The Bert Show – "Vault: Jeff's Best Proposal Ever"
Date: November 3, 2025
Hosts: Bert, Jeff, Melissa, (other cast: Kristin, Abby, Cassie, Tommy – not all present in this episode)
Theme: The Most Epic Romantic Proposal Stories (and Why Jeff’s Story Is “the Best”)
Episode Overview
This episode centers on the pursuit of the most romantic proposal story among listeners, with a build-up to Jeff’s legendary tale. The hosts and callers share stories ranging from grand gestures to slow-burning, deeply personal commitments, bantering about what truly makes for an epic engagement or romantic move. The topic produces laughter, teasing, and mild cynicism about where sincerity and "epicness" overlap.
Key Segments and Stories
1. Setting the Scene: The Proposal "Poker Game" (01:02–02:01)
- Bert warns listeners, lightheartedly, about “playing a dangerous game” of comparing their romantic stories to Jeff’s:
"Because it may bum you out. It may just bum you out." — Bert (01:02)
- The cast debates whether romance is about money or intention, hinting that Jeff’s story may have both.
2. Listener Stories – Challenging Jeff’s “Epic” Proposal
A. The Over-the-Top First Date (02:03–03:03)
- Caller: Shares how her now brother-in-law sent three separate dozen roses, each with labels for reasons he liked her sister, and cooked a fancy meal for their first date.
- Memorable moment:
"That's their first date." — Host (02:41)
"Not even close." — Jeff, unimpressed (02:58)
B. Tattooed Devotion (03:29–04:28)
- Caller: Her ex-husband tattooed her name over his heart after only three months of dating.
- Hosts joke about the “psycho” move and the aftermath now that they’re divorced.
- Notable quote:
"That's hardcore right there." — Bert (04:45)
C. The Slow Burn (05:23–06:58)
- Caller: She and her (now) husband didn't kiss for nine months, waiting until he was sure she was “the one.”
- Cynical but playful skepticism:
“Are you sure he wasn’t having an outbreak?” — Jeff (06:40)
D. Long Distance Leap (08:03–08:57)
- Caller: Met her now-husband over the phone across the country; he eventually flew her out to meet him.
- Jeff’s response: Dismisses it as “a Hallmark movie,” but “not as good.” (09:02)
E. The Painted Swing (09:10–10:15)
- Caller: Husband confessed love at Clemson on a porch swing, then later hired an artist to paint the swing as a graduation gift, proposing at the spot a month later.
- Hosts react with genuine awe:
"I got chill bumps." — Melissa (09:49)
"That is good... Beat that, Jeff." — Bert (09:56/09:57)
3. The Build-Up: Jeff’s “Unbeatable” Proposal Story (10:20–14:28)
Jeff launches into his highly anticipated story, repeatedly assuring the others it “trumps” every tale so far:
Jeff's Proposal Story: The Spontaneous Parisian Adventure
- Background: Jeff’s friend and his now-wife dated on and off, were technically broken up, and she was seeing someone else.
- The Move: At dinner together (while she was seeing another guy), Jeff’s friend spontaneously books two midnight plane tickets to New York, tells her "I'll call your boss," and insists, "let's get away—now."
- They buy everything needed for a weeklong trip. That night, after a show, he surprises her with a limo, a Central Park hotel, and the next morning, books tickets to Paris.
- In Paris, despite fights and emotional rollercoasters, they realize they’re meant for each other.
- Aftermath: Ten years later, they are still married.
- Notable quotes:
"He said, call him from New York." — Jeff, on the friend’s attitude toward her boyfriend (12:23)
"They spent five or six nights in Paris... At the end... decided they were right for each other." — Jeff (13:16)
4. Debate: Romance or Drama?
Melissa and callers push back, noting:
- The story’s extravagance—"just pull out the big platinum credit card"—may be less impressive than something thoughtful (16:03–16:37).
- The involvement of another boyfriend makes it less "pure" as a love story.
- Simplicity and sincerity (the "swing and portrait" story) might trump drama and expense.
Listeners weigh in:
- Some think Jeff’s story has too much drama and “negative emotions,” favoring the simplicity and honesty of the swing story (18:24–18:57).
- Melissa:
"Jeff's story is only romantic because they've been married for 10 years." (18:57)
"It could've been the most money ever spent on a failed relationship." — Jeff (19:16)
Notable Quotes & Moments
-
On over-the-top gestures:
"This guy had three dozen reasons on a first date. Feeling a little lame." — Bert (03:13)
-
On wild commitment:
"That's almost psycho." — Jeff (03:53)
-
On old-fashioned romance:
"No, no, no, no. He was just very respectful, very slow..." — Caller (06:45)
-
On Jeff’s friend’s audacity:
"I'll call your boss. I'll take care of it. I'll handle everything." — Jeff, impersonating his friend (12:23)
-
On hindsight:
"If you are the ex boyfriend, when she called to let him know she was in New York… No, she called from Paris." — Bert (17:32, 17:41)
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On what makes a great story:
"If it's a movie, then this is the best story because there's heartbreak and plane flights... If you're Nicholas Sparks, paint the picture of the swing." — Bert (18:07)
Timestamps for Key Segments
- (01:02) Setting up the "proposal poker game"
- (02:03) Caller story – first date with three sets of roses
- (03:29) Caller story – boyfriend’s name tattooed over heart
- (05:23) Caller story – no kiss for nine months
- (08:03) Caller story – long-distance flying romance
- (09:10) Caller story – the painted porch swing
- (10:20–14:28) Jeff’s “epic” Paris proposal story
- (14:29–19:16) Debate about drama, sincerity, and what really makes something romantic
- (18:24) Caller: “I think number two is more honest and didn’t have deceit.”
- (18:57) Melissa: “Jeff's story is only romantic because they've been married for 10 years.”
Tone & Style
As always, the Bert Show delivers sincere but irreverent commentary, balancing awe at big romantic gestures with ribbing, skepticism, clever one-liners, and honest debate about what romance truly is. Jeff’s stubborn championing of his story versus the crowd’s preference for simpler, more "pure" gestures keeps things fun and relatable.
Summary
This episode is a celebration—a playful showdown—of legendary romantic gestures. While Jeff’s friend’s adventure in love stands out for its grandiosity (midnight flights, impromptu trips to Paris, fate-defying persistence), many listeners and co-hosts champion quieter, more thoughtful proposals as the gold standard. In the end, the show nods to all forms of love—grand, steady, spontaneous, symbolic—as deserving of their own kind of epic.
For listeners who missed out:
If you've ever debated whether romance requires a bold, expensive move or simply thoughtful intention, this episode offers a funny, heartwarming, and sometimes critical look at just how many ways proposals can become “the best ever” (and who gets to decide).