The Bert Show: Vault - We Answer The Questions Our Listeners Are DYING To Know

Podcast: The Bert Show
Host: Pionaire Podcasting
Episode Date: December 15, 2025

Episode Overview

This episode dives into a fan-favorite Bert Show segment: honest, unfiltered listener Q&A. Blending two formats—“Let’s Be Honest” (where cast members answer anonymously submitted, revealing questions) and “Ask Us Anything” (where listeners call in)—the Bert Show cast delivers spontaneous, candid, and often hilarious responses. The episode provides a behind-the-scenes peek at the personalities of Bert, Jen Hobby, Melissa Carter, Jeff, and callers, as they navigate personal revelations, embarrassing confessions, and the chemistry that defines morning radio.

Key Discussion Points and Insights

Setting the Stage

• Interactive Format: The team alternates between answering random, anonymously submitted questions from a "terracotta pot" (02:05) and listener call-ins. Nothing is off-limits—personal, professional, and borderline outrageous questions are welcome.
• Promise of Honesty: The cast commits to answering everything truthfully, regardless of discomfort, continuing the show’s tradition of candid, relatable entertainment (02:33).

Noteworthy Q&A Segments

1. Virginity—If You Could Do It Over

• Question: “If you could have lost your virginity to someone you’ve met since, who would it be?” (02:43)
• Jen Hobby’s Response:
  • Chooses “Pink,” the singer, noting she’s actually met her:

    “Oh, yeah. Pink.”
    — Jen Hobby (03:09)

  • Cast jokes about Pink’s personality:

    “She’d be rough.”
    — Melissa Carter (03:10)
    “Yeah, I like it like that. Do you?”
    — Bert (03:13)

• Discussion: Playful banter on celebrity crushes that are also real-life acquaintances.

2. Keeping Pictures of Exes

• Question: “Do you still have a picture of an ex? Who is it and where do you keep the photo?” (03:24)
• Jeff’s Response:
  • Has a photo with “Tina,” a college girlfriend, in the attic.
  • Wife Jessica found it, but Jeff insists, “That's the only one I know of.” (03:54)
  • Admits to having had topless photos of another girlfriend, but says they’re now gone (04:15).
• Jen jokes:

  “In his mind when he fantasizes.”
  — Jen Hobby (03:32)

• Honesty & Discomfort: The cast dives into the awkward repercussions of such discoveries in marriages.

3. Revisiting On-Air Conflict

• Listener Asks: About Bert and Jeff’s previous explosive on-air argument and if the anger was real (04:29).
• Jen Hobby’s Detailed Account:
  • Confirms Bert was furious and describes it as “the most uncomfortable moment in the studio off the air that I've ever experienced.” (04:52-05:03)
  • Vivid atmosphere:

    “You could cut the air with a knife. It scared me.”
    — Jen Hobby (05:03)

• Listener’s Perspective:

  “I felt like I was in a room with my parents fighting. …Are they getting divorced?”
  — Caller (05:35)

• Resolution: Melissa attributes the harshness to bad timing around Valentine’s Day (06:08).

4. Radio Names—Real or Stage?

• Listener Q: Do radio DJs use real names or pseudonyms? (06:24)
• Cast Explains:
  • Bert uses his real name; Jen Hobby opts for her maiden name for simplicity and familiarity.
  • Noted that name changes in radio are more old-school, often for anonymity or simplicity (06:45-07:59).

  • “If it's a really complicated name…for now if someone changes their name, it's just to make it easy on the ear for the listener.”
    — Melissa Carter (07:17)

  • “I started the show as Jen Hobby and it's easy to remember.”
    — Jen Hobby (08:01)

5. Private Oddities – At Home vs. On-Air

• Question for Bert: “What do you do in the privacy of your own home that you would never do in front of us for fear of eternal ridicule?” (08:14)
• Hilarious Confessions:
  • Bert openly discusses body grooming:

    “Yeah, I shave, sure. I trim…my twigs and berries.”
    — Bert (08:54)

  • The cast spirals into speculation about other odd behaviors (biting toenails, eating on the toilet, dancing with a hairbrush).

    “Do you dance around with a hairbrush to old time Rock and Roll? Do you put your stuff in between your legs, look like a woman?”
    — Jeff (09:09)

• Bert shrugs off embarrassment, noting:

  “There’s just not a lot that I don’t tell you guys about.” (09:21)

6. Would You Do It For Money?

• Question: For $2 million, would you “go below the border” (have a sex act) with another man? If not, what's your price? (10:14, 10:27)
• Cast Reactions:
  • Jeff: An immediate “No” unless on the receiving end, then with resignation, “Sure, sure” (10:45).
  • Jen Hobby: Admits she’d do it for enough money to secure her children’s and grandchildren’s future (“it’d have to be a lot of money, but hell yeah, it would have to be…” 11:23, 11:27).
  • Bert: Skeptical that anyone would never do it “for a trillion dollars.”
  • Jeff adds humor: “Four whole margaritas!”
    — Jeff, joking about Jen’s threshold (11:30)
• Memorable Analysis:

  “My friend Chris says any guy that answers no...is a liar because he thinks every guy has his price to do something like that.”
  — Bert (11:55)

7. Radio Callbacks and Sex Education

• Question: “If you were to call Sue Johansson (sex educator), what would you ask?” (12:28)
• Cast Suggestive: Jen proposes “Let’s ask her about the back door” before the segment ends (12:53).

Notable Quotes & Memorable Moments

• On On-Air Tension:

  “You could cut the air with a knife. It scared me.”
  — Jen Hobby (05:03)

• On Honesty:

  “There’s just not a lot that I don’t tell you guys about. There’s not a lot that really embarrasses me.”
  — Bert (09:21)

• On Money and Morals:

  “Any guy that answers no...there’s no amount of money...is a liar because he thinks every guy has his price.”
  — Bert (11:55)

• Cast's Banter:

  “My slappin tickles.”
  — Jeff (09:01)
  “Oh, she met Pink.”
  — Jeff (03:07)

Timestamps for Key Segments

• [02:05] Starting Q&A and setting ground rules
• [02:43] First risqué question: who you’d pick to lose your virginity to
• [03:24] Pictures of exes—who still has them and where
• [04:29] Listener calls out on-air conflict; cast recounts explosive aftermath
• [06:24] Do radio personalities use their real names?
• [08:14] Private weird habits at home vs. what’s shared on-air
• [10:14] For $2 million, would you do it? Hilarious debate about money and sexual boundaries
• [12:28] What would you ask sex educator Sue Johansson?

Episode Tone & Takeaways

The Bert Show once again proves why it’s a staple in morning entertainment: totally authentic, slightly outrageous, always entertaining. The cast’s willingness to answer anything honestly results in a lively episode packed with laughter, confessions, and “did they really just say that?” moments. Their chemistry and sense of humor shine, making the episode a prime example of why listeners feel like part of the family.

If you missed it: Expect comedy, some blush-inducing honesty, and an entertaining “nothing is off-limits” energy throughout.