08:46–08:59: Jeff confesses to a sexual dream about his sister-in-law.
• 10:54–11:05: Bert shares his top work-related complaint.
• 12:14: Melissa talks about being open regarding her sexuality.
• 13:53: Wendy chooses Jen as the cast member she’d kiss.

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Tone & Dynamic

The episode is classic Bert Show: unfiltered, honest, playful, sometimes cringeworthy, and underpinned by the deep affection and respect the cast have for one another. Even the most awkward admissions are balanced by humor and understanding, with moments of support and insight arising from the discomfort. The cast’s willingness to both laugh and get real with each other invites listeners to feel like part of the inner circle.

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Final Thoughts

Longtime fans will love this episode’s rawness and the cast’s chemistry, while new listeners get a lively introduction to what makes The Bert Show unique: a blend of humor, honesty, and heart—all mixed into morning radio mayhem.

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Transcript

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[Bert]

probacion les refiones the bircha.

[Jeff]

So Melissa's right. Why do we continue to do these? Like, they always seem like a great idea in the post show meeting, but then it gets time to do them and I'm like, what?

[Melissa]

Somebody's having to show the rest of

[Bert]

the show, so let's not do it.

[Jeff]

Someone's gonna be hurt. It's probably gonna be you.

[Bert]

I don't. I've never been hurt by these.

[Jeff]

I know you haven't.

[Wendy]

And when coming up with these questions, I wanted mine to be like the best uncomfortable questions. So they were really good. But then I'm like, why did I just do that?

[Jen]

I don't wanna.

[Bert]

Tracy, by the way, said yours were the best worst.

[Melissa]

Oh, really?

[Wendy]

Yeah.

[Melissa]

So congratulations.

[Jeff]

Wendy went deep on this one, I

[Wendy]

wanted to win the competition. That wasn't really a competition, but now I'm regretting it.

[Jeff]

Well, it was a tricky assignment because you had to write questions that were gonna be uncomfortable for others, but not so uncomfortable that if you got your own question, you had to answer it.

[Melissa]

Right. So, yeah, I mean, is it possible for us to hurt our own feelings in this game?

[Jen]

Yes, possibly.

[Melissa]

I'm offended by this question, and I wrote it.

[Jeff]

Should we just go right in order?

[Jen]

Yeah, let's start. Do you want to say where it came from? Do you remember where it came from?

[Melissa]

Torture and hell.

[Jen]

Wasn't one of your wives or one of your friends. Wives.

[Bert]

It was somebody who asked a question about. And then Burt brought up that question where Jessica asked me to compare her ass to some other girl's ass when we were walking to the mall.

[Jen]

It was the one where, if your wife came to you and said, if I wasn't here and you had to hook up with one of my friends, who would it be?

[Jeff]

Right.

[Jen]

And you have to answer it like, which one of your wife's friends you would want to make out with, and

[Jeff]

it's gonna be an uncomfortable. And you really don't want the answer

[Jen]

that kind of question. Right.

[Jeff]

All right, Jeff, since you are unbreakable, why don't you go first?

[Bert]

Don't I draw it and read it,

[Jeff]

or Bert's going first or I'm going to. If you had to call one member of the show to bail you out of jail, who would you call and why?

[Bert]

Tracy. Cause she's the one who would not be drunk.

[Jeff]

She'd be like, I can't leave my baby. There's no chance I'm leaving my baby.

[Bert]

She'd bring her baby to jail.

[Wendy]

That was an easy question.

[Jen]

See, I was writing.

[Melissa]

Well, obviously it wasn't yours.

[Jen]

I was writing nice ones.

[Bert]

Oh, that was yours.

[Melissa]

Are we gonna get to the point now? We just own our question?

[Jeff]

Oh, sorry, Jen.

[Jen]

Okay, what is this one?

[Jeff]

Which Burt show member do you like the least and why?

[Jen]

Oh, do I like that?

[Melissa]

Uncomfortable.

[Jen]

Why do I like the least? God, I don't like anybody the least.

