Vault: Jeff Gets A Taste Of His Own Medicine

Summary

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The Bert Show

Episode: Vault: Jeff Gets A Taste Of His Own Medicine
Date: December 12, 2025
Host: Bert and Cast (Kristin, Abby, Cassie, Tommy, Jeff, others as referenced)

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Episode Overview

This episode centers around a moment of comeuppance for show member Jeff Dollar after a controversial on-air stunt. Previously, Jeff orchestrated a prank that left a group of women disappointed when they believed they were about to be proposed to at a restaurant, only to discover it was a ruse. The episode recaps the backlash Jeff received—and culminates in the team delivering priceless payback by subjecting Jeff to the kind of phone scam misery he’s usually the mastermind of.

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Key Discussion Points & Insights

1. Recap of Jeff’s Controversial Prank (02:05-03:56)

• The Incident: Jeff sent several women to Maggiano’s restaurant under the false pretense of being proposed to, leaving them publicly disappointed.
• Reaction: The Bert Show team and its audience were divided—half defended Jeff’s “comedic” intentions, while the other half expressed anger and distaste for his actions.
  • Quote:
    Bert (D) at 02:32:
    “So a whole bunch of women left, Maggiano's disappointed that they weren't being proposed to, and Jeff got a real good laugh out of it. And the rest of us on the show really thought it was in poor, poor taste.”
• Audience Feedback: Audience response was highly polarized, some brushing it off, others even expressing hatred toward Jeff.

2. The Team’s Fallout and Planning Revenge (03:56-05:40)

• In-House Conflict: After the show, Bert and Jeff had a heated discussion with their program director, visible to other staff through office glass walls.

  • Quote:
    Cassie (C) at 04:34:
    “There was definitely some shouting coming through that glass. I was like, oh, no.”

• A Need for Empathy: Bert realizes Jeff lacks empathy for the recipients of his pranks and devises a plan to give him a taste of his own medicine.

  • Quote:
    Bert (D) at 04:58:
    “What I realized is that Jeff didn't understand how mean it was to do to these women, because Jeff doesn't have the ability to empathize... he's never been burned, never been disappointed, especially when it comes to phone scams. So I'm thinking, all right, I need to teach him a lesson in empathy.”

3. Enlisting Jessica, Jeff’s Wife, for the Scam (05:23-06:36)

• The Setup: Bert calls Jeff’s wife, Jessica, to gather intel on Jeff’s biggest frustrations for an effective prank. Jessica is eager to participate.
  • Quote:
    Bert (D) at 05:40:
    “So while she was standing by her man and she was doing the unconditional love thing, there was part of her that really thought it was mean also.”
• Jeff’s Hot Button: Jessica reveals Jeff’s biggest pet peeve is being left on hold during phone calls—he can’t stand it for more than a few seconds.
  • Quote:
    Jessica (via Bert) at 06:36:
    “Jeff can't stand being left on hold for any amount of time. A second feels like an hour to Jeff.”

4. The Phone Scam: Revenge in Action (08:28-16:40)

The Setup (08:28-08:56)

• A radio friend from Washington D.C. is recruited to portray a cruise line representative calling Jeff, playing into his highly-anticipated family cruise plans.

The Painful Call (09:21-16:28)

• Endless Holds: Jeff is put on hold for extended periods, escalating his frustration. At one point, he’s on hold for a full half hour, with the total call extending beyond two hours.
  • Quote:
    Jeff (B) at 10:27:
    “We've been talking for a total of three minutes. I've been on hold for 20-something.”
  • Quote:
    Jeff (B) at 11:05:
    “Just so you know, you're aware that during this entire conversation I've been on hold over 45 minutes?”
  • Quote:
    Jeff (B) at 13:34:
    “Just for your record, you said you ended that with 'hold one more minute.' That was 21 minutes.”
• Absurdity Increases: The agent insists there’s no record of his paid cruise, suggests buying two additional (inferior) cabins, and repeatedly fails to help.
  • Quote:
    Agent (C) at 14:17:
    “Of course we would refund your money.”
  • Quote:
    Agent (C) at 14:25:
    “No, the cabins that are available now are not ba. They are cabins on the inside, on the lower deck, and they're not close to each other.”
• Final Straws: When Jeff finally agrees to buy the backup cabins, they have—of course—just been sold to someone else while the agent was on a personal call.
  • Quote:
    Agent (C) at 16:04:
    “Oh, my god. Jeffrey, those two cabins were just sold right out from under me.”
• Jeff’s Exasperation Peaks: The tables have turned, and Jeff’s infamous patience for pranks is nowhere to be found.
  • Quote:
    Jeff (B) at 13:52:
    “You're helping me out? I've been on hold for two hours, and we're no further than we were when you first called.”

