Vault: What Not To Ask Your Current Boyfriend

Summary

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The Bert Show: Vault — "What Not To Ask Your Current Boyfriend"

Date: November 7, 2025
Cast: Bert, Kristin, Abby, Cassie, Tommy, Producer Tracy, and callers Lauren, Cynthia, Nathan
Main Theme:
This episode revolves around the minefield of “dangerous questions” in relationships: things you should absolutely never ask your current boyfriend, girlfriend, spouse, or partner. The Bert Show cast and listeners contribute to an evolving, lighthearted but honesty-fueled list of these no-win curiosity traps.

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Key Discussion Points & Insights

Why We Ask Dangerous Questions (01:40–02:49)

• Bert introduces the topic by confessing to asking his wife, Stacy, a question he knew he didn’t want the answer to: “If I wasn’t around, which ex-boyfriend would you have ended up with?”
  • Quote (Bert, 02:10): “For her, it’s a no win because I’m not going to be happy with the answer. I don’t even really want to know the answer. So why do you even ask?”
• The cast jokes about the name “Glenn,” Stacy’s answer (with playful banter about mustaches and small penises).

The Classic Traps: Numbers & Ex-Comparisons (03:16–04:27)

• Never ask:

  • “How many people have you slept with?”
  • “Am I the best you’ve ever been with?”
  • “Who was the best?”

• The cast discusses how these questions usually lead to insecurity, jealousy, and the temptation to ask further comparison questions.

• Quote (Kristin, 04:18): “You don’t wanna go down that road… You open the door of ‘how many people,’ then that gate is open and all sorts of things can escape.”

Digging Up the Past (04:40–05:25)

• Bert and the cast expand the list:
  • “Which of my friends would you date if I wasn’t around?”
  • “What’s your least favorite body part about me?”
• Bert shares how he was “trapped” by Melissa into admitting his least-favorite thing about his wife (on air).

Listener Call-Ins: Real-Life Regrets (05:16–07:40)

• Lauren: Never ask if your partner has slept with any of your friends. She says if you know it might haunt you, better not to know.
  • Real tension: Some cast members would rather know (to avoid being “the fool”), while others want the bliss of ignorance.
• Cynthia: Made the mistake of asking her boyfriend what his exes looked like—regretted triggering unhealthy comparisons.
  • Quote (Cynthia, 07:05): “In my head… I think of some homely looking girl that is 10 times worse than I am just to kind of boost my self esteem a little bit. But if I ask… I go against everything I thought and I don’t want to know that… but my curiosity just kills me.”

The Spiral of Insecurity (07:31–08:02)

• The cast cautions against leading questions like:
  • “Who had better [body part]?”
  • “What’s the wildest thing you did with your ex in bed?”
  • These are almost guaranteed to have answers that hurt or haunt you.

Morbid Hypotheticals & Extreme Scenarios (08:26–10:46)

• Producer Tracy’s additions:

  • “If I died, how long would you wait to start dating again?”
  • “If I died, who would you be with?”
  • “If we broke up, how long before you started seeing someone else?”

• Nathan (caller):

  • “Would you still love me if I became a quadriplegic?”

• The team jokes about physical caretaking (e.g., “Would you wipe my ass if both my arms were broken?”), mixing honest reflections with irreverent humor.

• Quote (Cassie, 10:36): “In this situation, are you financially well off to hire a caretaker to wipe the butt?”

When Even the Honest Answer Doesn't Help (08:59–09:29)

• Pro Vita (caller): Shares the futility of asking, “Was that person better than me?”—no one tells the truth, and even if they did, no good can come of the answer.
  • Quote (Pro Vita, 09:18): “Don’t ask a question because I don’t think people will really honestly answer it.”

The Ex Factor (09:29–09:41)

• All agree: Most disastrous questions relate to partners’ exes.
  • Quote (Cassie, 09:29): “Every single one we’ve written down has to do with the ex. That’s what causes problems in these questions.”

