Awkward Tuesday: AI Messed Up

Summary

Brooke and Jeffrey: Second Date Update

Awkward Tuesday: AI Messed Up

Date: June 23, 2026
Podcast: Brooke and Jeffrey (iHeartPodcasts)
Episode Type: Awkward Tuesday Phone Call

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Episode Overview

This episode tackles a hilariously disastrous relationship snafu involving a listener, Seth, who faces eviction from his girlfriend Lola’s apartment after a digital mishap and a tangled web of lies. In a classic “Awkward Tuesday” segment, the team helps Seth make an on-air phone call to Lola to explain a suspicious, AI-generated photo and confess his actual whereabouts—with plenty of comic misadventure, unexpected emotional moments, and sharp commentary from the hosts.

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Key Discussion Points and Insights

Introducing Seth’s Predicament

[05:47] Jose: Explains Seth’s urgent email: he has just hours before getting kicked out and desperately needs advice.

• Seth has trust issues in his year-long, on-and-off relationship with Lola, partly due to lingering business with his ex.
• [06:48] Seth: “I've been trying to kind of clean things up with my ex...get stuff from her...trying to get closure and fully, like, move on.”
• Seth admits he and Lola live together, raising the stakes.

The Lie and the AI-Generated Photo

[08:49] Seth: Details his attempt to cover up a meetup with his ex by enlisting a friend to “prove” he was somewhere else—resulting in a bizarre AI-generated party photo on social media.

• The composite photo showed Seth, his friend, and an attractive woman at a casino, all digitally rendered.
• [09:53] Seth: “Well, she said, why are you gambling? Who is that woman that you are flirting with? I couldn't even say. Well, she's not even real.”
• [10:33] Brooke (sarcastically): “No wonder your girlfriend has trust issues. Yeah, I'm kind of happy she's kicking you out.”

The Hosts’ Advice (and Antics)

[13:12] Brooke: Suggests full honesty:

• Address the AI photo (“It’s not real!”)
• Admit Seth actually met his ex, but it’s the “final” closure
  [14:11] Jeffrey: Jokes about making up an even bigger lie to cover the first one (claim they were ring shopping).

[15:03] Seth: “God, I'm just. I'm very over. Yeah, this whole situation, I just want to move forward.”

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The Awkward Tuesday Phone Call

The Confrontation

[15:23] Seth calls Lola (live on air):

• Lola immediately rebuffs him, citing a pattern of dishonesty.
• [15:35] Lola: “No, I don't want to hold on anymore at all. Like, you lie to me, like, all the time.”
• Seth tries to appeal to empathy, calling himself “a bad teddy bear.”
• Lola fiercely rejects the cutesy tone:
  • [15:52] Lola: “Don't use, like, cute nicknames on me. Like, I'm over all of this.”

The Photo’s Fallout

[16:05] Lola: Outraged by the image, even assuming the woman is a prostitute.

• [16:22] Seth: Responds, “Don't say that. She doesn't even have feelings.”
• [16:54] Lola: Baffled—“She has feelings. She's a beautiful woman. She's human, right?”

The Truth Comes Out

[17:03] Seth (finally): Admits the woman was an AI-generated fake, and the friend used Photoshop.

• Lola is incredulous and frustrated: why make things more confusing with tech-based lies?
• The hosts break in, revealing the call is on a radio segment, adding to Lola’s confusion.

Full Confession

[18:29] Seth: Comes clean about meeting his ex, explaining the AI ruse was to prevent Lola from getting mad.

• [19:06] Lola: “I don't know whether to be mad at you or, like, just think you're stupid.”
• She accuses him of backing himself into a corner with lies—and extending contact with his ex unnecessarily.

Lola’s Final Verdict

• Lola will allow Seth back into the apartment, but only to retrieve all his possessions at once:
  • [19:38] Lola: “He has prolonged giving back...stuff to his ex for a year...Please. I will let you into the apartment to pick up your stuff, but with one condition...If I have to return it to you, you will take that with you. No trickling things along!”
• The hosts and Lola joke about how Seth has to move out in one go, and Lola asserts her boundaries.

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Notable Quotes & Memorable Moments

• [08:49] Seth: “He posted this AR photo of me and him with our friends all partying and drinking at a casino table with a hot woman.”
• [10:33] Brooke: “No wonder your girlfriend has trust issues. Yeah, I'm kind of happy she's kicking you out.”
• [13:47] Lola: “A picture is worth a thousand words, Seth. Why? Why do I have to hear you out?...Looks like you hired some prostitute or something.”
• [16:54] Lola: “She has feelings. She's a beautiful woman. She's human, right?”
• [19:06] Lola: “I don't know whether to be mad at you or, like, just think you're stupid.”
• [19:38] Lola: “I will let you into the apartment to pick up your stuff, but with one condition...No more trickling things along with your ex!”

