Vault: She Has One Target...Her Best Friend's Son!

Summary

The Bert Show – Vault: She Has One Target...Her Best Friend's Son!

Episode Date: April 10, 2026

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Episode Overview

This candid and lively episode of The Bert Show dives into the dynamics of age-gap relationships—specifically, the sexual and emotional nuance when older women show interest in much younger men. The hosts are joined by listeners, including a 22-year-old man nicknamed "Joe the Cougar Slayer" and a woman named Bridget with a particularly tricky crush: her best friend’s son. The panel explores double standards, “sexual peaks,” and the awkward, often taboo, realities that come with crossing generational dating lines.

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Key Discussion Points & Insights

1. Age Gaps & Double Standards (00:47–02:59)

• The hosts note that if the situation involved an older man pursuing a much younger woman, there likely wouldn’t be as much acceptance. However, since it's an older woman showing interest in a younger man, the conversation feels more “empowering.”
  • “If this was a 50 something year old dude going after a little 20 something year old female, I'd be like, gross, herby. But in this case, it's a woman going for a... It seems more empowering.” – Host 1 (00:52)
• The cast delves into sexual peaks:
  • For men: Early 20s (19–20).
  • For women: Early 40s and up.
  • “I think women, don't they peak in like their early 40s?” – Host 2 (01:50)
  • “A woman doesn't have confidence in her sexuality till she's in her 30s ... of course she's gonna peak higher.” – Host 1 (01:57)
• There’s exchange on whether rising sexual desire for older women is chemical or tied to confidence/freedom from shame.

2. Listener "Joe the Cougar Slayer" Joins the Show (04:09–08:57)

• Joe, a 22-year-old who suspects he is the “target” of an older woman at work (his 52-year-old subordinate), describes the situation.
  • “I've never been with anybody that old and ... I don't know how often this happens.” – Joe the Cougar Slayer (04:33)
• The group jokingly discusses men’s “mental trophy case” regarding sexual experiences:
  • “Dudes have a sort of like a mental trophy case when it comes to sex ... each and every experience that you have, you sort of put on your mental trophy case.” – Host 2 (06:29)
• Joe admits some apprehension about mixing work with pleasure, referencing bad past experiences.

3. Bridget’s Confession: Flirting with Her Best Friend’s Son (09:45–14:23)

• Bridget, a listener in her 50s, is dissatisfied with men her age and is increasingly tempted by younger admirers, especially her best friend’s 21-year-old son.
  • She recounts a provocative encounter: “I said, uh huh, keep that up and I'm gonna end up scooping you up and taking you home with me ... he just looked at me with this devilish grin and just says, I bet you could teach me something.” – Bridget (11:39)
• She is conflicted, feeling this attraction is “so wrong” due to her long-standing relationship with her friend and the boy’s age, despite them both being consenting adults.
• The conversation turns to performance concerns with older men and how sexual desire and ability fluctuate with age.

4. Panel’s Opinions and Playful Banter (12:59–14:09)

• Hosts have varying comfort levels with the topic:
  • “I'm not comfortable with this ... talking about where to pick up young boys on this Michael Jackson kind of tribute day.” – Host 3 (13:13)
• Bridget clarifies: “We're not talking young boys and our adults.” (13:21)
• The cast jokes about the “danger” of Bridget deflowering a young man:
  • “Let him lose his virginity to somebody his own age.” – Host 1 (14:21)
• Bridget reiterates she wouldn’t want to cross that line and ruin a good friendship, nor would she take a young man’s virginity.

5. Ralph Calls In: An Older Man’s Perspective (14:36–16:15)

• Ralph, 61, calls in to challenge the notion that older men can't “perform,” sharing that he and his wife maintain an active sex life.
  • “I'm 61, baby, and I'm still growing strong.” – Ralph (14:52)
  • “Everybody kept telling you where you're gonna reach your peak. ... I said, hey, dude ... it's not happening [for me].” – Ralph (15:21)
• Ralph’s account shows that sexual desire and activity can be very individual, regardless of age.