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Notable Quotes & Moments

• Bert (02:10): “For her, it’s a no win because I’m not going to be happy with the answer. I don’t even really want to know the answer. So why do you even ask?”
• Kristin (04:18): “You don’t wanna go down that road… You open the door of ‘how many people,’ then that gate is open and all sorts of things can escape.”
• Cynthia (07:05): “In my head… I think of some homely looking girl that is 10 times worse than I am just to kind of boost my self esteem a little bit. But if I ask… I go against everything I thought and I don’t want to know that…but my curiosity just kills me.”
• Cassie (10:36): “In this situation, are you financially well off to hire a caretaker to wipe the butt?”
• Pro Vita (09:18): “Don’t ask a question because I don’t think people will really honestly answer it.”

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Timestamps for Important Segments

• Main topic intro: 01:40
• Bert’s Europe story & ex-boyfriend question: 01:57–02:49
• Opening the floodgates with “How many people?” 03:16–04:27
• Comparison questions (“Am I the best?”): 04:15–04:27
• Listeners Call-In: Lauren on friends and exes: 05:16–06:31
• Cynthia on asking about exes’ looks: 06:51–07:40
• Wildest ex stories in bed: 07:52–08:02
• Producer Tracy’s morbid hypotheticals: 08:26–08:38
• Physical caretaking scenarios: 09:46–11:40

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Takeaways & Tone

• Tone: Playful, self-deprecating, and honest—with humor used to take the edge off uncomfortable truths.
• Key Message:
  Certain questions in relationships serve no constructive purpose and are usually asked out of insecurity or morbid curiosity. Most revolve around exes, comparisons, and extreme “what ifs.” The show encourages self-restraint and healthy boundaries for the sake of your own—and your partner’s—emotional well-being.
• Final Word:
  If you know the answer won’t help (or could only do harm), it’s best not to ask.

---

Transcript

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[Host (possibly named Bird or related to 'Bird Show')]

This is the Bird Show. Hey, before we get out of here today, I think we could help each other out. If you are in a relationship right now, and all four of us are, there are things that you should never, ever, ever, ever ever ask of each other when you're dating or you're married.

[Melissa]

Okay?

[Host (possibly named Bird or related to 'Bird Show')]

And I would like to compile that list and put it up on our website for us idiots, me specifically, that have asked these questions over the last couple of years and have been burned every single time I ask them. But there are way more than the superficial ones I asked. I told you guys when I was in Europe with Stacy, my wife Stacy about week and a half ago just with some silence. It was really nice, should have embraced it, but it felt like an uncomfortable lull in the conversation. So I, for whatever reason, said to her, you know, if I wasn't around, which ex boyfriend of yours do you think you would have ended up spending the rest of your life with? And for her, it's a no win because I'm not going to be happy with the answer. I don't even really want to know the answer. So why do you even ask?

[Another female panelist (possibly Lauren or Melissa)]

Right?

[Host (possibly named Bird or related to 'Bird Show')]

So of course she asked. She said, this dude Glenn, I probably got some jealousy, a jealous streak in me about it. Yeah, this dude back in high school and stuff. Yeah, it's really. With the name Glenn, I don't know.

[Male panelist (possibly named Jeff)]

That just reeks of mustache and small penis Glenn.

[Melissa]

Yeah, I'm sure all the mothers with brand new babies named Glenn are really thrilled to hear you say that.

[Male panelist (possibly named Jeff)]

Well, they make judges.

[Host (possibly named Bird or related to 'Bird Show')]

Well, they came out obviously, with a small penis and a mustache, and that's why they named them Glenn. But I'm curious if there are. There's got to be a whole list of questions that you should never ask each other. You in a relationship. Some of them are very obvious. How many people have you slept with?

[Another female panelist (possibly Lauren or Melissa)]

How many people have you slept with?

[Host (possibly named Bird or related to 'Bird Show')]

447. Oh, come on. 404, 741, 1005. How can that not? How can that turn out?

[Melissa]

Well, I just don't think that that's that bad. I think that maybe it's not a great question for the first part of your relationship, but if it's somebody you're going to spend the rest of your life with, I don't think that's big of an issue. I really don't.