[Bert]

Are you counting interns?

[Jen]

Current or former? Because I can pick out the former ones real quick.

[Jeff]

Ones we haven't talked to in five years, so there's nothing uncomfortable about it at all.

[Bert]

Say, Jamie Massey.

[Jen]

Does it have to be who wrote it? Does it have to be current?

[Jeff]

If we are trying to make this as uncomfortable as we can for each other, I think it's got to be 1s1.

[Bert]

It's got to be a current number.

[Jen]

Five.

[Bert]

Yeah.

[Jen]

I don't really like any of you guys the least, I would say. I mean, I just.

[Bert]

You look uncomfortable.

[Jeff]

Well, it's a crappy question.

[Wendy]

It is a crappy question.

[Jen]

It's an uncomfortable question. I'm trying to think, because the first thing that came to my mind was. Was Jeff. But I like Jeff the least in certain situations because he is the most honest with me, and it makes me squirm the most. So I would say sometimes when Jeff is bitingly honest, it gets mean, and it hurts my feelings sometimes. So I would say I would like Jeff's advice the least, but it's probably the best because it's the most honest. Does that make any sense?

[Bert]

Real talk? Yeah. That's a good, safe answer.

[Jeff]

That was a safe answer.

[Jen]

Like when you sat me down at Sean's that night, and after we had had lots and lots of beer that

[Bert]

day, that made me uncomfortable, and you

[Jen]

were, like, really, really harsh. It was really, really great advice, like relationship advice and just life advice to me. But it kind of stung for days.

[Jeff]

If I were you, Jeff, I'd take that as a compliment. Like, if there's somebody in your life that you could totally trust, no matter what, even if they hurt your feelings about it, but they'll give you brutal honesty. That's a person you keep close to.

[Bert]

Bert, just so you know going forward that I will take any criticism of me and manipulate it into a compliment,

[Jeff]

I don't have to do it for you.

[Bert]

You don't have to give me that advice, Captain.

[Kiana]

I got it.

[Jeff]

I wouldn't have been able to think that fast. I'm very proud of you.

[Wendy]

That was good.

[Jen]

Well, because it sounded like. I really love you guys. I mean, I really love everybody in this room.

[Jeff]

Oh, I think I know.

[Melissa]

Oh, what?

[Jeff]

I think you've showed up.

[Melissa]

I don't know what that means.

[Jeff]

I just know that she loves.

[Bert]

Well, I just want to modify my answer to say I would call Tracy to bail me out of jail, and I certainly will not call Jen now, because she'll be like, oh, really? Well, you have a good time there in the drunk tank. As I recollect our conversation at Sean's.

[Jeff]

Melissa, have you had a sexual dream about another Burt show member who?

[Melissa]

I had a sexual dream about Jen since we've been on the show, but it didn't go this morning. It didn't go real far. It was the got there, and then I woke up before any action.

[Jeff]

Don't you hate that?

[Melissa]

But that's. I'm trying to think if I've had a sex dream about anybody else.

[Jeff]

Did you try to put yourself back to sleep so you could be in the same situation?

[Melissa]

I don't have to answer follow up questions.

[Jen]

Can I ask a follow up question?

[Jeff]

It's like a senate hearing. You're looking for counsel?

[Melissa]

No comment.

[Jen]

In your dreams that I have bigger boobs?

[Melissa]

I don't have a problem with your boobs.

[Jen]

Oh, man. I was just hoping at least in somebody's dream I could have big boobs.

[Jeff]

She's more offended by that, that you don't have a problem with her boobs than anything else. Wendy.

[Melissa]

Good lord.

[Bert]

I hope Wendy draws one of her own just to teach her a lesson about really, really investing in these events.

[Jeff]

I have a feeling this one came from Wendy. If you could take back your virginity from your first partner, would you.

[Wendy]

Oh, yeah, I'll call myself my question now.

[Melissa]

Yeah.

[Jeff]

That is your question.

[Jen]

It is my question.

[Jeff]

That is instant karma.

