Vault: She Wants To Blackmail Her Boss With Compromising Pics?!

Summary

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The Bert Show: Vault: She Wants To Blackmail Her Boss With Compromising Pics?!

Episode Date: March 11, 2026
Featured Voices: Bert (Host), Carly (Caller), Melissa, Kenneka, other Bert Show commentators and callers

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Episode Overview

In this episode, The Bert Show delves into an ethically-charged and dramatic situation: a caller named Carly is contemplating using compromising photos of her boss to secure her job amid rumored company layoffs. The conversation explores the implications, risks, legality, and morality of workplace blackmail, taking input from hosts, the caller, and listeners with HR experience. The hosts maintain their trademark blend of humor, candid debate, and real talk.

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Key Discussion Points & Insights

1. The Situation Unfolds

[01:41]

• Carly joins the show using a voice disguiser, explaining her company's impending layoffs and the rumors circulating about who will be affected.
• She reveals she possesses incriminating photos of her district manager (former direct supervisor), believed to be influential in the layoff decisions.

Notable Quote:

“My company, there are rumors that there are going to be some layoffs...so they're thinking...maybe Wednesday they're gonna start to do the first round of cuts...I've been with this company for a while, and I have a couple coworkers that are really close with me. I have something incriminating that could jeopardize my boss's marriage.” — Carly (Caller), [01:45]

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2. Details of the Compromising Evidence

[02:53]

• Carly describes a work outing where she and colleagues observed (and surreptitiously photographed) their supervisor acting in a way inconsistent with his marital commitments.
• The photos show intimate gestures with another woman, including “hand on her inner thigh.”

Notable Quote:

“There’s one picture where his hand is on her leg, her inner thigh, and she had a skirt on. So he's leaning and talking to her, but his hand is going up her inner thigh.” — Carly (Caller), [04:11]

• Hosts and callers debate how damaging the photos truly are and whether they would justify her plan.

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3. Weighing Blackmail—Risks and Consequences

[05:03, 06:17]

• Question raised: does anyone else have this information (vital for the leverage value)?
• Carly confirms only three people know, but one is hesitant to be involved.
• Moderators and listeners force the issue: what about the aftermath? Even if she keeps her job, will her work environment become unbearable or dangerous?

Memorable Discussion:

“Well, the only thing you have to think about is like two or three steps ahead, because, okay, say you blackmail him and you keep your job...How is the work environment going to be after that?” — Caller/Commentator, [06:17]
“Doesn’t matter. She’s still getting a check at this point.” — Caller/Advisor, [06:30]

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4. The HR Perspective

[07:13]

• Kenneka, an HR professional, calls in to say the layoff decisions are often out of any one manager’s hands. Even if Carly tries to blackmail, the person she’s targeting may not have the power to protect her role.
• Additional insight: attempting the blackmail could backfire, possibly resulting in more trouble for Carly.

Notable Quote:

“If you go in and have this story...they're still gonna lay you off. And you might even get in trouble yourself for bringing this up.” — Kenneka (HR Caller), [07:16]

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5. Moral Dilemma and Alternatives

[08:29, 10:15]

• Co-hosts and callers debate the ethics, with some devil's advocate positions. Is it justifiable to “fight dirty” to preserve your livelihood in a harsh job market?
• They also discuss the real-world strength of the blackmail material, especially if the boss’s wife is forgiving—or if the company is forced to layoff regardless.

Notable Exchange:

“At least she’s still getting a paycheck and has insurance. You know what I mean? So...even though she may get laid off anyway, why not try to save your job?” — Melissa, [08:29]
“Hand going up the skirt and then leaving together. It’s pretty intense.” — Caller/Advisor, [10:10]
“Is blackmail illegal?” — Caller/Commentator, [10:15]
“Yeah, absolutely.” — Caller/Advisor, [10:16]

---

6. Plotting the Move—How to Use the Evidence

[11:00]

• The group discusses the logistics: Should Carly walk into his office? Send an anonymous note, or print the photo? Most agree on NOT using email, to avoid a traceable record.

Memorable Moment:

“Are you giving her blackmail advice? I’m just trying to figure out exactly what’s going on here.” — Host (Burt), [11:52]
“Yeah, I asked you if I could beforehand.” — Caller/Advisor, [11:55]

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7. What Happens Next?

