Vault: Is She Making A Mistake By Proposing To Her Boyfriend?

Summary

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Podcast Summary: The Bert Show

Episode: Vault: Is She Making A Mistake By Proposing To Her Boyfriend?

Date: March 11, 2026

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Main Theme

This episode centers around a listener, Kimberly, who seeks advice from The Bert Show team and its audience about her plan to propose to her boyfriend. The discussion explores the evolving dynamics of relationship roles, the significance (or insignificance) of marriage as a “piece of paper,” and the risks and considerations involved in Kimberly’s unconventional approach.

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Key Discussion Points & Insights

1. Kimberly’s Situation (01:15–02:15)

• Kimberly calls in excited, sharing her intention to propose to her boyfriend.
• Steven, the boyfriend, previously expressed the belief that marriage was “just a piece of paper” and not necessary for commitment.
• Despite this, Kimberly feels confident:

  “I really feel, I mean, with 100% certainty that he's going to say yes. I mean, he's the love of my life and he's terrific and I’m really excited now.”
  – Kimberly (01:33)

• The couple has been together for about a year and four months, including around six months apart due to long distance.

2. Relationship Timeline and Family Background

• Kimberly describes how her own parents married after knowing each other for only two months and have been together for 26 years, shaping her belief in personal timelines over societal norms (02:03–02:15).
• The couple started dating soon after Steven moved to Kimberly’s city.
• Steven has since had to move back to the East Coast for work, prompting Kimberly to consider moving—but she wants greater commitment first.
• She’s planning to propose during her first in-person meeting with his family.

3. Proposing in Front of His Family (03:09–04:55)

• Hosts express reservations about Kimberly’s plan to propose in front of Steven’s family, whom she has never met in person.
• Radio Co-host: “Now that is the part that I'm nervous about ... it should never be a public proposal in front of the family that you meet for the first time, man or woman.” (03:28, 07:22)
• Kimberly shares she’s spoken to his mother and sister by phone, but has not yet met them.

4. Why Not Wait for Him?

• The hosts ask Kimberly why she won’t wait for Steven to propose.
• Kimberly reiterates that he downplayed marriage, but she feels it’s important for her, and she wants assurance before moving.

  “…I really love this guy, I'm willing to, like, move halfway, you know, across the country, you know, to be with this guy. And if I'm going to do that, I don't want it to be just because he's my boyfriend. You know, I want definitely more of a commitment.”
  – Kimberly (04:55)

• Kimberly plans to talk to Steven’s dad and ask his permission before proposing — "traditional roles just flip flopped." (04:52–04:55)

5. The “Mangagement” Ring (05:00)

• Kimberly picked out a titanium band for Steven, noting the store called it a “mangagement ring.”

• “I definitely wanted to get him something that was, you know, masculine and strong and represented what I felt was the strength of our relationship.”
  – Kimberly (05:14)

6. Listener Feedback and Debate (05:35, 08:54)

• Another caller, Melissa, calls in to say her quick relationship turned out well, countering the claim that it’s “too soon.”
• Hosts debate the timing and meaning of marriage for Steven:

  “It’s not the timing … it’s the statement … his take on marriage sounds very different than yours. His take is it’s just a piece of paper. I don’t need that to be with you for the rest of my life.”
  – Radio Host (05:51)

• Kimberly believes Steven will marry because it matters to her, and because it's “not that big a deal” to him.
• Hosts emphasize the risk of a “public proposal” and that some people’s values about marriage simply can’t be changed.

7. Navigating Life Choices: Ultimatums and Moving (07:22–08:47)

• One host frames Kimberly’s proposal as a “creative ultimatum”: she won’t move without marriage.
• Kimberly discusses her willingness to move for Steven, but not without marriage, given her career flexibility vs. uprooting her life.
• Her reasoning: "I don't want to give up my friends, my family, like, the whole life that I've had, you know, just to go see some girlfriend. ... I definitely want to take it another step." (07:46–08:47)

8. Audience Reaction

• The hosts report their audience is about evenly split:

  “It's about split right now, about half. People saying, no way. It's just the wrong place, wrong time ... And the other saying just absolutely go for it. Why not? Seriously?”
  – Radio Host (08:54)

• The percentages?