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Key Timestamps

• 05:42 – Introduction of Seth’s predicament
• 08:49 – The AI-generated photo incident explained
• 13:12 – Advice: Should Seth confess or keep lying?
• 15:23 – Seth calls Lola
• 16:05 – Lola confronts Seth about the AI photo
• 17:03 – Seth explains the photo is fake
• 18:29 – Seth’s full confession about meeting his ex
• 19:38 – Lola allows Seth to collect his things, lays down strict rules
• 20:54 – Hosts reflect on the outcome

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Tone and Language

• The hosts maintain a humorous, sarcastic, occasionally compassionate tone, often ribbing Seth for his predicament and questionable decisions.
• Lola’s language is direct, often exasperated, underscoring her frustration but also her independence.

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Summary Flow

This episode delivers a sharp, comedic, and cringe-inducing account of miscommunication, technology gone wrong, and relationship messiness. Seth’s attempt to avoid drama with an AI-powered lie backfires, only compounding Lola’s mistrust. The hosts provide a mix of real talk and comic relief, while Lola ultimately seizes the upper hand, offering closure—with conditions.
For anyone navigating modern dating, trust issues, or the dangers of AI fakery, this is a cautionary tale delivered with plenty of laughs.

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Transcript

[Brooke]

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[Brooke]

We got a new episode for you today and I'm guessing the guy today is not going to have a lot of fans in the comment section. Don't think so. I mean, I could be wrong. I could be wrong. But yeah, I don't know. Yeah, it's one of those where I'm happy. I'm not the one that has to come up with advice. Just you guys. Yeah, that's right. So we're going to get to that in just a second. But first, comments. Alexis, what do you see? Yes. Ws and then a lot of numbers and letters said, omg, it happened to me. I can finally call the station and ask for a second date update. That's wild. Terrible. That sucks. But, you know, but congratulations.

[Jeffrey]

I wonder if they did that on their date when it ended so awful, they were just like, yes, yes.

[Brooke]

They went to brookandef.com submit. Yeah, yeah, that's where you do it. That's where you do it. You go to our website. And you can also, while you're there, just check out our socials. I mean, that's why not. You know, at BrookeandJeffrey, people always tell

[Jeffrey]

us we do not look like what you think.

[Brooke]

Yeah, exactly. All right, let's go to it. Your brand new Awkward Tuesday starts right now.

[Jose]

You know that friend who's always saying, relax, I've got this.

[Jeffrey]

Yeah.

[Jose]

Well, this is why you should never relax when your friend says that to you. Because one of our listeners trusted his idiot friend to help cover for him. And now he could be out of an apartment and out of a girlfriend, too. So he's turned to us, hoping we can save him in your awkward Tuesday phone call right after this.

[Jeffrey]

It's awkward.

[Lola]

It's Tuesday.

[Jeffrey]

It's awkward Tuesday phone call.

[Jose]

Got an urgent message that showed up at the top of our inbox this morning.

[Jeffrey]

Oh, my gosh.

[Jose]

From a listener named Seth who says, hey, I'm about seven, six hours away from getting kicked out of my girlfriend's apartment. Is there any way you could hurry this up and help me out?

[Jeffrey]

Is it hours?

[Brooke]

Oh, God. Just do your fair share, Seth.

[Lola]

Okay?

[Brooke]

Pick up the laundry. What you do? Clean your dishes.

[Jeffrey]

I feel like we're past that point.

[Brooke]

I'm kidding.

[Nissan Rogue Ad Host]

We don't even know what he did.

[Jose]

But with that type of request, how could we say no? Seth, welcome to the show, man.

[Seth]

Hey, it's great to be here.

[Brooke]

Is it?

[Jose]

Yeah.

[Brooke]

Because it sounds like it's a terrible reason to be here.

[Jeffrey]

Sounds like it's crazy to be where you're at.

[Jose]

You sound thrilled.

[Seth]

You guys are cheaper than therapy, though.

[Brooke]

We are cheaper because we're free.

[Jeffrey]

Yeah.

[Jose]

Well, what's going on? You have a six hour deadline till you're getting kicked out of your girlfriend's place. What happened?

