The Bert Show – Full Show PT 1: Friday, December 5, 2025

Podcast: The Bert Show
Host: Pionaire Podcasting
Episode Date: December 5, 2025

Episode Overview

This episode brings the signature, unfiltered humor and authenticity of The Bert Show as the crew wraps up a "little black book" relationship experiment that had captured listeners all week. Show regulars (Bert, Kristin, Abby, Cassie, Tommy, and others) revisit an outrageous saga involving a girlfriend, her boyfriend, and several of his ex-girlfriends—most notably a particularly persistent and opinionated ex named Stacy. After untangling this relational love triangle, the hosts veer into a lively debate on bar etiquette: is a woman obligated to talk to a guy who buys her a drink? The episode is chock-full of memorable lines, unscripted drama, and classic Bert Show banter.

Key Segments & Discussions

1. Little Black Book Finale: Jessica, Kevin, and the Exes

Timestamps: 01:57–16:31

Background

• Jessica, wanting to know her boyfriend Kevin better, spent the week talking to one of his ex-girlfriends each day.
• “Psycho Stacy,” an ex from three years prior, became a recurring (and uninvited) presence, continuing to contact Jessica and the show even after her initial scheduled appearance.

Email Feedback & Recap

• Jen reads an email (02:05):
  “You guys took America's most boring couple and turned it into a week long succession of bits. Congratulations, you guys are really talented. Thank God for Psycho Stacy.”
  — Listener Email

Key Moments & Quotes

• Jessica’s Recap (03:37–04:22):

  • Jessica clarifies that Stacy exaggerated the length of her call with Kevin.
  • “He was basically just trying to politely get off the phone with her.” — Jessica [04:12]

• Kevin’s Feelings (04:25–06:54):

  • Kevin reveals it felt “kind of creepy” to hear his personal life on the radio, emphasizing his preference for privacy.
  • “It was just weird for me to hear my own, you know, personal life just on the radio… It’s just kind of like Twilight Zoning or something.” — Kevin [06:23]
  • He objects to an ex (Annie) bringing up his mother's feelings, calling it “lame.”

• Relationship Dynamics & Sex Talk (08:15–09:56):

  • Discussion arises on the perceived lack of excitement in Jessica and Kevin’s relationship.
  • Jessica broaches the topic of Kevin’s “Playboy collection,” likening it to “practicing your golf swing the wrong way” [09:30].

• Stacy Crashes the Party (10:13–16:29):

  • Stacy calls in to contradict Kevin about the phone call length:
    “It was not a 10 minute conversation on Thursday. It was a 30 minute conversation. I don’t know why Kevin’s saying it was only 10.” — Stacy [10:29]
  • The exchange devolves into accusations, with Kevin calling Stacy “some sort of a weird psycho girl who at 19, was frigged up in the head and I made a big mistake…” [13:25]
  • Stacy defends her ongoing relationship with Kevin’s mother:
    “Just because you break up with someone doesn’t mean you break up with their family. Okay?” — Stacy [14:22]
  • Stacy gets emotional at the end, feeling she’s been treated unfairly and “very meanly.” She insists she was just trying to help, saying,
    “I think it's really unfair, and I think that they've been very mean, and they should… If they didn't want the truth about what was going on, they never should have done this on the air.” — Stacy [16:14]

Takeaways

• The experiment leads to messy, real-time drama and raw emotion, highlighting the show's love of “bringing listeners into our world.”

2. Bar Etiquette Debate: Obligations After a Free Drink

Timestamps: 18:57–30:11

Scenario

• Bert observes a common bar scene: guy and woman lock eyes, he sends her a drink, but she accepts with no intention of speaking to him.

• Bert's Position (19:36–22:15):

  • “If a guy buys you a drink, you are at least obligated to engage us in conversation to find out if we're the real deal or not. Am I wrong?” — Bert [20:36]
  • Panel generally agrees; accepting the drink is “agreeing to conversation” [22:15–22:29].

• Caller Candice Disagrees (22:29–22:51):

  • “That's just an assumption. You're assuming that if I buy her this drink, she's going to at least talk to me. I don't have to say anything to you. I can say thanks for the drink and keep it moving.” — Candice [22:40]
  • Show finds this “so rude”—“I don't think you should accept it.” [22:44]

• Graceful Exits and Social Cues

  • There’s spirited debate on whether a woman can “cheers” from across the bar and walk away (“still rude”), and the importance of saving face for the guy with his friends.

• Comic Escalation (25:02–26:17):

  • Bert jokes:
    “If I buy you a drink that costs more than $9, you're obligated to French kiss me.” [25:40]
  • Panel spins this further — “If your drink costs $10 or more, I get to touch one boob.” [26:04]

• "Drink Hoe" vs. "Gold Diggin Hoe" (29:23–29:50)

  • Caller T.C.: “The title that y'all are talking about is a ‘drink hoe.’ That's exactly what it is. She's just there to get a drink, and that's it.” [29:23]
  • Panel differentiates: drink hoe = 1 drink, gold digging hoe = many drinks.
  • “That's so wrong… what's three minutes? I buy you a drink, I would like to find the woman that has gone the longest, the longest time period not buying herself a drink.” — Bert [29:50]

Takeaways

• The show highlights gendered expectations in social settings and the unwritten rules of dating etiquette, mixing genuine disagreement with over-the-top jokes and self-awareness.

Most Notable Quotes & Moments

• “You guys took America's most boring couple and turned it into a week long succession of bits. Thank God for Psycho Stacy.”
  — Listener Email, read by Jen [02:05]

• “It was just weird for me to hear my own, you know, personal life just on the radio. But it didn’t really bother me. It’s just kind of like Twilight Zoning or something.”
  — Kevin [06:23]

• “Just because you break up with someone doesn’t mean you break up with their family. Okay?”
  — Stacy [14:22]

• “If a guy buys you a drink, you are at least obligated to engage us in conversation to find out if we're the real deal or not. Am I wrong?”
  — Bert [20:36]

• “That's just an assumption. I can say thanks for the drink and keep it moving.”
  — Candice, caller [22:40]

• “If I buy you a drink that costs more than $9, you're obligated to French kiss me.”
  — Bert [25:40] (jokingly)

Structure & Tone

• Tone: Playful, direct, brash, and self-deprecating, with room for genuine emotion and candid sharing.
• Flow: Discussions move briskly between outrageous humor, listener participation, and authentic arguments, capturing classic morning radio energy.
• Language: Relatable everyday speak, sprinkled with tongue-in-cheek exchanges and occasional pointed jabs.

Overall:
This episode distills everything the Bert Show is known for: bold relationship experiments, candid commentary, and a lively (sometimes controversial) exploration of dating culture. Through the real-life drama of Jessica, Kevin, and Stacy, and a spirited debate about bar etiquette, listeners are treated to a mix of laughs, awkwardness, and earnest (if sometimes exaggerated) real talk.