Vault: Jeff's Prank Takes A Turn For The Worst

Summary

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The Bert Show — “Vault: Jeff's Prank Takes A Turn For The Worst”

Original Air Date: December 11, 2025
Podcast Host: The Bert Show Team (Bert, Bird, Jeff, Phil, Anna, etc.)

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Main Theme & Episode Overview

This Bert Show vault episode revisits one of the show’s most infamous pranks, masterminded by Jeff. The premise: he fakes a romantic proposal email and has the team, and listeners, convinced it’s real. When unsuspecting women show up at a restaurant expecting a proposal, the stunt spirals out of control, exposing raw emotions, division among the cast, and the unforeseen consequences of “harmless” radio pranks. The episode explores themes of trust, responsibility, and how even small on-air tricks can deeply affect real people.

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Key Discussion Points & Insights

1. The Prank Unfolds

• Setup: Jeff sends an email to the show, written as a heartfelt message from a man planning to propose to his girlfriend at Maggiano’s restaurant. The catch: Jeff wrote it himself, intending to see who would show up expecting a proposal.
• Execution: The team interrupts a song to “make an important announcement,” building anticipation. Multiple women arrive at Maggiano’s, believing the proposal might be for them.

Bert [02:05]: “Is there any better way to get people’s attention than interrupt a song in the middle? Okay, how many people are down there, Phil?”

2. Immediate Backlash

• On-Air Discovery: Jeff admits on-air that he wrote the email, not a lovestruck suitor.

Jeff [02:41]: “Yes, I did. I just wanted to see how many desperate women show up on the day before Valentine’s Day thinking they’re gonna get engaged.”

• Shock from the Team: The hosts are stunned and disturbed by the fallout, especially when Anna, a listener, calls in, visibly upset at having been lured into a fake romantic moment.

Anna [07:38]: “I mean, I don’t know if any apology would even be sufficient. I mean, I can’t go to work now. I am too upset.”

3. Impact on Listeners

• Real Emotions: Anna shares how she and her sister made preparations, even taking off work, hoping for a proposal. Her distress is palpable, and she angrily vows never to listen to the show again.
• Host Sympathy: Bert and Bird empathize with Anna, contrasting Jeff's rationale.

Bert [08:09]: “I can understand really wanting to be that other piece of the puzzle, making a magical moment come true. … I don’t think she’s desperate to get married. I think that she thought this was a magical moment.”

• Discussion of Women’s Expectations: The team debates whether hope for romantic gestures is “desperate” or just meaningful to many women, especially around Valentine’s Day.

4. Internal Friction & Ethical Debate

• Breaching Trust: Bird and Bert push back hard against Jeff, emphasizing the show’s responsibility to its listeners.

Bird [09:30]: “Part of Jeff’s responsibility as executive producer of the show is to protect us and make sure that listeners trust us. … What you’ve done today is you have totally breached that responsibility.”

• Minimal Regret from Jeff: Jeff remains unapologetic, insisting the stunt “proves a point” about women seeking engagement.

Jeff [10:08]: “I feel like I’ve proven a point.”

• Calls from Listeners: Mixed reactions pour in—some defend Jeff’s right to prank, others slam his insensitivity.

5. Cast Reflection & Closing Thoughts

• Summary and Recap: The incident leaves the cast divided, solemn, and with frayed trust.

Bird [16:17]: “It’s just not the kind of show I want to do… where you set up women that are all excited about being proposed to and you squash their dreams. That’s just not what I want to do. I’m pissed.”

• Lasting Consequences: The team acknowledges they’ve ended the week and the pre-Valentine’s Day show on a sour, fractured note.

Bert [16:35]: “The thing that bothers me is that we have ended the week on this note. … You got it, Jeff. You hate this holiday and now you have ruined the vibe of the room. … You’re the bully of the room and the bully of the room has won.”