[Host (possibly named Bird or related to 'Bird Show')]

Well, that means you slept with a lot of people.

[Melissa]

I really don't. I mean, I really didn't.

[Host (possibly named Bird or related to 'Bird Show')]

You're never gonna get the right answer anyway.

[Another female panelist (possibly Lauren or Melissa)]

Well, and also, I mean, this is. If you're in a relationship, not every relationship is gonna end up being. And sometimes these questions are the reason why they don't end up being the rest of your life relationships. But I think for some, because there's a leading question into other things. Like it's, you know, how many people have you slept with? Well, or, you know, am I the best you've ever been with?

[Host (possibly named Bird or related to 'Bird Show')]

There you go. That's a question you should never ask.

[Male panelist (possibly named Jeff)]

You don't wanna go down that road. What Melissa's saying is, you don't open the door of how many people have you slept with? Because then that gate is open and all sorts of things can escape.

[Melissa]

Then it's, who was the best? Who would you Go back to, like, what bird asked.

[Host (possibly named Bird or related to 'Bird Show')]

Well, let's specifically go through these. Who was the best? Is another question you should never ask. What else?

[Another female panelist (possibly Lauren or Melissa)]

The one you said, if I wasn't around, which ex would you be with?

[Host (possibly named Bird or related to 'Bird Show')]

Yeah. Which one of my friends? Which one of my friends? If I'm not around, which one of my friends. I mean, sometimes you throw these out there just to start conversation because there's that lull and.

[Melissa]

Right.

[Host (possibly named Bird or related to 'Bird Show')]

And it's just so dangerous. And I just want to get to know you. Silence.

[Another female panelist (possibly Lauren or Melissa)]

But I just want to get to know you better.

[Melissa]

What about, like, what's your least favorite body part about me?

[Host (possibly named Bird or related to 'Bird Show')]

Oh, no, I've been. Melissa trapped me into that one on the air one day about my wife. Yeah, but we won't read. We weren't. We won't.

[Melissa]

I know.

[Another female panelist (possibly Lauren or Melissa)]

Yeah. That was a part of a whole. Yeah. I'm just not the evil one. It was part of a. Yeah.

[Host (possibly named Bird or related to 'Bird Show')]

Hello, Lauren. You're on the bird showing all the hints. Q100. Hi.

[Caller Lauren]

Hi. How are you?

[Host (possibly named Bird or related to 'Bird Show')]

I'm good. Let's go ahead. Help each other out. The questions that you should never, ever, ever ask a boyfriend or a girlfriend. Husband, wife. Never.

[Caller Lauren]

You should never ask if you guys. If you've ever had sex with any of their friends. Like, if you guys roll in the same circles, if you've known each other for a long time, never if you've ever hooked up with any of the friends.

[Host (possibly named Bird or related to 'Bird Show')]

I think the prerequisite for this is if you know that you're not going to get the truth, then why even ask the question?

[Caller Lauren]

That's a good point.

[Melissa]

See, I disagree with that one. Because don't you want to know, like, if you started dating a guy who had slept with one of your friends, wouldn't you want to know that information?

[Caller Lauren]

Yeah, but then imagine when you guys are together, all you think about is them and that girl, so you're not together.

[Melissa]

Like, I'd rather have that information than.

[Male panelist (possibly named Jeff)]

Be the fool, than be the one who doesn't know.

[Melissa]

Then be the one that doesn't know.

[Caller Lauren]

I've been there, and it is an ugly scenario. You can't get it out of your head. Cannot. It's so hard to not think about it.

[Host (possibly named Bird or related to 'Bird Show')]

Then why ask? Right?

[Caller Lauren]

Yeah. Yeah.

[Host (possibly named Bird or related to 'Bird Show')]

So you would. You would rather have her there not knowing that she slept with her boyfriend than know that they went down that road together?

[Caller Lauren]

Definitely. I mean, they're not together anymore, so you don't really have to worry about it. But having that in the back of your head is torture.

