The Bert Show – Full Show PT 3: Thursday, November 6 [Vault]

Date: November 6, 2025
Podcast Host: Pionaire Podcasting

Episode Overview

This episode is packed with real-life confessions and funny, jaw-dropping stories about “vacationships”—flings and hookups that start (and sometimes awkwardly continue) after vacations. The hosts and listeners swap tales of vacation romances that either fizzled out harmlessly or returned to haunt them, often with hilarious or jaw-dropping consequences. The latter half of the episode follows up on a headline-making scenario: what happens when a man sleeps with his sister-in-law while his brother is out of town—a raw and messy situation unfolds, showcasing the show's love for drama, laughs, and relatable chaos.

Key Discussion Points & Insights

1. “Vacationships”: Why Do Vacation Hookups Go Wrong? (01:31–19:21)

• Defining Vacationships:
  The cast coins the term “vacationship” for flings that occur on vacation and then, sometimes painfully, try to follow people home.

  • “Is anything gonna happen with this? … No, it was just a locationship. And I said, what about a vacation ship?” – Female Co-host (01:46)
  • “Vacation ships gone wrong… like ones that follow you home.” – Female Co-host (02:00)

• The Problems of Bringing the Vacation Home:
  Standards and expectations are different while on vacation; back in the real world, complications arise:

  • “Your standards are just different when you're on vacation… things you normally would not accept.” – Burt (02:56)

• Lying and “Beefing Up” Stories:
  The hosts joke that people often exaggerate or fib about themselves during vacationships:

  • “I think the majority, more people than not, tell little fibs.” – Male Co-host (03:31)

Listener Call-ins: Vacation Flings That Haunted

1. The Persistent Ex (Jessica/Sarah – 06:09)

   • A drunken hookup gives out her number, is tracked down in real life, and stalked.
     • “A month later, after spring break is over, he shows up at my door at college… he lived in New York and I lived in Virginia.” – Jessica/Sarah (06:54)

2. The “Haunter” (Nate/JJ – 08:18)

   • Listener admits to moving across the country for a vacation crush, only to be dumped.
     • “I became a professional stalker. I since now been reformed.” – Nate (09:04)

3. Teenage Trouble (Greg – 10:55)

   • A man unknowingly hooks up with a 15-year-old who lied about her age, leading to a comical but stressful encounter with her dad:
     • “She told me she was 19 and I was 20… it comes to find out she was 15 years old.” – Greg (11:45)

4. Green Card Marriage (Sarah – 13:34)

   • A woman marries a man she met in London; after he receives his green card, he leaves.
     • “Vacationship was a week. Relationship was less than a year.” – Sarah (14:15)
     • “As soon as he got his green card, he left.” – Sarah (13:48)

5. Digital Desperation (Amanda – 14:44)

   • A cruise ship hookup who, five years later, is still messaging her online.

6. Manipulation & Blackmail (Casey – 15:50)

   • Casey's brother-in-law is threatened with statutory rape unless he moves across the country for his young vacationship partner.
     • “She tells him that he needs to move to Green Bay, Wisconsin… if you don’t move… I’m gonna file statutory rape against you.” – Casey (16:23)

7. Letter Writing Gone Wrong (Male Co-host – 17:19)

   • The host's story of a flirtation that turned into months of romantic letters—until the pen-pal-turned-freeloader stays for two awkward weeks.

Moral of the Stories:

Most hosts agree:
“Keep the vacation ships on vacation. We have learned that today.” – Burt (17:08)

2. Revisiting the Secret Sibling Affair (19:37–30:26)

Background Recap (Melissa, 19:37–22:11)

• Listener “JJ” slept with his sister-in-law while his brother was away.
• The sister-in-law was initially adamant about confessing, JJ debated whether he should tell his brother first.
• The anxiety caused the sister-in-law to have a panic attack and end up in the hospital.

The Latest Chapter: Will the Secret Stay Buried? (22:27–28:22)

• JJ’s Call-In Update:
  After her panic attack and soul searching, the sister-in-law chooses to keep the affair secret:

  • “She said the more she thought about it she didn’t want to ruin her marriage, she didn’t want to ruin my relationship with my brother. … She is happy going taking this to secret with her to the grave is what she told me.” – JJ (23:13)
  • “She said the only thing she wanted to do was she wanted to get past the initial stage where it would be awkward for us...” – JJ (23:29)
  • They even shared a meal with her husband present, trying to act natural.

• Burt’s Skepticism:
  Burt challenges JJ:

  • “I know there’s about half of the Bert Show community right now breathing a sigh of relief because they really think that you should have kept this secret. … I just couldn’t live with the knowledge that at any moment, this secret can come up…” – Burt (25:36)
  • JJ stands his ground: “That’s a gamble I’m willing to take.” (26:23)

• Call-In Reactions:
  A caller argues some mistakes should remain secret, while Melissa and others debate whether secrets that big ever really stay buried, and if the betrayed spouse deserves to know.

  • “The reason they don’t have to tell. One of the things is when you do something like that, your payment is the guilt that you feel.” – Caller (28:26)
  • “But when there’s no children involved and you slept with...I would want to know that.” – Melissa (30:07)

Notable Quotes & Memorable Moments

• On vacation logic:
  “If it’s an away game and you’re on vacation, you may just go, you know what?...even though he smokes or drinks or is married, I can get past this for three days.” – Burt (02:56)

• When vacation ships become stalker ships:
  “Then they become stalker ships.” – Male Co-host (02:47)

• Listener’s green card romance:
  “I married him. And as soon as he got his green card, he left.” – Sarah (13:48)

• Practical vacation advice:
  “Keep the vacation ships on vacation. We have learned that today.” – Burt (17:08)

• Complexity of secrets:
  “I just couldn’t live with the knowledge that at any moment, this secret can come up at any single time.” – Burt (25:36) “That’s a gamble I’m willing to take… I’m taking her cue, and she’s the one who’s done a complete 180 on this, and I’m for it.” – JJ (26:23)

Timestamps for Key Segments

• 01:31: Main show starts – Vacation hookup stories begin
• 06:09: First major caller: Persistent hookup disaster
• 08:18: Listener admits to being the “haunter”
• 10:55: Tale of accidental underage hookup
• 13:34: Green card marriage gone wrong
• 15:50: Cruise fling threatens legal action
• 17:19: Host’s love-letter vacation story
• 19:37: Recap and deep-dive: The sibling-in-law affair saga
• 22:27: JJ’s update: Concealing the secret
• 25:36: Burt voices unease about secret keeping
• 28:26: Callers debate: secrets vs. confessions

Tone & Style

• Conversational, real, often self-deprecating and playful.
• Mix of personal anecdote, humor, cautionary tales, and direct listener engagement.
• The hosts don’t shy away from commenting on the ethics of each story, sometimes splitting on what the “right thing” is—always with a sense of humanity and relatability.

Summary Takeaway

If you ever wondered if that vacation fling could end up haunting you, The Bert Show’s collection of vacation love-gone-wrong stories will have you laughing and cringing in equal measure. The episode is a smorgasbord of wild, memorable listener call-ins and personal confessions, topped off with a deep-dish serving of moral ambiguity as the cast debates secrecy, honesty, and what we owe those we love. As always, the show is unfiltered, deeply relatable, and full of laughs—even when things get unexpectedly real.