Vault: Bert Solves Wendy's Dating Desperation

Summary

The Bert Show – ‘Vault: Bert Solves Wendy’s Dating Desperation’ (March 25, 2026)

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Episode Overview

This lively Bert Show classic centers on helping Wendy overcome her persistent dating struggles, which the team lovingly dubs “dating desperation.” Hosts Bert, Kristin, and additional cast members offer Wendy blunt but supportive advice: how to let go of desperation, stop trying too hard, and allow romance to unfold naturally. They invent a unique experiment—Bert will take over Wendy’s dating messages for a weekend, to demonstrate “the game” and reclaim her dating mojo.

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Key Discussion Points & Insights

1. Wendy’s Dating “Desperation” and its Perception

• The hosts confront Wendy about projecting desperation when single, with Bert stating plainly that “guys can smell it.”
  • Bert: “I’m not trying to come down hard on you, but the truth of the matter is… you come from a place of desperation, and guys can. We can smell it.” (00:56)
• Kristin (and others) clarify their critique is meant to empower Wendy, reminding her she has plenty to offer and doesn’t “need” to try so hard.

2. Specific Behaviors That Signal Trying Too Hard

• The group recalls an incident where Wendy dressed up far too formally for a casual lake outing—an example of trying to impress too much.
  • [A]: “Everybody’s in the driveway with flip flops... and you come down in a black dress, full makeup, and heels. Like, that is a desperate move right there.” (02:02)

3. The Dating “Game”—Is it Necessary?

• The hosts debate the need for game-playing in modern dating.
  • Wendy resists the idea, wanting to be honest and authentic:
    • C: “Games are stupid. Someone’s gonna like you whether you play a game or not, right?” (03:59)
  • Bert and the others push back, insisting that withholding some interest or access increases attraction:
    • B: “In the dating world, that doesn’t work. You gotta play the game.” (03:47)
  • The “Rules” book is discussed, illustrating old-fashioned “don’t call back right away” strategies. The group admits results vary, but maintains boundaries are key.

4. Demonstrated Experiments: Bert Takes Over Wendy’s Dating

• The on-air team recounts a prior instance of Bert managing a man’s romantic communications with success—until the man reverted to old, too-eager habits, and the relationship fizzled.
  • [A]: “…it worked perfectly—95% of the time. …It all fell to pieces when…he took matters into his own hands, and he lost the girl in, like, 24 hours.” (06:19–06:43)
• A new experiment is proposed: Bert will handle all text exchanges with men Wendy meets, using a secondary phone. The plan is to:
  • “reel in” prospects by controlling the pace,
  • show Wendy, via example, how to avoid over-eagerness and preserve intrigue.
  • B: “I am going to be you texting all weekend long, and I’m going to show you how this is done.” (07:48)

5. Listener Wisdom: Let Men “Hunt”

• Brandy, a caller, chimes in to agree that “the chase” is still essential for men.
  • C (Jen): “Men are hunters. Let them hunt.” (09:45)
• The group extends the analogy, humorously likening Wendy’s approach to being a deer that jumps willingly into the hunter’s truck—thus spoiling the challenge.
  • C: “You jump into their truck and you say, here I am. You’re a deer that jumps into the back of the truck…” (09:49)
  • A: “They have the rope in their mouth and, like, tie me to the hood.” (10:02)

6. Encouragement and Final Notes

• The segment wraps with both good-natured teasing and genuine encouragement, reinforcing that Wendy deserves someone who will make an effort for her.
  • A: “You deserve a guy that’s willing to climb in the tree and cover himself in urine…that’s what you deserve.”
  • B: “Just let me get them on the boat. …You can make them a trophy, you can eat them, whatever. But I’m going to bring them in.” (09:08)

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Notable Quotes & Memorable Moments

• On Desperation:
  • Bert: "You come from a place of desperation and guys know it. Am I wrong here?" (01:59)
  • [A]: “That is a desperate move right there.” (02:02)
• On Playing the Game:
  • Bert: “You have to act. That’s…the game we’re trying to tell you.” (03:47)
  • Kristin: “Games are stupid. Someone’s gonna like you whether you play a game or not, right?” (03:59)
• Analogy – The Deer in the Truck:
  • Jen: "Men are hunters. Let them hunt." (09:45)
  • Kristin: "You're a deer that jumps into the back of the truck and goes, just says, here, I'm already here. I'm already dead." (09:57)
• Experiment Plan:
  • Bert: “When you meet guys this weekend, you give them this phone number, okay? They’re gonna think they’re texting you, but they’re really texting me. And I’m gonna play it all weekend long.” (07:20)

