Vault: Have You Dated Someone Who Was Engaged A Lot?

Summary

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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.

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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.

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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]

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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]

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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]

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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]

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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.

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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]

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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]

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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

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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.

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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.

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Transcript

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[C]

The Burt Show. All right, I wanna go back to this Nikki Hilton story.

[D]

Now. We were telling you yesterday that Nikki Hilton's former best friend was absolutely shocked to hear that she married this guy Todd Meister because she had been engaged to him before. She is 19 year old Charlotte friend and she was reportedly beside herself at the. She dated him for two years and he even proposed to her last March. But I guess she felt she was too young. So she broke off the engagement because she was 19 and he was 30. Um, but anyway, yeah, so he had been engaged before marrying Nikki Hilton. He's 31 now and Nikki Hilton is 20.

[C]

It's the engagement part really. It's not the age thing. I mean, there's so many different things to focus in on this right on this couple and this relationship. But the one that interests me here is the former engagement. Now I know for me, if I was dating somebody that had been engaged one time before and the engagement broke off, not a big deal. Okay? But what I want to know is if you're dating somebody and they've been engaged more than one time, does that send you a big old red flag once you start dating them? 404-741-1005 or would you be like, not a big deal? I'll give you an even worse case example. One of my really good friends out in San Francisco Tony has a sister named Deedee who. Who's been engaged now three different times before she got married. She finally pulled the trigger on the fourth one. But she was engaged three times, and they broke. All of them broke off before the actual wedding.

[D]

Did she break them off each time?

[C]

She broke them off each time.

So I'm asking if the detective is found.

[B]

It's blue.

[C]

If you guys found out you were dating somebody that had been engaged more than one time, would you break off the relationship knowing that chances were pretty good once you got engaged, they were Gonna ask you anyway? 404-741-1005 I think from a.

[E]

Like, if the guy had been engaged a lot and I was in that relationship, it goes back to the feeling being, you know, the wanting to feel special. 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, like, it just. I don't know.

[D]

It would.

[E]

I think it would throw up a red flag, you know?

[C]

Is. Is it possible that women that are engaged more than one time have the same feeling that they do? Like those women that we know that love the feeling of planning a wedding. Like Jlo, right?

[D]

But Jlo just actually gets married, right?

[C]

She gets married and has enough money to blow where she can spend all that cash on a wedding, and it doesn't matter to her.

[D]

Right?

[C]

But isn't there, like a whole different set of feel when everybody's coming up to you, congratulating you on your engagement, all, let me see the ring. Blah, blah, blah, blah, blah.

[D]

Oh, yeah, you're the center of attention. When you're the bride and you're engaged for a year, you are like, on. I mean, you're the center of attention of all conversations, you know, by the.

[C]

Third time, isn't it kind of like.

[B]

Oh, here she is again?

[D]

But I think it's that they probably love the excitement of the whole thing because it is so exciting. And you walk into a party or a group of friends and everybody wants to know about you and what's going on with you and what's going on with the wedding and all that stuff. So they must just want to repeat that and repeat that and repeat that.

[C]

Shannon says wouldn't bother her. Hey, Shannon.

[F]

Hey. Good morning, guys.

[C]

Good morning.

[F]

No, I don't think it would bother me. My idea would be if that person was dating the other person for a long period of time, and then maybe they broke it off, you know, several relationships. But I think that would be better that they got out of a relationship before they got married as opposed to, like, getting divorced.

[C]

Wouldn't you be a little skeptical, though? Let's say, Shannon, you're dating Jeff over here, right? And you guys go out.

[E]

That's disturbing enough.

[F]

Yeah, yeah.

[C]

I'm already challenging your character.

[F]

That's cool.

[C]

All right, so you and Jeff are going out, and you know in his past that he's engaged, he was engaged to three different women.

[G]

Hi.

[B]

Hi.

[E]

Hi.

[C]

And he proposes to you. Do you take that proposal serious? Are you, like, chances are pretty good this is never going to end up in a marriage?

[F]

No, no, I would take it serious. I think I would. I mean, because each relationship is different. I really believe that. I really believe each relationship is different. Not necessarily. How many times they, you know, he was engaged to someone else?

[C]

Oh, I'd be red flagging that thing.

[E]

And then also, you have to wonder why he is so ready to get married. Like some. I don't know. I don't know. Because sometimes if I see a guy be married, and then. Well, of course, this is marriage and then divorce and then marriage again. But 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. You know what I'm saying?

[C]

Well, we've learned, though, that we can keep you all in a relationship for a long, long time without actually engaged and getting engaged.

[D]

Yeah, but you're right, though. It does throw. I think Melissa's right. I think that that does throw up red flags. Like, what role am I gonna play? Am I gonna be his mommy? Does he want somebody to mommy him?

[E]

Need somebody to clean up?

[D]

Does he need somebody to do his laundry? Like, what is he looking for here? If he's looking for it in every single woman that he's been with and, you know, been engaged three times.

[C]

Hey, Charity. Hey, good morning. How are you this morning?

[F]

I'm good. I've been engaged five times, which I say, so called engaged. And I tell every time somebody asks me if, blah, blah, blah, it's if you don't have a ring, you're really not engaged. I've been proposed to, but I never got a ring till my husband gave me a ring. So it was the thing where I don't want her to leave. I want us to be together. So let me go ahead and tell her I want to marry her, and then it'll prolong the relationship, like, kind of like what Bert said. But they feel like, if you say you're engaged, you know, it's like, okay, yes, we're finally going to do it. And then, you know, eventually I'm like, okay, I don't have time for this. I don't have a ring. You're not showing me anything. I'm gone. And so I don't. It really depends on the situation. I don't think there's something wrong with the person because I don't think there's anything wrong with me. It's just the men I got with every time is like, well, I don't want her to leave. She's talking about she don't want to be in a relationship. So I'm gonna propose to her without a ring. Which means you broke behind. Didn't really want to marry me anyway.

[E]

So is your husband number five?

[D]

Is that the fifth guy?

[G]

Yeah. Okay.

[E]

All right.

[F]

When he did, we weren't even together at time. He came with the ring and everything and I was like, oh, this is real.

[D]

Okay.

[F]

So I got my cousins, my sisters and everything. Like, he proposed, but he didn't give me a ring. I said, he don't want to marry you.

[C]

Yeah, to me, that's the definition right there.

[F]

I seen the camera come out of bubblegum machine.

[A]

I.

[C]

Charity, thanks for calling. See you later. The virtual.

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