[Melissa]

See, I think that's like the ignorance, ignorance is bliss thing, but I wouldn't take that approach. I would rather know. I would rather not be the idiot in the room that didn't know he slept with like one of my good friends. Ew.

[Host (possibly named Bird or related to 'Bird Show')]

You're damned if you do, you're damned if you don't.

[Male panelist (possibly named Jeff)]

You're so particular. You're so high maintenance.

[Host (possibly named Bird or related to 'Bird Show')]

Cynthia.

[Caller Pro Vita]

Yeah.

[Host (possibly named Bird or related to 'Bird Show')]

Questions you should never ever, ever, ever ask.

[Caller Lauren]

Oh God. I made this mistake the other day with my current boyfriend. What his ex girlfriends look like.

[Host (possibly named Bird or related to 'Bird Show')]

What's the why? Cuz all of them did or did not look like.

[Caller Lauren]

No. In my head when I'm with him, I think of some homely looking girl that is 10 times worse than I am just to kind of boost my self esteem a little bit. But if I ask and he tells me, oh, she's got, you know, long hair and it's brown and she's got a, like a regular, you know, normal girlish figure, you know, that's going against everything I thought and I don't want to know that, but I have to ask. My curiosity just killed me.

[Another female panelist (possibly Lauren or Melissa)]

I think also, like, yeah, I think also kind of going along the same lines in the past. I know there's been a conversation before where if someone feels insecure, they start trying to compare themselves. Who had the better blank or who. Like if you know, once you know what the ex looks like, then that leads down the path of, well, who had better legs or who had better this or who? You know, that kind of thing.

[Melissa]

I have another one to add about the exes is don't ever ask what's the wildest thing they did with the ex in bed?

[Host (possibly named Bird or related to 'Bird Show')]

Oh no.

[Male panelist (possibly named Jeff)]

Yeah, yeah, yeah.

[Melissa]

Because I have asked that question before and I did not want the answer I got.

[Host (possibly named Bird or related to 'Bird Show')]

Why would you see like. And as the question is coming out, you realize you don't really want to know the answer. And then when they say you don't want me to answer that, all of a sudden you really wanted to answer.

[Melissa]

That you want to know and you.

[Male panelist (possibly named Jeff)]

Can'T really take it back like once it's out. Cause you gotta pretend you're cool with it, right? Like, hey, what's the wildest thing you ah, dammit guys did when you were all clothed?

[Host (possibly named Bird or related to 'Bird Show')]

Producer Tracy has a great one. This is perfect. If I died, how long would you wait to start dating?

[Male panelist (possibly named Jeff)]

Ooh, how about this? If I died.

[Melissa]

She's morbid. She always has those morbid thought, if.

[Male panelist (possibly named Jeff)]

I died, who would you be with?

[Host (possibly named Bird or related to 'Bird Show')]

Right? Which or the same Thing. Which one of my friends?

[Melissa]

Ooh.

[Another female panelist (possibly Lauren or Melissa)]

Well, it could even be less morbid than that, though. If you're dating, you could say, if we broke up, how long do you think it would be before you start seeing somebody else?

[Host (possibly named Bird or related to 'Bird Show')]

Same along the same lines again, you're not gonna get an honest answer, so don't ask the question. Morning. Bircho all the hits Q100. Hi.

[Caller Pro Vita]

Hi.

[Host (possibly named Bird or related to 'Bird Show')]

Hey.

[Ryan Seacrest]

Hi.

[Caller Pro Vita]

This is Pro Vita.

[Host (possibly named Bird or related to 'Bird Show')]

Hello.

[Caller Pro Vita]

Hey. I say to never ask an ex, was that person better than me? Especially somebody that you were in love with.

[Host (possibly named Bird or related to 'Bird Show')]

Have you ever had somebody say yes they were?

[Caller Pro Vita]

No, of course not.

[Host (possibly named Bird or related to 'Bird Show')]

Right. So they're not going to answer.

[Male panelist (possibly named Jeff)]

So why ask questions?

