Vault: These Men Had No Idea The Women They Were Dating Were Way Younger Than Them

Summary

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Podcast Summary: The Bert Show

Episode: Vault: These Men Had No Idea The Women They Were Dating Were Way Younger Than Them
Date: March 23, 2026

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Overview

This episode of The Bert Show dives into the controversial and complex world of age-gap dating—specifically focusing on older men dating much younger women. The hosts invite callers to share their real-life experiences, unpack the psychology and social implications, and candidly react to the potential power imbalances and ethical questions that arise in these relationships. The discussion features a humorous yet honest tone, tackling awkward stories, confessions, and the uncomfortable realities behind significant age differences in dating.

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Key Discussion Points & Insights

1. Setting the Stage: Age-Gap Relationships in Pop Culture

• The hosts reference real-life celebrity relationships that have caused public uproar, including Paul Walker (then 35) dating a 19-year-old and Milo Ventimiglia (31) with Hayden Panettiere (19) ([01:00]).
• The segment transitions to inviting listeners to share if they've dated significantly younger women, highlighting societal double standards and stigmas.

2. Caller Stories: First-Person Experiences

Caller "Johnny" (Voice Disguised)

Age Difference: 41M / 22F; Relationship started when she was 18, he was 38 ([01:44])

• Relationship Start: "At first it was a sexual relationship and it turned into something a little bit more." – Johnny ([02:08])
• Meeting Story: Met through mutual friends while Johnny was seeing someone else ([02:59]).
• Hosts' Reactions:
  • Skepticism and discomfort about the age gap and what an 18-year-old and 38-year-old could have in common.
  • “I wouldn’t even give myself the license to call an 18 year old. That just, it just seems too… It's too young for me.” — Main Host ([03:29])
• Relationship Dynamics:
  • Johnny claims the relationship grew “deeper” over time. She’s in college; he’s in the corporate world ([04:13]).
  • They have an open agreement: “I do what I want to when I'm here, she does what she wants to when she's there.” — Johnny ([04:48]).
  • Hosts question if the girlfriend knows about dating others; Johnny reveals she accidentally exposed another romantic call ([05:31]).
• Notable Moment: “I know that she's seeing other people because one time we were on the phone and she got another phone call and she thought she had clicked over and she didn't. And I just sit there and listen to the conversation.” — Johnny ([05:31])
  • Embarrassed reaction from hosts and callers: “What a great reaction. I guess she did.” — Main Host ([05:58])

Caller "Dwayne" (No Disguise)

Age Difference: Met at 14F/18M; Now 27M/23F, married with children ([06:46])

• How They Met: Dwayne was 18, just started college; she was 14 ([07:03]).
• Backstory: Actually met when she was 12 and he was 16—Dwayne clarifies they began dating at 14/18 ([07:19]).
• Outlook & Reflection: "We had to get married when I was 19. She was 15 because she got pregnant, and we've been married for nine years now." — Dwayne ([07:40]).
• Hosts’ Response: There’s acknowledgement that while it “started young,” Dwayne “manned up” by marrying and supporting her ([07:46]). A debate ensues about “puppy love” vs. problematic age gaps.
• Societal Perspective: "If she's 14 and you're out of high school, that's hands off." — Main Host ([08:04])
• Hosts Discuss Stigma: Joking about returning to prom as a college student—“It looks pretty pathetic.” ([08:16])

Caller "Randy"

Age Difference: 27M/17F; Relationship evolved after meeting post-military ([08:28])

• Initial Meeting: 27-year-old ex-military, started “hanging out” with a waitress next door who was 17 ([08:32]).
• Terminology Critique: Randy describes her as a “little girl,” leading to instant discomfort—“It's kind of gross the way you said that…” — Co-host ([08:48])
• Relationship Course: They dated for two years before getting married; the marriage lasted “about four more years” ([09:02], [09:22]).
• Twist Ending: Now, Randy is dating a woman 12 years his senior — “She's telling somebody right now, hey, met me a little boy.” — Show Host ([09:34])

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Notable Quotes & Memorable Moments

