The Bert Show – "Vault: Summer Flings That Won't Die"

Date: November 6, 2025
Host: Burt with The Bert Show Cast
Theme: Vacation Flings That Won't Let Go

Episode Overview

This lively episode dives into the hilarious, cringe-worthy, and sometimes unsettling world of "vacationships"—those whirlwind summer romances or hook-ups that happen while on vacation and unexpectedly linger after everyone’s back in the real world. The hosts share their own experiences and invite listeners to call in with stories about vacation flings that came home, revealing the comedic and sometimes haunting aftermath.

Key Discussion Points and Insights

1. Defining the "Vacation Ship"

• Term Introduction:
  The crew coins "vacationship," differentiating it as a romantic connection made during travel, often fleeting and meant to be left as a fond (or embarrassing) memory.

  • "And so that’s what we’re coining his relationship with this cute girl in Charleston—just a vacation ship." (01:33)

• Why They’re Different:
  Hosts and callers agree standards change when traveling, leading to decisions never made at home.

  • "Standards are just different when you’re on vacation… If it’s an away game, and you’re on vacation, you may just go, you know what? I can get past this for three days." —Burt (02:35)

2. When Vacation Ships Haunt You

• Turning into “Stalker-Ships”:
  Sometimes one party isn’t ready to leave it behind, leading to awkward or outright scary situations.

  • "Then they become stalker ships." (02:25)

• Caller Stories:
  Multiple callers share tales of vacation flings that lingered, sometimes with comical persistence, sometimes crossing boundaries.

Notable Listener Stories & Memorable Moments

Burt's Hawaii "Wingman" Nightmare

Timestamps: 04:39–05:36

• Story: Burt recounts going to Hawaii for his 21st birthday. He plays wingman for his friend Johnny, putting up with Johnny’s love interest's "grenade" friend for days, only for this dynamic to follow him home when the girls visit San Diego.
  • "I have to spend another three days with her, like, every month for three or four months." —Burt (05:19)
  • "It haunted me. Totally haunted me." —Burt (05:33)

"The Unwanted Visit"

Timestamps: 05:43–07:03

• Story: Jessica shares how a one-time drunk hook-up during spring break led to her fling showing up at her college dorm, having tracked her down from another state.
  • "He had looked me up on our student directory and shown up. He lived in New York and I lived in Virginia." —Jessica (06:06)

The Vacation Ship You Can’t Forget

Timestamps: 07:53–09:59

• Story: A caller admits she was the "haunter." At 17, she followed her vacation crush to college, only to be heartbroken and, in retrospect, a “professional stalker.”
  • "I became a professional stalker. I have since now been reformed." —Caller (08:43)
  • "Hindsight, 20." —Caller (08:55)

Age and Awkward Discoveries

Timestamps: 10:33–12:46

• Story: Rafael connects with a girl at a Dominican Republic resort. Post-vacation, he learns she’s actually 15, not 19 as claimed, and meets her father in an unexpected, tense confrontation.
  • "She told me on the trip she was 19 and I was 20 at the time. It comes to find out she was 15 years old." —Rafael (11:26)

“I Married My Vacation Fling—for His Green Card”

Timestamps: 13:12–14:13

• Story: Sarah describes meeting a charming Buckingham Palace guard in London, marrying him, and being left as soon as he got his green card.
  • "As soon as he got his green card, he left. He disappeared." —Sarah (13:28)
  • "The day after he gets his green card. Buh. Bye." —Burt (13:58)

“Five Years of AIM”

Timestamps: 14:22–15:13

• Story: Amanda’s vacation crush from a cruise still messages her five years later, hoping to visit—a joke among the hosts about flings that really can't let go.
  • "Still to this day, I will sign online and he will have sent me a message saying, ‘Hey, I might be coming through Atlanta.’” —Amanda (14:44)

Blackmail and Moving Cross-Country

Timestamps: 15:28–16:51

• Story: A caller relays her brother-in-law’s ordeal—a cruise romance ends in the girl threatening statutory rape charges unless he relocates to Wisconsin, trapping him there for months.
  • "If you don't move to Green Bay, Wisconsin, I'm gonna file statutory rape against you." —Caller (15:53)

The Romantic Letter Writer

Timestamps: 16:57–18:59

• Story: Caller shares an unexpectedly wholesome saga of writing love letters to an Alaskan fishing guide… until he comes to visit, overstays his welcome, and the magic dies.
  • "I mean, I never even gotten closer than a handshake to this guy. So he decides he’s gonna come visit over Thanksgiving." —Caller (17:34)
  • "Three days. And then he stayed the whole two weeks." —Caller (18:40)

Notable Quotes

• On Living in the Moment:
  • "Standards are just different when you're on vacation." —Burt (02:35)
• On Flings Lingering:
  • "These are vacation ships. You know, standards are just a little different when you’re on vacation. Stay on vacation." —Burt (07:05)
• On Friend Duties:
  • "Your wingmanship...it has to be said that it’s on vacation. You can’t expect your wingman to continue it for you when you get back home." —Burt (10:06)

Episode Takeaways

• Vacation flings sound dreamy, but reality sets in fast when you’re home.
• Boundaries blur far from home, but consequences (and awkwardness) often follow you back.
• Many callers’ tales highlight the wackiness, heartache, and sometimes real dangers of not leaving vacation romances behind.
• Hosts and listeners alike endorse: “Keep the vacation ships on vacation!”

Timeline of Key Segments

| Timestamp | Segment | |--------------|------------------------------------------------------| | 01:09 | Discussion begins: vacations and spontaneous flings | | 02:23 | “Vacation ships” can – and often do – go wrong | | 04:39 | Burt’s Hawaii vacation wingman story | | 05:43 | Jessica’s unwanted “spring break” visitor | | 07:53 | Caller confesses to being the haunting vacation ship| | 10:33 | Rafael’s age-mix-up heartbreak | | 13:12 | Sarah’s green-card marriage vacation ship | | 14:22 | Amanda’s 5-year online persistent vacation ship | | 15:28 | Wisconsin statutory-threat saga | | 16:57 | Letter-writing romance from Alaska |

Final Thought

The Bert Show approaches awkward, funny, and even scary stories about summer flings with their trademark wit, proving some adventures are best left in the sand. If you’re contemplating extending a vacation romance, maybe—just maybe—you’ll think twice after hearing these stories!