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Memorable Quotes & Moments (w/ Timestamps)

• Jeff’s Reveal & Philosophy

  “There’s no engagement. I just wanted to see how many desperate women show up the day before Valentine’s Day thinking they’re gonna get engaged.”
  – Jeff, [02:53]

• Anna’s Heartbreak

  “I am too upset. I don’t know. Are you making fun of people wanting to get married? … I should just tell people right now they should never listen to the Bert Show again. Never.”
  – Anna, [07:38 to 07:57]

• Bird Confronts Jeff

  “That, to me, is just evil. How could you laugh at that?”
  – Bird, [03:02]

• Bert Explains the Weight of the Moment

  “I think that she thought this was going to be a magical moment. And if she didn’t do her part to make the puzzle piece come together, then she would have ruined a magical proposal.”
  – Bert, [08:28]

• Listener Phil (sympathizing with hurt women)

  “There’s enough people that do love romance and believe in it that they showed up and they were disappointed. You disappointed a lot of people.”
  – Phil, [10:48]

• Bird’s Final Reflection

  “We strive to have a relationship with our listeners where they trust. … That’s why we don’t do wacky things on April Fool’s Day. … I’m afraid, when’s the next time Jeff’s going to do that and who’s going to be hurt by it?”
  – Bird, [11:17 - 15:49]

• Bert’s Summary of the Fallout

  “The one bad apple in the room today has caused the whole vibe of the room to be sour.”
  – Bert, [17:00]

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Noteworthy Segment Timestamps

| Segment | Time | |-------------------------------------|--------------| | Prank introduction, song interruption | 01:33 – 02:10 | | Jeff admits the prank | 02:41 – 03:09 | | Anna, the upset listener, calls in | 04:39 – 08:47 | | Heated ethical debate in the studio | 08:54 – 13:01 | | Host reflections, recap, and fallout | 13:17 – 17:07 |

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Summary & Takeaways

This episode is a stark exploration of how media stunts—intended as pranks—can have real emotional consequences on listeners. The Bert Show team grapples live with questions of ethics, trust, and the responsibility they hold over their audience. Anna’s genuine heartbreak, the on-air regret (and lack thereof), and the somber mood closing out the show serve as a reminder: what’s “just a joke” in the studio isn’t always funny for those who feel the impact. The cast’s candor and emotional debate make for compelling listening—a cautionary tale for creators everywhere.

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Transcript

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[Bird]

Purch the bird show the goose has landed. Copy copy Red Leader.

Alright, so he's there.

[Phil]

No, Jeff just wanted me to stop the song in the middle of the.

[Bird]

Song cause he's there and is he proposing.

[Phil]

No, Jeff just told me to stop the song.

[Bird]

What the hell?

[Bert]

What?

[Jeff]

Well I just wanted. I thought first of all I think it's cool when we interrupt songs.

[Bird]

I think a half left in the song.

[Jeff]

I've got a very important announcement to make.

[Bird]

There's a minute you have a heart.

[Bert]

Grinch that your heart grew three sizes bigger? Is that what you're about to ask?

[Jeff]

I would like to make an important announcement and is there any better way to get people's Attention. Than interrupt a song in the middle of a song. Okay, so how many people are down there, Phil?

[Phil]

Again, from standing around? There's a couple people still milling about in that walk around, and I think they're, like me, waiting to see what happens.

[Anna]

There is.

[Phil]

I did see one lady drive up in a car during the commercials. She's parked to the side, and there's still that. Yes.

[Bert]

I just.

[Jeff]

I actually want to know how many people leave once I announce that I wrote that email.

[Bert]

Oh, my God. No, you did not.

[Jeff]

Yes, I did.

[Bert]

No, you did not. You cannot come up with words like that. Hey, Jessica, did you write this email? Because, I mean, every time you sing, it is like, angel that can't come have come from Jeff dollar.