[Seth]

Well, I've been dating this girl for a while. It's been about a year, but we've been off and on again the whole time because she doesn't fully trust me yet.

[Brooke]

Okay, why? Why doesn't she trust you? Is it because of past relationships or is it because of something you did?

[Jose]

What's wrong with her that she doesn't trust you? That's what Brooke means.

[Seth]

Sure it is an ex situation. Because I've been trying to kind of clean things up with my ex. Oh.

[Brooke]

Oh, not her ex. That it was her ex. Was it?

[Jeffrey]

What do you mean by clean things up?

[Seth]

Well, you know, just, like, get stuff from her. Like, just exchange stuff that was ours after the break. I'm trying to get closure and fully, like, move on.

[Jose]

Okay, this is. This is an ex that you were in pretty deep with, that you have a lot of roots with you have to untangle.

[Seth]

Yes. We had a long history. It was a three year relationship.

[Brooke]

Usually you get the closure, move on before you start dating again? No, before you move in with a new girlfriend. Because. Are you living with this new girlfriend?

[Seth]

Yes.

[Brooke]

Okay.

[Discover Ad Host]

Wow.

[Jose]

I don't see anything wrong with the choices that you've made in your life. Seth, I support you regardless of what happens.

[Ebglis Medication Informant]

Okay.

[Jose]

Although I will admit, it is a very, very messy thing that you're describing to us. So why is it causing a problem in your current relationship now?

[Seth]

Well, there's just like, we'll find stuff that we know is important to the other person. And so I just feel like I owe it to her to, like, get her this stuff, and then that sparks a conversation, just, how are you? And then we, like, just start talking about the past. But I'm trying to get over that. And one of the times that I was giving her stuff, Lola had my location on her phone. And so she was asking me about where I was, and she, like, knew about where she lived, so I had to say, oh, man. Yeah, I was meeting up with her and she got really upset about it.

[Brooke]

Yeah, you had to tell the truth. Well, I hope that you were always honest with her when you were there.

[Seth]

Well, this is why I'm having an urgent issue today is I wasn't honest.

[Jeffrey]

Oh, you lied.

[Brooke]

Okay.

[Jose]

What were you not honest about this time?

[Seth]

Also, last week, I finally had a Friday night and we were just exchanging the last few items, like, this would be it. And I didn't want my girlfriend to be mad. I asked my buddy to cover for me, and I was like, hey, just, like, post a photo of me and you hanging out somewhere complicated, wherever. And I don't know what. He misunderstood. I don't know what happened, but he posted this AR photo of me and him with our Friends all partying and drinking at a casino table with a hot woman.

[Brooke]

He's like, yeah, I got your bag.

[Lola]

Okay.

[Brooke]

AI. Okay, Maybe he's mad you asked him. He's like, this is how I'm gonna get him. I don't think so. I think he just went into AI and said, show me fun. Boys night out.

[Jeffrey]

You are so right now.

[Seth]

I guess I don't know what he put in the thing, but, like.

[Ebglis Medication Informant]

Dude.

[Jose]

Okay, so I'm assuming that your girlfriend Lola saw the picture that your friend posted and that's what set her off.

[Seth]

Yes.

[Brooke]

So what she say when she saw the fake photo?

[Seth]

Well, she said, why are you gambling? Who is that woman that you are flirting with? I couldn't even say. Well, she's not even real.

[Brooke]

Yeah, dude, because the answer's worse. Did you. Before we get too far into this, did you cheat with your ex?

[Lola]

No.

[Seth]

No, I don't. I don't think so. Like. Like when?

[Jose]

Oh, no, the.

[Brooke]

The time on Friday.

[Jeffrey]

Yeah.

[Jose]

When you were exchanging your last items that time.

[Jeffrey]

No, I don't believe here's.

[Brooke]

No wonder your girlfriend has trust issues. Yeah, I'm kind of happy she's kicking you out.

[Jose]

Okay, you're not helping your trust issues with her after that photo.

[Seth]

Yeah, well, no, she thinks I was gambling at a casino with a hot woman. And really, I was just with my ex. I just need to smooth this over, and we will be good going forward. Like, I feel like this is just. This is the last piece.

[Jeffrey]

Oh, man.

[Seth]

I just need this to go well. And I don't know if I should admit it.

[Brooke]

It is really hard for me not to have your girlfriend. Lola's back.

[Jeffrey]

Yeah. You want to take the moral high ground?

[Seth]

You can have her back. I just want to be able to stay in the house.