The Reveal (16:31-16:40)

• Bert unmasks the prank:
  Bert (D) at 16:39:
  “Yeah, my name's Bert.”
  Jeff (B): “God. We will. We will scam you. The Bert Show.”

---

Notable Quotes

• Bert (D) at 04:58:
  “What I realized is that Jeff didn't understand how mean it was to do to these women... So I'm thinking, all right, I need to teach him a lesson in empathy.”
• Jessica (via Bert) at 06:36:
  “Jeff can't stand being left on hold for any amount of time. A second feels like an hour to Jeff.”
• Jeff (B) at 13:34:
  “Just for your record, you said you ended that with 'hold one more minute.' That was 21 minutes.”
• Agent (C) at 16:04:
  “Oh, my god. Jeffrey, those two cabins were just sold right out from under me.”

---

Memorable Moments

• The detailed description of Jeff’s cruise planning (07:54-08:28), including his three-ring binder and paranoia about lost birth certificates, which makes the prank’s stakes comically high.
• The escalation of Jeff’s anger as he endures the ridiculous and interminable holds—an exact reversal of his usual on-air prankster persona.
• The entire phone scam segment (08:28-16:40), particularly Jeff’s comedic exasperation and futility, serves as the centerpiece of the episode.

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Timestamps of Important Segments

• 02:05–03:56 – Recap and fallout from Jeff’s Maggiano’s prank
• 03:56–04:49 – Tense debriefing in the office and Bert’s angry reaction
• 05:23–06:36 – Jessica’s insights into Jeff’s top annoyances
• 08:28–08:56 – The setup for the revenge phone scam
• 09:21–16:28 – The full phone scam climax; Jeff’s patience tested to the extreme
• 16:31–16:40 – The prank reveal/conclusion

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Tone and Style

The episode balances humor with pointed commentary about empathy and boundaries in comedy. The cast’s camaraderie, sarcasm, and affection shine through the episode, lightening the mood even as they hold each other accountable. The dynamic shifts swiftly between comedic roasting and genuine insight into office relationships and motivations.

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In summary, this episode is both a hilarious and revealing look at how The Bert Show deals with internal conflicts, audience outcry, and the value of giving someone a taste of their own medicine. Jeff’s legendary intolerance for being put on hold makes for a satisfying, well-orchestrated prank—and a minor lesson in radio karma.

Transcript

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[B]

The Birch Show.

[D]

Look, the last thing we need to do if you listen at this time every day is rehash everything that went down on Friday. Yeah, just the really short version of it. If you weren't listening. Jeff thought it would be really funny to kind of scam women that thought that they were being proposed to send them down to Maggiano's on Friday, only to find out it was a big joke and have them disappointed as they left.

[B]

I call that a hearty har har har moment.

[D]

Real knee slapper for all of us. So a whole bunch of women left, Maggiana's disappointed that they weren't being proposed to, and Jeff got a real good laugh out of it. And the rest of us on the show really thought it was in poor, poor taste. And we took tons of emails on it. And you guys were no help in solving the problem because 50% of you said, leave Jeff alone. He just exposed women that were desperate. And the other 50% of you said, I hate Jeff Dollar and always hate have hated Jeff Dollar. I'm gonna burn his house down. So it really didn't help at all.

[B]

Oh, by the way, I'd like to thank the people from WeHateJeff$com who sent me an email yesterday and said, what was the first part of it?

[D]

You mean the one that I read on the radio yesterday?

[B]

No, the one that I read to you and Tracy in our meeting.

[D]

Oh, the one that asked if you were pregnant or something.

[B]

It started out what it started out with. We think you're ugly and you stink. You should lose weight. Too fatty. Yeah, that's the whole email.

[D]

Oh, Cinda, come on. You don't gotta be honest.

[C]

I just love it that they registered the email address.

[B]

Yeah, I love we hate Jen Heller.

[D]

That should stand on its own.

[C]

But you don't have to.