[Jeff]

There's no engagement. I just wanted to see how many desperate women show up on the day before Valentine's Day thinking they're gonna get engaged.

[Anna]

Oh, my God.

[Bert]

How me?

[Bird]

Yeah. That, to me, is just evil.

That's so mean. How could you laugh at that? That's amazing.

[Bert]

I'm just like. Because I'm stunned. I mean, we should have known.

[Phil]

I'll tell you this now. There is one less car in the parking lot that is pulling out and pulling off.

[Bird]

Now, Jeff, you do these things, and you never even think about anybody else.

[Jeff]

What am I. Who am I thinking about? An imaginary girl?

[Bird]

No. So here's a woman that shows up that is, like, really thinking that her boyfriend is doing something romantic for. And she shows up, right. And is completely devastated and disappointed. Now, that's a dick move.

[Jeff]

No, it's not.

[Bird]

It totally is.

[Jeff]

It is proving that women. Look, at Valentine's Day is the day that all the special crap is gonna happen, and they will do anything to force themselves into a situation where they will get engaged.

[Bert]

Now, do you think that a lot of the women that showed up there were honestly thought they were gonna get engaged to. Or do you think they were just, like, being rubberneckers where they wanted to see it take place?

[Bird]

One woman shows up.

[Bert]

Yeah.

[Bird]

It's heartbreaking.

[Bert]

I am just honestly most surprised that Jeff was able to come up with something so romantic and sweet.

[Bird]

Hold on, Phil. Okay.

[Bert]

Are you sure Stops moving when. Yeah, those were. Yeah. Jeff didn't. Are you sure producer Tracy didn't write that?

[Jeff]

Come on.

[Bird]

And how did you, like. Jeff didn't say, let's read this on the air tomorrow. He sent it, and I. I bit hook, line, and sinker.

[Bert]

Oh, you're kidding.

[Bird]

So this. This came to me, and I'm like.

[Bert]

Print it and hand it to you?

[Bird]

No, no, no, no. This came to me in my email box and I'm like, this is.

Good morning. All the hits. Q100.

[Anna]

Hello.

[Bert]

Hello.

[Anna]

Yeah, how are you guys? Cause I am really ticked off.

[Bert]

Go ahead. What's going on?

[Anna]

Well, I've been sitting in the Maggiano's parking lot and, you know, waiting for my boyfriend to show up.

[Bird]

I don't know why you find that funny, because.

[Bert]

Sorry to hear that.

[Jeff]

And why did you decide to wait for your boyfriend?

[Anna]

Because, hello, he wrote that email.

[Bert]

He did? Yeah.

[Bird]

When?

[Anna]

Well, obviously recently, if you read it on the air.

[Jeff]

Well, you thought that he wrote it, so. Let me ask you some questions, Anna. What's so special about Maggiano's and you?

[Phil]

What do you mean?

[Anna]

I mean, I haven't even eaten there.

[Jeff]

So why would you go? It says in the email that I made up that nobody wrote but me.

[Anna]

You know what? I am totally confused. How do I know that my boyfriend didn't write that email and you told him not to go? And now that you know, because you wanted it to sound better on the air and that you're just making a big joke out of it.

[Jeff]

What is my. Do you sing?

[Bird]

I still don't understand what your point is.

[Anna]

No, I don't sing. But, you know, the parking lot thing didn't really throw me off because my younger brother proposed to his girlfriend in the church parking lot. So I thought, oh, well, he's doing something like my brother did.

[Jeff]

So you know what? This girl. What's her name again? Ann. Anna. Anna.

[Bird]

Anna.

[Jeff]

Amy.

She is proving my point. Think about it. You've got a woman who is so desperate to be engaged that she. Do you sing?

[Anna]

No, I don't.

[Jeff]

Then why did you go to Maggiano's when the email said that you sang?

[Anna]

I just want to tell you this. You know, of course that email was about me because I listen to your show all the time and he knows I do. Okay? So you know what I do? I totally take a day off from work to go down there.

