The Bert Show (Pionaire Podcasting)

Full Show PT 3: Wednesday, December 10 [Vault]

Original Air Date: December 10, 2025

Episode Overview

This episode of The Bert Show serves up a blend of signature morning show mischief, spirited group games, personal confessions, and a deep-dive into a dramatic relationship dilemma submitted by a listener, all delivered in the cast’s trademark real, unfiltered, and humorous style. The cast—Bert, Kristin, Abby, Cassie, Tommy, and more—deliver both laughs and candid personal insights, creating a relatable, entertaining, and occasionally heartwarming escape for listeners.

Key Segments & Discussion Points

1. "The Bra Unhooking Showdown"

[01:36 – 13:32]

• Inspired by classic '80s movies, Jen pitches a playfully awkward contest: who among the show's men can unhook a bra the fastest, replicating the legendary pressures of youthful dating.

  • Teams are divided: Crash & Melissa, Jen & Jeff, with Mandy as the real sport, volunteering her back-clasp bra for the challenge.
  • The contest is filled with comedic banter, nostalgia, pokes at masculinity, and self-deprecation.

  Memorable Quotes:

  • “Like, is there any more pressure for a guy than unhooking a bra?” — Jen [03:52]
  • “I feel like I’m in seventh grade.” — Burt [05:46]
  • “I finally get to go up Melissa’s shirt. I’m not getting out fast.” — Jeff [06:01]
  • “It’s so awkward. I wasn’t even close.” — Melissa [10:30]

• Results:

  • Jeff demonstrates impressive skill, drawing both congratulations and friendly jabs.
  • Listeners and hosts swap stories and tips, blending education with embarrassment.

  Listener Tip:

  • On how to unhook a bra smoothly: “Take your index finger, pop it under the strap, then middle finger and thumb… and it pops right open.” — Listener Jeremiah [12:45]

2. "Let’s Be Honest"—Anonymous Question Pot

[16:06 – 28:42]

• The cast pulls anonymous, squirm-inducing questions from a "Let’s Be Honest" pot, promising unflinching honesty with their answers.

Highlights:

• If you could have lost your virginity to anyone you’ve since met, who would it be?
  Jen: “Jessica Simpson.” [17:14]

• Running Mate for President?
  Burt, evaluating his castmates’ skeletons and personalities, humorously weighs his options before choosing Jen Hobby:
  “I’d go with Jen Hobby as my Vice President. As soon as they dig up my past, you’re screwed!” [19:10]

• If you had to sleep with another cast member’s significant other, who?
  Crash jokes: “Ryan. I’ve always wanted to do a rock star,” but Jeff quickly chimes in with, “Stacy. She’s just ultra cute and sexy.” [20:13–20:28]

• Relationship Reflection:
  Questioned about past breakups, Crash admits the end of his relationship was “my fault,” citing how a near-death illness changed his life’s perspective and needs.
  “I would put the blame on me, because I’m the one that initiated the change in momentum in our relationship.” [23:27]

• Private Behavior Confession:
  When asked what private act she’d never do in front of the group, Jen admits:
  “I can sit in the mirror for hours and analyze and reanalyze my eyebrows and every little hair on my face… I have, like, man hairs that come up on my face. So I’m always checking.” [26:51]
  The cast riffs on “face pubes” and “nipple snakes,” ending the segment on a hilarious, self-deprecating note.

3. Listener Drama: The Super Bowl Ticket Ultimatum

[31:08 – 49:10]

Setup:

Listener Sarah’s coworker calls in about Sarah’s controversial plan to withhold her husband’s Super Bowl ticket in protest of his chronic failure to complete household projects.

The Situation:

• Sarah details a year and a half of marriage where her husband starts house projects (fixing a tile, cleaning, dishes) but never finishes them.

  • “He starts things and doesn’t finish them…he’ll put his dishes by the sink and just doesn’t wash them.” — Sarah [32:51]

• She sees withholding the ticket as a means to “teach him a lesson.”

  • “I’m just gonna give back to him exactly what he gives to me right now.” [35:57]

Feedback From Cast & Listeners:

• The cast is incredulous—Melissa warns, “You are gonna lose a great guy.” [34:30]

• Callers offer strong opinions:

  • Annette (long-married): “This is gonna stink in your marriage forever if you do this over projects.” [35:44]
  • Angela: “Matt is not your child. He is your husband.” [36:06]

• Sarah remains unmoved, supported only by her single/married girlfriends and argues, “It’s my relationship… I know better than anyone else how to work it.” [38:42]

The Twist:

• The cast reads an email from Sarah’s brother Kyle, revealing he found her hidden ticket, FedExed it to her husband, and her husband got to attend the game after all.

  • “Long story short…he got the ticket and went to the game.” — Kyle (email) [44:52]

• Sarah’s shock, denial, and fury at the (well-intentioned) family intervention is palpable:

  • “I’m so angry right now…to step into my personal space, into my house, without my knowing it. I’m beside myself.” — Sarah [46:33]

Aftermath:

• Callers reflect and poke fun:
  • “Sad Sack Sarah. That’s what we’re gonna call her.” — Shara [49:03]
  • “She better hold on to her man.” — Shara [49:03]

Notable Quotes & Moments

• Instant Nostalgia and Group Chemistry:
  “This is like a surreal moment on the Bert Show. This is weird. This is worse than the football kissing game.” — Burt [07:03]

• On Growing from Trauma:
  “After surgery…I was the only one who had that perspective of facing death and then coming out. At least it didn’t have that.” — Crash [23:29]

• On Relationship Overreach:
  “It’s not a business. Honey, you don’t run a marriage, that’s just like the wrong way to look at it. Your marriage is a partnership.” — Burt to Sarah [46:40]

Section Timestamps

| Segment | Start | End | |------------------------------|----------|----------| | Bra Unhooking Challenge | 01:36 | 13:32 | | "Let's Be Honest" Q&A | 16:06 | 28:42 | | Listener/Caller Drama | 31:08 | 49:10 |

Takeaways

• The Bert Show delivers big on authentic, raucous group dynamics and a willingness to go embarrassingly personal in the name of entertainment.
• The “bra off” bit, and the honest Q&A, showcase the cast’s comfort with each other and their knack for spinning relatable, awkward experiences into collectively funny moments.
• The listener drama strikes a more serious, sometimes contentious note—casting light on control issues, communication pitfalls, and boundaries in marriage, all while keeping the audience engaged with twists and real talk.
• Throughout, the episode lives up to its promise: blending genuine humor, listener interaction, and real-life messiness, delivered with warmth and wit.

Best for listeners who love:

• Real-life drama and open conversations
• Humor that’s a little awkward but always honest
• A vibrant group dynamic that invites you to laugh—and squirm—along