6. Advice, Reflections & Final Thoughts (16:15–16:51)

• The hosts agree that Bridget’s main issue is the scarcity of available, high-performing men her age—most are married or partnered.
• Encouragement (bordering on humorous provocation) is given for Bridget to pursue younger men—but not her best friend’s son or any virgins.
  • “Go trolling this weekend for some young guy and tell us about it on Monday!” – Host 2 (16:23)

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Notable Quotes & Memorable Moments

• On Double Standards:
  “If this was a 50 something year old dude going after a little 20 something year old female, I'd be like, gross, herby.” – Host 1 (00:52)

• On Sexual Trophy Cases:
  “Dudes have a sort of like a mental trophy case when it comes to sex.” – Host 2 (06:29)

• Bridget’s Temptation:
  “I said, uh huh, keep that up and I'm gonna end up scooping you up and taking you home with me.” – Bridget (11:39)

• The Younger Man’s Perspective:
  “I've never been with anybody that old ... but she's extremely interested in me.” – Joe the Cougar Slayer (04:33)

• On Sexual Confidence:
  “A woman doesn't have confidence in her sexuality till she's in her 30s.” – Host 1 (01:57)

• On Older Men's Sexuality:
  “I'm 61, baby, and I'm still growing strong.” – Ralph (14:52)

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Important Timestamps

• [00:47] – Debate on age/gender double standards begins
• [04:09] – Joe the Cougar Slayer joins, details his workplace age-gap crush
• [09:45] – Bridget’s call: admits feelings for her best friend’s son
• [12:59] – Hosts discuss the morality and awkwardness of such hookups
• [14:36] – Ralph shares that older men can still very much “perform”
• [16:23] – Hosts encourage Bridget to pursue what she wants (except her friend’s son!)

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Episode Summary: Tone & Takeaways

This episode is sharp, cheeky, and frank. The Bert Show hosts skillfully balance humor ("Cougar Slayer," “mental trophy case”) with genuine exploration of the taboos and realities around older woman/younger man dynamics. Both Joe’s and Bridget’s calls bring relatable, real-world nuance to these questions. The cast acknowledges shifting desires, cultural double standards, and the unique conflict when family friendships are involved, ultimately suggesting that as long as everyone is a consenting adult and boundaries are respected—notably, not crossing the “best friend’s son” line—it’s all fair game.

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For those who missed it: This episode shines for its honest talk, laugh-out-loud banter, and for giving voice to the complicated feelings around desire, age, friendship, and sex in modern dating.

Transcript

[Host 1]

Are you really buying a car online

[Joe the Cougar Slayer]

on autotrader right now?

[Host 1]

Really? I can get super specific with dealer

[Host 2]

listings and see cars based on my budget.

[Host 1]

You can really have it delivered or pick it up. I think kid is walking up the slide.

[Host 3]

Really?

[Host 2]

Autotrader, buy your car online.

[Host 1]

Really?

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[Host 2]

All right, let's be totally honest. If this call was going the other way around here, we probably wouldn't even take it.

[Host 1]

I know I said when you say get your man or whatever's like. Yeah. And then I thought, now safe. It was a 50 something year old dude going after a little 20 something year old female. I'd be like, gross, herby.

[Host 2]

But in this case, it's a woman going for a.

[Host 1]

It seems more empowering when there's a woman doing it.

[Host 4]

Well, it does seem that there's a bell curve of interest in sexuality that starts much younger for men and gets better as women get older. Like, we should make sure that, you know, like if you had a pie chart and one started on the left and the other started on the right and they had to cross where you like actually meet. I wonder what ages those would be. Like, where women are at their peak and men are at their peak. Because I'm guessing for men it's in their 20s or early 30s. And I'm guessing for women it's a lot closer to 40 or 50.

[Host 2]

Are you talking about like, sexual peak?

[Host 4]

Yeah, that's what I just said.

