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

Summary

The Bert Show – Vault: Massey's New 20 Year-Old Virgin Date

Release Date: November 7, 2025
Host: Jamie Massey with Jeff, Melissa, Caitlyn, plus listener call-ins
Podcast: The Bert Show, Pionaire Podcasting

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Episode Overview

This episode centers on Jamie Massey’s latest dating adventure: going out with a younger guy—a 20-year-old virgin. The cast dives deep into the age gap, dating motivations, taboos, and societal double standards, all in the show's trademark spirited, bantering tone. Lively debates arise about what's "icky," what counts as a deal-breaker, and how personal and cultural values shape approaches to relationships—particularly when sex and age are involved.

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Key Discussion Points & Insights

1. Jamie’s Dating Track Record & The Premise

• Jamie Massey recounts her dysfunctional dating history:
  • “We have told you before that the history of Jamie Massey's dating life is not sad. It's laughable.” (Jamie, 01:00)
  • Past issues: men revealing they’re married mid-date, guys ditching her with the check, etc.
• Jamie tries “something new” by dating a younger man, after previous attempts at dating older or married men haven’t worked out.

2. The Age Difference Debate (28 vs. 20)

• Jamie reveals she’s 28, dating a 20-year-old she met through friends.
• The cast jokes about the generational gap:
  • “You were walking in the Seafire side of the Caribbean and he was there to see cars.” (Jamie, 02:10)
  • “She was going to an R rated movie and he wanted to sneak in on her ID.” (Jeff, 02:15)
• Is it different if an older woman dates a younger man?
  • Caitlyn: “If I'm 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.” (03:31)
  • Jeff points out an “ickiness” scale: “You're borderline icky… it's like a piece of chicken that's just raw still. Like in the very middle.” (04:11)

The "Icky Factor" Mathematical Formula

• Melissa introduces the “half your age plus seven” formula:
  • “The icky formula is what? Take half of your age, which is 20. Plus seven.” (04:00)
  • Calculated as 14+7=21; at 20, he’s one year below Jamie’s “minimum.”

3. Motivations & Double Standards

• Discussion about why older women date younger men:
  • “Let's be honest, there's one reason why you go out with a guy that's young. It's because he's good looking.” (Jamie, 05:19)
• Jokes about lessons learned and casting Jamie as a "predator" (in jest).

4. The Bombshell: He’s a Virgin (Saving Himself for Marriage)

• Jamie reveals her date is saving himself for marriage:
  • “He. I've. You say, but I don't want to say because I would look like—” (Jamie, 05:55)
  • “Is he a virgin?” (Jeff, 05:59)
  • “Yes.” (Jamie, 06:00)
  • “Are you going to deflower him?” (Jeff, 06:01)
  • “No.” (Jamie, 06:03)
• Jamie struggles with dating but not being able to have sex:
  • “If you're sexually frustrated now, wouldn't you rather be sexually frustrated alone rather than this hot piece of 20 year old meat in front of you that you can't do anything with?” (Jamie, 06:11)
• Jeff jokes about “high school stuff”:
  • “He can still do the old high school stuff… touch you above your bra, the dirty paint, pant rub, all those things.” (Jeff, 06:33)

5. The “V Bomb” Aftermath & Perspectives

• The cast interrogates Jamie about how the topic arose; Jamie explains it came up in casual religious conversation.
  • “He said, yeah, by the way, I'm saving myself for marriage. And I was like, saving what?” (Jamie, 07:46)
• Jamie reflects on the pressure of possibly being “the one” who changes his vow:
  • “I could not do that because… if he filled guilty about it, he would resent me for the rest of his life.” (Jamie, 09:06)
• Cast asks Jamie if she’ll still date him or “dump” him.
  • “Don’t I turn into like a complete—if all of a sudden I’m like, won’t date him anymore because he doesn’t do that?” (Jamie, 09:32)

6. Listeners Call In: Real-Life Experiences

• Dolores shares her story:
  • She married a 23-year-old who was a virgin when they met; he was also 20 when they started dating.
  • Overcame religious reasons eventually; no guilt involved.
    • “It was one of those where I had been married… he just said that, you know, he really had never found someone… who made him say, you know, yeah, I’m willing to go that far.” (Dolores, 11:15)
• Dolores’ advice: “Don't do it. Let somebody else be the person to take it from him, but don't do it.” (Dolores, 12:42)
  • Jamie: “Yeah, no, I don't want to be that person. That's too much pressure.” (Jamie, 12:48)

7. Final Thoughts: Should She Continue or Let Go?

• A second caller advises moving on:

