Vault: Is She About To Make A Mistake With The Guy She's Dating?

Summary

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The Bert Show — Vault: Is She About To Make A Mistake With The Guy She's Dating?

Air Date: January 8, 2026
Host: The Bert Show Cast (Bert, Kristin, Abby, Cassie, Tommy, et al.)

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Episode Overview

In this episode, The Bert Show team catches up with Dana, a 27-year-old woman who, after never having dated before, has become involved in a serious relationship with Matlock—a 58-year-old friend of her parents. The hosts and listeners weigh in on Dana's rapid romance, exploring concerns about age differences, the nature of first love, skepticism from friends and family, and whether Dana is making the right decision as her relationship accelerates.

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Key Discussion Points & Insights

1. Dana’s Unusual First Relationship

• Dana, 27, had never been on a date before meeting Matlock (58), who is a friend of her parents.
• She describes being "so in love" and spending time with him nightly. The relationship quickly became serious—including talks of moving in, plans for a vacation, and the gift of a promise ring.
  • Quote (Dana, 02:23):
    "Honestly, I really didn't think I would be where I am right now. Just from one date... I'm so in love with him."

2. The Relationship’s Rapid Progression

• Vacation to the Bahamas already planned over Memorial Day.
• Promise ring given by Matlock and discussions about moving in together as her lease ends in June.
  • Quote (Dana, 04:15):
    "Everything is so great... He's even given me a promise ring, which is just incredible."
• Dana's parents remain skeptical and believe the relationship may be a "phase" (05:33).

3. Intimacy and Daily Life

• Dana recounts being at Matlock's home every night and states the intimacy is “great” (03:32).
• She insists the relationship is mutually caring and not one-sided in decision-making.
  • Quote (Dana, 07:22):
    "...when it comes to making decisions, I put my two cents worth in... I don't feel like I'm being led in any direction by him."

4. Skepticism from Friends and Hosts

• Dana’s friends are divided between supporting her happiness and cautioning her about heartbreak (08:25).
• The hosts debate whether the central issue is the age gap or the fact that it's Dana's first relationship.
  • Quote (Host B, 06:38):
    "I feel like if it was two 27-year-olds... that's just them being infatuated and not thinking clearly. But... I just feel like he's taking advantage of her naivety."
• Concerns are raised about potential power imbalances and whether Dana is trading naivety for security.

5. Financial & Domestic Concerns

• Listeners (e.g., Terry, 10:10) call in to speculate Dana may be after Matlock's money, but she refutes being a “gold digger,” mentioning her job as a clothing buyer and her financial independence (10:29).
• Hosts raise questions about whether moving in means she’ll become a caretaker (09:15), but Dana asserts Matlock is self-sufficient.

6. Promise Ring Controversy

• Promise rings become a source of lighthearted debate.
  • Quote (Host B, 11:36):
    “I think promise rings are full of crap.”
  • Quote (Host C, 11:47):
    “It's a promise. It's what you give when you're not [old] enough to get engaged.”
• The cast jokes about the appropriateness and meaning of a promise ring given by a 58-year-old.

7. Listener Perspectives

• Some listeners phone in, expressing both support and skepticism.
  • Quote (Caller, 11:01):
    "I just wanted to say that I support her and... when you find love, I think you should hold on to it."

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Notable Quotes & Memorable Moments

• Dana on falling in love:
  “I just feel like... I definitely have an amazing thing here.” (02:55)
• Host B on skepticism:
  “Are you sure he doesn't... need somebody to take care of him?... I'm just wondering if the roles are going to change a little bit once you get in there.” (08:45)
• Dana on domestic roles:
  “He actually makes things for me and I make things for him... everything else he does himself.” (09:38)
• Promise ring skepticism:
  Host B: “I think promise rings are full of crap.” (11:36)
  Host C: “Promise rings are okay if you're 16.” (11:40)

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Timestamps for Important Segments

• [01:41] — Start of Dana's story recap
• [02:23] — Dana’s reflections on her new relationship
• [03:32] — Discussion of intimacy
• [04:15] — News of promise ring and moving-in talk
• [05:57] — Discussion of parents’ reaction
• [06:35] — Hosts debate issues: age or lack of dating experience?
• [08:45] — Host raises concerns about power dynamic and caretaking
• [10:10] — Listener accuses Dana of being after money; Dana responds
• [11:36] — Promise ring debate

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Tone and Final Thoughts

The episode is playful yet probing, blending concern with lighthearted teasing. The cast routinely challenges Dana, but she remains insistent about her agency and happiness. Listeners and hosts alike are sharply divided—some warning of heartbreak and manipulation, others rooting for unconventional love.

To Be Continued: The Bert Show promises a follow-up with Dana in two weeks to see if things have changed as her relationship and vacation plans move ahead.

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Transcript

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[C]

Get it? The Birch Show. All right, let's get back to Dana here because it's. We've been talking to Dana now for a couple of months, correct?

