Podcast Summary: The Bert Show — Vault: Gentle Hints

Episode Date: October 27, 2025
Hosts: Bert, Kristin, Abby, Cassie, Tommy & The Bert Show Cast
Featured Guest/Voice: Melissa, Jeff
Theme: Delivering Delicate News Anonymously (with Humor)

Episode Overview

This episode centers on the awkwardness—and comedy—of telling someone about an embarrassing personal issue without taking the blame. The cast explores "gentlehints.com," a website that sends anonymous alerts about issues like bad breath, and decides to handle a real-life scenario on air. In classic Bert Show style, they turn a cringeworthy social dilemma into a hilarious, unscripted on-air experiment.

Key Discussion Points & Insights

1. Introduction to GentleHints.com (00:01–00:19)

• Jeff introduces gentlehints.com, explaining: “What it'll do is it'll email somebody in your office that has really bad breath anonymously, so you don't take the rap for it.” (B, 00:01)
• Instead of paying for the service, the team decides Melissa will make the call live, putting the spotlight on both her skills and the public service angle.

2. Preparation & Nerves (00:20–01:18)

• Melissa asks for legal guidance on how to introduce herself, getting clear instruction:
  “The first thing you have to say is, 'Hey, it's Melissa from Q100. You're on the air.'” (D, 00:25)
• Playful banter as the team weighs who should make the call. “Cam, she's a rookie. We can't put her through that.” (A, 01:16)
• Melissa expresses her dread: “This is going to suck.” (C, 00:37)

3. The Prank Call – Delivering the “Gentle Hint” (01:29–03:46)

• Opening: Melissa calls Jeff, delivers legal disclaimer:
  “Hi, Jeff. It's Melissa from Q100. You're on the air right now. How are you today?” (C, 01:45)
• The Message: She smoothly transitions into the purpose:
  “We’ve had an anonymous caller... someone who cares about you and wanted to let you know about your chronic halitosis.” (C, 01:50)
• Confusion & Denial:
  Jeff recoils, “Chronic what?” (E, 02:01)
  Melissa clarifies: “Chronic halitosis. Bad breath.” (C, 02:02)
• Anonymous Source: Jeff repeatedly questions who submitted the complaint:
  “Who wanted you to call? ... It's a person I work with.” (E, 02:24 & 03:09)
  Melissa stays vague, reiterating: “It was an anonymous caller. ...I'm not sure. It was an anonymous call.” (C, 02:08 & 03:12)
• Offer of Goods: Melissa tries to soften the blow:
  “We're happy to send you any materials that would help out, if that's okay with you... toothbrush, toothpaste, mouthwash.” (C, 02:47)
• Jeff Reacts: Realization dawns, and he’s not having it:
  “The radio? ... What service is this? ... Oh, what? This is a... This is the radio, Q100? Oh, this is bull.” (E, 03:19-03:46)

Notable Quotes & Moments

• On the social challenge:
  “Rather than spend the 20 bucks on the website, we just have Melissa make the call for you.” (B, 00:01)
• Apprehension about the task:
  “This is going to suck.” (C, 00:37)
• Maintaining composure:
  “Don't forget, you gotta tell him that he's on the air first.” (A, 01:32)
• Jeff’s confusion escalates:
  “Chronic what?” (E, 02:01)
  “Who are you?” (E, 03:18)
  “Oh, this is bull.” (E, 03:46)

Timestamps for Important Segments

• 00:01 — Introduction to gentlehints.com and decision for a live call
• 00:37 — Melissa’s apprehension, prep, and legal guidance
• 01:29–03:46 — The call with Jeff: delivery, confusion, and conclusion

Flow and Tone

True to The Bert Show's playful, authentic style, the segment captures the discomfort and humor in addressing awkward topics. While poking fun at social etiquette, the hosts create an empathetic (if mischievous) space reminding everyone that we all have cringey moments—and laughter helps ease the sting.

For listeners, this episode delivers a masterclass in turning awkwardness into entertainment, and showcases The Bert Show’s trademark blend of real-life situations, empathy, and comedy.