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)

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.

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.

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

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.

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.