[B]

Correct. I mean, she first came to us because she said she was 27 years old and she'd never been on a date before, ever, ever, ever in her life. And so she was gonna go on her first date with a man who just happened to be 58 and a friend of her parents.

[C]

Yeah.

[B]

And so she ended up going out with him and she's still going out with him.

[C]

Things have progressed. I mean, she's fallen for this guy. It's the first dude she's ever gone out with, you know, so we talked to her about two weeks ago. And let's just all get caught up. Here's about 60 seconds of the conversation we had with her two weeks ago.

[D]

Honestly, I really didn't. That I would be where I am right now. Just from one day, I have spent, like, we hang out every night at his house, and it's getting more serious and more serious, and I just. Everything is so amazing right now. I really didn't believe that I would get all of this out of one date. And I just. I'm so in love with him. And we. He actually. This is amazing, too. He's actually planning a vacation for us in Atlantis at the Bahamas.

[B]

Wow.

[D]

So I just. I mean, it's so amazing that he's so giving and he's so sweet to me, and I just. I mean, I never would have imagined I would be where I am right now. And that's why I didn't take a lot of people's advice when they were saying, you should really not do this because he's older. But I just. Like I said, for the first time I met him, he was just so easy to talk to, and I had such a great time with him, and he takes such good care of me, and he really just wants to make me happy. And so I just feel like, you know, that I definitely have an amazing thing here that's kind of where I'm at.

[B]

How's the intimacy department?

[D]

It's great. I mean, I'm over at his house every night, so it's kind of a.

[C]

Nice visual right there. You guys want to take any kind of predictions?

[B]

I think. I mean, I think they're still going well because they have a vacation, from what I remember, planned here soon. So I think everything will be fine until that vacation. I wonder if she's met any of his friends or if he's met any of her friends. That's what I'm curious about.

[C]

She has cheated on him with a friend of hers. Grandfather. Good morning, Dana.

[D]

Hi. Good morning.

[C]

How are you?

[D]

I'm good. How are you doing?

[C]

I can instantly tell with the excitement of your voice that things are going very well with Matlock.

[D]

Yes, they are. Definitely. Definitely. Everything is so great. And I know everybody's been really skeptical, and people are wondering what's going on, but everything is absolutely great. Like I said a couple of weeks ago, I really didn't imagine that I would get everything I got out of one date. I'm so happy right now. I really am. I'm still happy. Everything's great. My lease is actually up in June on my apartment and we've been talking about moving in together and he's even given me a promise ring, which is just incredible. What?

[C]

58 year old man giving you a promise ring?

[D]

Yes, yes.

[B]

You're going to move in with him in June?

[D]

We're talking about it. I'm seeing if it's, you know, we're just kind of discussing back and forth, just some options and we just, we've talked about it. So I'm leaning towards doing it. Yes.

[B]

When, when is your vacation with him?

[D]

The vacation is over Memorial Day.

[C]

Do your parents have any idea of how fast things are moving?

[D]

They know that I really, really like him and that I'm falling in love with him. Yes.

[C]

And what's their reaction been? Because initially they said maybe you want to slow things down here, maybe this isn't right.

[D]

I think that they still think that it's just going to be kind of a first date issue and then it'll all fizzle out. I think that's what they think. I think that's what they're hoping for. But, but I've been really honest with them and telling him that I'm really falling in love with him and you know, that I really like him. So we'll see. I mean, they think it's just going to be a phase and that, you know, I'll get over it.

[B]

Do they know that you're going to move in with him?

[D]

No, because we're still discussing it. So I, you know, once we get things situated completely, then I'll tell them. But since we're just kind of discussing it, I'm not going to tell them yet.

[B]

What is it? What does he do for a living?

[D]

He sells stock, things like that. He used to run a company when he was younger. It was a private owned business, but now he's into stock stock trading.

[C]

So I mean, he's doing well for himself. I mean, you can see yourself very, very secure financially with this guy. What's our biggest problem with this? Is it his age or is it the fact that this is her first relationship? The first relationship.

[B]

I think it's the first relationship. I mean, both.

[C]

Well, what if he was younger? Wouldn't we be going, oh my God, that's so cool you found love with your first relationship.

[B]

If he's progressing this fast. But I think the added element of his age just makes it a little more bothersome for me. But. Because I, because I feel like if it was two 27 year olds who were getting all caught up in it and thinking about moving in and stuff. That's just them being infatuated and not thinking clearly. But I just. He's a 58 year old man who, I don't know, I just feel like he's taking advantage of her naivety.

[C]

And this is based on absolutely nothing really that you've said. But I just imagine this relationship kind of being him dictating everything and you just being very accommodating because you're just so happy to be in any relationship.

[D]

I don't really think so. I mean, I definitely, when it comes to making decisions and things like that, I put my two cents worth in. I mean, even the moving in situation. He suggested if I wanted to move in with him, you know, that I could. And I'm the one that's kind of waiting to see if I should do that or not. So I don't feel like I'm being led in any direction by him. I mean, he's just great. Like, you know, he gave me a promise ring and you know, he's given me time to think about that and.

