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The Bert Show

Vault: Massey's New 20 Year-Old Virgin Date

The Bert Show

The Bert Show

Entertainment News, Society & Culture, Comedy, News

4.14.4K Ratings

🗓️ 7 November 2025

⏱️ 14 minutes

🧾️ Download transcript

Summary

Vault: Massey's New 20 Year-Old Virgin Date

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Transcript

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0:00.0

You're on the Bert Show.

0:02.1

Jamie Massey here.

0:03.7

We have told you before that the history of Jamie Massey's dating life is not sad.

0:11.4

It's laughable.

0:12.9

No, it's pretty sad too.

0:14.5

But it gets to a point where it's so sad that you just have to embrace it and laugh about it.

0:18.7

Well, it's kind of dysfunctional.

0:20.2

I can't figure out why. Like, I don't know if you have a type or, like, something that attracts you to these guys, that they just end up being losers. Yeah, I definitely have been on a run. Well, isn't like the true definition of, like, craziness is when you do the same things over and over and over again and you expect different results right well at least Jamie Massey here is trying

0:40.9

something new why don't you tell them what you're trying Jamie because married guys aren't

0:45.9

working out for you yeah there was the date with the guy who told me in the middle of dinner

0:49.8

he was married there was the guy that stiffed me for the chick. And so, you know, gone a little

0:57.5

younger. How old are you? Yeah, yeah, exactly. First of all, I'm 28 years old and I'm, I threw a

1:03.6

friend of a friend was, I met this boy and he's a boy. Literally, dude. He's not, no, he's not a boy.

1:09.8

You were walking in to see fires out of the Caribbean and he was there to see cars. Shut up. And she was going to an R-rated movie and he went to sneak in on her ID. He is, he's 20. 20 years old. 20 years old. It's not quite Mary Kay LaTerno material, but it's close. He is so hot. I can't help it. See the rules are totally broken. Where did you see him in Hollister? I, like I said, I met him to a friend of a friend. And, yeah, I've gone out with him like three times. This is the guy you've gone out with three times now. Dude, he's the best. He gets, like, out of all the drivers at his store, he earns the most tips. He's awesome. Sometimes you let him drive? Are you teaching him how to drive a clutch? Okay, so 28 and 20 is not that bad. He's like, your little hot summer fling, right? Yeah. Do you love him? Hold on a second. Hold on. We got to back up a second. Because in the post-show meeting yesterday, 28 and 20 was a way bigger deal than it appears to be on the air right now. Well, what really got me thinking about it was the fact that when I got my first car and I learned to drive at 16, he was eight.

2:18.1

Okay. Well, it's not the age different that flips me out. It's the thing that she's not confessing about the 20-year-old. Oh, we just haven't gotten there yet. Okay, good. We're still on the age thing. Now, even before we get to that, Melissa, you think 28 and 20, it doesn't matter if the woman is older. Yeah, I try to be consistent. Like if I'm, you know, icked out by a 28-year-old guy chasing after a 20-year-old girl, then I can't be different if it's a 28-year-old woman and a 20-year-old guy. It is different. No. You don't think it's any different? Yeah, it's, wait, hold on, whose side of mind? Melissa still thinks it's, it's icky?

2:52.1

Yes.

2:52.6

Yeah, it's still icky. You still think it's okay. Okay, wait a second. The icky formula is what? Half of your age, which is 20, okay, plus seven. I haven't done this yet. What? You're okay. So she's okay because 17 is the youngest she can go, but still. That's really icky.

3:06.9

See, that would be icky.

3:08.4

28 and 20, he's very mature.

3:10.3

But you're like,

3:10.9

but he's still usually. 17 is the youngest she can go, but still. That's really icky. See, that would be icky.

3:08.3

28 and 20, he's very mature. But you're like, you're, but he's still using his fake ID. Your borderline icky to the point where it's still gross. Like, it's like a piece of chicken that's just raw still like in the very middle. Like, you're still going to eat it. You're probably not going to get that sick, but you'll still throw up a little in your mouth.

...

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