Vault: She's getting hit on by rich old men at work

Summary

---

Episode Overview

Episode Title: Vault: She's getting hit on by rich old men at work
Date: June 29, 2026
Podcast: The Bert Show

In this lively and relatable segment, the Bert Show crew dives into a listener drama centered on Wendy, an intern, who shares her experience of being frequently hit on by older, often wealthy men at her workplace. The conversation, full of humor and candid reflections, explores generational flirtation, boundaries at work, and the sometimes uncomfortable realities young women face in customer service roles. The dynamic cast (including Bert, Kristin, Abby, Cassie, Tommy, and Wendy) engage Wendy’s story with empathy and laughter, debating age gaps, motivations, and the etiquette of receiving gifts from admirers.

---

Key Discussion Points & Insights

1. Wendy's Story: Getting Hit On at Work

• [01:27] Wendy explains: Since working at a mailbox center for five years, she’s often hit on by much older men—“old, and I mean very old guys”—sometimes as old as 50 or 60 (01:31).
• Recognizing Regulars: Wendy notes that she’s friendly with the regular mailbox holders, so many are aware of personal milestones, like her graduation from broadcasting school.
• Receiving Gifts: “This one guy, he gave me like a hundred dollars because I graduated... then he came the next week and kept giving me money.” (02:16)

2. How Far Is Too Far? Creepy or Flattering?

• The Double-Edged Sword: Wendy shares, “I’m a nice person... we have to be nice and stuff... but I don’t flirt back with them at all.” (02:44, 04:09)
• The hosts debate whether this behavior is more creepy or flattering. Wendy is clear: “Yeah, it’s disgusting... I can’t be rude or nothing, but I don’t flirt back with them at all.” (04:09)
• Radio Host 4: “I think older guys just want that they still got it. So they gotta hit on the young thing... if they can, that’s what they’re looking for.” (05:10)

3. Age Gaps and Family Experiences

• Generational Trends: Wendy notes, “My sister’s 25 and she’s marrying a 47 year old... my family date older men, but I just can’t get with it.” (04:23)
• Discussion turns to societal expectations and motivations for both older men and younger women engaging in relationships with significant age gaps.
• Host Reflection: “There’s such a big gap in what you know and your knowledge between 60 years old and 20 years old. It’s just creepy.” (04:34)

4. Motivations: A Game or Genuine Intentions?

• Is it a game?: The hosts muse on whether the older men really expect success or are just “having fun for a minute.”
  • “Is it sort of just a fun game for them? Like they’re like a cat batting you around like catnip... play with her and have fun for a minute.” (05:24)
• Material Benefits: Host points out, “He’s handing you $100 bills. I think for some women, (they think) well, 22-year-old boys not doing that to me.” (05:34)
• Wendy clarifies that her boyfriend is her age and generous, “No, he’s 21. Okay, thank God.” (05:52)

5. Humor and Matchmaking at the Mailbox Center

• Wendy as Matchmaker: She describes trying to set up a regular customer, but he turns it around, suggesting he likes her instead.
  • “I’m trying to hook him up with this white lady, right? He says, ‘No, I like sisters.’... He starts pointing. I’m like, oh my God. I’m trying to help you out here, you’re trying to hit on me.” (06:21)
• The hosts joke about whether the desire for feminine attention ever fades—at 66, 76, or “16.”

6. Should You Take the Money?

• Wendy's Dilemma: Asked if she takes the cash gifts, Wendy replies, “Not all of them.” (07:00) The hosts tease her: “Yes, you are!” (07:01)
• She admits to taking about two hundred-dollar bills, but clarifies, “He only gave me like...” before being cut off by playful ribbing. (07:07)

