Vault: She Accidentally Hooked Up With Her Boss's Ex?!

Summary

Episode Overview

Episode Title: Vault: She Accidentally Hooked Up With Her Boss's Ex?!
Date: March 16, 2026
Hosted by: The Bert Show Cast (Bert, Kristin, Abby, Cassie, Tommy, etc.)

In this episode, a listener named Jillian calls in seeking advice about a complicated romantic mishap—she unknowingly hooked up with her supervisor’s ex-husband. The cast dives into whether Jillian should come clean to her boss, navigate the workplace fallout, or continue her new relationship quietly. The segment is classic Bert Show: candid, supportive, playful, and full of real-life awkwardness.

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Key Discussion Points & Insights

1. Jillian’s Story Unfolds

• [00:29–01:43]
  • Jillian, under a voice disguiser, recounts her Thursday night out, where she met and hooked up with a man she genuinely liked.
  • The next morning, after exchanging numbers, the man later reveals via phone that he’s her supervisor’s ex-husband—a total shock to Jillian.
  • Quote:
    • “I had absolutely no idea that this is my supervisor's ex husband.” — Jillian [02:56]

2. How Did This Happen?

• [02:59–03:35]
  • The show explores how the man recognized Jillian; turns out, they met once years ago at a company event while he was still married.
  • Jillian doesn’t recall the meeting, and the man withheld this info during their night together.
  • Playful banter from cast:
    • “Why complicate things with details that may take your mind off the goal at hand?” — Cast [03:32]

3. Can She Still Date Him?

• [04:03–05:56]
  • Jillian reveals she genuinely likes him and went on another date over the weekend.
  • She barely talks to this supervisor and wasn’t aware of her boss’s current relationship status.
  • She seeks the cast (and audience) validation:
    • “Can I still see him?... I need somebody to really tell me that I can't. There's no way that that's okay.” — Jillian [05:24]

4. Should She Disclose to the Supervisor?

• [05:58–08:11]
  • The cast debates:
    • If the supervisor isn’t an immediate manager, is any disclosure necessary?
    • “If she's not your immediate boss... I think you're free and clear.” — Cast [06:27]
  • Most argue that, since the divorce was two years ago and there’s minimal work overlap, Jillian doesn’t owe her boss any explanation yet.

5. Audience Weighs In

• [06:33–10:13]
  • Callers offer their takes:
    • If the supervisor’s involvement is minimal and there are no kids, Jillian’s “fair game.”
      • “I'd say they're fair game.” — Caller [09:30]
    • If the relationship becomes serious, that’s when disclosure should happen:
      • “At some point, you're gonna have to say something because you’re gonna end up at an office party together.” — Bert [07:10]
    • Since this is just two hookups, no conversation is needed now.
      • “We're talking about two nights, so. Yeah, telling her now would be way jumping the gun on that.” — Cast [09:50]

6. When and How to Disclose, If Ever

• [10:13–10:53]
  • Consensus: If this turns into an exclusive, serious relationship, a conversation with the supervisor should happen then.
    • “So once it gets exclusive, that's the time to bring the supervisor in on it?” — Bert [10:23]
      • “Yeah, pretty much.” — Caller [10:27]
    • “Handle it delicately. But you don't owe him or anything just yet.” — Bert [10:50]

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Notable Quotes & Memorable Moments

• Jillian realizes the identity:
  • “I had absolutely no idea that this is my supervisor's ex husband.” — Jillian [02:56]
• Cast jokes about hookups and company events:
  • “Why complicate things with details that may take your mind off the goal at hand?” — Cast [03:32]
• On timing disclosure:
  • “We're talking about two nights, so. Yeah, telling her now would be way jumping the gun on that.” — Cast [09:50]
• Funny take on alcohol and romance:
  • “I like him. Especially after seven beers.” — Cast [10:41]