[12:15]

• The hosts propose a check-in: They want Carly to report the results of her plan on the next day's show.

Key Moment:

“Let’s talk to you tomorrow morning after you go in the office today and find out how it went, okay?” — Host (Burt), [12:15]

---

Notable Quotes

• “You don’t ever really think that blackmail is happening in real life.” — Host (Burt), [04:55]
• “I want to be able to leave this company when I get another job when I want to. I don’t want to buy myself two months.” — Carly (Caller), [06:57]

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Timestamps for Important Segments

• 01:41 — Carly explains her layoff fears and possession of incriminating pics
• 02:53 – 04:31 — Details of the compromising incident and what’s on the photos
• 05:03 – 06:34 — Hosts and callers discuss the implications and risks of blackmail
• 07:13 — HR voice weighs in: layoffs often not decided by the person being targeted
• 08:29 – 10:16 — Callers and hosts debate the morality and effectiveness of blackmail
• 11:00 – 12:15 — Advice segment: how to deliver the “evidence,” and next steps
• 12:15 — Show wraps initial discussion and plans follow-up

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Episode Tone & Atmosphere

The tone mixes real concern for Carly’s precarious position with the Bert Show’s classic, conversational humor and opinionated banter. There is an undercurrent of “this can’t be real life!” paired with genuine empathy for people facing job insecurity.

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Takeaway

This episode offers an unfiltered look into a workplace dilemma that blurs legal, ethical, and emotional boundaries. Listeners are left grappling with the slippery slope of leveraging personal knowledge for professional security—a scenario both sensational and rooted in the real-world anxieties of a tough economy. The Bert Show doesn’t provide tidy answers but creates a safe space for raw discussion, laughter, and support—inviting listeners back for the dramatic aftermath.

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Transcript

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[Host (Burt)]

Carly here wants to be on the voice disguiser for good reason. A lot of businesses are making cuts right now, big time. And you would think, like the timing of it has always like been a little strange to me. Like, why wait until like a week before Christmas?

[Caller/Advisor]

It's the new year.

[Host (Burt)]

I guess you gotta wait until the new year. But can't you do it on like December 3rd or something?

[Caller/Commentator]

I don't know what's better or worse. Because you want people to get their paychecks for as long as they can.

[Caller/Melissa]

Yeah.

[Host (Burt)]

Give them the action at the beginning of December and give them two weeks, seven.

[Caller/Advisor]

You gotta be off the books by January 1st.

[Host (Burt)]

Yeah, it sucks.

[Danielle Fishel]

It does.

[Host (Burt)]

Well, Carly here says that she's got some job security and her boss doesn't even know about it and she wants to obviously be on the voice discussor. So here we are. Hey, Carly.

[Carly (Caller)]

Hi, guys.

[Host (Burt)]

Hey.

[Carly (Caller)]

So, yeah, my company, there are rumors that there are going to be some layoffs because they're really trying to cut back and so they're thinking it's going to be. Well, they're saying maybe Wednesday they're going to start to do the first round of cuts. So I've been with this company for a while and I have a couple of co workers that are really close with me. I'm sorry, I'm just so nervous. And so today we're going to go in maybe and this other woman and we're going to. We'll see. Our district manager used to be my direct supervisor and I have Some. Something incriminating that could jeopardize his marriage. And I was going to basically go in there and say, I want to be ensured that my job is safe. And the other co worker.

[Host (Burt)]

Okay, we need some specifics here.

[Carly (Caller)]

Well, okay. We went on a work kind of outing and one night we were at this bar, restaurant and a bunch of people left and I was with two other people and we were about to go, but then we said, you know what, why don't we. There's like a little loungey part in the back. Let's just kind of go over there and have a couple more. So we were there and this person, this manager, he ended up staying. I guess he was just sitting at the bar and he started talking to this woman who was there. And you know, over the next couple of hours he got really flirty and he ended up leaving with her. And we have some pictures of just like. I don't want to get too specific, but just. It's pretty obvious that something's going on that they did at least walk out to the parking lot maybe. Very touchy feely type pictures.

[Host (Burt)]

He's not gonna care. There's nothing really incriminating there.