[Brooke]

Okay.

[Jeffrey]

Okay. So no matter what, you just.

[Seth]

You guys should know, too. Like, again, this is over with the ex. You know, like, we. We exchanged our last thing. Like, I made it clear. Like this. This is it.

[Cat Treat Ad Host]

We're done.

[Ebglis Medication Informant]

Okay.

[Seth]

My focus is gonna be on Lola.

[Brooke]

Okay.

[Jeffrey]

All right.

[Lola]

Yeah.

[Brooke]

That he lives with.

[Starbucks Ad Host]

Yeah.

[Brooke]

Good. So good of you. Yeah, man. She's a lucky woman.

[Lola]

Yeah.

[Brooke]

Very lucky woman.

[Cat Treat Ad Host]

She is.

[Jeffrey]

We just have to show her we

[Jose]

believe in you is what we're trying to say. And we're gonna have great advice when we come back. Call your girlfriend and convince her to not kick you out of your apartment with your awkward Tuesday phone call right after this.

[Seth]

Oh, you guys are the best.

[Jose]

I don't feel great about it, but let's do it.

[Jeffrey]

It's awkward.

[Brooke]

It's Tuesday.

[Jeffrey]

It's awkward.

[Geico Gecko]

Tuesday.

[Jeffrey]

Phone call.

[Jose]

They say it takes a real man to admit when he's made a mistake. So our listener Seth, must be Superman with the number of mistakes he's admitting to today. He's been seeing a woman named Lola for about a year now. There's been some trust issues because live

[Brooke]

together is an important piece of this.

[Jose]

Yeah, and he's also trying to clean things up with his previous relationship. And that untangling process has lasted longer than expected.

[Brooke]

Let's just say so long.

[Jose]

It got a whole lot worse when he asked his buddy to cover for him while he went and picked up the last few items from his ex's place the other night. And his buddy covered by posting an AI generated photo of them drinking and gambling at a casino with some AI generated baddies sitting on his lap. So girlfriend saw that pic and didn't love it to the point where she's about to kick Seth out of their apartment. And that's why he's come to us seeking advice on how to stop that from happening.

[Brooke]

You know what? We never found out. We know Lola's pissed, but what was your response to Lola about that picture, Seth?

[Seth]

She did not even let me get a word out about the photo. She just immediately was kicking me out and said, like, I don't want to see you again.

[Brooke]

Okay, well, so that's the first thing is you need to address that, and you need to say, listen, you didn't give me a chance to explain. It's AI I'm sure you can tell in that photo. Like, I don't know, one of your buddies has four fingers or somebody's missing a nose.

[Jeffrey]

There's always the eyes. The eyes got to look a weird.

[Brooke]

Totally. Totally. But then after that, you need to tell her. However, I need to finally be fully honest with you and let you know that I saw my ex. But it's a good thing because I have complete closure and now I'm fully invested in our relationship.

[Geico Gecko]

Wow.

[Seth]

Okay. I like the first part of what you said a lot better than the second part.

[Jose]

Yeah, the first part seems like it might get him back into his apartment. The second part seems like it's going to really be a part. Yeah, the relationship.

[Brooke]

But the thing is, what are you going to tell her you were doing Friday if it's not the honest truth,

[Jose]

that's a conversation for another day.

[Brooke]

I don't think so, Jeff.

[Jeffrey]

Well, I actually have an idea what I think you should say.

[Jose]

Okay. What do you think, Jose?

[Jeffrey]

So you're going to say, yeah, the casino picture, it was real.

[Brooke]

We're going to lie.

[Jeffrey]

You just didn't see the other pictures. The second picture after it, that was of me ring shopping.

[Brooke]

You're going to get engaged based on a lie?

[Jeffrey]

No, we're not saying it's an engagement ring.

[Jose]

He was just shopping.

[Jeffrey]

Yeah, I just happen to be shopping for jewelry for my lovely girlfriend.

[Brooke]

Drunk post. Casino ring shopping is romantic because he

[Jeffrey]

loves her so much. I gotta go get her necklace or something.

[Jose]

Seth, what do you think of that?

[Jeffrey]

I'm trying to help.

[Seth]

Well, I'd have to, like, get her a ring then, right?

[Jeffrey]

No, no, no. You just need to get your buddy to make the AI picture of you

[Jose]

shopping for a ring.

[Jeffrey]

Okay?

[Seth]

Okay.

[Jose]

The advice is definitely different between Brooke and Jose, but you and choose whatever you want. Seth.