[Host 2]

I don't even think dudes are. Yeah, I think it's proven that dudes are in their sexual peak, like at 20, 19 and 20.

[Host 4]

Really?

[Host 2]

Yes. Oh, yeah. 30s. You're. Yeah. Put us out to pasture.

[Commercial Announcer]

It's over at that point.

[Host 2]

And I think women, don't they peak in like their early 40s, right?

[Host 1]

Something like that. And I think.

[Host 4]

I don't know what's proven, but it's just interesting where they. Where those two would meet.

[Host 1]

I think it's also. There's gotta Be a correlation too. And sexual confidence. Because a woman doesn't have confidence in her sexuality till she's in her 30s. So for her to just start, you know, out the gate in her 30s realizing, wait a second, I'm gonna take control of this, then of course she's gonna peak higher.

[Host 4]

And I think it's more about desire. Desire changes from 20s to 30s. Totally.

[Host 2]

In what way?

[Host 3]

For men or for women?

[Host 4]

For women it just increases more. Like you don't want to do it as much in your 20s as well. I'm experiencing, but you know what I mean? Like, I just really do think it changes. And I don't necessarily think it has to do with confidence or who you're with or experience or whatever. I really think that there's something chemical.

[Host 2]

You don't think that it's like, I mean, women basically have been told their entire lives that you're supposed to be virgins and you're supposed to feel guilty about your sexuality. And then in your 30s, do you just feel. You don't think that you just become more comfortable with like, I'm not a hoe because I enjoy sex.

[Host 4]

I'm sure it comes along with it. That confidence, I'm sure helps, but I think it is physical. I think it's based in your body.

[Host 1]

Yeah, you agree with that? No, but I think it's a combination of both. I mean, but we just both present our points. Yeah, I think it's. I think you're women are their sexuality so attached to their mind that if you're not free in your head, you're not gonna be free with your body.

[Host 4]

Yeah, but you're free in your head as a woman when you get married. Cause then all of a sudden you not being able. Not being supposed to do it until you get married. And then when you get married, you're supposed to be an expert at it. So I think all of that guilt or shame or whatever it is about sexuality goes away when you're married. I'm saying it still changes as you get older.

[Host 2]

Hey, Bridget. Hey. Can you hold on one second for me? Okay. And when we put you back on, I'm gonna need you to talk a little bit louder, okay?

[Bridget]

Okay.

[Host 2]

Thank you. I'm gonna do things in reverse order here. I don't even wanna get Bridget on yet because there's a dude online too that even before we talk to Bridget, thinks he's the early 20 year old something. Oh, really?

[Host 1]

Oh, that's funny.

[Host 2]

Bridget may be stalking this weekend.

[Commercial Announcer]

Hey, what's going on?

[Host 3]

I'm in my 20s and I know that all the older ladies want me. My name is Jimmy and I'm the Cougar Slayer. Welcome to my lair.

[Host 1]

Save that.

[Host 2]

Here is Joe the Cougar Slayer. Hey Joe.

[Joe the Cougar Slayer]

Hey.

[Host 2]

Can you speak up a little bit?

[Joe the Cougar Slayer]

Can you hear me better now?

[Host 2]

Yeah. And you're on the voice disguiser so nobody can recognize your voice, handsome. So we haven't even had Bridget on yet. But you are pretty sure that you are the young 20 year old something that our 50 year something wants to hook up with this weekend?

[Joe the Cougar Slayer]

I'm not sure. I've talked to a lot of my friends about this and everybody says I should go for it, but I think it's kind of awkward. I've never been with anybody that old and I mean she's a good looking lady and I don't know how often this happens. If this would be, I don't know if she would call up a radio station to talk about it. But she's extremely interested in me and I don't know if this happens to a lot of people.

[Host 2]

Now how old are you?

[Joe the Cougar Slayer]

22.

[Host 2]

You're 22. And the 50 something year old woman is exactly how old?