  “About 50-50. Is that what our audience is about? 50-50? It's always 50-50. Shocker.”
  – Mike & Radio Host (09:03–09:10)

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Notable Quotes & Memorable Moments

• “He’s not the marrying type ... but I really feel with 100% certainty he’s going to say yes.”
  – Kimberly (01:30)

• “It should never be a public proposal in front of the family that you meet for the first time, man or woman.”
  – Radio Co-host (07:22)

• “To me, it’s like a more creative ultimatum.”
  – Radio Co-host (07:32)

• “I want to move, but not just to be somebody’s girlfriend.”
  – Kimberly (08:47)

• On the ring:
  “I definitely wanted to get him something that was masculine and strong and represented … our relationship.”
  – Kimberly (05:14)

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Timestamps - Important Segments

• 01:15: Kimberly introduces her proposal idea and background
• 02:03: Relationship timeline; reflections on parents' marriage
• 03:28: Host expresses concern about proposing in front of family
• 04:55: Kimberly outlines why she won’t wait for Steven to propose
• 05:00: Discussion of the “mangagement” ring
• 05:35: Listener Melissa calls with quick-marriage success story
• 05:51: Host focuses on Steven’s beliefs about marriage
• 07:22–07:32: Ultimatum discussion; questioning public proposals
• 08:54: Hosts summarize audience split

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Tone & Style

The exchange is lively, warm, and pragmatic. The hosts balance humor (“mangagement ring,” “creative ultimatum”) with genuine concern for Kimberly’s well-being. The style is conversational but occasionally pointed, especially around the risks of public proposals and making major life choices for love.

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This episode offers an engaging, candid look at evolving relationship traditions, highlighting the complexities of love, commitment, and gender roles—all through the lens of one listener’s bold plan.

Transcript

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[Radio Host]

THE Fruit show hi, Kimberly. Hi. Hi. How are you today?

[Caller Kimberly]

I am doing great.

[Radio Host]

You are ready to get engaged?

[Caller Kimberly]

Yes, I am.

[Radio Co-host]

Congratulations.

[Radio Host]

She's taking matters into her own hands.

[Radio Co-host]

Well, I go ahead. But I have friends that did a similar thing and are still married and very successful.

[Caller Kimberly]

That's great. I mean, you know, it's interesting because he had said before that he wasn't the marrying type and you know, the whole like, oh, you know, a piece of paper, just a piece of paper. You know, if you're together, you're together. But I really feel, I mean, with 100% certainty that he's going to say yes. I mean, he's the love of my life and he's terrific and I'm really excited now.

[Radio Host]

How long have y' all been going out?

[Caller Kimberly]

Probably almost a year and four months.

[Weight Watchers Announcer]

That's still pretty early.

[Caller Kimberly]

Well, you know, I think it really depends because I know like my, my parents were. They knew each other for two Months before they got married. And they've been together for 26 years.

[Radio Host]

Okay.

[Caller Kimberly]

So, you know, I mean, I think that, you know, it really depends on the couple, definitely. And one of the biggest factors that really made me think that this was not just a fantasy but could actually happen was he moved. He's originally from Connecticut and he moved out here, like I said, a little over a year ago. And we started to date. And after about nine months, his job called him back to move back. And I thought, you know, I've been in long distance relationships before. Like when I was in college and didn't work out well. And I told myself, I was like, you know, what if things are going really strong still after six months? This is something I said to myself. I didn't say it to him. I said, you know, what if after six months of being long distance and apart and it's still going strong, I'm going to ask him and it's been great.

[Radio Host]

And you're that sure he's going to say yes? You're that sure he's going to be as excited as you are?

[Caller Kimberly]

I am positive. Well, the excitement, like, I don't know if he's like a scream and jump up and down like a, like a girl would. I think he's definitely gonna say yes. I mean, his. This is gonna be in front of his whole family too.

[Radio Co-host]

Now that is the part that I'm nervous about.

[Radio Host]

That's how we fit the branches.

[Weight Watchers Announcer]

A lot of parts I'm nervous about.

[Radio Co-host]

I mean, I'm not, I'm not, you know, I'm not such a traditionalist, obviously that I don't agree with you proposing to him. However, doing it in front of his family, that my understanding is you've never met.

[Caller Kimberly]

No, I've talked to his mom many, many times and like his sister on the telephone, but we've never actually met in person. So he's been out here to see me a few times. But he invited me this year to go to his family's house. And why wouldn't you just wait for him to ask you? Well, like I said, I mean, he'd always said that it was just a piece of paper, that it didn't matter to him. But I think what my thinking is, and I feel like I said really, really strongly that he's going to say yes, is that he'll realize that it's important to me and to my family. Like, I just don't want to, I don't want to just move in with him. And I really love this guy, I'm willing to, like, move halfway, you know, across the country, you know, to be with this guy. And if I'm going to do that, I don't want it to be just because he's my boyfriend. You know, I want definitely more of a commitment. And it's. When you were talking about, like, meeting his family on Christmas Eve, I'm actually gonna talk to his dad and ask his permission if, you know, how he feels about it.

