The Bert Show – "Vault: Jeff's Pot Of Questions"

Date: December 9, 2025
Host: Pionaire Podcasting
Episode Theme:
A laugh-filled, candid deep dive into the infamous “Pot of Questions”—the tradition where The Bert Show cast anonymously pulls tough, squirm-inducing questions aimed at each other, promising real, unfiltered answers.
Cast Members Appearing: Bert, Jeff, Jen, Melissa, Crash

Episode Overview

In this episode, the cast revives the "Let’s Be Honest" segment featuring Jeff’s terracotta “Pot of Questions.” The purpose: challenge each other with semi-anonymous, awkward, and often hilarious personal questions—none of which are off-limits. The hosts agree to answer honestly, making for unscripted, revealing, and sometimes uproarious moments.

Key Discussion Points & Insights

1. The Pot of Questions Returns

• [00:00–00:16] The show kicks off with Bert (A) explaining the premise:

  “We all come in here with questions for each other, but they're anonymous and they're pretty. I mean, they're. They're questions that are basically designed to make you squirm. Alright, so Jeff has a whole pot full of questions.”

• Jeff (B) comically describes the object:

  “It's a terracotta pot... with Q100 painted on it.” [00:16]

2. The Rules and Their Past Experience

• [00:21–00:40] The group reminds listeners of honesty being the only rule—they note prior sessions got “really hard and hurt people around us,” so the segment was previously retired, but is now back.
• The air is tense as they anticipate the questions, with a lot of nervous laughter.

3. Question One: The Re-Do on Virginity

• [00:43–01:39]
  • The first question pulled by Jeff (for himself): “If you could have lost your virginity to someone you have met since, who would it be and why?” [00:56]
  • Jeff deadpans his answer:

    “Jessica Simpson.” [01:08]

  • When asked why, Jeff is blunt:

    “Because she looks like Jessica Simpson.” [01:32]

  • Group jokes about the celebrity loophole:
    • Bert: “Does it say they don't?” [01:12]
    • “Don’t have to say anything more as far as I’m concerned. There you go.” [01:35]
  • Notable for how the answer stays unfiltered, with everyone clearly enjoying the silly honesty of the segment.

4. Question Two: Presidential Running Mate

• [01:44–03:34]
  • The next question is aimed at Bert:

    “It’s an election year and you are running for president. Which member of the show do you choose as your running mate and why?” [01:50]

  • Bert ticks off reasons against picking each cast member:
    • Melissa: “I can’t have Melissa because 3/4 of the country wouldn’t allow a gay vice president.” [02:04]
      (“Melissa, I love you, but I can’t. I’m not that progressive yet, and I really want the presidency.”)
    • Jen: “You can't go with Jen because of the Howard Dean incident. I think she's prone to outbursts.” [02:17]
    • Crash: “I couldn't pick Crash because... Crash has something in his past that would ruin our candidacy. Or he'd be drunk at a debate.” [02:24-02:34]
    • Jeff: “I'd always feel like there was some kind of phone scam around the corner or some manipulation going on that was gonna make me look like an ass on national television.” [02:36]
  • After all the banter, Bert’s pick:

    “I’d go with Jen Hobby then, I think, as my vice president.” [03:02]

  • Jen immediately warns:

    “But as soon as they dig up my past, you're screwed.” [03:03]

  • Bert, joking about vetting:

    “You are screwed.” [03:07]

  • There’s suggestion that even innocent-seeming producer Tracy might have skeletons—group pokes fun about how everyone could have their campaign derailed.

5. Rapid Fire Question for Crash

• [03:36–03:48]
  • The pot delivers a classic zinger for Crash, but the group momentarily hesitates, with Jeff riffing:

    “No, I’m not drunk right now. Next story. Let’s be honest, okay?”

  • This bit underscores the group’s comfort ribbing each other, and the quick wit on display in these unscripted moments.

Notable Quotes & Memorable Moments

On the Pot of Questions Itself

• Jeff (deadpan):

  “It's a terracotta pot... with Q100 painted on it.” [00:16]

On Celebrity Crushes

• Jeff, on why he'd choose Jessica Simpson:

  “Because she looks like Jessica Simpson.” [01:32]

Presidential Picks and Campaign Baggage

• Bert (rationalizing his vice-presidential choice):

  “It’s the innocent ones you gotta watch out for, you know? And then it’s not her background I’m worried about. You have to take a look at your spouse’s and girlfriend’s and boyfriend’s background, too. And I know that Scott guy’s into some weird crap.” [03:14–03:22]

Crash’s Wild Card Reputation

• Group riffing on Crash’s “debate buzz”:

  “Or he would be drunk at a debate.” [02:34]
  “Right, the debate buzz.” [02:34]

Timestamps for Important Segments

• [00:00–00:16] – Introduction to the Pot of Questions
• [00:43–01:39] – Jeff’s question: Lost virginity “re-do”
• [01:44–03:34] – Bert’s running mate dilemma and cast roast
• [03:36–03:48] – Brief “Crash is not drunk (right now)” quip

Episode Tone & Style

The cast maintains a playful, irreverent, and authentic tone throughout. Their ribbing is good-natured but real, reminding listeners why this segment was both loved and feared. The pace is quick, the energy high, and the camaraderie palpable.

Summary

“Vault: Jeff’s Pot Of Questions” delivers classic Bert Show laughs and brutal honesty, as each host faces tongue-in-cheek, boundary-pushing questions. From re-writing their first time to vetting their podcast “cabinet” for hidden scandals, the episode serves as both a comedic therapy session and a showcase of the hosts’ chemistry, quick wit, and authenticity.

For listeners new and old, this episode is a perfect encapsulation of the group’s willingness to poke fun at themselves and each other—all while keeping the laughs (and squirming) coming.