  • “Let that go real quick. Honey, run in the other direction and find you another 20. 21, 2019, for God's sakes. But get you some ass and get it quick.” (Dolores, 14:23)

• Jamie seems undecided about whether to break up:

  • “I mean it's, it's not even to the breakup dumping point, you know…” (Jamie, 14:48)

8. Notable Quotes & Jokes

• On the age gap:
  • “28 and 20, he's very mature.” (Jamie, 04:05)
  • “Did you take him to the Disney store?” (Melissa, 04:42)
• On sexual tension:
  • “He's denying you that based on the Bible.” (Jamie, 13:39)
• On coping:
  • “If you've learned nothing from listening to the Burt Show today, I'll remember that last night.” (Melissa, 14:38)
  • “Go get you some hats and get it quick.” (Dolores, 14:42)

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Timestamps for Key Segments

• Jamie Explains Her Dating Past & Younger Guy Reveal:
  01:00–02:35

• Debating the Age Gap, “Icky” Formula, and Double Standards:
  03:00–05:00

• Virgin Reveal, Jamie’s Dilemma, and Banter on Sexual Tension:
  05:38–09:06

• Listener Dolores Shares a Similar Experience:
  10:50–12:39

• Callers Advise Jamie (Should She Drop Him?):
  13:31–14:46

---

Memorable Moments & Quotes

• On the “Icky Formula”:

  • “So you're in the icky factor.” (Melissa, 13:14)

• On self-awareness:

  • “I cannot be the one to do that. Because, like, say he was. Felt guilty about it. He would resent me for the rest of his life.” (Jamie, 09:06)

• On learning from others:

  • “Don't do it. Let somebody else be the person to take it from him, but don't do it.” (Dolores, 12:42)

• Banter Highlight:

  • “Go get you some ass and get it quick.” (Dolores, 14:32)

---

Summary

This episode captures the Bert Show’s honest and irreverent approach to taboo dating situations, focusing on Jamie Massey’s new flame: a much younger, deeply principled (and very attractive) 20-year-old virgin. The panel’s laughter, teasing, and sincerity turn a potentially awkward topic into an entertaining and relatable exploration of age, sex, values, and the complexities women face in the dating world.

Listeners leave with:

• Food for thought on age gaps and double standards
• Firsthand accounts of handling sexual boundaries
• Plenty of laughs, sharp one-liners, and Jamie’s relatable journey to figure out what she wants

Essential takeaway:
While the group offers plenty of ribbing, they ultimately respect Jamie's decision—highlighting that it’s okay for dating to be a process, even if it’s not the fairytale ending we expect.

Transcript

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[Jamie Massey]

You're on the Burt Show. Jamie Massey here. We have told you before that the history of Jamie Massey's dating life is not sad. It's laughable.

[Jeff]

No, it's pretty sad too, but it.

[Jamie Massey]

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

[Melissa]

Well, it's kind of dysfunctional. I can't figure out why, like, I don't know if you have a type of or like something that attracts you to these guys, that they just end up being losers.

[Jamie Massey]

Yeah, I definitely have been on a run.

Well, isn't, 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 something new. Why don't you tell him what you're trying, Jamie? Cause married guys aren't working out for you.

Yeah, yeah. There was the date with the guy who told me in the middle of dinner he was married. There was the guy that stiffed me for the check and so, you know, gone a little younger.

[Jeff]

How old are you?

[Melissa]

Yeah, yeah, exactly.

[Jamie Massey]

First of all, I'm 28 years old and I'm through a friend of a friend. I met this boy and he's so cute. No, he's not a boy.

You were walking in the Seafire side of the Caribbean and he was there to see cars.

Shut up.

[Jeff]

She was going to an R rated movie and he wanted to sneak in on her ID.

[Jamie Massey]

He is. He's 20.

20 years old.

20 years old.

[Melissa]

It's not quite Mary Kay Letourneau material, but it's close.

[Jamie Massey]

He is so hot. I can't help it.

See how the rules are totally broken.

[Jeff]

Where'd you see him? In Hollister?

[Jamie Massey]

Like I said, I met him through a friend of a friend. And yeah, I've gone out with him like three times.

This is a guy you've gone out with three times now?

[Jeff]

Dude, he's the best. He gets like out of all the drivers at his store, he earns the most tips. He's awesome.

[Jamie Massey]

Sometimes you let him drive? Are you teaching him how to drive a clutch?

[Melissa]

Okay, so 28 and 20 is not that bad. He's like your little hot summer fling, right?