[Bert]

That sounds funny.

[Anna]

Okay. And then my sister takes a video cam and goes with me. All right? She has two small kids, she's a stay at home mom, so she had to get a sitter so that she could go with me and film this. Sent my parents in Florida.

[Bird]

And that's funny to you?

[Jeff]

Why did she go? Why is. Why did you go down there?

[Bird]

Doesn't matter.

[Anna]

What do you mean, why did I go down there? Because I thought the email was about me. Because I Thought I was getting a ring at Christmas. And when he didn't give me a ring at Christmas, I knew it was Valentine's Day. I knew it was gonna be Valentine's Day weekend.

[Bert]

I don't think you see, some guys, I don't think understand like if it was something that was important to you, like a gift, a gadget or something. I wish I could think of something that was more comparable, but. And you drop a hint to your girlfriend or your wife that this is something that you really want and you really think she's gonna get it for you. And then the Christmas comes, your birthday comes and goes, and it's. And it's not there and you get really disappointed. I mean, the thing is, you sound like it's women forcing men to propose, but I think that it's just. I mean, this is something that is again the most important day to a woman's life. So I mean, I can understand where if she thought there was a hint of a possibility, it obviously meant enough to her to take off work to arrange for videotape of the event. So, I mean. Yeah, it is.

[Anna]

Well, I mean, I can't go to work now.

[Bird]

I gotta. I just have to apologize.

[Anna]

I mean, I don't know if any apology would even be sufficient. I mean, I can't go to work now. I am too upset. I don't know. Are you making fun of people wanting to get married? And I mean, I'm assuming. Am I on the air right now?

[Bert]

Uh huh. Well, I can.

[Anna]

Well, I should just tell people right now that they should never listen to the Burt show again. Never. Well, I'm not listening to you all. You know the set button on my car radio? I am setting it somewhere else.

[Bert]

Well, I just wanted to apologize. Cause I can understand really wanting to be that other piece of the puzzle, making a magical moment come true. Cause I think that that's what she was trying to do. I don't think that she's desperate to get married. I think that she thought, okay, this is a magical moment.

[Jeff]

You can flank.

[Bert]

Let me finish what I'm gonna say for the first time this week.

[Bird]

Okay.

[Jeff]

Oh God, here we go.

[Bert]

Let me finish what I'm gonna say. Okay. I think that she thought this was going to be a magical moment. And if she didn' do her part to make the puzzle piece come together, then she would have ruined a magical proposal. Ruined a magical part. I don't think that it means that she's desperate to get married.

[Bird]

Anna. I'm sorry. There's nothing I Can say, I don't.

[Anna]

Know if that's gonna cut it with me, because, you know, I thought he wrote that email. And now I'm really confused, because you guys are on there going, this is a challenge.

[Bert]

First of all. No. First of all, I take offense at the fact that you don't want to listen to the Burt show anymore, because we have four people on this show, and one person is the one that lied, not only to you, but the other three on the show. So you can't blame Burt or myself or Jen for this, because we were just as involved as you were. And I know, Bert, I know that we have to take responsibility for Jeff's actions, but I.

[Bird]

No, I don't. And I'll tell you why. And I'll tell you why I don't. Part of Jeff's responsibility. And I'm gonna let you go. Okay, I'm sorry.

[Anna]

Well, I don't know. I'll have to think about whether I'm ever gonna listen to you all again, because I am just hacked off. I just think you're making a mockery of people who want to get married. And I thought this was a special day for me.

[Bird]

I understand. All right. Thank you. Part of Jeff's responsibility as the executive producer of the show is to protect us and make sure that listeners trust us. That is his responsibility. And what you've done today is you have totally breached that responsibility.

[Jeff]

This is the same thing.

[Bird]

No, Jeff, you totally have, and there's nothing you can say about it.

[Jeff]

This is the same thing as.

