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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.
Hers Weight Loss Advertiser
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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Date: June 15, 2026
Cast: Bert, Jeff, Melissa, Jen, Wendy, Tracy, Kiana
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!
Jen on Jeff’s tough love:
Melissa on her sexuality:
Bert on working radio hours:
Wendy’s instant karma:
Jen’s deadpan on paying-for-sex question:
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.
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.