[Joe the Cougar Slayer]

I believe she's 52.

[Host 2]

And how did you guys meet in the first place?

[Joe the Cougar Slayer]

Work.

[Host 1]

Okay, so your co workers like your principal, is she your boss?

[Joe the Cougar Slayer]

No, I'm her boss.

[Host 2]

Oh, okay. That's an interesting layer. This is going to be fun.

[Host 3]

Now don't you have the concerns that all guys have that women are just sexualizing them in order to advance her career?

[Joe the Cougar Slayer]

I'm pretty sure she isn't 99% sure.

[Host 2]

Did she come on to you or did you flirt with her first?

[Joe the Cougar Slayer]

I can't really remember.

[Host 2]

But you think she's hot?

[Joe the Cougar Slayer]

Yeah.

[Host 2]

Okay.

[Host 3]

Do you think it's your engaging personality that drew her into you?

[Host 2]

He's on the radio and nervous and stuff. So is there a chance that this is going to happen this weekend?

[Joe the Cougar Slayer]

I don't know. I mean I kind of do but I don't want it to be like, like I kind of at first wanted to do it just because I'd be like, you know, guys have records of how many people they've been with or what the oldest and youngest and I don't know if I would want to do it for that reason and then feel bad afterwards.

[Host 2]

It's almost, you know. He brings up a really good point. I want to mention this to women that you don't know about guys. Jeff, back me on this. Go. But I think that Dudes have sort of like a mental trophy case when it comes to sex, that each and every experience that you have, you sort of put on your mental trophy case. So if you're a black dude and you hooked up with a white girl, that goes on your mental trophy case. If you're 22 years old and you hook up with. You have a one night stand after a night at five paces, one night stand is your goes in your mental trophy case. If you're 22 years old, you're sort of looking for somebody older because you don't have that trophy yet. And now that it's here, he may be able to put that in his trophy.

[Host 3]

It's like a giant. It's a giant game of Zelda. You're collecting the swords, you're collecting the gems, you're collecting the bow and arrow. And once you get it all, then you get to slay the master dragon.

[Host 4]

And I think for women, we put you in the category of I can't believe I did that or I go back and do that again.

[Host 2]

And that's it.

[Host 4]

That's it.

[Ralph]

Yes.

[Host 1]

Agreed.

[Host 2]

So, Joe, what is the. How old is the oldest woman that you have ever been with?

[Joe the Cougar Slayer]

31. And that was last year.

[Host 2]

Oh, you're crushing that record. And you said you're already physically attracted to her, so that part doesn't scare you at all?

[Joe the Cougar Slayer]

No.

[Host 1]

Is the awkwardness mainly from her age or the. Are you working together?

[Joe the Cougar Slayer]

A little bit of both, I guess. I've had experiences before with work where it really went bad and I don't want that to happen again. But once she's so. I don't want to say old, but older than me, I'm pretty sure she wouldn't start drama.

[Host 2]

Okay, let's do this. I'm gonna put you on hold. Well, let me ask you two more things. Your office is in what county?

[Joe the Cougar Slayer]

I don't know what county it is, but it's.

[Host 4]

How do you not know what county?

[Joe the Cougar Slayer]

It's up 985.

[Host 2]

Okay, that's all we need. I'm just trying to get a fact to figure out if this is the woman that you think it is.

[Host 3]

If it's not, and we don't come back to you and you do have this relationship, just make sure you're safe so you don't get any STDs, like arthritis or Alzheimer's or anything.

[Host 2]

Come on. Hey, I'm gonna put you on hold. Joke is, either way, we want to talk to you next week. Because even if Bridget is not the woman. You still have a story to tell.

[Host 1]

Exactly.

[Host 2]

All right, so hold on one sec. Okay.

[Host 4]

Have a good weekend.

[Host 2]

Go get. Go get your. Go get your Jaguar.

[Host 1]

Go get got.

[Host 3]

What if.

[Host 2]

Go get your git.

