The Bert Show — Vault: Have You Dated Someone Who Was Engaged A Lot?
Episode Date: December 5, 2025
Host: The Bert Show Cast (Bert, Kristin, Abby, Cassie, Tommy & More)
Main Theme: Examining whether having multiple broken engagements is a dating red flag — featuring listener calls and lively cast discussion.
Episode Overview
In this episode, The Bert Show tackles an age-old dating dilemma: Would you consider it a red flag if the person you're dating had been engaged more than once? Inspired by a story about Nicky Hilton’s new husband, who was engaged to his ex before marrying Hilton, the cast—and listeners—debate the implications of serial engagements, the motivations behind them, and how they impact trust in new relationships. The segment is filled with real stories, humor, and candid confessions from both the cast and callers.
Key Discussion Points & Insights
1. The Nicky Hilton Story & the Spark for Discussion
[01:31–02:09]
- The segment begins with mention of Nicky Hilton’s marriage to Todd Meister, who had previously been engaged to another woman (Charlotte Friend, then 19, he was 30).
- The focus shifts quickly from the controversial age gap to the fact that Todd was previously engaged, prompting the broader question: How many engagements are too many?
"It's the engagement part, really. It's not the age thing... But the one that interests me here is the former engagement."
— Bert, [02:09]
2. Is Multiple Engagements a Red Flag?
[02:09–03:25]
- Bert asks the table: Is having more than one broken engagement a major concern?
- He gives an example: His friend Deedee was engaged three times before marrying her fourth fiancé.
"If I was dating somebody that had been engaged one time before and the engagement broke off, not a big deal...But if they've been engaged more than once, does that send you a big old red flag?"
— Bert, [02:09]
3. Emotional Impact and "Feeling Special"
[03:25–03:45]
- One cast member (E) worries about being just another in a string of “almost-brides.”
- The sentiment is that repeat engagements could make the next fiancée feel less special or unique.
"Like, I would have a hard time because I'm thinking he has been that close to that many women that he's proposed to them, that when he gets to me... I don't know."
— Cast, [03:25]
4. The Allure of Weddings: For the Experience or the Relationship?
[03:45–04:25]
- Bert proposes some people—especially women, referencing J.Lo—may be “addicted” to the engagement/wedding experience itself.
- The thrill of being the center of attention is real, and multiple engagements may be a way to relive that.
"Is it possible that women that are engaged more than one time have the same feeling—that they love the feeling of planning a wedding, like J.Lo, right?"
— Bert, [03:45]
"By the third time, isn't it kind of like... oh, here she is again?"
— Bert, [04:21]
5. Cast and Caller Reactions: Skepticism, Sadness, and Pragmatism
[04:39–05:42]
- Caller Shannon says it wouldn't bother her; she'd see multiple broken engagements as better than multiple divorces.
- She believes each relationship is different.
- Cast members debate: Wouldn’t you be skeptical if you were the fourth or fifth person proposed to?
"No, I would take it serious. I really believe each relationship is different."
— Shannon (Caller), [05:29]
- Kristen and others point out the concern about what drives serial proposals (“Can’t be alone?” “Is he looking for a mommy or caretaker?”)
- The importance of knowing the “why” behind repeat engagements.
6. Candid Caller: Charity and Life with Five Engagements
[06:28–07:50]
- Caller Charity shares she’s been “so-called engaged” five times, but only got a ring from her (now) husband.
- She describes how past suitors used a “proposal” to keep her around without commitment. If there was no ring, she took it as a lack of real intent.
- She believes circumstances (and not her character) were responsible for her serial proposals.
"I've been engaged five times, which I say, so-called engaged... but I never got a ring till my husband gave me a ring."
— Charity (Caller), [06:31]
"If you don't have a ring, you're really not engaged."
— Charity, [06:32]
- Charity’s story draws laughs and agreement, and at [07:39], she delivers a zinger about fake proposals:
"He proposed, but he didn't give me a ring. I said, he don't want to marry you. I seen the camera come out of bubblegum machine."
— Charity, [07:52]
Notable Quotes & Memorable Moments
-
Bert on Serial Engagements:
"Oh, I'd be red flagging that thing."
— [05:42] -
On Seeking Attention:
"You are like the center of attention of all conversations... So they must just want to repeat that and repeat that and repeat that."
— Cast, [04:25] -
Kristin on Motivations:
"Sometimes if a guy can't be alone and he needs a woman in his life, and I would just wonder what my role would be in his world."
— Kristin, [05:44] -
Charity gets the last laugh:
"I seen the camera come out of bubblegum machine."
— Charity, [07:52]
Key Timestamps of Interest
- 01:31 — Segment topic introduced: multiple engagements as a red flag
- 02:09 — Personal anecdotes of serial engagements
- 03:25 — Cast discussion: Does it make your relationship less special?
- 04:39 — First caller (Shannon) weighs in with a contrary view
- 05:44 — Doubts about serial proposers’ motives
- 06:28 — Charity's story: five engagements, but only one ring
Tone & Language
- Lighthearted and playful: Cast members poke fun at the topic but also share earnest opinions.
- Candid and authentic: Both the show’s hosts and the callers share real-life experiences without filters.
- Supportive: The tone remains respectful even when opinions diverge.
Closing Thoughts
The episode is a lively, relatable exploration of modern relationship red flags—the cast draws a line between understandable romantic missteps and patterns that might raise valid concerns. While the conclusion isn’t definitive, listeners get a nuanced mix of laughter, empathy, and genuine insight.
Great for listeners who enjoy debates about relationships, social norms, and the meaning behind modern dating trends.