The Bert Show – “Vault: Bert Show's Big Secrets”

Date: November 18, 2025
Cast: Bert, Kristin, Abby, Cassie, Tommy & The Bert Show Cast
Host: Pionaire Podcasting

Episode Overview

In this “vault” episode, The Bert Show team pulls back the curtain on their personal lives by anonymously sharing some of their biggest secrets. The cast challenges themselves to be vulnerable and honest, all while having fun guessing (and overanalyzing) which juicy confession belongs to whom. The segment is lighthearted yet candid, providing listeners with surprising insights and plenty of laughs—underscored by the humor, camaraderie, and honesty that define the show.

Key Discussion Points & Insights

1. How Well Do We Know Each Other?

• [01:18 – 03:05]

  • The group reflects on how much time they spend together—sometimes more than with their own families.
  • They compare their closeness to a family or even a married couple.
  • The idea arises: “Would our significant others know these answers better than we do?”
  • Leads into the central game: anonymously sharing secrets.

  “I spend more time with you people for sure than I do my own family every day.” – A [01:26]

2. The Bert Show’s Big Secret Game

• [03:05 – 13:29]
  • Each cast member brings in an undisclosed, typed secret, placed in a bag to preserve anonymity.
  • The secrets are read aloud, and the group reacts—sometimes guessing, sometimes simply marveling (or cringing!).

Notable Secrets Shared & Group Reactions

• “I helped my roommate’s ex get my roommate in trouble. The ex was cheated on, so I gave the ex keys to my roommate’s car, and they hid drugs in the ashtray and trunk. They called campus security to report it, and my roommate was arrested.”
  • [04:05]
  • Group is stunned, calls it “brilliant” but also “crappy”.
  • Sparks debate on ethics versus effectiveness.
  • Later referenced as “classic” by a listener caller.

“If I were the rest of you guys on the show, I would be scared that I’m gonna do this to one of you guys in an upcoming month. That’s really awesome.” – A [04:41]

• “I’m a fraud. I am not as confident and happy as I portray myself to be.”

  • [05:28]
  • Immediate joking guess: “It’s Melissa. You’re right. Charlie Brown over here.” – E [05:56]
  • Team pokes fun but acknowledges the truth many feel at times.

• “I think one of my friends would be better off divorced.”

  • [06:19]
  • Universally relatable sentiment—several say it “could have been” theirs.

• “I once had a collection that consisted of the underwear of everybody I slept with.”

  • [06:44]
  • Group finds it hilarious and very much in the “guy” tradition, but speculation ensues.

• “When I was 13 I took $100 from my grandmother’s Christmas card from my aunt and uncle.”

  • [07:33]
  • Group reacts with laughter and commiserating stories.

• “My best friend and I slept with the same person.”

  • [08:14]
  • Prompts jokes about clarification ("at the same time?"), curiosity, and intrigue.

• “I am attracted to somebody I work with.”

  • [08:48]
  • Group notes it wasn’t specific and could reference anyone at the office.
  • Series of jokes follows about who it might be (including real and fictional baseball players).

• “My friend had an affair, and I liked who they were having the affair with more than their spouse.”

  • [12:05]
  • Team laughs, recognizing the complicated loyalty lines of friendship.

Game Dynamics

• Although there's a temptation to guess the submitter, most secrets are left anonymous (per the rules).
• Some secrets are fodder for ongoing jokes and playful side conversations.
• One caller argues someone should fess up to the “best” secrets, especially the car/drug plot, for "employee of the month" status.

  “If you hear this happening to Steve McCoy over the next couple of months, you’ll know one of us is behind it for sure.” – A [13:14]

Notable Quotes & Memorable Moments

• “It’s like watching a magician. You can’t enjoy the trick. You gotta know how it’s done.” – A [03:53]
• “If I were the rest of you guys on the show, I would be scared that I’m gonna do this to one of you guys in an upcoming month.” – A [04:41]
• “I once had a collection that consisted of the underwear of everybody I slept with.” – Secret [06:44]
• “My best friend and I slept with the same person.” – Secret [08:14]
• “You think it’s like watching… That’s the type of people we are.” – E [03:50]
• “It’s funny how you become, like, almost like an interrogation expert. Like, I’m looking in the eyes to see which lie. I’m seeing right through you.” – A [12:18]

Funny Sidebars & “Small Guy” Banter

• [09:18 – 11:17]
  Extended joking about baseball players with “small” stature, including:
  • “I’ve got a crush on that little Weiss fellow. He’s just so cute, that little guy.” – E [10:09]
  • Naming “Little Marcus” and riffing on calling people "little."
  • It ends with a funny but borderline inappropriate discussion distinguishing "midget" from "dwarf" (“can wipe their own ass or not”) [11:27 – 11:42]—which the group instantly recognizes as classic, if uncomfortable, Bert Show humor.

Listener Involvement

• Caller Ryan jumps in [12:31] demanding someone own up to the most shocking confession.
• The team stands firm on the rules: “We will just keep our secrets, our secret.” – A [13:29]

Segment Timestamps

• How well do we know each other? – [01:18 – 03:05]
• Game intro & setup – [03:05 – 04:05]
• Secret: Roommate & Drugs – [04:05 – 04:37]
• Secret: I’m not as confident as I pretend – [05:28 – 06:10]
• Secret: Think my friend should be divorced – [06:19 – 06:44]
• Secret: Underwear collection – [06:44 – 07:13]
• Secret: Took money as a kid – [07:33 – 08:07]
• Secret: Slept with same person as friend – [08:14 – 08:48]
• Secret: Attracted to coworker – [08:48 – 09:03]
• Baseball banter & ‘small guy‘ jokes – [09:18 – 11:17]
• Secret: Liked affair partner more than the spouse – [12:05 – 12:14]
• Caller tries to get confessions – [12:31 – 13:29]

Tone & Takeaway

The episode is classic Bert Show—humorous, real, and just a bit edgy. The “secret” game doubles as a celebration of trust and vulnerability among castmates, while the anonymity ensures no one is truly exposed (even as listeners and cast both itch to crack the mystery). Longtime fans will enjoy the mix of genuine confessions, playful ribbing, and random tangents—while newcomers get a revealing peek at the personalities behind the microphones.

Tagline:
Even the people you think you know best can still surprise you—especially on The Bert Show.