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Timestamps for Major Segments

• 00:47 — Show begins, addressing Wendy’s single status and “zero mojo”
• 02:02 — Example of ‘trying too hard’: Dress at the lake outing
• 03:47–04:04 — Debate about whether “the game” is necessary in dating
• 06:19–06:48 — Recap of prior experiment: Bert coaches a man in dating
• 07:20–09:14 — Announcement and setup of the new “Wendy’s Dating” experiment
• 09:29–10:52 — Hunting analogy & listener calls encourage letting men “chase”
• 11:10+ — Segment wraps with teasing and plans for experimenting

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Tone & Takeaways

The episode is frank, comedic, and supportive. While the team pokes fun at Wendy’s “desperation,” their intent is to empower her to be more confident and strategic. The “dating game” is dissected with both skepticism and real-world support. Memorable analogies and innovative radio experiments keep it engaging and relatable throughout.

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Key Takeaway:
To find genuine connection, stop projecting neediness and let potential partners come to you—sometimes, a little game playing helps maintain your own value and intrigue. And if you can’t do it yourself, maybe let Bert run your love life (at least for a weekend).

Transcript

[A]

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[A]

Listen, it's the vert show.

[B]

Where do we even start? I mean, Wendy, we've been preaching to you now for years. Have you been on the show years?

[C]

A year. Year, year.

[B]

Now that the problem with you being single here is you got zero mojo. You are coming from a place, and I'm saying this lovingly, I'm not trying to come down hard on you, but the truth of the matter is this, is that you come from a place of desperation and guys can. We can smell it.

[C]

Well, and here's. I think what you need to remind Wendy is that the point is she doesn't need to be that way because she's got everything going for her that you can imagine. So that's. That's the sentiment behind their criticism, is that, hey, don't act this way because you don't need to. Right? I mean, you've gotta talk to a girl in a way that you're talking to a girl. You can't talk to a girl like you talk to a guy.

[B]

Okay, let me.

[C]

So be careful with the way you word things or else she's gonna shut down and not have. Yeah, I'm trying not listen to anything you have to say.

[B]

Well, Wendy's told me before that she just wants it honest. Be totally and completely honest with her. So I could either sugarcoat this or I can be 100% and say, look,

[C]

as a guy, no, we're women. Sugarcoat.

[B]

Jeff, Jeff, you can't do.

[C]

You can do honesty.

[A]

I'm joking.

[C]

No, honesty. Because apparently I'm desperate. But I don't even see that I'm desperate.

[B]

You come from a. Of desperation and guys know it. Am I wrong here?

[A]

You do. Based on the way you behave. And. And here's the we see it, I think, more when you're not around the guys. But it always goes back to the example when we were up at the lake and we're going to the dive bar, and we're like, we're leaving in 10 minutes, and everybody's in the driveway with flip flops and T shirts and jeans or cargo shorts. And then you come down in a black dress, full makeup, and heels. Like, that is a desperate move right there.

[B]

Guys can see that, and they know that you want it too much.

[C]

But that the bar, you never know. We're gonna meet Mr. Wright.

[B]

It's not gonna be at that bar. And it's so funny, but he wasn't gonna be at Disney World a couple of weeks ago when you wore that

[A]

up to that the point you say that, but guess what? Like, Mr. Right. The Mr. Right, who's at the bar that's built on a pier, you know what I mean, that has water underneath it where you can actually fish while you eat. Like that place, the guys there aren't gonna be interested in a girl weari dress and heels and full makeup for other than one thing. Same thing at Disney world. Like the people walking around Disney world in leather pants. Like, the guys who see them. Like, you get. So that right there appears to be trying too hard.

[B]

And you've told us before, like, sometimes at our events is just to kiss a boy. I want to kiss boys tonight. Guys can smell that. They know. We know because you have. It takes away your mojo entirely. If you want it too much, guys can sense that.