[Jamie Massey]

Yeah.

[Jeff]

Do you love him?

[Jamie Massey]

Hold on a second, hold on. We gotta 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.

Well, what, what, what? 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 8.

[Melissa]

Okay, well, it's not the age difference that flips me out. It's the thing that she's not confessing about. The 20 year old.

[Jamie Massey]

Oh, we just haven't gotten there yet.

[Melissa]

Okay, good.

[Jamie Massey]

We're still on the age even before.

We get to that. Melissa, you think 28 and 20, it doesn't matter if the woman is older.

[Caitlyn]

Yeah, I. 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.

[Jamie Massey]

It is.

[Caitlyn]

You know, you call it.

[Jeff]

No.

[Jamie Massey]

You don't think it's any different?

[Jeff]

Yeah, it's. Wait, hold on. Whose side am I? Melissa still thinks it's. Melissa still thinks it's icky.

[Jamie Massey]

Yes.

[Jeff]

Yeah, it's still icky.

[Melissa]

Okay, wait a second. The icky formula is what? Take half of your age, which is 20. Okay. Plus seven.

[Jamie Massey]

I haven't done this yet.

[Melissa]

What?

[Caitlyn]

You're okay, so she's okay because 17 is the youngest she can go.

[Jamie Massey]

But still, that's really icky. See, that would be icky. 28 and 20, he's very mature.

[Jeff]

But you're like, you're borderline.

[Caitlyn]

He's still using his fake id.

[Jeff]

You're borderline icky to the point where it's still gross. Like, like, like it's like a piece of chicken that's just raw still. Like in the very middle. Like you're still gonna eat it. You're probably not gonna get that sick, but you'll still throw up a little in your mouth.

[Melissa]

We can't even go out with you.

[Jamie Massey]

Yeah. Like when you go to 1150 and do your, your gigs, I mean, they're gonna stop him right at the door.

We've only gone out like three times.

[Melissa]

And what did you guys do when you went out?

[Jeff]

Chuck E. Cheese.

[Jamie Massey]

Chuck E. Cheese. No.

Did he get stuck in the little tunnel to get stuff and save them?

[Melissa]

Did you take him to the Disney store?

[Jamie Massey]

Y' all are funny. No, it all started because he had never seen Lost Season 2. And I have it on my ipod. And I was like, well, you can come over sometime and watch it. And I didn't. I mean, I knew how old he was and I wasn't expecting it to be like a dating thing. And then I just kind of got a little crush on him.

[Melissa]

You are such a predator. That's what you are. So when you're a little boy, I.

[Caitlyn]

Have a toy that I want you to look at.

[Jeff]

So, like, when you. So, so you're. It's not, it's not a date. So you don't get all dressed up or anything. And he's coming over and then when his mom's car pulled up, did you get nervous or excited?

[Caitlyn]

Just get Ms. Passi. It's okay.

[Jamie Massey]

Well, she felt nervous because she had to have him home by 10 o' clock and it was already 8:30. Things had to progress quickly. Now, normally when you go out with a younger guy, let's be honest, there's one reason why you go out with a guy that's young. It's because he's good looking.

[Caitlyn]

You just said how hot he was and a lot of women in the audience were thinking, well, he's a youngster. Done. No wonder she's going out with him.

[Jamie Massey]

And dude can go the distance. That's the reason why older women go out with younger guys, because they can go the distance. How far is his distance? Jamie Massey?

He doesn't have a distance.

[Jeff]

What do you mean?

[Caitlyn]

What do you mean?

[Jamie Massey]

He. I've. You say, but I don't want to say because I would look like.

[Jeff]

Is he a virgin?

[Jamie Massey]

Yes.

[Jeff]

Are you going to deflower him?

[Jamie Massey]

No.

[Melissa]

So he's 20 and he's a virgin and he's saving himself.

[Jamie Massey]

Yes.

[Melissa]

For marriage?

[Jamie Massey]

Yes.

[Jeff]

Have you guys done anything?

[Jamie Massey]

That's the Point.

That's what I said. I said, look, if you're sexually frustrated now, wouldn't you rather be sexually frustrated alone rather than this hot piece of 20 year old meat in front of you that you can't do anything with?

[Melissa]

Well, that's the only reason you're dating hot piece of 20 year old meat in the first place, is to, you know.

[Jeff]

Well, he can still do the old high school stuff.

[Melissa]

Summer fling.

[Jeff]

Like he could.

[Jamie Massey]

Summer lovin'.

[Jeff]

Touch you above your bra, the dirty paint, pant rub, all those things.