[Melissa]

Right?

[Caller Pro Vita]

So don't ask a question. Especially like that. First of all, you might get an answer you're not prepared to get. And don't ask a question because I don't think people would really honestly answer it.

[Host (possibly named Bird or related to 'Bird Show')]

Sure.

[Another female panelist (possibly Lauren or Melissa)]

And you said, you know, every single one that we've written down has to do with the X. Okay. So, I mean, I go back to my problems with X's. That's what causes problems in these questions is every single one of them has to do with an ex.

[Host (possibly named Bird or related to 'Bird Show')]

This one does not. But it is dangerous. Hey, Nathan. Good morning. You're on the bird truck.

[Caller Pro Vita]

Hey, my question that you should never ask anyone is if pretty much like, would you still love me if I became a quadriplegic?

[Male panelist (possibly named Jeff)]

What the hell is wrong with you people?

[Host (possibly named Bird or related to 'Bird Show')]

The question is if I was in a car accident, right?

[Caller Pro Vita]

Yeah, yeah, basically. You know, it's like one of those things you really don't know until you think about it. You know, if a girl asked me that one time and I was like, that's a good question. You know, you just never think more of his stuff like that, right?

[Host (possibly named Bird or related to 'Bird Show')]

If I was.

[Caller Pro Vita]

And honestly, I don't even know where to begin to think that may be true. Or, you know, like her answer.

[Another female panelist (possibly Lauren or Melissa)]

I mean, honestly, everybody think about when Christopher Reeve first had his accident. Here is a tall, good looking guy, just got married to this beautiful woman, and then he has this accident, and now she's spending her life taking care of him. Like now, obviously they loved each other and obviously she stayed. But in certain situations, I think it would be the same result.

[Male panelist (possibly named Jeff)]

In this situation, are you financially well off to hire a caretaker to wipe the butt?

[Host (possibly named Bird or related to 'Bird Show')]

It's all about wiping the butt at the point, right?

[Male panelist (possibly named Jeff)]

Because if there's no ass wiping, then whatever.

[Host (possibly named Bird or related to 'Bird Show')]

But other than that, maybe that's a question you can't ask. Answer. Also, like, if I broke both of my arms. Would you wipe my ass?

[Another female panelist (possibly Lauren or Melissa)]

I don't even think you need the beginning of that. Just, would you wipe my ass? I think.

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[Male panelist (possibly named Jeff)]

That could be the test between two guy friends is the, you know, the both arms in a cast and standing at a urinal.

[Melissa]

Hey, buddy, would you shake a leaf?

[Host (possibly named Bird or related to 'Bird Show')]

Yeah.

[Male panelist (possibly named Jeff)]

Can you help me out?

[Host (possibly named Bird or related to 'Bird Show')]

I showed you. I had this very thing happen to the guy I worked with in Washington, dc. His wife was teaching their kids how to inline skate. So she puts her skates on for the very first time. She starts showing their kids. She falls backwards, isn't wearing any wrist guards or anything, breaks both of her arms.

[Melissa]

No, she did not.

[Host (possibly named Bird or related to 'Bird Show')]

She broke both of her arms. So that was his duty, so to speak, for the next. However long it took.

[Melissa]

He had to wipe her ass.

[Host (possibly named Bird or related to 'Bird Show')]

He had to wipe the ass.

[Male panelist (possibly named Jeff)]

It would take me 10 minutes. It would take me 10 minutes to get a bidet put in the house.

[Jessie or Lenny Ware]

No, it would.

[Another female panelist (possibly Lauren or Melissa)]

Jeff would just have her in the front yard and then just have the hose.

[Host (possibly named Bird or related to 'Bird Show')]

I got a power washer with that.

[Melissa]

Extra hard nozzle that sprays really hard.

[Male panelist (possibly named Jeff)]

I'll be with you as soon as I get this green stuff off the driveway.

[Host (possibly named Bird or related to 'Bird Show')]

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[Jessie or Lenny Ware]

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[Host (possibly named Bird or related to 'Bird Show')]

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