[Bird]

Why can't you ever just admit. You know what? I didn't think it through. I screwed up.

[Jeff]

This is the same thing as the gold diggers bit. It's just proving that women are out there who are desperate to get married and will force situations in order to make. And what better day to do it than Valentine's Day?

[Bird]

So you feel good about what you've done?

[Jeff]

I feel like I've proven a point.

[Bird]

Hi. All the hits. Q100.

[Phil]

Hey, my name's Joe, and I got your back on this one, Bird. I think he did screw up. And Jeff does some wonderful pranks, man.

[Announcer]

I agree.

[Bird]

Totally agree.

[Phil]

Laughed and thought that he's just the instigator. But even us guys like a romance, you know? I even thought of going there just to see. Just to watch.

[Bird]

Well, it's such a breach of trust that. I don't know, that's.

[Phil]

He just needs to admit that he screwed up.

[Jeff]

I just. I will if I can meet the girl who fits Every description in that movie.

[Phil]

She's not out there.

[Bird]

I don't know.

[Announcer]

Exactly.

[Phil]

And the quirk that called up.

[Anna]

Oh, my God.

[Phil]

Where'd she come from?

[Jeff]

Exactly.

[Phil]

She didn't have no criteria. But the thing is, there's enough people that do love romance and believe in it that they showed up and they were disappointed. You disappointed a lot of people.

[Bird]

Thank you for calling.

[Jeff]

All right.

[Bird]

Bye. Bye. Go ahead. Let me take all the I love Jeff calls.

[Jeff]

I didn't put it.

[Bird]

That have. That are as mean as you are.

[Jeff]

Dump them all then and pick them up randomly.

[Bird]

People are calling saying, I thought people see the point. Morning. All the hits. Q1.

[Bert]

It's just.

[Bird]

You know what? It's just not the kind of show I want to do. Maybe that's it. It's not the kind of show I want to do where you set up women that are all excited about being proposed to and you squash their dreams. That's just not what I want to do. I'm pissed. I'm really pissed. And we strive to have a relationship with our listeners where they trust. That's why we don't do wacky things on April Fool's Day. We come up with wacky kind of stunts where you buy into it and then you're disappointed at the end of the day because, Jeff, you've been in on this conversation. Also want our listeners to trust us.

[Jeff]

Are you mad?

[Bird]

And you have breached that.

[Jeff]

Are you just mad because I got you too with the email?

[Bird]

No. I mean, you phone scammed me before I did that.

[Anna]

I did not understand anything. Bert just nailed it right on the head. You have no empathy. You are so bitter about this whole ordeal that you wanted to cause other women pain. Do you know that that description, if it wasn't for the fact that my best friend was already engaged, fit her to a T. Do you know how many couples have had their first date or several important dates at Maggiano's? Do you know how many women sing to their boyfriends? I sing to my fiance. I mean, you just did not think of the damage that you could do. Women's emotions are so high around Valentine's Day and so temperamental that you care. You caused every one of your listeners who trusted you to no longer trust you. You know, well, that's the first rule.

[Jeff]

Don't trust me.

[Bird]

Had we known it was coming from you, we wouldn't have.

[Anna]

You should not be on a radio station if your listeners cannot trust you. That's what your listeners are here for.

[Bird]

Yeah. Had you read the Email, then we might be a little bit more skeptical, but because, you know, you sent it to me and I bought hook, line, and sinker, man. I'll give you that.

[Jeff]

I think that's why you're the most upset.

[Anna]

You're a callous, very bitter man. You're a very callous, bitter man. You have no business being on the radio station, playing games with people's heads.

[Bird]

No, I'm really not bitter about that. I mean, you know what? You're much smarter at putting stuff like that together than I am. I'll give you that. So that doesn't bother me.

[Bert]

Yeah, I just.