[Melissa]

Dirty pant rub.

[Jeff]

It's a nice way of saying dry hump.

[Jamie Massey]

Oh, delete that.

So you, I mean there's really. I don't understand.

Yeah, I know it's very frustrating and I'm still, I'm still figuring all this out. I mean it's only been like three times now.

[Caitlyn]

Wait, I'm figuring what out? That he's just, I mean, I just.

[Jamie Massey]

Am learning all of these, these things.

I don't know, there must have been a point where you were so aggressive that he had to say, wait, wait, wait, wait, wait, I am waiting until am going to be married. Yeah, because I mean, in three days. That normally wouldn't come up. So I'm assuming you jumped on him like a shark on chum and he said something like, wait a second, I gotta, I gotta set the record straight.

[Caitlyn]

Yeah, how did it come up?

[Melissa]

Yeah, I want to know how that conversation started.

[Jeff]

What's the normal amount of time that meets the passes between Jamie Massey meeting a feller and mounting him?

[Jamie Massey]

Oh my God, I am really uncomfortable with this conversation right now. No, it actually just came up in normal conversation.

How does it come up in normal conversation?

We were watching Teat Lost or something like that. And Dora, we're watching Dora. It was my favorite episode of spongebob.

No, this thing just doesn't come up in normal conversation.

Well, I think it became like kind of a religious talk. Like it turned to a bit of a religious talk. And he said, yeah, by the way, I'm saving myself for marriage. And I was like, saving what? So that's kind of how it turns out. Turned up.

[Melissa]

Okay, wait, now I want to know what you say after he says that. You're like, oh, fabulous.

[Jeff]

Hold on, let me get dressed. That's the first thing she says.

[Jamie Massey]

No, I just, I, to be honest with you, he said, I'm saving myself for marriage. And I was like, why? And I felt like, you know, you know, a 28 year old single woman with a hot 20 year old dude you're gonna be like, dude, why you.

Have to make a plea.

Sure, yeah, but see, then you come to the fact. And I thought about that, like making that plea, you know, Come on, dude, seriously, you know, and, and what Jeff said earlier. But if I was.

[Jeff]

What did I say earlier?

[Jamie Massey]

You were talking about deflowering a young man. But if, if he has made this decision and has lasted, you know, 20 years, good looking guy, gone all the way through high school and into college, you know, keeping him. I cannot be the one to do that.

[Jeff]

He lasted like 20 years.

[Jamie Massey]

He's lasted like six. Well, nowadays he's last.

Yeah, so. But I could not do that because, like, say he was. Felt guilty about it. He would resent me for the rest of his life.

[Melissa]

No, I don't think that you should do him. I think that you should stop dating him. Because I don't, I. What I don't understand is like after he drops the big V bomb, the virgin bomb, and that he's saving himself. Like, where does it go from there? Like, have you gone out with him again since then?

[Jamie Massey]

Don't I turn into like a complete. If like all of a sudden I'm like, won't date him anymore because he doesn't do that.

Yes.

[Melissa]

Yeah, but who cares?

[Jamie Massey]

Yeah, like, why 17 year old virgin friends?

[Melissa]

I mean, who cares? Like, are you looking for a long term meaningful relationship with a 20 year old?

[Jamie Massey]

No.

[Jeff]

You're gonna be the biggest bitch on MySpace. I wouldn't worry about it.

[Jamie Massey]

Let me ask you guys.

He was just like a nice guy. He was fun to hang out with. And I like, you know, it's not been like this big, serious, like, oh my God, I'm. You know.

Is there a possibility that he just said he was holding out to make himself even more attractive to her?

[Jeff]

That's brilliant.

[Melissa]

No.

[Jeff]

Yes.

[Caitlyn]

Are you sure he's not lying?

[Jamie Massey]

No, no, no, no, no, no, no, no.

[Melissa]

You don't play the religious cardi. I mean, that just doesn't go.

[Jeff]

Hold on a minute.

[Caitlyn]

How was it? What do you say? How was it confirmed?

[Jamie Massey]

The friend of a friend who introduced me told me, confirmed it because I asked and they were like, oh, yeah, he's like a really, really good guy.

[Caitlyn]

And he's really bad to have sex, but he's like, you're not looking for.

[Jamie Massey]

A really, really good guy right now. A 20 year old, really, really good guy. You're not looking for that. Yeah, well, hey, Melissa, you should go.

[Jeff]

On the other end of the spectrum. You should date 60 year olds.

[Jamie Massey]

Hey, Melissa, Go ahead.