[Caller/Advisor]

You don't know his wife.

[Host (Burt)]

I mean, how bad is it?

[Carly (Caller)]

I mean, there's one picture where his leg. I mean, his hand is on her leg, her inner thigh and she had a skirt on. So he's leaning and talking to her, but his hand is going up her inner thigh.

[Caller/Commentator]

You know, she has pretty bad.

[Carly (Caller)]

Yep. You know, nothing with them kissing, but leaning in really, really close, you know, and then he's helping put on her jacket and you know, has his arm around her and. No, there's definitely. You could see that there's. There's something.

[Caller/Advisor]

There's some chemistry there.

[Host (Burt)]

Yeah, sounds like such a made for TV movie type thing. You don't ever really think that blackmail is happening in real life.

[Caller/Commentator]

You know, here's the question. How many other people in the office know about this? Because I feel like this information is only really good for blackmail if it's only yours. I mean, if he has to make a lot of different cuts, but then the whole department's coming in to try to blackmail him. Like he's still gonna have to cut some people.

[Carly (Caller)]

Only three of us know about it. And it's not like we had planned to use this or anything. It just. We started taking pictures of each other and then noticed he was in the background and we were getting really drunk and we just said, oh. And we just start snapping Pictures every now and then. It's three people, including me, so me and two other women. And one woman, she's just. She doesn't really. She's not sure yet, but she definitely doesn't want to walk into the office with us. She's just really freaked out about it. And I am too. I just feel. I'm just so scared about losing my job. I mean, I don't know what, you're desperate. And I have another friend who used to work for the mayor and he hasn't been able to get work. He got laid off and he hasn't been able to get work for a year. And he has a master's degree.

[Caller/Commentator]

Well, the only thing you have to think about is like two or three steps ahead because, okay, say you blackmail him and you keep your job through the holidays or through this firing time. How is the work environment going to be after that when you still have to go to work with him?

[Caller/Advisor]

Doesn't matter. She's still getting a check at this point.

[Carly (Caller)]

He's not my direct supervisor anymore. He's been promoted. So he's still.

[Caller/Commentator]

I'm just saying in January you can come up with some other reason to let you go.

[Host (Burt)]

He's going to want those pictures. He's going to go, okay, this one time deal. At least this is how I would see it going down on Lifetime Network. He's going to want the pictures in exchange for doing this. So you can never blackmail him ever again.

[Carly (Caller)]

No, I wouldn't give up pictures. I mean, I want to be able to leave this company when I get another job when I want to. I don't want to buy myself two months.

[Host (Burt)]

Hey Kenneka, good morning. You're part of the Burt show, huh?

[Caller/Melissa]

Good morning.

[Caller/Kenneka]

I love your guys show.

[Host (Burt)]

Thank you.

[Caller/Kenneka]

I work in HR in a company here and all I wanted to say to this lady is that if you're working for a DM or whoever, they're told a specific name to cut you off. They don't just choose a random person to lay off. So if you go in and have this story for that person, they're still going to lay you off. And you might even get in trouble yourself for bringing this up.

[Host (Burt)]

So it might not. Is it. Do you know for sure it's his direct decision on who stays and who goes?

[Carly (Caller)]

I don't think it's his direct decision and I've definitely thought about what that caller said, that there are a lot of factors, but he has a great influence on, you know, I believe who stays and who doesn't. And I don't think he's going to want to come forth with that with anyone. I don't think he's going to say, hey Bob, I'm kind of, I don't know what to do because you know, someone has these pictures, you know, I don't think he's going to want anyone to know about that. So I think he'll try, you know, as hard as he can to come up with some reason why he can't, you know, let us go.

[Host (Burt)]

Go ahead, Melissa.

[Caller/Melissa]

Yeah. Devil's advocate. I mean again, moral issue, whether she should do it or not. But here's, here's the situation we're in in this country where so many people are losing their jobs and like she said, so many people say you lose your job at Company before then you might be able to get something even if it's part time. But that is not the case that we're in right now. So even if like you said Jen, the work environment, well, at least she's still getting a paycheck and has insurance. You know what I mean? So for some people that it may be, even though she may get laid off anyway, why not try to save your job? Devil's advocate. Just asking.