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Key Timestamps

• 00:29 – Caller Jillian joins in
• 01:43 – Jillian finds out the hookup was with her boss’s ex
• 02:59 – How they met before
• 04:03 – Jillian admits she went on a second date
• 05:24 – Jillian asks if it’s okay to keep seeing him
• 06:27 – Advice about workplace hierarchy
• 07:10 – If things get serious, disclosure is needed
• 09:30 – If no children are involved, “fair game”
• 10:27 – When relationship becomes exclusive, have the conversation
• 10:50 – Final advice: handle with care, but no disclosure needed yet

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Summary Tone

This episode strikes its usual entertaining, sympathetic tone—full of playful jokes, honest storytelling, and a touch of real-world awkwardness. The cast supports Jillian while poking gentle fun at the universal horror of discovering unexpected connections in your dating life.

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Takeaway

At the heart: Jillian doesn’t owe her supervisor an explanation yet, especially given the time since the divorce and their loose work relationship. If the office romance goes next-level, though, it’s time for an honest conversation—preferably before any public surprises at work. For now: don’t sweat it, but stay mindful.

Transcript

[A]

The bird show. I mean, think about what that must feel like. Like that, that anxiety pit in your stomach when you realize that you just got off a date or you just hooked up with your boss's ex and

[B]

you can't do anything to take it back. I mean, you can't change it history of what you just did. And so, yeah,

[A]

all sorts of angles probably to take it this, you tell the boss, you let it go. Do you pretend it never happened? Hey, Jillian, you're on the voice disguiser.

[C]

Oh, good.

[A]

Hi.

[C]

Good morning.

[A]

Morning. How are you?

[C]

Good, how are you?

[A]

We're okay. You're on the voice disguiser. We can't recognize your voice.

[C]

Yeah, thanks for pointing out the knot in the pit of my stomach.

[A]

Yeah, I bet.

[D]

Oh, no, tell us the story. How did it happen?

[C]

So I went out. This is last. This is past Thursday night. So we went out with some girlfriends. We were just hanging out, drinking. I got a little tipsy. We were at this bar and I met this guy and so I was drinking a little bit, but I actually really did like him. And I know I did something kind of. Kind of slutty, but I ended up going back to his place and hooking up with him, like all the way.

[D]

Hooking up?

[A]

Yeah. Let's define hooking up.

[C]

Sleeping with him.

[A]

Okay, but sleeping, but not really sleeping. Gotcha. The night. Sleep, sleep.

[D]

No cuddling.

[E]

Just so you know, I don't think that was slutty because you were buzzed, so that makes it not slutty. Just for reference.

[D]

Sweet.

[A]

Chad's numbers just went down by dozens.

[C]

Oh my gosh, that's awesome.

[D]

Good news.

[A]

All right, so you go to the bar, you get your buzz on pretty good and you end up okay. Gotcha.

[C]

Right, so. But the thing is, I ended up. I mean, I stayed over and then I got up the next morning and we switched numbers. Like it wasn't. It was. You know, we actually did like each other. So we had. We had breakfast. I left.

[E]

Hey, as a courtesy move, when you're doing that early morning number switch, write down your name Also, just generally speaking,

[D]

that's a good idea, both of you.

[E]

Because if not about 10:30 in the morning, you'll get a hang up call and that's him hearing the name on your voicemail, just so you know. True.

[A]

All right, so continue on.

[C]

So anyways, the next day I'm at work and I get this text from him and it's like, hey, I had a really great time. Hope to see you again soon. And then like right after that it's a second text that says, so do you know, do you feel awkward at work today? And I wrote back, and I was like, no, works cool. Why? And then I didn't hear anything back from him until later that night, and he called me to tell me what was going on. And I had absolutely no idea that this is my supervisor's ex husband.

[A]

So did I miss something that had.

[B]

He knew that you were his ex's employee? Yeah.

[A]

I feel like I missed something here.

[C]

Yeah. But I. Okay, first of all, I have. It's not like I just have one supervisor. I have six supervisors.