• On Age-Gap Relationships:
  “I wouldn’t even give myself the license to call an 18 year old. That just, it just seems too… It's too young for me.” — Main Host ([03:29])

• On Relationship Agreements:
  “I know that she's seeing other people because one time we were on the phone and she got another phone call and she thought she had clicked over and she didn't.” — Johnny ([05:31])

• On Early Relationships & Responsibility:
  “We had to get married when I was 19. She was 15 because she got pregnant, and we've been married for nine years now.” — Dwayne ([07:40])

• On Social Perception:
  "If she's 14 and you're out of high school, that's hands off." — Main Host ([08:04])

• Funny/Self-Aware Reaction:
  “You just referred to her as a little girl… it’s kind of gross the way you said that.” — Co-host ([08:48])

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Important Segment Timestamps

• [01:00–01:31]: Introduction to age-gap relationships with celebrity examples.
• [01:44–06:07]: Caller "Johnny" details his relationship with a much younger woman.
• [06:46–07:52]: Caller "Dwayne" shares story of marrying his teenage girlfriend.
• [08:28–09:38]: Caller "Randy" recounts dating a 17-year-old at 27 and subsequent relationships.

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Tone and Takeaways

• The hosts maintain a mix of frank honesty, humor, and discomfort, highlighting the complexity and social awkwardness of large age-gap relationships.
• The episode doesn’t shy away from pointing out questionable behavior ("little girl" remark), yet also recognizes different life circumstances, such as relationships that endure despite their controversial beginnings.
• Callers illustrate a range of motivations and outcomes—from open relationships to marriages with kids—while the hosts remind listeners of the ethical and emotional stakes.

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Summary:
This episode provides candid, sometimes cringeworthy, and thought-provoking perspectives on significant age gaps in dating. While the conversation is often light and laced with humor, moments of genuine discomfort and challenge punctuate the discussion, making listeners reflect on the boundaries and realities of romance across generations.

Transcript

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[Main Host]

Listen, it's the vert show. Before we completely separate ourselves from this here, Paul Walker, the dude from Fast and the Furious, really good looking blonde dude. I mean, model, 35 years old, just got engaged to a 19 year old. But they've been dating three years, since she was 16 years old. And then you got that Vito Lasagna guy.

[Co-host 1]

Milo Ventimiglia.

[Main Host]

Yeah, that guy.

[Co-host 1]

He's 31. And Hayden Panettiere is 19. But they just.

[Main Host]

So we were talking to our virtual listeners that were underage and dating older guys, and now we're gonna go the other way with it. Older guys dating younger women. Okay, that's who Wendy wanted to hear from.

[Co-host 2]

I do. I want to get into the mindset of what they're thinking.

[Main Host]

He's gonna put himself on the voice disguiser. And his name is Johnny. Hey, Johnny, how you doing? Good, man. How are you?

[Caller Johnny]

I'm doing okay.

[Main Host]

All right. Is this a current relationship or a past relationship?

[Caller Johnny]

It is a current relationship.

[Main Host]

Current relationship.

[Co-host 2]

And you are how old?

[Caller Johnny]

I am 41 and she is 22.

[Main Host]

Okay, is this a purely a sexual relationship or is there something deeper going on here?

[Caller Johnny]

It's something deeper.

[Main Host]

Something.

[Caller Johnny]

At first it was a sexual relationship and it turned into something a little bit more.

[Co-host 3]

How long have y' all been dating?

[Caller Johnny]

Three years.

[Co-host 3]

Three years.

[Co-host 1]

Wait, and why are you on the voice disguiser then?

[Show Host]

Well, because when he started, it was a felony.

[Main Host]

Now he's 18. She was 18, right?

[Caller Johnny]

Yeah, she was 18.

[Show Host]

She's 18 now or she was 18.

[Caller Johnny]

She was 18.

[Show Host]

Okay.

[Main Host]

And you were 38 at the time?

[Caller Johnny]

Yeah.

[Main Host]

So what could a 38 year old do, possibly, possibly have in common with an 18 year old?