[Host 3]

What if he. What if you're a 22 year old and you. And you hook up and you hook up with. With a cougar like that, you know, or jaguar or whatever, lioness or whatever we're calling her, and. And he has some erectile dysfunction problems with his. Gonna be like, he's the one who can't perform.

[Host 4]

She'll be like, oh, well, back to Johnny's hideaway. Same thing there.

[Host 2]

All right, so this can go in a couple of different ways. Either Bridget is the woman and then we get to put them both on the air together at the same time here. Or she's not, and we get two stories on Monday. Hey, Bridget.

[Bridget]

Yes?

[Host 2]

Did anything that that dude just said, Joe, the jaguar slayer, say anything that makes you think that you are the jaguar that he to slay this weekend?

[Bridget]

Well, I don't work with him because I don't work off a 985.

[Host 2]

Okay.

[Bridget]

I do live off a 985, but I work in Atlanta.

[Host 2]

Okay, so it's not the same thing because Joe. There is a right, because Joe's hooking up with his boss. So it's not the same. All right, so what's your story then, Bridget?

[Bridget]

Well, actually, I kind of go to a regular place that I hang out at and a lot of young boys, I guess I'll say, always hitting on me. And lately here I've been very frustrated and dissatisfied with guys my own age that I've managed to hook up with. And I'd say it was my own bad taste or my own poor judgment. However, not too long ago I dated a 34 year old, or probably, I don't know, we kept something going for about three years and I kept breaking up with him because of his age, not because he was immature or anything. I just kind of felt, hey, I can't get good family. I'm not going to have any more kids. Da, da, da, da. You know, and I kind of figured he needed to meet some girls his own age too. However, the, you know, the one time thing or whatever, as far as that hurting a girl's feelings. From what he said, a lady my age. No, it won't. If he's going to put a trophy up on us, we'd be the Grammy. But I'm just. I don't know, it's to Me, I'm thinking this is like so wrong to be thinking this. And I think this because one of the kids hitting on me happens to be one of my best friend's son and he got a bit carried away about a week ago and leaned over me at the bar and I mean leaned over me, all his 21 year old glory and all pretty much stayed there until he knew he'd get a reaction out of me. And I just managed to say something to him and I said, uh huh, keep that up and I'm gonna end up scooping you up and taking you home with me. And he just looked at me with this devilish grin and just says, I bet you could teach me something.

[Host 1]

Ew.

[Host 2]

But this is your. You say this is your boyfriend's son?

[Bridget]

It's my best friend's son.

[Host 2]

Best friend's son. All right, that's it.

[Bridget]

And I was real tempted at that point. He's a dollar.

[Host 1]

But you've known him since he's in diapers, I bet.

[Bridget]

So I'm thinking to myself, I've really got to meet some guys that are my age that actually don't just talk and think about it, that can actually perform. However, in listening to y' all earlier, yeah. I think men, at about the age of 40, they start to decline in that area. I don't know if it's because they just don't care or they get too tired or just their body parts just don't seem to work. However, women, I'd say, yeah, between 40 and 45, they do hit their sexual peak. And that's. I don't know. That's wrong. That is wrong. Whoever designed that did it really backwards. So I guess I'm trying to figure out do I need to get advice from the listeners on some other places to go and, or do I need to consider taking advantage of what I can.

[Host 2]

I don't, I just don't. I don't know, maybe I'm more liberal in my thinking. I just don't think it's a big deal. You're a 50 year old woman or whatever. You want to hook up with a young 22 year old something you want to get a need filled. So do it.

[Host 3]

I'm not comfortable with this.

[Bridget]

Really?

[Host 1]

Why?

[Host 3]

Just talking about where to pick up young boys on this Michael Jackson kind of tribute day.

[Host 2]

Come on.

[Host 3]

Just makes me uneasy.

[Bridget]

Well, we're not, we're not talking young boys and our adults.

[Host 2]

I know, just being funny.