[C]

And you want less. You have to care so much less than you do. I can't not care.

[B]

Then you have to pretend. Then you have to act.

[C]

Oh, okay. Well, how do you pretend to not care if you care? I don't know the answer to that one.

[B]

You have to act. You have to. That's. This is the game that we're trying to tell you that people say that, oh, I don't want to play the game. I just want to be totally and completely honest. And in the dating world, that doesn't work. You got to play the game.

[C]

Games are stupid. Someone's gonna like you whether you play a game or not, right?

[B]

Nope.

[A]

It's yes, they'll like you. But getting into it, right? You're not going to. You don't. Here's the deal. If a guy. If you're hanging out at the. At the bar that you can fish from, right, and you're having a good time and everything's cool, the guy who comes up and meets you there and gets your number that night and makes out with you that night and probably calls you the next day and sees you the next day is gonna do the same thing to a different girl next week. That's not what you're looking for. You're looking for a guy who's gonna be into you. Which means you gotta make him dance a little. Make him hustle.

[B]

Do you remember that book that came out a couple of years ago called the Rules that everybody was so critical about? This game playing book that came out.

[A]

Remember Wendy was in fourth grade when it came out. So she doesn't.

[B]

It said it was a book on basically how to get a guy by just not caring. There are certain rules. If he calls you you don't call him back immediately. If he texts you.

[C]

That doesn't work. It didn't work.

[B]

You don't immediately didn't work. Go ahead.

[C]

It did not work. It's a game of numbers though.

[A]

But you don't. It did work because you weeded that guy out. You don't want him. It did work. You're saying that you like we're. The cream rises to the top. Look it. I am being praised like I am in church right now. Listen.

[C]

Listen to it.

[A]

But what you're saying it didn't work because you didn't get the guy. The rest of us are all saying it did work because you don't want that guy.

[B]

That guy. You were a booty call for that guy.

[A]

If the guy couldn't call you back and make a relationship with you because you waited 24 hours or not even that 15 hours to text him back then you don't want that guy.

[C]

But I think that goes for a phone call. Like text is almost immediate in general.

[B]

I'm glad we're getting into this now. Cause Jeff brought up a point. You know I forget what we do on a day to day basis here. But when we had Phil Turana on the show years ago.

[A]

That's what we do. We help.

[B]

That's all we can try to do. Jeff.

[A]

Look at our hearts.

[C]

Look at them extending their helping hand.

[A]

Wendy. Put your hand on my chest and feel how my heart beats for you.

[B]

Bill Turano a couple of years ago on the show. Same situation. Dude. The nicest guy in the world. Heart of Gold. Zero game. 000 game. So we did this bit to where I guided him through a relationship with a girl. He was not allowed to make any decisions at all. I made all the decisions for him for how many weeks?

[A]

I mean for whatever the period of time was, it worked perfectly for 95% of the time.

[B]

It was flawless. I was reeling her in.

[A]

I mean, we were reeling her in. And it was the first. The first 95%. Because it all fell to pieces when one thing happened, didn't I?

[B]

Like, went out of town or something like that, and he went off script.

[A]

You were unavailable.

[B]

He was unavailable. And he took matters into his own hands, and he lost the girl in, like, 24 hours.

[A]

And that's not a joke. Like, it was seriously a situation where it's serious. Really. It's the same thing.

[C]

It's overeager.

[A]

He would call Bert, like, on a Saturday afternoon and go, dude, she just called me and asked me if I wanted to meet her at Applebee's for drinks before we go out tonight. What do I say? And Bert would give her guidance. Well, one day, Bert was doing something stupid like playing with his kids or whatever and couldn't take the phone call. And so Phil just said on his own. You know what? I think? You know what? Breakfast right now is a good idea. And went to breakfast with her. And whatever happened, she seriously dumped him the next day.

[B]

He made himself too available too soon.

[C]

Oh, no.

[B]

Okay, so here's what I want to do with you, okay? Jeff got this AT&T phone, okay? I am gonna give you the phone number to this phone, okay? When you meet guys this weekend, you give them this phone number, okay? They are gonna think they're texting you, but they're really texting me. And I'm gonna play it all weekend long.

[C]

I am gonna be you, okay?

[B]

All weekend.

