Vault: Did The Bert Show give her the wrong advice?

Summary

The Bert Show — Vault: Did The Bert Show give her the wrong advice?

Date: May 8, 2026

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Episode Overview

This episode of The Bert Show revisits a listener drama involving Terry, who sought advice about reaching out to a "pseudo-ex" she hoped would visit Atlanta for the weekend. The team reflects on their previous guidance and whether their advice helped or hindered her situation, all while peppered with their signature humor and off-the-cuff banter. The discussion explores dating nuances, digital communication etiquette, and generational differences in pursuing relationships.

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Key Discussion Points and Insights

Recap of Terry's Situation (00:57–01:52)

• Background: Terry had been communicating with a guy she dated years prior and was unsure if he'd visit Atlanta. She reached out via multiple channels (instant message, email, Facebook).
• Host Reaction: The team reflects on whether Terry’s persistent messaging was too much, especially since she didn't even have his cell number.
  • "I think she just assaulted him online and sent him a bunch of IMs and emails and then Facebooked him." — F (01:58)

Listener's Update Reveals a Twist (02:11–04:26)

• Terry’s Message: She sent an email saying, “You guys were wrong. I didn’t screw things up. I think he likes me. I think this is gonna be a good weekend. If I don’t let you guys screw it up for me. :)” (02:47)
• Team’s Initial Reaction: Hosts thought her attempts had ended things, but then realize she forwarded an email from the guy, who apologized for not responding and confirmed plans to visit Atlanta:
  • "Hey, sorry for not getting back to you. Last weekend was crazy... Good news is I’ll be there on Saturday. Will you be around? I’ll look for you online in the morning." — Terry, quoting the guy's email (04:07)
• Hosts’ Self-Reflection: They joke about their mistaken advice and how Terry may blame them for almost derailing things.
  • "She thinks we jacked up for her." — B (03:17)

Analyzing Terry’s Next Move (05:04–05:55)

• Banter about Playful Stalking: The group riffs on Terry potentially waiting at the Georgia border with a welcome banner.
  • "She’s gonna replace the welcome to Georgia, Georgia’s on your mind sign with her own personal size." — B (05:38)
  • "Also home of love of your life, Terry." — F (05:46)
• Advice on Being Unavailable: D suggests Terry should appear less available and not overplay her interest.

Audience Calls and Gender/Dating Dynamics (06:00–08:45)

• Caller Reno’s Perspective: Suggests men will tolerate persistent behavior if they're into the person, otherwise it’s off-putting.
  • "If he genuinely likes her, he's gonna put up with more of this stuff." — I/Reno (06:11)
• Caller Tim’s Critique: Asserts the show's advice was “high school” for an adult situation. Encourages more maturity in approach.
  • "You guys were kind of giving her... like high school advice on an adult problem." — H/Tim (07:19)
• Host-Caller Banter: The generational gap in dating communication is playfully discussed.
  • "You had to write him a letter with your feather pen under a candlelight, seal it with wax, and then give it to the Pony Express." — F, to Tim (09:05)
• Hosts Debate Whether Modern Dating is Just a New Game: While technology changes, the "game" of dating may remain fundamentally similar.

The Outcome and What Comes Next (08:52–End)

• Will Terry Check Back In? The group predicts Terry will only update if things go well.
  • "If it went well, we will hear from her. If it didn’t go well, we will absolutely not hear from her." — B (09:26)
• Host Guilt: Jen (E) feels remorse for possibly giving bad advice, which is lightheartedly ribbed by the team.

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Notable Quotes and Memorable Moments

• "I think she just assaulted him online and sent him a bunch of IMs and emails and then Facebooked him." — F (01:58)
• "You guys were wrong. I didn’t screw things up. I think he likes me. :) If I don’t let you guys screw it up for me. :)" — Terry (02:47)
• "She’s gonna replace the welcome to Georgia, Georgia’s on your mind sign with her own personal size." — B (05:38)
• "If he genuinely likes her, he's gonna put up with more of this stuff." — I/Reno (06:11)
• "You guys were kind of giving her... like high school advice on an adult problem." — H/Tim (07:19)
• "You had to write him a letter with your feather pen under a candlelight, seal it with wax, and then give it to the Pony Express." — F, to Tim (09:05)

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Timestamps for Key Segments

• Recap and Terry’s Concern: 00:57–01:52
• Terry’s Defiant Email: 02:11–02:52
• Forwarded Email from the Guy: 03:44–04:24
• Hosts’ Banter about Waiting in Georgia: 05:04–05:55
• Callers Weigh In (Reno and Tim): 06:00–08:45
• Predicting the Outcome and Closing Thoughts: 08:52–End

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Tone and Style

• The hosts are witty, self-deprecating, and irreverent, poking fun at themselves and each other while examining Terry’s predicament.
• The language is casual, humorous, and authentic, peppered with callbacks, impressions, and asides.