[D]

Gentleman likes it. Cause she's got one.

[B]

Yeah, she's got. She just wants to hang out now because she's got ihategenhobby.com. no, it's can't standjenhobbyahoo.com. get it straight. I like that better.

[D]

Can't stand.

[B]

So hers is I can't stand Gen hobby. Mine's we hate. Why do I have plural?

[D]

So we debated it back and forth, and we took your emails, and by the time we get out of here on Friday, we were really kind of at. At Jeff's throats, I should say. And I mean, it was serious because even after the show, Jeff and I went back and we talked to the program director. And I was really, really pissed. I was really mad. I thought it was kind of a betrayal of trust.

[B]

And we have these offices here at.

[C]

All the hits Q100 that have, like, glass walls.

[B]

So even though somebody's behind the closed.

[C]

Doors of an office, you can see what's going on. And I happen to walk by the.

[B]

Program director's office, and Jeff and.

[C]

And the program director were standing on.

[B]

You know, standing up, and there was.

[D]

Definitely some shouting coming through that glass. I was like, oh, no.

[B]

I ran to Melissa's office.

[C]

I'm like, dude, they're down there in the other office. What's really going on?

[D]

And then my butt went numb. So it really wasn't purdy at all. The butt numbing part and the fight.

[C]

Cause when I get scared, my butt goes numb. I think it's from being a kid in anticipation of getting paddled.

[D]

So what I realized is that Jeff didn't understand how mean was to do to these women, because Jeff doesn't have the ability to empathize. He doesn't know what it's like to be burned like that, to be disappointed like that, whatever. He's never been burned, never been disappointed, especially when it comes to phone scam. So I'm thinking, all right, I need to teach him a lesson and empathy. But I was so. I was so angry, I couldn't come up with anything good.

[B]

I'm glad you called, Jessica, because I. If not, I would be getting a spanking today.

[D]

So.

[B]

Whooping.

[D]

What I did was I called Jeff's wife, Jessica, and I'm like, can you help me out with this? And she was more than eager to help out.

[B]

After all those years with Jeff, she's.

[C]

Like, finally, finally, my moment has come.

[D]

So while she was standing by her man and she was doing the unconditional love thing, there was part of her that really thought it was mean also. So I'm like, can you help me out here? What's Jeff's hot button? Because in working with Jeff, what we realized is he never gets too high, never gets too low. He's, like, right in the middle all the time.

[C]

He's very consistent in his mood.

[D]

He's very just like, you know, it's probably from lack of caring about anything. The man has no emotions. He has no heart.

[C]

So he just.

[B]

I'm just kidding.

[D]

I said earlier, he's like Spock. He's like a Klingon. He just Vulcan no emotion. Vulcan. Okay. Glad I don't know that. So I called Jessica up, and I'm like, jessica, can you give me a little help here? I really want to teach Jeff a little bit about empathy here. How can I phone scam this guy? And she laughs, and she's like, well, Jeff's got a couple of hot buttons, and one that was kind of random that she brought up was Jeff can't stand being left on hold for any amount of time. A second feels like an hour to Jeff.

[B]

I hate it. And that really is the only thing that will get me angry. Like, if it is a situation. Like if I'm calling you up, you know, and ordering something out of your catalog or whatever. If you put me on hold, you've got about 10 seconds. Like, if you put me on hold, it better be to reach across your desk and get a pen and then you're back. Because if I'm giving you business, I shouldn't be on hold. I hate call waiting. I hate. I won't be patient with call waiting. I hang up on people if, you know, they click over. I hate the fact that we only have call waiting because Jessica likes it. Like, I would love. I have no problem with no call waiting. Like, I just. I don't know why.

[E]

Pet feet.

[D]

Out of all the things to be angry about in the world, the only thing that sets Jeff off is being on hold. You know, that's his kryptonite right there.

[B]

Well, that and people with really thick accents that. That I can't understand. And I have to keep going.

[E]

Huh.

[D]

I couldn't find a friend to fake an accent like that. Sorry. So I'm like, well, Jessica, that sounds all right, but I don't know. That's enough for a phone scam. Is there anything else? Well, Jeff, for Christmas, gave his parents a family cruise that he's gonna be taking with his folks starting next week. And they're going all throughout the Caribbean for, like, 10 days. And Jeff has been, like, a crazy detailed person about this vacation. Wants to make sure it's really special for his par.