[Caller Johnny]

Well, like I said, it started out as a sexual thing and it turned into something more after we got to know each other a little bit more. It turned into something a little bit

[Co-host 3]

more because she's mature for her age.

[Caller Johnny]

Yeah.

[Co-host 1]

How did y' all meet?

[Caller Johnny]

When we met, I actually was actually seeing somebody else. And we met because a friend of mine that she was seeing, we were going to have a little get together.

[Co-host 1]

Friend of mine that she was seeing. So you knew her old boyfriend?

[Caller Johnny]

Yeah.

[Main Host]

And he was how old?

[Caller Johnny]

I'm not quite sure how old he was. He was a lot younger than I was.

[Main Host]

In his 30s, in his late 20s, teens, probably.

[Caller Johnny]

Late 20s, early 30s.

[Main Host]

All right, so she has this history. I wouldn't even give myself the license. Here's the thing. You and I are roughly the same age. I wouldn't even give myself the license to call an 18 year old. That just, it just seems too. It's too young for me.

[Show Host]

Well, here, let's roll. Phone rings and then somebody answers.

[Caller Dwayne]

Hello?

[Show Host]

Hi, can I talk to, I don't know, what's an 18 year old's name?

[Co-host 2]

Susie.

[Show Host]

Can I talk to Susie, please? Yeah, this is Susie. Mom, hang up. It's for me.

[Caller Johnny]

Mom.

[Co-host 1]

That's freaky.

[Main Host]

And on a day to day while you guys are in this relationship together, you're not bored out of your mind?

[Caller Johnny]

No, not at all.

[Show Host]

What do you guys talk about?

[Caller Johnny]

Yeah, we talk about everything. She is actually in college right now. This is her last year.

[Co-host 1]

Oh, God.

[Co-host 2]

And you're like corporate in the corporate world?

[Caller Johnny]

Well, yeah, pretty much.

[Co-host 2]

Oh, I just, I don't.

[Co-host 3]

I just feel it is, it is robbing her of her. I mean, I.

[Co-host 2]

What?

[Co-host 3]

She's done it to herself though. But she's robbed herself of any true experience as a college student. Because I think for whatever reason she is in a phase in which she needs to have that mature, quote unquote male figure in her life. But I guarantee that, yeah, she's. She's gonna grow out of this.

[Caller Johnny]

Well, I don't think so because, I mean, I let her do what she wants to do and she's away. I mean, you know, I do what I want to when I'm here, she does what she wants to when she's there.

[Main Host]

All right, so you have an agreement with her that she can date other guys while she's at school. And you're allowed to date other women when she's not around?

[Caller Johnny]

Yeah.

[Co-host 2]

Does she know that?

[Caller Dwayne]

Yeah.

[Co-host 2]

Are you sure?

[Caller Johnny]

Oh, crap.

[Show Host]

I forgot to tell you that.

[Co-host 1]

And you're not the jealous type.

[Caller Johnny]

No, I'm not.

[Main Host]

Are you just her sugar daddy?

[Caller Johnny]

No, I'm not. Definitely not a sugar daddy.

[Main Host]

Okay.

[Caller Dwayne]

All right.

[Main Host]

You wanted to talk to the older guy dating a younger woman, so there you have it.

[Co-host 1]

I just don't think.

[Co-host 2]

I just don't think she knows that she can see other people. Because I would be naive at. Even at 23 if some older man

[Caller Johnny]

said, matter of fact, I know that she's seeing other people because one time we were on the phone and she got another phone call and she thought she had clicked over and she didn't. And I just sit there and listen to the conversation.

[Main Host]

Oh, no. What were they saying?

[Caller Johnny]

She was just talking about how she loved and this, that, the other. And you know. And I finally went and said, and you know who you're talking to, and she hung up. Oops.

[Co-host 3]

Oops.

[Co-host 1]

That's so funny.

[Main Host]

What a great reaction. I guess she did. All right, Johnny, thanks for calling, man.

[Caller Dwayne]

No kidding.

[Caller Johnny]

See you.

[Main Host]

Oh, what do I do? Hang up. That is the ultimate panic right there.

