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.)
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.
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.”
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]
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 |
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.