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Summary

In this lively episode, The Bert Show hosts revisit a piece of listener drama, wrestling with whether their advice (to avoid over-pursuing an ex-flame) was off the mark. An update from Terry surprises them, revealing things might not be as doomed as they thought. Through candid discussion, guest calls, and generational ribbing, the episode captures the challenges of modern dating and the pitfalls of giving (and taking) advice—reminding listeners that success in love often comes down to timing, chemistry, and a sense of humor.

Transcript

[A]

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[B]

This is going to be very quick here. Very quick. We've detailed for you the instant message history here with Terry. We helped her out twice during the show. Things were going fine. And then going into the weekend, she wasn't sure if this pseudo ex of hers was coming to Atlanta or not. So she wanted some answers Friday.

[C]

Since I didn't know if he was coming or not, I. I sent him an instant message because I hadn't heard from him, and I guess I kind of felt like, well, maybe he, you know, maybe he didn't think I was like that into him.

[B]

Because that's where you want him.

[D]

That's where you want him.

[B]

That's exactly where you want him.

[E]

Well, I just. Once you ask him that question, did he respond at all?

[C]

No.

[E]

Oh, my gosh. Maybe the text didn't go through. So she found him on Facebook and Facebooked him, and he accepted her Facebook requests as a friend, but he didn't respond to her message.

[F]

Actually, I don't think she sent him a text because I don't think that she even has a cell phone number.

[E]

I thought she texted him, too. Maybe I made that up.

[F]

Yeah, I think she. Because that makes it even creepier if she's reaching out all those ways and doesn't even have his cell number. I think she just assaulted him online and sent him a bunch of IMs and emails and then Facebooked him.

[B]

Well, she's not answering this morning, so we can't ask her all these questions. But this is the email that she sent out last night. Just check this out. You guys were wrong. I didn't screw things up. Which we told her time and time again, it's done. I mean, he doesn't respond to four different messages. Doesn't matter if it's an instant message. It's an email. The combination of four with no response. You're done. Check this out. You guys were wrong. Exclamation point. I didn't screw things up. Exclamation point. I think he likes me. Smiley face. Yep. I think this is gonna be a good weekend. Exclamation point. If I don't let you guys screw it up for me. Smiley face.

[F]

Mm.

[B]

I'm really nervous he won't IM me in the morning. I don't think I'll be able to sleep tonight. From Terry.

[D]

That's it.

[B]

I don't.

[E]

That's it.

[B]

I'm really nervous. He won't in the morning. I don't think I'll be able to sleep tonight.

[E]

I wonder if he's coming to Atlanta this weekend. It sounds like she got some news from him. In one way or another, she heard the whole thing.

[B]

That's it.

[D]

And so she doesn't want us to

[E]

screw it up, and that's why she's not.

[B]

Oh, I wasn't even putting that together. So she thinks we jacked up for her.

[D]

Well, she's the one.

[F]

We're in trouble now.

[B]

Alligator arms, dude.

[D]

But she's the one who text him every. Tracy Facebooked him and ruined it herself.

[G]

You didn't read the whole thing? It was a forward from him. If you go further down, the email's below that.

[D]

Oh, so he contacted her.

[B]

Why are you breathing so heavy?

[G]

Because I ran down here.

[F]

Well, here, you read. Well, you reading it.

[D]

We're screwing it all up, Bert.

[G]

Okay, well, you read the part that she sent. The reason she sent that is cause she forwarded an email from him that was sent a couple hours before that.

[F]

Tracy's inhaler.

[G]

I just made it down here in two seconds. It says, hey, sorry for not getting back to you. Last weekend was crazy. And this week was even more crazy. So much work. I never made it to Atlanta. Good news is I'll be there on Saturday. Will you be around? I'll look for you online in the morning.

[B]

Sorry, Tracy.

[D]

He was unavailable.

[B]

That condescending look.

[F]

I know.

[G]

Well, I thought you were gonna, like, go into commercials, and then we missed the whole point of everything.

[B]

Sorry.

[G]

Sorry.

[B]

I'm not good at this.

[G]

Get it right.

[F]

So, you know, we've actually just so everybody knows.

[B]

What?

[F]

Tracy went. Cumulus has sublet her office to a family who's Living in there. And she is working out of her car in the parking lot. So she ran up five flights of stairs.

[D]

So he contacted her.

[E]

Yeah.

[B]

Sorry for not getting back to you. Last weekend was crazy, and this week was even more crazy. So much work. I never made it to Atlanta. Good news is that I'll be there on Saturday. Will you be around? I'll look for you online in the morning. So she's sitting there waiting for him right now?

[D]

No, she still can't do that. You have to seem somewhat unavailable or have a limited amount of time.

[F]

So do you think she's intentionally not answering because she's like, I got this.

[B]

Yeah, she thinks we were the ones that screwed it up.

[E]

She's gonna send some good morning, sunshine crap all over again.

