The Bert Show - Full Show PT 1: Tuesday, February 24 [Vault]
Date: February 24, 2026

Episode Overview

This episode of The Bert Show dives into two engaging and humorous discussions that showcase the show's blend of authenticity, humor, and audience participation. The central theme is unusual romantic relationships—specifically extreme age gaps—and the complex, often comedic social reactions to them. In the second significant segment, the cast provides an update on "the No-Texting Challenge," delving into dating behaviors, self-control, and the supportive (or enabling) nature of friendships. The episode is marked by candid exchanges, listener call-ins, and playful banter among the Bert Show team.

Key Discussion Points & Insights

1. Exploring Extreme Age Gaps in Relationships

[02:00-15:39]

• Bert introduces a recent news story about Ronnie Wood from the Rolling Stones (61 years old) dating a 20-year-old and asks listeners about similar or more extreme examples in their own lives.

• The cast discusses their fascination with such relationships, often questioning motives (e.g., love vs. money) and the ability to overlook large generational differences.

Memorable Listener Call-Ins:

• [04:44] Charles: Shares about his grandfather, who dated a 28-year-old when he was nearly 70—a 41-year gap. The family was upset, and ultimately, the younger woman exploited his grandfather financially.

  • Quote: "There was some severe talk with my grandfather about the whole thing... she rolled up his credit cards on her kids and he realized he was just being taken for a ride." (Charles, 05:21)

• [06:02] Christine: Reveals her sister (29) is in a long-term relationship with a 73-year-old, a famous actor from a globally-renowned movie.

  • Quote: "You would definitely know the movie immediately... it is one of the best movies of all time." (Christine, 06:53)
  • This prompts curiosity and speculation among the cast about the celebrity's identity.

• [08:24] Amy: Claims her 23-year-old cousin had a baby with a 78-year-old man (55-year gap).

  • Quote: "You don't really have a daddy complex. You have a granddaddy complex." (Cast, 09:25)

• [10:41] Marlena: Describes her cousin who started dating a man in his 50s when she was just 15. They later married and had children—a story met with shock and humor.

• [11:52] Cassie: Shares about her cousin (18) marrying an 81-year-old multimillionaire (63-year gap), who already has a 62-year-old child.

  • Quote: "He is a multimillionaire. And she has totally changed since they got together... he actually walks with a walker and sometimes in a wheelchair." (Cassie, 12:28)
  • The cast jokes about motivations and potential inheritance.

• [14:21] Adrian: Offers the reverse scenario—her 26-year-old brother-in-law dating a 68-year-old wealthy woman.

  • Quote: "It's definitely for money. He's not a good person." (Adrian, 14:41)

Show Themes & Reactions:

• Humorous disbelief at the age gaps.
• Persistent question of whether these relationships are for love or money—and skepticism about the former.
  • Quote: "Come on now. That's a 55-year age difference. We can't beat that. Can't be done." (Bert, 10:32)
• Cast openly jokes about “granddaddy complexes” and “making it rain” with retirement money, pushing the line between social commentary and comedy.

2. The No-Texting Challenge & Relationship Dynamics

[17:35-25:37]

• The second major segment follows an ongoing personal challenge for member Wendy: not to text any men she’s interested in over the weekend.
• The intention is to help Wendy avoid seeming too eager or “desperate” in new relationships.

Highlights from Discussion:

• [17:40] Wendy confesses her usual pattern is to respond promptly to texts, often not waiting even when dating advice suggests otherwise.

  • Quote: “Usually I’ll contact right back. I guess I looked eager. So Melissa had to take my phone.” (Wendy, 17:56)

• [19:09] Wendy explains she met a new guy on Friday and, although she technically replied to his text, she kept her message brief and didn’t initiate further contact.

  • Quote: “He texted me and asked if I got home okay. So I was like on a technicality, I say text back and I just go, yes, I made it home safe.” (Wendy, 19:19)

• [20:12] Wendy admits to a “drunk dial” on Saturday, unable to make it one weekend without breaking the challenge.

  • Quote: “I did send a drunk dial.” (Wendy, 20:12)
  • The group teases Wendy about her willpower, but also jokes about how women might enable each other to “bend the rules.”

• [21:17] Group Discussion: The cast elaborates on modern dating communication norms—delayed responses, “playing it cool,” and the pressure to avoid looking desperate.

  • Quote: “You can’t err on the side of waiting too long for a guy... but I’m just being friendly.” (Wendy, 22:36)
  • Countered by: “You’re not. You’re being desperate. That’s what I’m trying to get you out of.” (Bert, 22:40)

• [24:22] Bert bluntly queries Wendy about whether her texting patterns have served her well romantically.

  • Quote: “Has the way you’ve been doing this so far worked for you, been successful for you when it comes to relationships?” (Bert, 24:11)

• The segment closes with self-deprecating humor as Wendy acknowledges her track record, and the group reflects on the difference between nurturing and enabling in friend groups.

Notable Quotes & Memorable Moments

• On Relationships with Huge Age Gaps:

  • “There’s no reason a young girl is going to be with a man that old. Unless it’s for his money.” (B, 05:43)
  • “You don’t really have a daddy complex. You have a granddaddy complex.” (E, 09:25)
  • “81 and 18. So there must be just a load of money we’re talking about right now.” (D, 12:19)
  • “See what you can get when you can make it rain?” (G, 13:49)

• On Texting & Dating:

  • “The assignment for the weekend was not to text.” (B, 23:03)
  • “One text message is 20 steps backwards.” (G, 23:14)
  • “Women do nurture each other.” (B, 25:03)

• Funniest Banter:

  • “She must have been like a caretaker or something... she was a dancer.” (G, 13:30)
  • “He has to let go. It’s tough because he has to let go of his walker.” (G, 14:04)
  • Wendy’s shame about texting and the group’s teasing: “I'm really ashamed. I'm ashamed of myself.” (H, 19:56)

Timestamps for Key Segments

• [02:00] – Introduction to extreme age gap relationships and call for listener stories.
• [04:44] – Charles’s family story: 70-year-old grandfather, 28-year-old girlfriend.
• [06:02] – Christine’s sister: 29 with a 73-year-old famous actor.
• [08:24] – Amy: 23-year-old cousin has a baby with a 78-year-old.
• [10:41] – Marlena: small-town drama, 15-year-old cousin with man in his 50s.
• [11:52] – Cassie: cousin (18) marries multimillionaire (81).
• [14:21] – Adrian: brother-in-law (26), girlfriend (68).
• [17:35] – Transition to Wendy’s No-Texting Challenge.
• [19:09] – Wendy’s Friday night update and rationalizations.
• [20:12] – Wendy confesses the “drunk dial.”
• [22:36] – Discussion about text response timing and desperation.
• [24:11] – Bert challenges Wendy: Has her dating strategy actually worked?

Episode Tone & Style

The conversation is candid, fast-paced, and laced with humor—true to The Bert Show’s reputation for authentic and relatable dialogue. The cast oscillates between playful teasing and genuine curiosity, making space for both laughter and cringe-worthy revelations. The listeners’ stories bring drama and amusement, while the cast’s commentary stays unfiltered and accessible.

In Summary:
This episode delivers a roller-coaster of jaw-dropping real-life relationship stories and painfully relatable dating mishaps, driven by sharp cast chemistry and enthusiastic listener participation. It's both an escapist romp and a sly commentary on love, money, and the games people play.