[B]

I got a three ring binder. Seriously, that has, like, copies of all of our tickets. It's got the paperwork, it's got, you know, all the, like, anything that we could need, even to the point where, like, we have duplicate copies of our birth certificates. I mean, nothing can go wrong. And I think it's just because I decided I gave this as my parents for Christmas. I bought it in, like, October, so I've had, like, six months to plan it. So you know, that's done by like October 10th. Then you look for something else do. Hey, what if we all get birth certificate duplicates in case something happens, in case somebody breaks into the ship in Barbados and takes our birth certificate?

[D]

And his parents are from upstate New York in this small little town, Nedro. And they're just very simple people. So this is going to be like a kid going to Disney World. So the combination of those two things, and I'm thinking, okay, we've got something here now. We've got something here. So I call a friend that's in radio up in Washington, D.C. and she calls Jeff on Friday. Now, would it be smart for me to tell how long this entire conversation lasted up front or should we wait till the end of the conversation?

[B]

We'll tell them at the end. But I will tell you that you're going to hear me put on hold here several times during the conversation. And I would say probably the shortest amount of time that she left me on hold was five minutes. And at one time she left me on hold for a full half hour. Hi, it's Jeff.

[C]

Hi, Jeff. This is Julie with Semiology Orange.

[B]

Hi, Julie. How are you?

[C]

I'm good. How are you?

[B]

I'm well, thank you.

[C]

I'm just checking on the cruise you're taking. The depart date is February 22nd.

[B]

Yes.

[C]

I'm just confirming that you're still going on that cruise as well as your parents, another couple?

[B]

Yes, that's correct. Why would you be confirming?

[C]

I'm checking to see about your deposit here.

[B]

I don't think I understand.

[C]

Well, can I put you on hold for a minute?

[B]

Sure.

[C]

Okay, one sec. Hi, I'm Beck. You still there?

[B]

I am.

[C]

So you are still planning on taking the cruise?

[B]

Yes.

[C]

You did put a deposit down?

[B]

Yes, I mean, I put more than a deposit down. The whole cruise is paid for in full, huh?

[C]

It's not paid in full. I can't seem to find it. Paid in full. Well, can you hold on for another minute?

[B]

Sure.

[C]

Hi. Okay, I'm back. You still there?

[B]

Yeah. I have a confirmation number.

[C]

Why don't you give me that confirmation number?

[B]

Well, is there a way that this could. We could do where I could give you whatever and then you could call me back because we've been on the phone, We've been talking for a total of three minutes. I've been on hold for 20 something.

[C]

I really only see a deposit and there's two cabins and they really need to pay.

[B]

The confirmation number is 2. It is paid in full. First of all but the confirmation number.

[C]

Okay, hold on one more minute. Thank you.

[B]

Yep.

[C]

Okay, I'm back. And who did you book this through?

[B]

Okay, just so you know, you're aware that during this entire conversation I've been on hold over 45 minutes?

[C]

Um, yes.

[B]

Okay, I booked it through. Susan.

[C]

Susan. Hold on, let me see if I can find her.

[B]

I don't want to.

[C]

Hold on one second. Did you say Susan?

[B]

Do you have any idea how long you're leaving me on hold for?

[C]

No, I'm really, you know, I'm real sorry. We're having some problems with our, you know, our database here, and I'm really trying to help you out. You know, Susan's. She's on vacation until March. Is there anyone else you spoke to?

[B]

I spoke with Heather in her office.

[C]

Heather? Let me see if I can find her. Hold on one minute.

[B]

It's the same exact extension.

[C]

Okay.

[B]

It took you 10 minutes. I'm sorry.

[C]

Look, I really want to help you out here. And the crew seems to be sold out, but there's two cabins left. So what I'm thinking is maybe the deposit that you put on we could now put towards the two cabins that are left and you can buy those two cabins and then if we find your other reservation, we can cancel that and use the new ones that you're.

[B]

So you want me to buy two additional cabins?

[C]

I think you're going to have to, Jeffrey, because I can't seem to find.

[B]

I have paperwork. I have emails and stuff back and forth. It's done and it's paid for. I have a credit card receipt.

[C]

You know, let me see what I can do. I'm going to put you on hold, but just stay there because our phones are acting a little bit weird and I don't know if I can call you back. Hold on.

[B]

Wait, what do you mean you don't know if you can call me back? Hello?