[Co-host 3]

Yeah, and I wish flee.

[Main Host]

I can't flee fast enough.

[Co-host 3]

I wish we could do that in person where we just turn around and run away.

[Show Host]

Why don't we try that? Like, why don't next time we're in an uncomfortable situation, we just get up and walk away?

[Main Host]

Yeah, we're gonna have Neo in studio here for his concert. If one of the questions gets uncomfort, I think we just all get up and we run out of time.

[Co-host 3]

When is he coming?

[Main Host]

I think next week.

[Co-host 2]

Oh, super.

[Main Host]

Hey, Dwayne. Good morning.

[Caller Dwayne]

Good morning.

[Main Host]

Good morning. You're on the voice disguiser. Do you want to be?

[Caller Johnny]

Nah.

[Main Host]

Okay.

[Caller Dwayne]

Nah.

[Main Host]

You are. You are how old? And you are dating somebody how old?

[Caller Dwayne]

Well, currently I'm 27 and my wife is 23.

[Main Host]

27. 23.

[Caller Dwayne]

When we got together, she was 14 and I was 18. Just started college.

[Main Host]

14 and 18, that sliding scale we're always talking about.

[Co-host 1]

Yeah, there's a little bit of a difference there. But you were still in high school, right?

[Caller Dwayne]

No, I was just starting college.

[Co-host 1]

Starting college.

[Caller Dwayne]

And we actually met when she was 12 and I was 16.

[Main Host]

You guys didn't start hanging out though, when she was 12 and you were 16?

[Caller Dwayne]

I was actually dating her sister's best friend.

[Co-host 1]

Okay. Okay, to me, that still sounds like young love. I mean, that age difference. There's definitely a gap there with the 14 to 18 thing, for sure.

[Caller Dwayne]

We had to get married when I was 19. She was 15 because she got pregnant, and we've been married for nine years now.

[Co-host 1]

Well, at least you manned up making it work.

[Co-host 3]

Absolutely.

[Main Host]

All right, thank you for the call.

[Caller Dwayne]

Yeah.

[Co-host 3]

I'm going to reward him for staying.

[Co-host 1]

Absolutely. I mean, it does start young, but I feel like when you're young like that, and it's kind of like that puppy love thing, I don't think there's as much wrong with it. Remember that. What was the case?

[Caller Dwayne]

I don't know, man.

[Main Host]

When you're. If she is 14 and you're out of high school, that's hands off. Yes, that's hands.

[Show Host]

You don't want it. Like, you don't want to be the guy coming back to junior prom from college.

[Main Host]

You're a freshman in college, and you're. And you tell your buddies that you're dating a freshman in high school. That looks pretty pathetic.

[Co-host 3]

Not as pathetic as the 30 and 40 year olds, though.

[Main Host]

Hey, Randy, go ahead. You'll be the last call on this. What's happening?

[Caller Dwayne]

Not a whole lot.

[Co-host 2]

I dated.

[Caller Dwayne]

I was 27. I just spent 10 years in service and got out and was working at a sporting goods shop. Met a little girl that worked at a restaurant next door. We started dating. She was 17, just out of high school.

[Co-host 1]

Yeah, you just said little girl.

[Main Host]

You just referred to her as a little girl.

[Caller Johnny]

Just so you know.

[Show Host]

It's kind of gross the way you said that. In case you're wondering,

[Caller Dwayne]

a younger girl.

[Main Host]

Okay, little girl. And you met her. She was 17 years old, you were 27, and you decided to go for it.

[Caller Dwayne]

Yeah, I mean, we just started out as, you know, just dating and kind of hanging out because, like I said, I just gotten out of the service and didn't know a whole lot of people where I was at. And we dated for about two years before we. We did get married, and then it passed about four more years after that.

[Co-host 2]

All right, well, you're still married.

[Caller Johnny]

No, no. Yeah.

[Caller Dwayne]

Now, the ironic thing is I'm dating one that's 12 years older than me.

[Show Host]

She's telling somebody right now, hey, met me a little boy.

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