Vault: She's in love with a married man

Summary

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The Bert Show

Episode: Vault: She's in Love with a Married Man

Date: June 11, 2026

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Episode Overview

In this episode, the Bert Show team digs into a listener dilemma: Jill, a bartender, confides that she's fallen for a married regular at her bar. She calls in using a voice disguiser to seek advice from the hosts and audience. The conversation centers on boundaries, personal responsibility, and the complexities of workplace relationships, especially when strong feelings and existing marriages are involved. The episode features authentic, candid back-and-forth among the cast as they challenge Jill and each other on accountability, temptation, and the right path forward.

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Main Discussion & Key Insights

Jill’s Story: The Situation Unfolds

• [01:32–04:35] Jill’s Introduction & Confession
  • Jill has known the married man for over a year; he is a regular at the bar where she works (mainly as a bartender).
  • The man comes in frequently (up to 3 times a week), sometimes with his wife, but mostly with his male friends.
  • The bar staff and regulars are a close-knit group ("like a family"), blurring the lines between work, friendship, and attraction.
  • Jill describes genuine chemistry: “Most recently... I just like almost leaned in and kissed him and it was just overwhelming to me, like how strong a feeling it was and it just felt absolutely like the right thing to do in any other situation. And I had to really, really check myself.” (Jill, 03:16)
  • She’s agonizing over her next move: quitting isn’t an option, so she considers asking him not to come in anymore.

Challenging Jill: Accountability & Boundaries

• [04:35–06:09] Cast Pushback

  • Bert and Jeff question why Jill’s thinking about making her feelings the man’s problem, rather than addressing her own boundaries.
  • Jeff speculates there must be mutual attraction for such closeness, but Jen and Shannon push back, arguing that Jill’s feelings alone don’t prove reciprocity.
  • The team highlights that this is a slippery slope and emphasizes individual agency.

• Key Exchange:

  • Bert: “Why are you making your problem his? Like, why does he have to not go to your bar?” (Bert, 04:35)
  • Shannon: “You realize that you’re tempted by him... so you have to make the decisions to change that process and then you won’t do it.” (Shannon, 06:48)

The Complexity of the Social Scene

• [06:41–07:44] Jill on Social Rut

  • Jill argues that asking her to avoid the bar would mean losing her close friends and entire social structure.
  • The cast counters that she can and should control her own actions without demanding others change for her.

• Notable Quote:

  • Bert: “You aren't like, yeah, I mean, you're not a victim here. You could go or not go.” (Bert, 07:37)

What’s the Responsible Path Forward?

• [08:08–09:00] The Conversation Jill Wants

  • Jeff asks Jill what she pictures would happen if she confessed her feelings.
  • Jill admits she thinks he’d be “grateful to know” but might be annoyed—still, “could easily find another place to hang out with his friends.” (Jill, 08:31)
  • She vacillates—she doesn’t want to lose him or disrupt her social group, but also doesn’t want to be “that girl.”

• Candid Moment:

  • Bert: “Put your big girl panties on and work there and be there while he's there and don't say anything to him about it. You're not allowed to.” (Bert, 08:02)

Perspective Swap: How Would the Married Men Feel?

• [09:11–09:52] Cast Role-Play
  • Jeff asks Bert and Jeff (both married) how they’d feel if a coworker confessed similar feelings.
  • Bert shares: “My stock answer is this. I always want to know when there's somebody attracted to me. I can deal.” (Bert, 09:39)

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Notable Quotes & Moments

• “Falling in love are like pretty strong words. Have you had one-on-one with him or you just have fallen in love sort of watching him from afar?” (Bert, 03:07)
• “This is why I’m getting worried is because... I just like almost leaned in and kissed him… I had to really, really check myself.” (Jill, 03:16)
• “Affairs don’t happen. Just all of a sudden. People make decisions to have affairs. That’s why they hurt so badly.” (Shannon, 06:48)
• “If I stopped going in, that would be a huge social rut… I wouldn’t see the people who I’m close to.” (Jill, 07:28)

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Timestamps – Important Segments

• [01:32] – Jill’s introduction and confession
• [03:07] – Bert probes the depth of Jill's feelings
• [03:16] – Jill describes the near-kiss and her worries
• [04:35] – Panel challenges Jill’s proposed solution
• [06:48] – Shannon discusses personal responsibility and affair dynamics
• [07:37] – Bert emphasizes Jill’s agency
• [08:08] – Jeff asks Jill what outcome she wants
• [09:39] – Perspective from the married male hosts
• [09:52] – Jill’s dilemma summarized for callers’ feedback

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Episode Takeaways

• The situation highlights the reality of complex emotional dynamics in close-knit workplace environments.
• The Bert Show hosts encourage accountability and urge Jill to own her feelings rather than imposing responsibility on the married man.
• Listeners are left pondering the blurred lines of friendship, work, and love, as well as the mature choices required to avoid hurting oneself and others.
• The conversation is candid, a bit irreverent, and ultimately puts the onus on Jill to set boundaries—and stay accountable.