---

Notable Quotes and Memorable Moments

• On Being Hit On by Older Men:
  • Wendy: “It’s like I’m a magnet for old pervs.” (04:09)
• On Family Patterns:
  • Wendy: “My mother... all my family date older men, but I just can’t get with it.” (04:23)
• On Generational Dating Gaps:
  • Radio Host 6: “There’s such a big gap in what you know and your knowledge between 60 years old and 20 years old. It’s just creepy.” (04:34)
• On Motivations:
  • Radio Host 4: “I think older guys just want that they still got it... if they can get to you, that’s what they’re looking for.” (05:10)
• On Customer Gifts:
  • Wendy: “Well, this one guy, he gave me like a hundred dollars... then he came the next week and kept giving me money.” (02:16)
• Playful Teasing:
  • Radio Host 4 (about taking the money): “You’re wearing headphones. Don’t pretend you didn’t hear.” (07:09)

---

Timestamps for Key Segments

• [01:27] Wendy introduces her workplace dilemma
• [02:16] Story of the $100 graduation gift
• [03:36] Wendy describes the number of men hitting on her
• [04:09] Hosts and Wendy debate if it’s creepy or flattering
• [04:23] Wendy’s family and age gap relationships
• [05:10] Panel theorizes on older men’s motives
• [05:34] Wealth vs. youth in romantic gestures
• [06:21] “I’m trying to hook him up... he starts pointing” (Matchmaking gone wrong)
• [07:00] Wendy’s honesty about accepting/not accepting the cash

---

Tone & Atmosphere

True to The Bert Show’s signature style, the discussion is lighthearted yet candid, mixing humor (“I’m a magnet for old pervs.”) with genuine curiosity and occasional incredulity at generational dating trends. The camaraderie allows space for honest reflection, teasing, and a healthy dose of self-deprecation, making a relatable workplace situation both entertaining and thought-provoking.

---

Summary Takeaway

This episode offers a humorous and sincere look at the lighter and more awkward sides of customer service, intergenerational flirtation, and workplace boundaries. Wendy’s willingness to share, combined with the hosts’ playful banter, brings out the relatable dilemmas of being young, female, and working in public. The conversation sheds light on how women navigate unwanted attention and highlights the complexities and sometimes absurdities of age-gap advances—all with laughter and warmth.

Transcript

[Wix Advertiser]

My new website's been getting a lot of attention lately, and here's my secret. I used WIX Harmony. It's one of my favorite tools because it feels like such a natural way to create. And I have so much control over my website. I can just tell Aria, my AI agent, to create whatever I'm imagining in my head, or I can click anywhere on my site and change things myself. Try it for [e-mail] Harmony that's wix.com Harmony.

[Radio Host 1]

Forget whatever plans you have this weekend because you're staying at home and playing on spinquest. And there's never been a better time to sign up than right now. New users get $30 coin packs for just $10. All the table games you love with hundreds of slot games and real cash Prizes. That's at spinquest.com S P I N

[Commercial Announcer]

Q U E-T.com Spin Spin Quest is a free to play social casino void where prohibited. Visit spinquest.com for more details.

[Radio Host 1]

This is the Bird show.

[Radio Host 2]

I'd Intern Bianca's up. Each one of our interns has their at mic music and intern Bianca's is Rihanna. Bianca. Bianca's loving the attention on one hand but not the attention on another.

[Wendy]

Okay.

[Radio Host 2]

It's always a little flattering, right? When somebody comes on to you. Maybe a little bit.

[Wendy]

A little bit.

[Radio Host 2]

A little bit.

[Radio Host 3]

What's going on?

[Wendy]

Since I work, these old and I mean very old guys keep hitting on me.

[Radio Host 2]

Like 40.

[Wendy]

No, higher.

[Radio Host 2]

Higher.

[Wendy]

Yes. Gray hair.

[Radio Host 4]

50 here at the 60.

[Wendy]

50. 60.

[Radio Host 4]

You're talking about here at the radio station. Because he does that to everybody.

[Radio Host 2]

Oh.

[Wendy]

Oh, well, now I feel better now. Sorry, Burt.

[Commercial Announcer]

I wasn't talking about Burt.

[Radio Host 4]

But it applies there. Good.

[Radio Host 2]

Where are you talking about? And I mean, is this a boss or is this just.

