The Bert Show: Vault — "Let's Be Honest"
Date: December 10, 2025
Podcast by: Pionaire Podcasting
Episode Overview
This episode revisits the show's popular, occasionally infamous "Let's Be Honest" segment, where co-hosts anonymously submit and answer deeply personal, sometimes squirm-inducing questions. The tradition of bare-all honesty, with a comedic and authentic twist, delivers both laughs and genuine moments as each cast member faces questions aimed at vulnerability, truth, and a bit of embarrassment.
Key Discussion Points & Insights
1. The "Let's Be Honest" Pot Returns
[01:20 – 01:47]
- Jeff introduces the format: a "terracotta pot" filled with anonymous, personal questions—meant to make the team squirm.
- “They're questions that are basically designed to make you squirm.” — Jeff [01:20]
- The crew recalls how tough the last session was, which led to some fallout, but they're giving it another go.
2. Who Would You Have Lost Your Virginity To?
[02:13 – 02:59]
- Crash’s question: If you could have lost your virginity to someone you've since met, who would it be and why?
- Crash answers: “Jessica Simpson.”
- Jen clarifies if celebrities count; Crash argues the question doesn't exclude them.
- Jeff and others joke about the “easy question,” and Crash simply replies:
- “Because she looks like Jessica Simpson.” — Crash [02:53]
- The group jokes about who would have answered differently and riffs about dodging trouble.
3. Choosing Your Vice President—Bert’s Presidential Pick
[03:11 – 04:24]
- If running for President, which co-host would you choose as your running mate—and why?
- Jeff methodically eliminates each person for humorous, mock-political reasons:
- “I can't have Melissa because three fourths of the country wouldn't allow a gay vice president.” — Jeff [03:24]
- “I couldn't pick Crash because inevitably, you know, Crash has something in his past that would come out and ruin our candidacy. Or he'd be drunk at a debate.” — Jeff [03:45, 03:53]
- “Buzz ... there’s always some kind of phone scam around the corner.” — Jeff [03:56]
- Picks Jen Hobby as the most politically correct.
- “I'd go with Jen Hobby then, I think as my vice president.” — Jeff [04:21]
- Jen retorts about her own “past”: “As soon as they dig up my past, you're screwed.” [04:24]
4. If You Had to Sleep With Someone’s Significant Other
[05:09 – 05:36]
- Crash faces: “If you had to sleep with the significant other of someone on the Bert Show, who would you choose and why?”
- Ryan quips: “It would be Ryan. I've always wanted to do a rock star, baby.” [05:23]
- Crash admits: “I'd do Stacy. She's too cute, she's little... There's just something about Stacy... ultra cute and sexy.” — Crash [05:36]
5. The Impact of Breakup — Melissa’s Honest Take
[06:46 – 08:59]
- Melissa is asked: If someone retold the story of her breakup with “not Lisa” in full detail, who was more at fault? “Equal” is not allowed.
- After some hesitation and group banter, Melissa answers:
- “I'd say me. Because ... after the illness, I'm the one that totally changed my vibe ... I had a new lease on life ... and not Lisa didn't have that. So I would put the blame on me, because I'm the one that initiated the change.” — Melissa [08:00]
- They talk candidly about the changes illness can bring to perspective and relationships.
- Jeff: “Your perspective is different after the illness.” [08:57]
- Melissa reflects on her healing and moving past the hurt.
6. Private Habits Confessed — Jen Hobby
[11:24 – 13:51]
- Jen faces: “What do you do in private you’d never do in front of us for fear of endless ridicule?”
- After quips about past “Am I Normal?” segments, Jen reveals:
- “I can seriously sit in the mirror for hours and analyze and reanalyze my eyebrows and every little hair on my face ... I have, like, man hairs ... and so I'm always checking ... to pluck the random man hairs that come out of my face.” — Jen Hobby [12:05]
- The group jokes about “face pubes” and “nipple snakes,” making light of the confession.
- “For future reference, that's called a face pube.” — Crash [13:15]
- “If you have them on your nipples, they're nipple snakes.” — Jen Hobby [13:20]
Notable Quotes & Memorable Moments
- On the purpose of honesty:
- "We will answer these questions honestly. And the last time we did this, it got really ugly because the questions were really hard and they made you squirm and they hurt people around us. So we swore it off and then decided to bring it back." — Jeff [01:47]
- Crash’s celebrity crush:
- "Jessica Simpson ... because she looks like Jessica Simpson." — Crash [02:53]
- Jeff’s diffusing candor about politics:
- "I can't have Melissa because three fourths of the country wouldn't allow a gay vice president." — Jeff [03:24]
- Honest, raw self-accountability:
- "I'd say me. ... after the illness ... I'm the only one that had that perspective of facing death and then coming out on the other side." — Melissa [08:00]
- Self-deprecating humor about unwanted facial hair:
- "I can sit in the mirror for hours and analyze ... man hairs that come up on my face." — Jen Hobby [12:05]
- “If you have them on your nipples, they're nipple snakes.” — Jen Hobby [13:20]
Important Timestamps
| Segment | Timestamp | |-----------------------------------------------|-------------| | The "Let's Be Honest" game starts | 01:20 | | Crash answers the virginity question | 02:15–02:59 | | Jeff discusses his vice president pick | 03:11–04:24 | | Sleeping with a co-worker’s significant other | 05:09–05:36 | | Melissa on her breakup with "not Lisa" | 06:46–08:59 | | Jen's secret grooming habits | 11:24–13:51 |
Episode Tone & Takeaway
With classic Bert Show wit, self-deprecation, and mutual ribbing, this episode exemplifies the balance of authenticity, vulnerability, and humor that has defined the show's reputation. The "Let's Be Honest" segment both exposes and bonds the team, while showing listeners that even morning radio hosts are as messy, awkward, and human as the rest of us.