[Host 4]

Yeah, you're talking about consenting adult who's how old again, 22.

[Bridget]

He's. Well, there's one that hits on me. That's 21. Another one that's 22. And one other. That's 23.

[Host 2]

Wow.

[Host 4]

Oh, you should compare them.

[Bridget]

I definitely can't go there.

[Host 1]

Yeah, I agree.

[Joe the Cougar Slayer]

Stay away.

[Bridget]

I would totally screw up a good friendship. Amongst other things being if he's a virgin, and I won't do that either.

[Host 2]

Oh, no.

[Host 1]

Virginity.

[Host 2]

You're a virgin. You're, like 22 years old, and you hook up with a 50 something that is like. It's a little bit like never picking up a bat. And the first time you play a baseball game, you're trying to hit against John Smalls.

[Bridget]

Yeah.

[Host 3]

I don't know what it was about the word virgin that made all of us turn into, like, a World cup soccer match audience.

[Ralph]

Yeah.

[Host 1]

Let him lose his virginity to somebody his own age.

[Bridget]

There's got to be some men out there that can still perform. I mean, I'm convinced that there are.

[Host 1]

Well, if you're worried about that, don't pick the virgin.

[Host 2]

Hold on. I think I found one for you.

[Joe the Cougar Slayer]

Hold on.

[Host 2]

Hey, good morning. Ralph, you're on Q100. Hi.

[Ralph]

Good morning. Hey. I can't believe what I'm hearing.

[Host 2]

Yeah. Ralph, Bridget is 50 years old, and she says there aren't any old dudes that can keep up with her anymore.

[Ralph]

Oh, man. She's hooking up with the wrong guys.

[Host 2]

How old are you, dude?

[Ralph]

I'm 61, baby, and I'm still growing strong.

[Host 2]

Love it.

[Bridget]

Ralph.

[Host 1]

You go get you some Ralph.

[Host 2]

Go get your Jaguars. Are you a married guy?

[Ralph]

Yeah, she's. She's got me pinned down. But I'm telling you, it's. You know, everybody says, when you get older, once a baby every night.

[Host 4]

See, you know what? That's why he's still married, probably. Right? Right.

[Host 2]

Is it still at the point where you're like, is she like, leave me alone already? It's been 20 years.

[Ralph]

Well, I'm. He's 11 years younger than I am, and she's. She just. He's after it, too. I just thought. I just got lucky, I guess. I don't know, but I think I got. I got a beautiful woman, but I've been with her for 14 years, and we knew each other for a long time, but I was single for a long, long time. And, you know, everybody kept telling you where you're gonna reach your peak. You're gonna reach your peak. I said, hey, dude, I don't know what's. What's going on I said, but I'm not ready. You know, it's not happening. And it's just. And I know a lot of my friends are the same way. They keep talking about, well, what are they talking about? Sexual peak. And I said, I don't know. I said, just forget it. They must be talking to someone else in a different country.

[Host 2]

He's ready to go. See, so they're out there, but where do they go?

[Bridget]

Where do they go, Ralph?

[Host 2]

I don't know. He's gone.

[Bridget]

Well, he's married to people at my age that. At least some of the good ones, they're married and still married if they're definitely still performing.

[Host 2]

Yeah, I think that's the problem that you're gonna run into is that most people in their 50s and 60s are probably coupled, and if not, they're over at Johnny's Hideaway. You need to go get a. Get. Go get yourself a young guy. Go trolling this weekend for some young guy and tell us about it on Monday. Go. You know, that's what you want to do.

[Bridget]

I just wanted to make sure. I know. I think it's wrong. But then again, I'm beginning to think it's not so wrong after all.

[Host 1]

It would be wrong if you went after your best friend's son.

[Bridget]

That would be so wrong.

[Host 2]

And not the virgin. So virgin and virgin. This is the Birch show to realize the future America needs. We understand what's needed from us to face each threat head on. We've earned our place in the fight for our nation's future. We are Marines. We were made for this.