The Bert Show (Pionaire Podcasting)

Episode: Vault: Jeff's Unhooking Bra Race
Date: December 10, 2025

Episode Overview

In this lively and nostalgic episode, the cast of The Bert Show recreates a humorous rite of passage: the challenge men face unhooking a bra, as inspired by scenes from classic 80s teen movies. With plenty of banter, confessions, and competitive spirit, the cast organizes a hands-on race—literally—to see who among them can unhook a bra the fastest, with hilarious results and plenty of playful ribbing. The show leans into awkward adolescent memories, team rivalries, and a behind-the-scenes look at their own brand of humor and camaraderie.

Key Discussion Points & Highlights

1. Setting Up the Challenge

(01:33 – 04:30)

• Nostalgia Trigger: Jen brings up how 80s movies often dramatize the awkwardness of unhooking a bra, prompting memories of adolescent pressure for guys (“Is there any more pressure for a guy than unhooking a bra?” — Jen, 03:52).
• Team Formation: The cast splits into teams: Bert & Tracy, Crash & Melissa, and Jen & Jeff.
• Anticipation & Anxiety:
  • Crash jokes about the “sexual tension” and “anxiety” of the challenge, setting a light, competitive tone.
  • Tracy and Melissa poke fun at the situation, teasing Crash for his supposed enthusiasm and experience.

2. Rules, Rivalries, and Logistics

(04:31 – 09:00)

• The Rules: The challenge must be completed using only one hand, echoing the constraints of teenage make-out sessions.
  • “I think it should be a one-handed thing, because when you were making out back in the day…” — Crash, 05:33
• Authenticity Concerns: There’s joking about which bra clasps count (“There are some bras… women with smaller breasts have less clasps than women with larger breasts, correct?” — Crash, 07:28).
• Good Sportsmanship: Despite the tease, everyone gets on board and recognizes the whole thing is for bragging rights.

3. The Unhooking Bra Race

(09:00 – 10:45)

• The Countdown: Jen orchestrates the countdown to begin the “race.” The room is thick with silly anticipation (“Is anybody else feeling the seventh-grade tension…?” — Jen, 10:01).
• The Results: Jeff surprises everyone by finishing first, despite earlier nervousness.
  • “Jeff’s done.” — Jen, 10:27
  • “I can’t tell you how awkward that was. I couldn’t get anywhere near it. I wasn’t even close.” — Crash, 10:30
• Debrief: Teammates high-five and share laughs over the outcome, with Crash lamenting his poor performance (“I didn’t even get one unclassed.” — Crash, 10:49).

4. Technique Breakdown and Show Banter

(10:46 – 12:24)

• Technique Talk: Jeff explains his two-finger snap method for unlatching bras, making it sound almost like an urban legend.
  • “You take your thumb and finger, put them in between, you snap your fingers and that moves them both at the same time. That’s exactly the technique I did...” — Jeff, 11:23
• Banter on Awkward Moments:
  • Remembering movies where the guy can’t figure out a front-clasp bra (“…you’re searching, you’re rubbing the back, you’re looking for the clasp, and then the girl, it’s in the front.” — Jen, 12:04)
  • Tracy jokes about letting guys “sweat a little bit” before revealing the trick.

5. Listener Call-In: Expert Tips

(12:24 – 13:32)

• Jeremiah’s Call: A listener, Jeremiah, calls in to walk the crew through proper bra-unhooking technique step by step, playfully coaching the group on air.
  • “Take your left hand and put it around her back and stick your index finger between the bra strap and her back… you snap it right open.” — Jeremiah, 12:45

6. Wrap-Up and Aftermath

(13:32 – 14:06)

• Praise and Laughter: The group congratulates Jeff for his deftness and jokes about rotating positions for another round, staying in typical Bert Show comedic flow.

Notable Quotes & Memorable Moments

• Jen (on the pressure of the moment):
  “Is there any more pressure for a guy than unhooking a bra?” (03:52)

• Crash (on competitive nerves):
  “I just now got all sorts of anxiety.” (03:57)

• Tracy (on Crash’s supposed experience):
  “Office mates in Crash have been trying to get my bra off for years, so he’s gonna be speedy on this.” (04:33)

• Crash (post-race, humbled):
  “I couldn’t get anywhere near it. I wasn’t even close.” (10:30)

• Melissa (evaluating Jeff’s skills):
  “He was actually really good at it, you guys.” (10:47)

• Jeff (explaining his method):
  “You take your thumb and finger… you snap your fingers and that moves them both at the same time.” (11:23)

• Jen (on the classic movie blunders):
  “You’re searching, you’re rubbing the back, you’re looking for the clasp, and then the girl, it’s in the front.” (12:04)

Timestamps for Main Segments

• 01:33-04:30: Setup and nostalgia—how the challenge idea came up
• 04:31-09:00: Teams, rules, and competitive banter
• 09:00-10:45: The live unhooking bra race and outcomes
• 10:46-12:24: Technique talk and pop culture recollections
• 12:24-13:32: Listener (Jeremiah) calls with expert tips
• 13:32-14:06: Aftermath and closing laughter

Tone & Style

The episode is infused with the Bert Show’s signature mix of authenticity, playful teasing, and frank reminiscence, punctuated by moments of absurdity and warmth. The cast keeps the tone light and inclusive, poking fun at themselves and their own adolescent awkwardness. The topic, while slightly risqué, is handled with humor and camaraderie, making it a memorable (and replay-worthy) bit for fans.

For listeners who missed it:
This episode is a throwback to hilarious teenage mishaps, packed with competitive antics and offbeat wisdom about that classic movie trope—the struggle of unhooking “the bra.” Through their candid conversation and in-studio race, The Bert Show cast delivers both laughs and a reminder of life’s most human, awkward, and universal moments.