[D]

But she's got to let us know, though, what happened. She's got to let us know on Monday if she saw him.

[B]

Yeah, she does.

[D]

Well, she's gonna be waiting at the border of Alabama and Georgia for his

[E]

car to come through the big welcome banner.

[D]

Yes, here I am. It's Terri. Im's screen name is this. And this. Good morning, sunshine. Welcome to Georgia.

[B]

She's gonna replace the welcome to Georgia, Georgia's on your mind sign with her own personal size.

[H]

I'm here.

[B]

I'm waiting for you. She'll screw this up by herself down

[F]

at welcome to the state where it says Governor Sonny, or, you know, Sonny Perdue, governor underneath, that'll say, also home of love of your life, Terry.

[E]

But this is good news for her, though. I mean, we want her to get the guy. So I'm excited for.

[B]

Reno agrees. She thinks we jacked this whole thing.

[D]

We did. Geez.

[F]

Hey, Reno.

[B]

Good morning.

[C]

Hey.

[I]

Hey. Well, not necessarily. I mean, I think she's going a little overboard, definitely, but I think that. Don't you guys think that a guy will put up with a lot more stuff from someone that he really. So if you gen. If he genuinely likes her, he's gonna put up with more of this stuff. But if you don't like a girl initially, this just becomes annoying.

[F]

He doesn't even know, like, her.

[I]

Well, he does know her. I mean, he's dated her, seen her at some. I mean, Right.

[E]

They made out before.

[F]

Years ago.

[I]

He accepted her friend request on Facebook, which is kind of.

[D]

That makes you real friends.

[I]

I don't know about that, but I'm just saying, like, there's a level like that you put up with if you like a girl a lot.

[B]

Well, isn't this all about how hot she is? I mean, because he hasn't seen her in years. They. They only hooked up like a couple of times and then it's been years. So if she. She Facebooks him, he accepts it. She looks hot. Yeah. He's setting it up.

[I]

I definitely think that that has a lot to do with it very well. If he doesn't know her that well as far as a relationship wise, even though he should probably walk on eggshells a little bit because she does. I mean, like I said, she is going overboard, but I don't know, man. I don't know.

[B]

Here's Tim. Same thing.

[E]

Okay.

[B]

Thinks that Jen. Jen specifically screwed this all up.

[D]

Okay.

[B]

Hey, Tim. Good Morning. You're on Q100.

[H]

Yeah, thanks for that intro. So, yeah, you guys were kind of giving her. I'm glad she. This guy's showing some interest because it seemed to me that you guys were kind of giving her like high school advice on an adult problem.

[I]

Right.

[H]

To play all these games and. Okay, yeah, she was 21 and all, but I think you all steering her in the wrong direction.

[E]

Hey, Tim.

[H]

Yeah.

[E]

Are you a married guy?

[H]

Yes.

[E]

Okay. And how long you been married?

[H]

A long time.

[E]

So you didn't have to play the dating game with texting an im, did you?

[I]

No. No, I did not.

[E]

See, the landscape has just changed, Tim.

[B]

You're like a good lawyer right now. The case closed, Tim.

[F]

You couldn't even text when you picked up the phone and you were like,

[E]

I understand where he's coming from. Because you didn't have to deal with that when you were dating. Like, you liked a girl, you asked, you're out, or whatever. Like, there's so many different forms of communication that make it so much easier for both guys and girls now to not have to have that personal level of communication and to be able to sort of be smarter and wittier about it. Like, you have to play this game.

[B]

Let me, let me stick up for the old guys here for a second, Tim.

[H]

Thanks.

[B]

Because I don't think the game has changed. And I mean, it's evolved, but it's certainly the tone of the game is still the same.

[E]

Sure. But I'm just saying the type of communication is different and there's something different to that.

[B]

We're dinosaurs, Tim. It's over, man. We both got school.

[E]

I didn't mean to be insulting to him. I was just trying to prove my point. I wasn't. Yeah, was I insulting, Tim?

[B]

I don't know.

[F]

Hey, Tim, you didn't even have electricity when you were a kid, did you.

[E]

That's not what I meant.

[F]

You had to write him a letter with your feather pen under a candlelight, seal it with wax, and then give it to the Pony Express.

[B]

All right. We'll see how she does on her own now. She wanted to leave the nest, so we'll see how she does this weekend.

[F]

She's never calling us again to be mean.

[B]

You weren't being mean. I'm just giving you a hard time. But we'll see how she does all by her own this weekend.

[F]

I bet we don't even hear from her.

[B]

If it went well, we will hear from her.

[E]

Agreed.

[B]

If it didn't go well, we will absolutely not hear from her.

[D]

Right.

[B]

Don't get all in your own head now. I can see. Like this remorse is washed over Jen. Like, I don't want to hurt anybody.

[E]

I didn't mean to hurt his feelings.

[F]

You spanked him.

[E]

Allison Winterland, Medicine Heady. So I'm weird.

[F]

The Birch Show.