[A]

But how did he know that you were an employee of one of those six supervisors?

[C]

Well, apparently, he met me almost three years ago when he was still married at a company event.

[D]

I know you didn't remember him.

[C]

I don't remember him telling me that.

[A]

And he never brought it up when you guys were at the bar getting your buzz on.

[D]

Of course not.

[A]

Never said anything.

[D]

Oh, you chosen to go there.

[E]

Well played by him. Nicely done. Why complicate things with details that may take your mind off the goal at hand?

[D]

Wow.

[A]

Oh, that sucks.

[E]

It's good for him.

[D]

So were you upset with him? Were you ticked off?

[C]

I was stressed out more than. I mean, I'm upset that he didn't tell me because I was in this position. But then. No pun intended. But then he also. I mean, I really like him. I ended up going out with him again.

[D]

You did?

[C]

Yeah.

[A]

Okay, that's gonna change things here a little bit.

[C]

Over the weekend, I went on again. I didn't go out with him. I went out with my friends. I wasn't gonna go out with him. And then I ended up going again. I really like him. We. We totally hit it off. And I mean, you know how hard it is to meet somebody.

[A]

When he told you that he had met you previously, was it a little bit like watching the end of the movie the Sixth Sense, where you're, like, putting everything. Oh, yeah. Did you remember that you met him before?

[C]

No.

[A]

You didn't. He still had no recollection.

[E]

Have you asked him if. Is it possible that you and he talked about your mutual friend on. What was it, Thursday night? The night of the original hookup, but because you were buzzed, you don't remember it? Are you 1000% certain? It didn't come up? Not that it makes a difference.

[C]

That's like. That's one of those. It's a little fuzzy, but I don't. I'm 95% sure.

[A]

So what is the Question that we're asking this morning. Do you tell the supervisor? Do you not tell the supervisor? I guess we need a little history of the supervisor and the ex. Were they married? How long have they been broken up?

[C]

They were married. They've been divorced for two years.

[A]

Two years.

[C]

Okay.

[E]

No need to tell.

[C]

The question is. And what I'm asking is, am I. I just want approval that I can. I mean, am I wrong? Can I still see him? And if I. If I can't still see him, I mean, I need somebody to really tell me that I can't. There's no way that that's okay.

[D]

Well, is your boss over it? Is she moved on?

[C]

I have no. I don't talk to. I mean, I barely work with that supervisor. You know, I obviously don't talk to her about my personal life.

[E]

Does she have the. Does she have the ability to fire you?

[C]

Yeah, I mean, all supervisors have that.

[E]

But I mean, like, yeah, in our department. Do you not talk to her enough that, like, would she be able to. On Wednesday if, for whatever reason, would she be able to call you in the office and go, I'm sorry, we have to let you go? Or would it be somebody else doing that? Because you're saying that she's a supervisor,

[C]

but, like, I worked there for years. I mean,

[E]

if she's not your immediate boss and she's just someone who's above you in the organization, I think you're free and clear.

[A]

Hey, Natasha.

[E]

Good morning.

[A]

You're part of the Burt show. Go ahead.

[F]

I would just say that if, like he just said, if it's not one of her direct supervisors, it's probably not going to come up enough for her to worry about. On top of that, if it's been two years, I would say she's probably well over it. And if she didn't even know, there's no reason for her to be worried about it. I have direct. I have more than one supervisor, too, and I'm not real close to any of them, but something like that, I would highly doubt that one of them could even. That would come up and just say, you're fired because of that. And if they did, the way that the laws are wrote, she could come back and, I mean, that would be the end of that.

[A]

At one point or another, though, if the relationship evolves into something more meaningful, at some point, you're gonna have to say something because you're gonna end up at an office party together or a Christmas party or something, and you'd want to give your supervisor the Heads up. That look, I don't want you to be shocked. That's uncomfortable tomorrow at the party when the ex husband.