[Host (Burt)]

Hey, Kirsten. Go ahead. You're on Q100.

[Caller/Kenneka]

Hey, good morning. I was just gonna say that what if the boss is on the chopping block too? I mean, I would assume he's not the be all end all. So what if he's on the chopping

[Caller/Advisor]

block then what difference does it make? Like he's the guy who's.

[Caller/Kenneka]

Because if you weren't on the chopping block, he's gonna make sure you are now.

[Host (Burt)]

Well, not if you got the pictures.

[Caller/Advisor]

Yeah, yeah. Not if you have the pictures. Why would he do that?

[Host (Burt)]

Can't. That's the only thing she's got.

[Caller/Advisor]

Like he wouldn't even then he might say, like then he would go to his supervisors and go, hey, you know what? That list I gave you, we gotta move a couple people off it. Cause I was wrong.

[Host (Burt)]

I have to see the pictures. But the case that you're stating for the pictures right now, at least what I have in my. He could just go to his wife and go, look, I just gotta be honest with you. One night I got buzzed with a whole bunch of workers and I didn't go over the line but I think I was inappropriate one with one of my co workers and there were some pictures taken. She's gonna get mad at him. They're gonna be Mad at each other for three days and then it's over. It's not like, you know, he's having an affair.

[Caller/Advisor]

Depends on how many pictures there are.

[Host (Burt)]

And I'd have to see him too, but at least what you're staying here. The way the picture that she painted doesn't sound devastating.

[Caller/Advisor]

Hand going up the skirt and then leaving together. It's pretty intense.

[Caller/Commentator]

Is blackmail illegal?

[Caller/Advisor]

Yeah, absolutely.

[Host (Burt)]

When are you supposed to do this?

[Caller/Advisor]

Unless you're one of the major car companies.

[Host (Burt)]

What's that? When are you gonna do this?

[Carly (Caller)]

We're gonna do it today. Today? Yeah.

[Caller/Advisor]

I have a suggestion. Is it wrong for me to give you a suggestion on how to do it?

[Carly (Caller)]

No, I. Yes, sure.

[Caller/Advisor]

Because my suggestion wouldn't be because you said you were gonna march into his office.

[Carly (Caller)]

Yeah. And it wasn't a co worker. It was just a woman who was at the bar. You know, she looked like kind of a business type woman. Maybe she was traveling or something on a. You know, for work.

[Host (Burt)]

So it's nobody. It's not somebody you know?

[Carly (Caller)]

No.

[Host (Burt)]

Okay.

[Caller/Advisor]

See, my thought is, don't walk into.

[Carly (Caller)]

I mean, that would be even better because that person could maybe say that,

[Host (Burt)]

but you don't have that.

[Carly (Caller)]

There was something going on, you know, but no, it's just a random woman. So what were you gonna tell me?

[Caller/Advisor]

I was gonna say I wouldn't walk into the office. I would write a strongly worded email and attach one of the photographs, the most incriminating, and say. And maybe even. Not even. Maybe even print it out so there's nothing like in the email system, and take it to him and then go in there and just say, hey, the email was from me and Melissa. Don't put your names on it or anything like that.

[Host (Burt)]

I wouldn't put anything in an email.

[Carly (Caller)]

No, I wouldn't either.

[Caller/Advisor]

Put it in writing and then go in there and say, hey, this is for me and Melissa. Don't put your name on it, because if you go in there in person, then he can start threatening and you can end up fired right away. But if you give it to him in writing and he's got to sit on it and he doesn't know who it is.

[Host (Burt)]

Are you giving her blackmail advice? I'm just trying to figure out exactly what's going on here.

[Caller/Advisor]

Yeah, I asked you if I could beforehand.

[Caller/Melissa]

He says, is it okay for me to give advice on how to do it?

[Caller/Advisor]

Yeah, because I think if you go, his gut reaction might be to, buh, bye, fire you immediately without. And then deal with the consequences afterwards. But if he has to sit on it for a few hours, that's when the full repercussions start to pop into his mind.

[Host (Burt)]

Let's talk to you tomorrow morning after you go in the office today and find out how it went, okay? Okay. Good luck.

[Caller/Kenneka]

Thank you.

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