[Jen]

That's good. That's actually a good question.

[Wendy]

No. Yes, I would. It was just nothing that I think I wanted to do at the time, but it's just something I felt I had to do so absolutely would take

[Jeff]

it back of women would probably say the same thing.

[Wendy]

Yeah, yeah.

[Bert]

What class did he teach?

[Wendy]

He was not a teacher.

[Bert]

Oh.

[Jen]

What sport did he coach?

[Wendy]

He was my age.

[Jeff]

Well, it looks like that's all the time we have for on this segment. I'm just kidding. Who in your personal life have you been surprised that you had a sexual dream about this?

[Melissa]

For burn.

[Bert]

Dad. We are pervy.

[Jen]

This is the 4, 8:30 show.

[Melissa]

7:30 in the morning.

[Bert]

Jail for friend. Pervy dream. Virginity. Pervy dream.

[Jeff]

Who in your personal life have you been surprised you had a sexual dream about? I want to answer honestly, but I'm like crucial surprise. None of them have surprised me.

[Melissa]

I've had,

[Jeff]

I had a. Oh, I remember. Yes. And I've talked about this on the air before. Remember I had a sexual dream about my sister in law.

[Bert]

You did?

[Jeff]

Yeah. This was years and years and years ago.

[Jen]

Your wife's brother.

[Jeff]

My wife's brother's wife. I couldn't figure out.

[Jen]

Yeah.

[Jeff]

For the life of me, even today I can't figure out why.

[Jen]

Had you just been like around each other.

[Jeff]

Around each other or something that weekend? Yeah. And then I came home that week and I'm like, what? Really? Somewhere deep down in there we're doing

[Wendy]

two rounds of this.

[Jeff]

Yeah.

[Jen]

Yours is an easy question.

[Jeff]

Oh, this one. This is a Great one.

[Jen]

I got the worst one so far, by the way.

[Jeff]

You did.

[Bert]

Are we doing this draft style? So now you answer too, and we go back the other way.

[Jeff]

I wasn't planning on it. This is a good one for you to take, though. All right. What's your top complaint about our listeners?

[Bert]

Oh, they're there all the time.

[Jeff]

Yeah. Doesn't that suck? Doesn't that suck being part of a show that has ratings?

[Melissa]

You had one yesterday.

[Bert]

I did.

[Melissa]

Or is that.

[Bert]

Yeah, no, I. No, I could bring that one up. I don't really have a complaint about the listeners because they honestly appreciate them, but I do. I have a complaint about people in general, and I think it applies more to professionals or professional peers, but I have a complaint. And thank you, Melissa, for reminding me of this. Cause I complained about it yesterday.

[Melissa]

He was going off about it yesterday, so that's fine.

[Bert]

When people think that between 5:30 and 10, when we're doing the show, that there is, like, access to us. So it's. Hey, I'm gonna stop by. Like, people show up in the studio sometimes with, you know, a clown to promote the circus. Yeah. I just need to get in the studio and let the birds show. Know the circuses in town. Like, seriously, come on. Like, we're doing a show. Like, it's not. I get. I think so. My complaint would be. And again, this doesn't. This applies more to business associates than peers. That while our job is very fun and very low key, and I think we do a great job of making it appear easy, that there is still work that goes into it. And I would like a little more appreciation for the fact that when we are working, it really is work.

[Jen]

Sort of respecting those boundaries.

[Bert]

Yes.

[Jeff]

The dude that I used to work with in Dallas used to tell his wife when they were first starting to go out, and she would call him during the show for personal stuff, like to pick something up. He'd say, look, if Bon Jovi was on stage, would his wife be on the side stage going, hey, don't forget to bring up some milk when you get off stage. It was the same thing for him. Like, this is his stage right here.

[Melissa]

I'm surprised she was calling him during the show.

[Jeff]

Jen.

[Melissa]

Yes.

[Jeff]

Have you ever. You guys are sexual, man. Have you guys ever. Have you ever paid for sex or any sexual services?

[Kiana]

No.

[Jen]

Why would a woman have to.