[Bird]

You can manipulate way better than I can. Let me just give a quick recap because we're getting a lot of people calling up, going, what are you guys talking about? We got this email yesterday. I got an email yesterday from this guy that I thought was just this complete hopeless romantic. And he wanted to propose to his girlfriend, but he was really, really general in the. In the email. Excuse me. And, you know, he was just. I mean, pouring his heart out in this email. And he said if I read it, he knew that his girlfriend would be listening because she's a big time listener of the show and she would show up at Maggiones at 9:15 because that restaurant holds a really special place in their heart. So I read the email yesterday, read it like twice today. We sent Phil Tyranna down there at 9:15 this morning to see this whole proposal go down. The parking lot gets filled up with women that maybe think it's them that their boyfriend is gonna be proposing to. And then once Phil is down there, Jeff makes the claim that the email he sent. He sent. Jeff wrote the email, sent it to me, and there was never a proposal going down. And he thinks it's a big joke and very funny that a whole bunch of women went down to Maggiana's today, had their dream squad.

[Bert]

I mean, this is my first Valentine single. And it's not, you know, it's. And I don't have that feeling. I don't want other people not to be romantic and other people not to be.

[Jeff]

I did it to hurt people. I did it to prove that there are women out there who will force themselves into the wrong. Like, you know, it's like that playing that game you had when you were a kid where you had to try to put the triangle in the triangle hole and the circle in the circle hole. It's like trying to cram the triangle into the circle hole. It doesn't like that woman did not fit the description. Why is that lost on everyone? She was trying to force herself into a situation where she could get engaged.

[Bird]

And so were the other five or six or seven or 10 women that went down there today that you really hurt?

[Jeff]

I would assume so, yes.

[Bird]

And you feel good that they walk down there and you. They're walking away because you hurt them today. You feel good that they're walking away.

[Jeff]

And you had, I hope, hopefully they're walking away going, you know what? I gotta back off on this engagement thing.

[Bird]

Hey, Tony, you're on all the hits. Q100.

[Jeff]

Yeah.

[Phil]

I cannot believe you guys are lambasting Jeff over this because he has not once all week, even though he's been bitter, has not said, you shouldn't give roses, you shouldn't be special, you shouldn't have an engagement. Not one is called with the right criteria. He was pretty vague, but he punked you guys. You guys have phone pranks. You do all that stuff. It does not hurt your credibility. There were not thousands of people. This was not, you know, this email could have come from any blank listener punking you and not have really shown up. Anyone could have done that. Those women didn't have any connection. There hasn't been 2, 3, 10 people that have called you with any validity even anywhere near matching this.

[Bird]

You have if it was just me getting punked. I mean, Jeff's done that before. He phone scammed me with that Jezebel thing. That doesn't bother me, not even a little bit. It's the fact that 10 or 12 or however many women walk down there. This is the thing that bothers me, that 10 that went down there and got really hurt today. And also the fact that I'm afraid, when's the next time Jeff's gonna do that and who's gonna be hurt? Who's gonna be hurt by it next time?

[Bert]

And it doesn't take a thousand people to justify. I mean, like, if it's just. If it was just one woman that went down there, is that not enough? And the thing is, it is Valentine's Day, and this was a day that was supposed to be themed about Valentine's Day. And the thing that is going to also have bragging rights on it is he's ended the show before Valentine's Day on a sour note.

[Bird]

So you got that on your side also.

[Bert]

The thing that bothers me is that we have ended the week on this note. We've ended a week on where we are fractured in this room. There are listeners are fractured. We're not leaving with a good feeling. We're not leaving with a feeling of love. So there you go, Jeff. You got it. You know what? You hate this holiday and now you have ruined the vibe of the room. I hope you're happy. You're the bully of the room and the bully of the room has won.

[Jeff]

Well, I certainly didn't mean to kill everybody's Valentine's Day.

[Bert]

The one bad apple in the room today has caused the whole vibe of the room to be sour.

[Bird]

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