[Wendy]

Oh, no, no, no. Well, at my job, I'm pretty sure they're listening now.

[Radio Host 2]

Well, don't tell us where. Just tell us what kind of job it is.

[Wendy]

Pack is mailboxes. We have mailboxes there. Can't really say too much.

[Radio Host 2]

Is there like other stuff like. Etc?

[Radio Host 5]

Yeah.

[Wendy]

No.

[Radio Host 2]

Okay.

[Wendy]

Yeah. So they're mailbox holders. And like, when I noticed, they keep looking at me. But I'm. I'm a nice person. You know, we have to be nice and stuff. So they come in. This one guy, he gave me like a hundred dollars because I graduated from my broadcasting school. And he came the next week and kept giving me money. Like, he was like, oh, did I give you money for your graduation? I said, yes. He's like, okay, well, you can have it anyway.

[Radio Host 2]

Well, how did he even know? He's just a customer.

[Radio Host 1]

Right?

[Wendy]

Well, I've been working there for five years, okay? So I know all the mailbox holders.

[Radio Host 6]

So you have regulars?

[Wendy]

Yeah, they're all regulars. And then there are occasional people that walk in, but it's this look they give you when they walk in there. Like they double look like, oh, yeah, I'm coming over there. And then they just come with this walk, like. Yeah. So.

[Radio Host 4]

Well, I think that, I mean, the mentality is if I'm going someplace to do a postal transaction of some sort, I'm not really expecting like a hot young girl to help me. I'm expecting like, you know, somebody, some old government employee who's seedy and doesn't really care to help me.

[Radio Host 2]

Yeah, like you're like some kind of superhero. Like, this is your day job. You're like saving kids and stuff.

[Radio Host 4]

She never said where it was, Bert.

[Radio Host 2]

Oh, yeah, sorry.

[Wendy]

Yeah, just mailbox.

[Radio Host 2]

So when these dudes come in and you're having these casual conversations with them, I mean, how many are we talking about these older guys hitting on you? Is it one, is it two?

[Wendy]

It's like seven that come in all the time.

[Radio Host 5]

And what do they say? Do they ask you out? They ask.

[Wendy]

Well, this one guy was like, where's your wife? Because he kept. He always comes in here and talks about his wife. So I'm like, where's your wife at? Why does she never come here? He's like, oh, I don't have a wife. I said, oh, okay. I remember you talking about it. He's like, but I'm looking for one. I'm like, oh, okay. Well, you know, if you need help, you know, I'll help you look around for some people. He was like, no, I'm looking right here. And I was like, oh, that's creepy.

[Radio Host 2]

And you're home. 20, 20, 50 year old dudes are coming.

[Wendy]

Yeah, it's disgusting. And I'm like, okay, you know, I can't be rude or nothing, but I don't flirt back with them at all. I don't know what it is. It's like I'm a magnet for old pervs.

[Radio Host 2]

That's pretty standard stuff, Wendy. Does that happen to you all the time?

[Wendy]

And it's with my sister too. She's 25 and, you know, she's marrying a 47 year old. Like my mother. She's. They all my family date older men, but I just can't get with it.

[Radio Host 6]

Yeah, I don't understand that mentality. There's such a big gap in what you know and your knowledge between 60 years old and 20 years old. It's just creepy.

[Radio Host 2]

Well, I mean, I understand from the 50 or 60 year old, the 20 year old wants to be with, you know, sexually, you want to be with somebody young and all that.

[Radio Host 3]

Right.

[Radio Host 2]

But from the younger to the older thing, I just don't understand how y' all detach from that. I've never understood that.

[Wendy]

I don't either.

[Radio Host 2]

Mm, mm.

[Wendy]

Maybe we should.

[Radio Host 4]

I would think by. I think by the time that I'm 60, I'm not gonna want someone young. I'm gonna be tired.

[Radio Host 2]

So, like, you don't want somebody 80?

[Radio Host 4]

Yeah, so I'd be okay with somebody who's rated the same level as me.