[C]

He gave me a what promise?

[B]

A promise ring, Yeah. I have a question about your friends. Have your friends met him and have you met his friends?

[D]

I've met a couple of his friends. Just. I mean, I know them because they hang around my parents and things like that. And I've met one of his really good friends since we've been dating. And then the other friends I already know because again, he was friends with.

[B]

My parents first and what about him meeting your friends?

[D]

No, I've just told them about him.

[B]

Everything. About him?

[D]

Yeah, about his age and everything like that. And most of them are skeptical as well. I have two friends that are really happy for me and think that it sounds great and the way that he takes care of me is amazing. But then I have other friends that really, you know, that are just skeptical about it and think that I'm gonna get my heart broken.

[B]

Well, I have. I'm probably in the skeptical camp, I gotta be honest, because I just want to plant a seed. Are you sure that he doesn't. He's not at a point in his life where he needs somebody to take care of him? Like, are you sure that once you move in with him that the tide's not gonna turn a little bit and he's. I mean, he's giving you promise ring, he's gonna take you on vacation. He' that suggested you move in with them after such a short period of time. And I'm just curious. I mean, here's a 58 year old man's never been married. I'm just wondering if the roles are going to change a little bit once you get in there.

[D]

I don't, I don't think he's at that stage of his life yet. I mean, I maybe like when he's in his 70s or something, but I don't see that he's in that stage of his life because I didn't mean.

[B]

That he's elderly and disabled. I mean, like he, you know, I mean, he's an older man who is, you know, I mean, you're gonna end up. I'm just wondering if you're end up doing all these things for him domestically. Yes.

[D]

I don't know. I don't do them now. I mean, like I said, the only thing I, you know, that I do domestically is if we decide to cook anything. He actually makes things for me and I make things for him. You know, I'll do like the dishes and stuff. But I mean, everything else he does himself. So I don't, I don't know, I don't think that that's. And his agenda, but I mean, because he's so used to doing things for himself that by this point I don't think that's what he's counting on.

[C]

All right, the skeptics are calling in, of course. Good morning, Terry.

[B]

Yeah.

[D]

I am having a problem buying this girl's story. I think she is not as naive as you think and I think she might be after the poor man's money.

[B]

You think he's the victim in this?

[C]

She thinks he's a. She thinks that Dana's a gold digger. Yeah. Hey, Dana, what do you do for a living? Are you supporting yourself now?

[D]

Yes, I do. I work at a clothing store and I help do. Excuse me. My voice is going in and out. I help do buying for them and I'm a buyer. I look at different clothing lines for them. I'm doing well. I don't need anybody to support me. And obviously I've never thought about being a gold digger or going after men because I've never had a relationship. So if I wanted to be a gold digger, I could have done that, you know, years ago. Not what I'm after.

[C]

Good morning. You're on all the hits. Q100.

[D]

Hey.

[C]

Hi.

[D]

I just wanted to say that I love your show and I just want to say that I support her and in her happiness and everything, but I wouldn't, you know, go with a guy that was 31 years older than Me, but whatever, you know, whatever makes her happy. I think, you know, when you find love, I think you should hold on to it. You know, it doesn't matter if it's the first person she dates, you know, just because it's that, I don't think she'll let it go.

[C]

So love is found in really, really strange places and really, really strange circumstances. I guess that's what we're hearing.

[B]

But I would like to say this, that I think promise rings are full of crap.

[C]

Promise rings are okay if you're 16. What do you mean they're full of crap?

[B]

They're just crap. What does that mean?

[C]

Because it's not an engagement ring.

[B]

I mean, what is that?

[C]

It's a promise. It's what you give when you're not.

[D]

Enough to get engaged.

[B]

I don't know. I think it's crap.

[C]

And he's plenty. I don't know what it says.

[B]

What is he promising you? Like, I don't. What's the significance of the ring?

[C]

It's a promise ring that you get when you. When you are not old enough to get engaged. It's right after prom? Generally, yes. Although I just found out our intern, Mary Kate, has one, so she's graduating and going to prom here in a couple of weeks also. All right, Dana. Well, I'm not exactly sure where to go with this, except to say we'll check in again with you in two weeks. I mean, it seems like every time we talk, this thing is, like, progressing in dog years, you know?

[B]

Well, in a couple weeks, you'll be getting ready for your trip, so. Yeah, we'll see how. Yeah, we'll see how that's going.

[D]

Okay.

[B]

Okay.

[C]

Okay.

[D]

Okay. Thanks, guys.

[B]

Thanks, Dana.

[C]

Bye. Bye.

[D]

Okay, bye.

[C]

See ya. Get it. The Bird Show. With endless scroll algorithms and AI flooding feeds, podcasting stands out. They're sought, not served. Audiences actively choose to hear trusted voices on topics they care about. In fact, 72% of listeners say podcasts shape cultural conversations. For marketers, that means podcasts shift brand perception like no other channel. Acast's podcast Pulse2025 report has the proof. Get all the [e-mail].