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Transcript

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[Bert]

Let me introduce you to all to Jill who wants to be on the Voice Disguiser. And she's fallen in love with a married dude and doesn't really know what to do with it. Hey, Jill.

[Jill]

Hi.

[Bert]

Hey. You're on the Voice Disguiser.

[Jill]

Okay, thanks.

[Bert]

So how long have you known this guy now?

[Jill]

A little over a year probably, I'd say.

[Bert]

Okay.

[Jeff]

How do you know each other?

[Jill]

Well, I work. I'm not gonna say where I work, but I work in like a bar, restaurant kind of place. And he comes in regularly, like mostly three times a week, sometimes with his wife, but most of the time with his other guy friends. And everyone who works there is really friendly and my age and we all hang out even when we're not working and it's just, you know what we do. We're like a family there and those guys are like regulars, you know, and we spend a lot of time talking and hanging out with them and you know, it's, it's just a sort of a friendly thing. And I've never seen any of them outside of the restaurant. But you know, three nights a week is a lot to see anybody. So are you a server?

[Jeff]

Are you a server or bartender?

[Jill]

I'm usually a bartender, but I've done both. I've done everything.

[Bert]

And have you ever had anything?

[Jill]

I've worked there a long time. It's, you know, I've worked my way up and I'm friends with everybody and nobody gets hired without my permission. Like, you know, it's like I said, my family so.

[Bert]

Well, falling in love are like pretty strong words. Have you had one on one with him or you just have fallen in love sort of watching him from afar?

[Jill]

We've had our one on one conversations. Yeah, quite a bit. Like I said, I'll go when I'm not working. So I've just sat with him at the bar and you know, we've had drinks, his friends have left and we've talked about all kinds of stuff. And this is why I'm getting worried is because most recently we were talking one night and I just like almost leaned in and kissed him and it was just overwhelming to me, like how strong a feeling it was and it just felt absolutely like the right thing to do in any other situation. And I had to really, really check myself. And I'm starting to feel really worried about the way that I am going to start acting around him. And like I'm afraid I'm going to lose control and I don't want to be the girl who is chasing after a married man. That's not who I am. That's not what I'm about in life. But I also, I'm not going to quit my job because I love it and I need it and I need to pay and there's just no way. I can't not work there. So I feel like I need to tell him so that I can ask him to stop coming in because that's my only, that's the only thing I can see as a solution at this point.

[Bert]

Why are you making your problem his? Like, why does he have to not go to your bar?

[Jeff]

Because, well, it sounds like he's into her too.

[Jen]

Why did he get that? Where did he get that from?

[Jeff]

Come on.

[Jen]

What she said. 0. He comes into the restaurant sometimes with his family.

[Jeff]

Is he into you too?

[Jill]

I wouldn't say that. I don't think that he's ever showed signs that he's into me beyond except

[Jeff]

coming to see you three times a week.

[Jen]

Well, there's nothing wrong with that.

[Bert]

He's not there by himself and he's not there visiting just her. Why are you putting it on him?

[Jeff]

I'm just saying it sounds like there's a mutual attraction there. If they're having one on one conversations and they're close enough and there's an intimate moment enough where she felt like it was the right moment to kiss each other. Like that's chemistry coming from both people. I'm not saying he's done anything wrong yet, but I'm just saying like, so

[Bert]

because she feels the need to kiss him, it's his fault.

[Jeff]

No, I'm just saying if they're having one on one conversations and they've gotten to a point of an intimate moment close enough that she feels there was

[Jen]

an intimate moment she felt like she.

[Shannon]

Yeah, I mean, I see where Jen's coming from. If they've had. If they've been alone talking and she felt comfortable enough to lean in and kiss him, I don't think that he's being stone cold over to the side. Non flirtatious. It's not a blame on him. It's just the fact that they are creating this very dangerous. They are creating this very dangerous situation. Can you be in that bar in a different part of the bar when he's in. I mean, like, because you're talking about how you're having one on one conversations with him. Well, don't have one on one conversations with him anymore.