[B]

It just depends on the nature of the relation, their work relationship. I mean, if it is truly one of many supervisors and it's the one supervisor she never sees, then what is the. You know, why would she have any obligation to say anything after two years? But if she is somebody that she has to deal with a lot and the woman's gonna find out some other way and it makes it awkward for them? I don't know. I don't know.

[D]

I think it all depends on the supervisor's state of mind with her divorce.

[A]

You just don't know, though, because your supervisor won't share that with you if you're an employee most of the time.

[C]

Right.

[D]

If she's, you know, if she's over it and she's moved on and maybe she's in another relationship, then I don't think she has anything to worry about.

[A]

Jillian, do you know if your supervisor is in a serious relationship with somebody else?

[C]

Not that I know of, but I really have no idea.

[A]

Okay, Justin, go ahead. You're part of the birth show, huh?

[F]

Oh, hey, I think she should have

[G]

the other guy tell her supervisor because he was the one in the relationship, you know?

[A]

So you say it's the ex's responsibility to say. To define what's going on?

[D]

Maybe it depends on if they still talk or not. I mean, they may not be in communication at all. If they are, that would be a great way to solve the problem.

[A]

404-741. Q100. Hey, Joe, go ahead.

[G]

I think that she needs to invite the supervisor over the next time he invites her over, and they need to have a bit of a reunion.

[A]

Oh, you're crazy.

[D]

You're so.

[A]

James, that is creating drama right there. Good morning, Patrick. You're on Q100. Hi.

[F]

Hi.

[G]

I was just wondering if there was children involved.

[A]

How does it sway you either way? How does it sway you either way? Like, let's say.

[G]

Well, I mean, I wouldn't want my stepchildren's parents to be my supervisor or vice versa. That would create a problem.

[E]

You're fascinating.

[C]

This.

[G]

If there's not children, then there's no history.

[B]

Well, I think. And also, if there's children, they're still in contact with each other.

[A]

Right.

[B]

If they're. If they don't have children, then they don't necessarily have a reason to be in contact.

[A]

Jillian, are there any children involved in this whole thing?

[C]

No, no kids. None.

[A]

No kids. No kids.

[G]

I'd say they're fair game.

[A]

Yeah. Most are calling up saying you don't have to say anything. I just do think that eventually you're gonna have to have that talk before he walks in the office or he's gonna pick you up to have lunch one day or something like that. And wouldn't you rather her know before it's a shock and she finds out in front of the rest of the office?

[D]

But you have to remember, they just hooked up Thursday and they went on one other date.

[A]

Yeah.

[D]

We're talking about two nights, so. Yeah, telling her now would be way jumping the gun on that.

[C]

You know, we haven't even gone on a date. A real date.

[E]

Yeah. You're just hooking up and you're drunk.

[A]

That's totally different. Last call. Good morning, Chandelle. You're part of the Burt Show. Hi.

[C]

Hey.

[G]

Morning.

[F]

I think that they should just keep it to themselves because they just hooked up. They're not in a relationship.

[B]

Right.

[A]

So when do you think it's time for you. For her to pull. For Jillian to pull the supervisor aside and go. Okay.

[F]

If they decide to stay in.

[D]

So they decide to what?

[F]

To start dating.

[A]

Start dating. So once it gets exclusive, that's the time to bring the supervisor in on it?

[F]

Yeah, pretty much.

[E]

Okay. All right.

[A]

Thank you, Jillian. Most are calling up saying you don't owe the supervisor anything, yet you hooked up with the guy twice. Everything's so exciting now. Yeah, of course. You like him so much, but who knows what's going to happen over the next couple of weeks.

[E]

I like him. Especially after seven beers.

[B]

Just don't screw him over because then he may call the ex wife and say something.

[A]

Handle it delicately. But you don't owe him or anything just yet. Okay?

[C]

Okay.

[A]

All right. Thank you for calling the Bird Show.