The Bert Show: “Vault: Listeners Share Their Biggest Relationship Age Difference”

Original Air Date: February 24, 2026
Podcast Host/Cast: Bert, Kristin, Abby, Cassie, Tommy & The Bert Show Cast

Episode Overview

In this lively and provocative episode, The Bert Show opens the phone lines for a listener roundtable on the most extreme age differences in romantic relationships. Sparked by recent celebrity gossip about Rolling Stones musician Ron Wood and his much younger partner, the team challenges their audience to call in with true stories of family or friends whose relationships have even larger age gaps. The resulting parade of stories is jaw-dropping, humorous, and, at times, deeply uncomfortable. The cast discusses motives—money, love, fame—and reacts to the wild tales with their trademark blend of candor and humor.

Key Discussion Points & Insights

1. Setting the Stage: Celebrity Age Gaps

• [02:21] Bert introduces the spark for the discussion: reports that Rolling Stones' Ron Wood (61) is in a romantic relationship with a 20-year-old woman.
• The crew reacts with a mix of disbelief and sarcasm, questioning whether such a pairing could be genuine or motivated by other factors, such as fame or money.
  • Bert: “His other 60 year old friends are high fiving him—if they can get their arm up that high.” ([03:52])
  • E: “She's gonna have to be his granddaughter.” ([02:49])

2. Listener Call-Ins: Real-Life Stories that Outdo Celebrities

• First caller, Charles ([04:45]): Shares that after his grandmother died, his 70-year-old grandfather dated a 28-year-old. Age difference: 41 years.

  • F: “Did your family freak out and lose their minds?” ([05:18])
  • G (Charles): “Yes, they did… she rolled up his credit cards on her kids and he realized he was just being taken for a ride.” ([05:21])

• Christine ([06:03]): Her 29-year-old sister has been seeing a 73-year-old former celebrity (44-year difference), identity withheld.

  • B: “That’s a 44 year age difference right there.” ([06:44])
  • Multiple playful, incredulous attempts to guess the celebrity: “Every time an angel is born, a bell rings—that movie.” ([07:08])

• Amy ([08:24]): Her 23-year-old cousin had a baby with a 78-year-old—a staggering 55-year gap.

  • I (Amy): “It’s kind of gross.” ([08:38])
  • F: “You don’t really have a daddy complex. You have a granddaddy complex.” ([09:25])
  • Discussion revolves around motives—money, emotional needs, or something deeper psychologically.

• Marlena ([10:41]): Shares about her cousin, who started dating a man in his 50s at age 15. They married and had a child, resulting in significant school and family drama.

  • I: “He actually had a live-in girlfriend that was... one of our substitute teachers.” ([10:46])
  • E: “I would slap my daddy.” ([11:33])

• Cassie ([11:52]): Reports her 18-year-old cousin married an 81-year-old multimillionaire. Age gap: 63 years.

  • I: “She’s had a ton of plastic surgery. He walks with a walker and sometimes uses a wheelchair.” ([12:28])
  • E: “He has one foot in the grave already and the other one's halfway in there.” ([13:01])
  • F: “Did she sign a prenuptial agreement?” ([13:03])
  • I: “No, they did not." ([13:05])

• Adrian ([14:15]): Her brother-in-law (26) is dating a 68-year-old woman, primarily for financial support.

  • I: “He’s not a good person... She supports habits and stuff. So... he doesn’t have to work or anything.” ([14:50])

3. Analysis and Cast Commentary

• The cast repeatedly circles back to the idea that, in these dramatic age-difference relationships, money and personal gain are almost always the motivating factor, and love is infrequently at the core.
  • E: “There’s no reason a young girl is going to be with a man that old. Unless it’s for his money.” ([05:37])
  • B: “That’s the thing that as a guy is so fascinating to me. Like a woman can mentally check out of making love... in order to get that money at the end of the rainbow.” ([05:48])
• They joke about the logistics (“Do they travel with a nurse?” [12:15]), and critique the obviousness of Anna-Nicole Smith–like scenarios coming up again and again.
• Multiple remarks about the familial reactions, from incredulity to indignation—“I would slap my sister.” ([10:19])

4. Gender Reversal

• The final caller’s story involves a younger man with an older, wealthy woman, flipping the common stereotype.
  • B: “Every now and then there is a guy with the same gear that a woman has—they can turn it off and make love to somebody way, way, way older than he is.” ([14:15])
  • F: “If she’s paying for everything for him, he better.” ([15:28])

Notable Quotes & Memorable Moments

• On family outrage:

  • F: “Did your family freak out and lose their minds?” ([05:18])
  • G (Charles): “She rolled up his credit cards on her kids and he realized that he was just being taken for a ride and it was annulled.” ([05:21])

• On motives:

  • E: “If people are calling and saying it’s about love, it’s not.” ([05:45])
  • I (Amy): “She doesn’t work. No.” ([10:17])

• Record-breaking age gap:

  • B: “That’s a 63-year age difference. Wow.” ([13:47])

• Turning a trope on its head:

  • B: “Every now and then there is a guy with the same gear that a woman has that they can turn it off and make love to somebody way, way, way older.” ([14:15])

Key Call Timestamps

• [04:45] – Charles: 70 & 28 (41 years)
• [06:03] – Christine: 29 & 73 (44 years, with a celebrity twist)
• [08:24] – Amy: 23 & 78 (55 years, also have a child together)
• [10:41] – Marlena: 15 & 50s (dating started in high school)
• [11:52] – Cassie: 18 & 81 (married, no prenup)
• [14:24] – Adrian: 26 & 68 (younger man/older woman)

Tone & Style

• The hosts balance shock and humor, rarely holding back their honest opinions or sly jokes.
• There’s a recurring theme of familial disbelief and judgment, both from the hosts and listeners.
• The cast doesn’t shy away from pointing out uncomfortable or taboo aspects—often using playful banter to offset just how wild some of the scenarios are.

Summary

This episode of The Bert Show is a rollicking, unfiltered window into the world of eyebrow-raising relationship age gaps. The cast’s curiosity about celebrity May-December romances opens a floodgate of audience confessions, some of which dwarf even the wildest tabloid stories. While the show keeps the mood light, it also lets moments of real discomfort and skepticism shine through, especially regarding motivations like money and fame. The result is an engaging, surprising episode that’ll leave listeners shaking their heads—and laughing at the irreverence of The Bert Show team.