[Jill]

Yeah, I mean it's, you know, like I said, it's everybody hanging out. So it's not like, I mean, the guys act the same way toward us when their wives are there. You know, it's not.

[Shannon]

But I'm going back. But I'm going back, you know, act

[Jill]

flirty and they still talk to us and you know, their wives are friendly and it's.

[Shannon]

But, but I'm going on what you told us about.

[Jill]

So this is where I go to hang out.

[Shannon]

My, my comment is that you talked about having one on one conversations with him. Going back on what Jen referenced about you feeling the need to lean in and kiss him, which probably did not happen in the group setting. So I'm Saying, can you stop those one on one conversations and sometimes be busy working or not go in when you're not working when he's there?

[Jill]

Like, I mean, yeah, I mean, yeah, I can try that. But I just feel like you're gonna have to.

[Bert]

Yeah, this is your problem.

[Shannon]

You're gonna have to. Because I don't, I absolutely don't think you should say anything to him because this is you. And you know, anytime affairs happen like this is, this shows the process that it takes to have an affair. Affairs don't happen. Just all of a sudden people make decisions to have affairs. That's why they hurt so badly. And I think that you have now you realize that you're tempted by him. And it has been over the course of a year hanging out with him and having one on one time with him and going in when you're not working to hang out with them. So you have to make the decisions to change that process and then you won't do it.

[Jill]

And I go in just to hang out with him. I hang out with everybody.

[Shannon]

You're not listening.

[Jill]

Those are my closest friends. You know, if I stopped going in, that would be a huge social rut. Like I wouldn't see the people who I'm close to.

[Bert]

Look, you're in control. You're in control of this situation. You aren't like, yeah, I mean, you're not a victim here. You could go or not go.

[Jeff]

When you think about.

[Jen]

I understand what she's saying though, because what she's saying is not going to her. Takes out a significant chunk of her existence. Like, number one, she's still gonna have to go to work. And number two, if she goes there after work or on days off because all of her friends work there and hang out there.

[Bert]

Put your big girl panties on and work there and be there while he's there and don't say anything to him about it. You're not allowed to.

[Jeff]

Let me ask you something. When you sort of imagine this conversation going on, you know, you sort of, sort of practice in your mind how what you would say, how you would say it in your mind. What, what does he say back to you? What do you think he would say back to you?

[Jill]

I don't know. I mean, I guess that's why I called. I.

[Jeff]

What do you want him to say back to you?

[Jill]

He would be grateful to know

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and

[Jill]

maybe would be a little bit annoyed, but could easily find another place to hang out with his friends.

[Bert]

So part of you is scared to say something to him because you'll think you'll lose him forever.

[Jill]

I mean, sure, but you're not wanting

[Shannon]

to actively stop him.

[Jill]

I don't want any part of that. I don't want to be that girl. I don't.

[Bert]

Yes, you do. Yeah, you do. Hold on a second, all right, Because a whole bunch of people want to talk to you about this. Believe you me. All right, So I want to know

[Jen]

what you guys did say.

[Bert]

Believe you me, I did.

[Jen]

I just turned around my grandpa.

[Jeff]

I want to know how you guys would feel if you were the guys in that situation. Because you guys are both married.

[Bert]

Yep.

[Jeff]

If it were somebody at the radio station who came up to you and said, we're just having these feelings, you know, because, I mean, it's obvious some of our interns are really all about it.

[Bert]

Why don't you just see by the way they all ignore me how much they dig me.

[Jen]

Instead of being like all hypothetical about it, why don't you just. Hey, Bert and Jeff, can you answer this question the way you answer it when it comes up?

[Bert]

Oh, when it all comes up, My stock answer is this. I always want to know when there's somebody attracted to me. I can deal.

[Jeff]

If you guys were the person in this situation. I want to know your answers.

[Bert]

Okay, we'll answer it coming back and we'll get your comments as well. She'll hang on. Jill here works at a bar and there's a regular that comes in there that she's having really strong feelings for. She says she loves this guy and she's thinking about telling him but she doesn't want to scare him away. But she also doesn't want to lose her social group too. That's in the very same bar. So what is she married and he's married guy? Yeah. So your comments for we'll put you on with her next.

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