[C]

Hi, Jeffrey, I'm back. What I'm thinking is I can't find anything on the database that has anything paid in full. All I can find is a deposit. So I really suggest that you buy these two other cabins so that you have two cabins. Unless you want to go on a different date. Can you.

[B]

How can I go on a different. I've got airfare. My parents are flying in from freaking New York.

[C]

Can you hold on?

[B]

We've got hotel in Puerto Rico. I don't want to hold anymore.

[C]

There's one more place I can hold. Just be patient with me. Hold one more minute.

[B]

What?

[C]

Okay, I can't Find you.

[B]

Just for your record, you said you ended that with hold one more minute.

[C]

Yeah.

[B]

That was 21 minutes.

[C]

Look, I'm really sorry, but I'm trying to help you out here. I really don't. You know, I'm trying to. I'm going overboard to help you out here.

[B]

First of, how are you helping me out?

[C]

Well, I'm helping you out by trying to get you on a cruise, and.

[B]

You'Re helping me out. I've been on hold for two hours, and we're no further than we were when you first called.

[C]

Well, that's really not my fault. I'm doing the best I can. I'm searching for you, say you paid in full. I don't have any record of that.

[B]

Listen to me. What happens if I buy these two cabins and then you find my other ones? I bring the paperwork with me. I fax it to you. I do whatever I have to do.

[C]

Of course we would refund your money.

[B]

So are these the same category of the ones that I had before?

[C]

What's the category that you had?

[B]

Balcony, upper deck.

[C]

No, the cabins that are available now are not ba. They are cabins on the inside, on the lower deck, and they're not close to each other.

[B]

And these are the last two cabins you have on the whole freaking ship.

[C]

Yes, they are.

[B]

Oh, my God.

[C]

So would you like to give me the credit card information for these two other cabins?

[B]

I'm gonna. Can you hold on a minute?

[C]

Because I can hold on, but I can only hold on for two minutes because I'm gonna lose the extension.

[B]

Okay, you can? All right. Ma', am, are you there?

[C]

Yes, I am. You know, you really can't put me on hold for that long. I don't have time.

[B]

You've gotta be kidding me.

[C]

No, I mean, I have an office full of business to do here, and I'm really. I'm really trying to help you out.

[B]

I can't hold for two hours with you.

[C]

I'm really sorry, but I just. You can't put me on hold like that. What am I. What am I gonna do? I'm at a job.

[B]

All right.

[C]

Would you like to take these?

[B]

Yes, we're gonna take the other cabins. Okay? And I'm gonna need a fax number because I'm faxing you this paperwork. My wife has the credit card statement. Everything is paid for.

[C]

Well, why don't you.

[B]

And I also want to be compensated for these two hours.

[C]

Oh, you know what? My cell is ringing. Can you just hold on one second?

[B]

Are you taking a personal call?

[D]

No, no, no.

[C]

It's not personal. One second, please.

[B]

Please. You've gotta be kidding me.

[C]

Hi. Are you kidding? Come on. How many times have we spent weekends with your parents?

[B]

Hello?

[C]

I don't understand you.

[D]

Holy.

[C]

I can spend one brunch with my mother.

[B]

Hello?

[C]

Yes, hello.

[B]

Can we take care of this? I've been on hold for two hours.

[C]

I need your visa information.

[B]

Right. For the last two cabins.

[C]

Oh, my God. Jeffrey, those two cabins were just sold right out from under me.

[B]

They weren't. They were sold while you were arguing with your husband or whoever it was.

[C]

That's impossible.

[B]

You just said they were sold within the past minute.

[C]

Oh. Oh, goodness. Oh, my God. What are we gonna do here?

[E]

We're gonna.

[B]

You know what? Let me talk to someone else, okay?

[C]

Let me put you on hold and see what I can do.

[D]

No.

[B]

No. Hello?

[A]

Holy. Hi.

[D]

Can I help you, please?

[B]

Can I have your name, please?

[D]

Yeah, my name's Burt.

[B]

God. We will. We will scam you. The Burt Show.

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Zoe, this thing weighs a ton.

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[B]

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[D]

Santa, did you get my let.

[B]

Talking to you britches?

[C]

I'm not that.

[A]

Of course he did. Right, Santa?

[B]

You know my elf, Drew here, he.

[D]

Handles the nice list.

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[E]

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