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That is very true.

[Bert]

So have you ever just.

[Wendy]

You can just go down to the Buckhead bars?

[Jeff]

Yeah.

[Jen]

I mean, I could walk to the 711 right now and walk to hey, would you like to. Yeah.

[Wendy]

Okay.

[Jeff]

That's actually our 815bit.

[Jen]

Oh, good.

[Melissa]

Okay.

[Bert]

711 random or whatever.

[Jen]

You know what I mean? Like that women don't. That's a. That's a bad question to direct at a woman.

[Jeff]

Melissa, true or false? I have a huge personal secret that I haven't shared with anybody on the bird show for fear it will be exposed on the air.

[Melissa]

No, because I think the biggest skeleton in my closet is that I'm gay. And I think everybody knows that by now.

[Jeff]

And you're serious about that thing?

[Melissa]

Yeah, there are some people that actually think that I'm lying. No, that would have been. I mean, that would have been the answer up until age 25, of course. But I think that by growing up with such what I considered a huge secret that would cause people not to love me anymore is what you think then. I think that since then it's, you know, that pretty much took the cake for my.

[Bert]

If we asked that question to 22 year old Melissa, would you have been paranoid that we knew?

[Melissa]

Yes. So you're always paranoid. Yeah.

[Bert]

Oh my God. They know.

[Melissa]

Yeah. When you're trying to hide something. And that's. I mean, that's. I think that's just the thing about hiding something is like, it may seem for some people, you know, kind of alluring or something in the beginning, but it's so energy draining that it just. It, it. You always are paranoid about it.

[Jeff]

If we were both 22 and you hadn't told us publicly, I would have assumed you were a lesbian because you would have been ignoring me sexually.

[Wendy]

But see, it's.

[Jeff]

The only reason why. Is because you're a lesbian, you're just not attracted to dudes, right?

[Melissa]

Well, at 20, up until 22, I was going out with guys. So I did. I did enough to get by.

[Jeff]

Okay.

[Melissa]

Yeah.

[Jeff]

This is a good one for you, Wendy. And it's probably one that came from you.

[Wendy]

Perfect.

[Jeff]

If you had to pick one person on the show to kiss for a solid two minutes, who would it be and why?

[Wendy]

Wait, I've already done that. I mean, I've kissed a couple of

[Jeff]

you guys, but this one, you get to choose.

[Jen]

You have to choose. And it's a solid two minutes.

[Jeff]

That's an eternity.

[Wendy]

Two minutes.

[Jeff]

Two minutes.

[Wendy]

Oh, Lord.

[Bert]

Feeling oddly competitive right now.

[Wendy]

Golly, I'd have to go with Jen because I don't want to kiss any of the guys.

[Jeff]

I knew she was gonna slam.

[Melissa]

I knew you were gonna take the

[Jeff]

easy way out on that.

[Wendy]

I've already Kissed Bert uncomfortable. Jeff didn't. Yeah, well.

[Melissa]

Cause she knows that Judah be equally uncomfortable. They'll do the whole, like break their lips out as much as possible.

[Jen]

You pick the one girl who's not into girls. I think you're the one person who's not into girls.

[Bert]

And the cool thing with Jen is you could go up her shirt and pretend it's a boy.

[Jeff]

Oh, dear.

[Melissa]

That was uncomfortable.

[Jen]

That is not true. I wear padded bras.

[Jeff]

I drew an easy one for the last one. Do you think you are the best looking member of the show? Absolutely. I mean, it's not even close. We still, I mean, we'll do these from time to time. They're still. I think that was an easy first round, to be honest with you. You drew a tough one.

[Melissa]

Tough one.

[Jeff]

But in general, I think that was a pretty easy first round.

[Melissa]

Why do you want to make it even more?

[Jeff]

I mean, cuz it's just not.

[Melissa]

Why do you want to sabotage the show?

[Bert]

Hey, the Birch Show.

[Wendy]

Hey, everybody.

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[Jeff]

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[Jeff]

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[Bert]

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