[C]

Awesome. Any guy. Any guy I meet this weekend, Any

[B]

guy that you're really interested in, okay?

[C]

Okay.

[B]

That you want to reel in, I am gonna be you texting all weekend long, and I'm gonna show you how this is done.

[C]

So you gotta give out that phone number a couple of times.

[A]

And you know what? It's all like, we'll set it up with. You'll put your own voicemail on there. So if they call you, Bert will set it up, so he'll have the password and everything. And so when they call you and they're like, hey, what's up, Wendy? It's Jeff. I met you last night at five paces of blah, blah, blah. He'll hear the message, and then he will write a text back to the dude. So then I would get a text back from you that says, hey, guy, got your voicemail. We'll try to call you tomorrow. Like, so he's Playing the role of you for. I mean, we have the phone as long as we need it. All right, so he starts this week at&T. Their heart also bleeds for you, Wendy.

[C]

Oh, man. So I can't talk to any of the dudes I meet?

[B]

No, no, no, no, no, no. I'm gonna reel them in, and then once I get them, then I will hand it over to you. But you can't get. You can't get through the first couple of phases.

[A]

And you can just say, can we

[C]

also do this when Wendy gets in a relationship and starts sexting them? No, no, no. I want to know what you would write.

[A]

And just so you know, the way it'll work is, like, if Burt plays it around for a couple weeks, and then you could just say, hey, I. You know, I switched my number. And he'll turn. He'll release the men over to you, and you just say, hey, I switched my number. I got an iPhone or whatever, and boom, you're done.

[B]

Just let me get them on the boat. And you could choose to do what you want with them. You can make them a trophy, you can eat them, whatever. But I'm gonna bring them in.

[A]

It's like. It's like fish, marlin. Like the guy, you're the captain of the boat who reels him in, but

[C]

Bert's never reeled one in. So what am I supposed to do? Bert's never reeled a marlin in. Great.

[B]

Hey, Brandy. Go ahead. You're on Q100.

[C]

Yeah, I was just gonna say that guys still like the chase. And I was totally in that place last year, and I started not caring, and I got tons and tons of calls right away and just ignored them for a while. And now I'm in a long term relationship.

[B]

So, Jen, what is your infamous line about guys and hunting?

[C]

Oh, men are hunters. Let them hunt.

[B]

You don't let them hunt.

[C]

I'm not good at that.

[B]

You jump into their truck and you say, here I am. You're a deer that jumps into the back of the truck and goes, just

[C]

says, here, I'm already here. I'm already dead.

[A]

They have.

[C]

I'm a venison burger.

[A]

They have the rope in their mouth and, like, tie me to the hood.

[B]

It's already done. So here's the. I will give you the phone number.

[C]

It's actually a good analogy.

[A]

What? The hunter.

[C]

I'm a deer. The deer that jumps in the back

[B]

of the truck jumps in the truck.

[A]

Here I am.

[C]

What fun is that?

[B]

No, you go ahead. You put the Gun away.

[C]

I mean, why put on the camouflage and all the other stuff if it's just gonna jump in the back of your truck?

[A]

Yeah, why waste a bullet?

[C]

Well, at least you have something in the bag just in case you can't catch anything.

[A]

Stop covering your truck.

[B]

Why?

[C]

You wanna be the. Just in case you wanna be the prize?

[B]

This is what we're talking about. You're coming from the desperate place.

[C]

Well, I'm looking at the positive side of it, Wendy.

[A]

You deserve a guy that's willing to climb in the tree and cover himself in urine and sit there for half

[B]

woman doesn't want that.

[A]

That's what you deserve.

[C]

I need a urine covered man.

[A]

Wendy, I want for you a urine soaked man. And with Bert's help, you will get one. You will get a man in camouflage.

[C]

I'm sure I will.

[A]

At Park Tavern with a bright orange hat and covered in deer urine.

[B]

I will. Actually. That's going to be funny because I will actually be at Park Tavern with you on Saturday. You're going to be giving your phone number out, and I'm going to get the text. All right, so here's the phone. You go ahead and you set up the voicemail and everything. You give the phone number out, and I will respond as Wendy for the next couple of weeks.

[C]

Oh, this is gonna be weeks.

[B]

See how long you think?

[A]

Oh, my God, could be years. Listen, it's the virt show.

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