[Radio Host 6]

I think older guys just want that they still got it. So they gotta hit on the young thing to see if they can still get at that. And if they can, they can get to you. Then that's what they're looking for.

[Radio Host 2]

Yeah. Watch how panic he would become if you actually said yes. Said yes.

[Radio Host 5]

Yeah, that's what I was gonna say. Do they really expect the girls to say yes, or is it sort of just a fun game for them? Like they're like a cat batting you around like catnip, like, oh, I'm just gonna play with her and have fun for a minute, whatever.

[Radio Host 3]

But you talk about from the women's standpoint, I mean, he's handing you $100 bills. I think for some women, they're like, well, 22 year old boy is not doing that to me, so.

[Wendy]

Well, my boyfriend does. Like, we go on trips like twice a year. I don't pay for anything. I'm glad he's here, you know, and He's.

[Radio Host 2]

And he's 48, right, your boyfriend?

[Wendy]

No, he's 21. Okay, thank God.

[Radio Host 2]

But yeah, I don't know how you put.

[Wendy]

I have to tell you about this burp. This one mailbox holder, he comes in all the time and I. I know he's listening. I love you if you're listening. You're the coolest person. But he comes in all the time and we're trying to hook him up with another mailbox holder. So we're trying to play matchmaker for them.

[Radio Host 4]

Hey, why don't you take.

[Radio Host 5]

That's great.

[Radio Host 4]

Where did she take a look at box 208? You know what I'm talking about?

[Wendy]

Anyway, he comes in and I'm trying to hook him up with this white lady, right? He Says, no, I like sisters. I'm like, oh, okay. Then I'm like, okay, what kind? He was like, you know, like he said, he starts pointing. I'm like, oh, my God. I'm trying to help you out here. You're trying to hit on me.

[Radio Host 2]

And again. He's how old?

[Wendy]

He's really old. He has to be 66. Oh, I know he's listening.

[Radio Host 2]

I don't think it goes. I wonder if it never goes away. Like if it doesn't matter if you're 66, 76 or 16, just that you want to be attracted attractive to a woman. Never goes away, I hope. Are you taking those hundred dollar bills as they're coming to you, by the way?

[Wendy]

Huh?

[Radio Host 4]

Yeah, you.

[Radio Host 2]

Are you taking those hundred dollars?

[Wendy]

Not all of them.

[Radio Host 4]

Yes, you are.

[Radio Host 2]

Not all of them.

[Radio Host 4]

How many have you turned down?

[Wendy]

I would take them about 2.

[Radio Host 4]

How many is he giving you total?

[Wendy]

Huh? He only gave me like.

[Radio Host 4]

You're wearing headphones. Don't pretend you didn't hear.

[Radio Host 1]

This is the Birch Show.

[Commercial Announcer]

What's up everybody? It's Bretzky. And America is turning 250. And I can't think of a better way to celebrate that than playing on an American owned Sport Social Casino. SPIN quest.com with all of your favorite games. Live crabs, bubble craps, live blackjack, there's no better place to play for free and win real cash prizes. Spinquest.com Spin Quest is a free to play social casino, Boyd. Where prohibited. Visit spinquest.com for more details.

[Geico Advertiser]

We've all been there. You pop into the shop for five minutes and all of a sudden you've forgotten where you parked.

[Commercial Announcer]

Car. Car.

[Geico Advertiser]

Unfortunately, that lost feeling is what it's like trying to manage your policy with other insurers here.

[Radio Host 5]

Car.

[Commercial Announcer]

Come out, come out, wherever you are.

[Radio Host 2]

Please.

[Geico Advertiser]

With Geico, you can use the app to easily manage all your policies in one place.

[Radio Host 2]

Did this parking lot have a waterfall?

[Geico Advertiser]

I think you've wandered too far, mate.

[Commercial Announcer]

It feels good to find what you're looking for. It feels good to. Geico. Ahora mascolos. Ye vacada proyecto al siente niver ahora quince porciento Nuna selection.