[Dolores]

I am about to turn 30 and I am actually married to a 23 year old. And he was a virgin when we started dating.

[Jamie Massey]

And how long did it take you to rob that of him?

[Dolores]

Six months.

[Jamie Massey]

Six months.

[Caitlyn]

How old was he when you first started dating?

[Dolores]

He was 20.

[Jamie Massey]

But you know, you weren't going. I mean, you knew that in your head as soon as he told you that he was a virgin, that that was gonna change if you were gonna continue to date him.

[Dolores]

It was one of those where I had been married. So I was like, I'm not, you know, maybe I'm not cut out to be your date. And I told him that and I had been divorced and so I just kind of was like, I'm obviously not. And he just said that, you know, he really had never found someone. Is what his point was, is he never found someone who made him say, you know, yeah, I'm willing to go that far.

[Jamie Massey]

But was his for religious reasons?

[Dolores]

Partially, but it was, it was more, it was. He got over the religious reasons when he fell in love.

[Jamie Massey]

I guess. I bet he did.

[Melissa]

When he found love. Uh huh. I don't think that's all he found.

[Jamie Massey]

Was there any amount of guilt on your part after the first time?

[Dolores]

No, actually there wasn't.

[Jamie Massey]

Was there any amount of guilt on his part after the first time?

[Dolores]

There wasn't. And it was actually six months later that he asked me to marry him. So we weren't even engaged. And I was actually really worried about the guilt. And he, he was just like, no, I'm totally in love with you and I feel completely comfortable.

[Jamie Massey]

So what have you learned from this, Jamie Massey? That if it does happen, it will be guilt free.

Awesome.

[Caitlyn]

And then he will ask you to marry him.

[Jamie Massey]

Not so awesome.

Hey Dolores.

Ever.

Hey Dolores. Good morning. You're on the Burt Show.

[Dolores]

Hey. No, I'm gonna tell Jamie. Don't do it. Just don't do it. Let somebody else be the person to take it from him, but don't do it.

[Jamie Massey]

Yeah, no, I don't want to be that person. That's too much pressure.

[Dolores]

That is too much pressure. But I mean, just mess around with him. Make out, but don't, don't take it from him.

[Jamie Massey]

So it's okay for a 28 year old to make out with a 20 year old, in her opinion, as long.

[Jeff]

As your braces don't get locked.

[Caitlyn]

We recalculated because I, in my mind I was basing it on his age, the icky factor, not her age. And we realized it's 28.

[Melissa]

It's her age in half. 14 plus 7 is 21.

[Jamie Massey]

So you're in the icky factor.

[Caitlyn]

So it is icky.

[Melissa]

It is icky.

[Jamie Massey]

That's the calculation for the icky factor. So you are.

[Melissa]

And that goes either way if the guy's older.

[Jamie Massey]

Yeah, I know how that works. Heard of that before.

She's done the math. She don't care. Caitlyn, good morning. You're on all the hits Q100.

[Dolores]

Good morning.

[Jamie Massey]

Morning.

[Dolores]

I think I should leave Jamie alone because if she's hot enough to get a 20 year old then you got to give her props.

[Jamie Massey]

Yes.

No. I mean I give her all the compliments in the world. I just think that she is adding to her frustration. I mean he's that good looking. You obviously don't have a lot in common with this guy. There's one reason to go out with him and he's denying you that based on the Bible.

[Dolores]

Well, I'm still a senior in high school and I like look for guys that are still virgins. Like that's good for me. So I don't think you should steal it from him because that's awesome that he's like chosen to wait for marriage.

[Caitlyn]

Well, Jamie can set y' all up.

[Jamie Massey]

He'll give you his number.

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

[Dolores]

Hi.

[Jeff]

Hey, what's up?

[Dolores]

Oh, really? Honestly, let that go.

[Caitlyn]

Let it go.

[Dolores]

Let it go real quick. Honey, run in the other direction and find you another 20. 21, 2019, for God's sakes. But get you some ass and get it quick.

[Jeff]

Hello.

[Jamie Massey]

If you've learned nothing from listening to.

[Melissa]

The bird show today, I'll remember that last night.

[Jamie Massey]

There's the nugget of wisdom.

[Melissa]

Go get you some hats and get it quick.

[Jamie Massey]

Awesome. Are you gonna officially dump them? Are you gonna ha. You go.

I mean it's, it's not even to the breakup dumping point, you know, I.

[Caitlyn]

Mean just write them a note, fold it up with a little tuck underneath it tab so you can pull it out.

[Jamie Massey]

You're on the Birch show.

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