[Weight Watchers Announcer]

So you're going like, traditional roles just flip flopped.

[Caller Kimberly]

Yeah, yeah, a little flip flopped.

[Weight Watchers Announcer]

Are you going to propose with a ring?

[Caller Kimberly]

Actually, yeah. You know, it's funny because when I was shopping, I hadn't ever heard this term before, but they called it a man gagement ring and mangagements. That's really funny. It's a funny term, but it's a really beautiful, like, titanium band. So it doesn't. It could just be, like, a regular decorative ring, too. Like, I don't know if he'd want that for his wedding ring, but I definitely wanted to get him something that was, you know, masculine and strong and represented what I felt was the strength of our relationship.

[Radio Host]

Hold on one second here. Good morning, Melissa. You're on Q100.

[Caller Kimberly]

Hey, guys. I love your show.

[Radio Host]

Thank you.

[Caller Kimberly]

I wanted to tell the caller that it's really not too early. I had a lot of my friends tell me that was too early, but it wasn't. We met April 2008, and we were married June 13 this year.

[Radio Co-host]

Wow, that was real fast.

[Radio Host]

See here, it's not the timing of it that scares me a little bit. It's the statement that. And I would have to see it or hear it for myself. His take on marriage sounds very different than yours. His take is it's just a piece of paper. I don't need that to be with you for the rest of my life. Now, I don't know how strongly he believes in that or not. There are guys that will absolutely, under no circumstance around the world. Susie was dating a guy for a long time that absolutely this was part of his world, that if you want to be with me, I can love you forever, we can have children. But as far as marriage goes, that's just not for me. And it sounds to me like he's telling you it's just a piece of paper. It doesn't mean anything to me.

[Caller Kimberly]

Well, that's why, like I said, I mean, he. Every step of our relationship, he's been really supportive. He's like, he's not one of those guys who's like, afraid to talk about his feelings, you know? And I know he loves me, and I'm really, really thinking that when he realizes that how important it is to me, that if it is just a piece of paper, it won't be that big a deal. I mean, I don't care about prenups or any of that. You know, like, my. I come from a really good family, so I don't need, you know, money or any of that stuff. That has nothing to do with it. So I think that's why most men are afraid of getting married. They're so worried.

[Radio Host]

There's just enough gray area here to make me think, you certainly shouldn't be a public proposal, and it shouldn't be in front of the state.

[Radio Co-host]

Well, it should never be a public proposal in front of the family that you meet for the first time, man or woman. But I think that's a good point to me, though. It's like a more creative ultimatum. Because, I mean, my only other suggestion is that if you don't feel comfortable moving and living with him as a girlfriend, then the only other option is you're gonna have to give him the ultimatum. Either I am married to you or I don't go.

[Caller Kimberly]

Well, I mean, it's. That sounds pretty harsh, but I guess it's true, because I don't want to do that. You know? I mean, he moved out here for work. We met here. So this is my life. And when he's here with me, it's fine, because I have my family, I have my friends, I have my career. I have all of that. But if I move back east, where I don't know anybody, I'm sure he's going to understand because we've talked about this, about me moving. I'm a pharmaceutical rep, so I can pretty much work anywhere. But he works. I won't say what company he works for, but he works for a very big company, and he has, you know, a lifetime career ahead of him. With this company, I can move around from company to company. It's not that big a deal, But I don't want to give up my friends, my family, like, the whole life that I've had, you know, just to go see some girlfriend. Not that, you know, I enjoy my relationship with them, but I definitely want to take it another step.

[Radio Host]

Kimberly, let me put you on hold for a second, because a whole bunch of people want to give you their opinion on it.

[Caller Kimberly]

It's not a problem.

[Radio Host]

It's about split right now, about half. People saying, no way. It's just the wrong place, wrong times, just not right. And the other saying just absolutely go for it. Why not? Seriously?

[Mike]

50 50.

[Radio Host]

About 50 50.

[Mike]

Is that what our audience is about?

[Radio Host]

50 50? It's always 50 50. Shocker.

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