[Brooke]

Dude, don't double down online. This is why you're here to begin with.

[Lola]

Okay?

[Seth]

God, I'm just. I'm very over. Yeah, this whole situation, I just want to move forward.

[Brooke]

This whole situation that I made for myself.

[Jose]

Well, let's just rip off the bandit now. I'm going to dial your girlfriend. Hopefully she picks up and you two can start talking. Here we go.

[Seth]

Okay.

[Lola]

Hello?

[Seth]

Alola, it's me. Please do not hang up.

[Lola]

I don't. I don't want to talk to you right now. I really don't need to talk to you right now.

[Seth]

Hold on a second, please.

[Lola]

No, I don't want to hold on anymore at all. Like, you lie to me, like, all the time.

[Seth]

No, listen, you're right. I have been a bad teddy bear, but I'm gonna be better, I promise.

[Lola]

Don't use, like, cute nicknames on me. Like, I'm over all of this.

[Seth]

That's. I understand. You have every right to be angry, but please, the least you can do is hear me out. Why?

[Lola]

A picture is worth a thousand words, Seth. Why? Why do I have to hear you out? You were out gambling with your buddies. I don't know who the heck you were with. Looks like you hired some prostitute or something. So, like, what do you want me to hang on for anymore?

[Seth]

Don't say that. Please don't say that.

[Lola]

What do you mean, don't say that? She has all her breasts hanging out of her dress and you're all smiling and rolling the dice. Like,

[Seth]

don't talk about her like that. It's not.

[Lola]

Why do you know her? Did you do stuff with her? Like, did you go to your room with her? Like, why are you defending her?

[Seth]

I'm not defending her. She doesn't even have feelings.

[Lola]

Oh, wow. Okay, this is a new low in your life. She has feelings. She's a beautiful woman. She's human. Right?

[Seth]

No, you don't understand. She is not a beautiful woman. She's not a real person. She's artificial intelligence. Okay, Dave Photoshopped me in the picture.

[Lola]

What? Like, why? Awkward.

[Brooke]

We're just gonna hit it right there, huh? Lola, I am so sorry.

[Lola]

What's going on?

[Jose]

Yeah, Lola, you're on a radio show right now. We're called Brooke and Jeffrey in the Morning.

[Geico Gecko]

Hi.

[Jeffrey]

Good morning, Lola.

[Lola]

Why am I on our radio show?

[Jose]

Seth is a listener of ours and he came to us as seeking help for this segment we're doing. It's called the Awkward Tuesday Phone Call.

[Jeffrey]

He's in a pickle, he's

[Jose]

pickled himself, and he feels terrible about everything that's happened.

[Lola]

Okay, so, honestly, confused, cuz, like, I have a radio show calling me a picture. So, like, what's the big deal about a fake picture? But it's not a fake picture. Is it a fake picture?

[Jose]

You're getting it now.

[Lola]

Big deal.

[Jose]

Exactly. We've cleared it up.

[Brooke]

Okay, I think that he needs to explain a little bit more. Where'd he go?

[Lola]

Stephanie?

[Jose]

Still there?

[Seth]

Yeah.

[Jose]

Okay, I feel like everybody in the room agrees this is your time to shine, bud.

[Jeffrey]

Let's keep the story going.

[Lola]

Oh, wait, there's more?

[Jose]

Well, just some clarity. Some clarity would be nice.

[Brooke]

I think there's a lot more.

[Seth]

Lola, I just want to come clean with you. And I know that this is probably not the best way that I could have done it, and I'm sorry, but no kidding. Dave really did use AI to create that photo. Because I didn't want you to get mad at me because I was exchanging stuff with my ex. But it was the last of the stuff. It was that it. I just needed to get some closure, and I didn't want you to get upset, so I just asked Dave to cover for me.

[Lola]

Oh. I don't know whether to be mad at you or, like, just think you're stupid.

[Brooke]

Both things could probably be true.

[Jose]

It's allowed.

[Lola]

Stupid like you made your friend cover for you because I was gonna be mad at you and that made it worse for you?

[Jeffrey]

Yep.

[Lola]

So you made a lie to cover a lie because you thought I was gonna get mad.

[Jose]

Jeff, you're right.

[Jeffrey]

She does get it.

[Jose]

I mean, yeah, you're totally locked into what's going on, Lola.

[Lola]

Right?

[Jose]

We're just trying to See if maybe there's a chance anywhere in your heart that you could forgive Seth enough to let him back into the apartment.

[Brooke]

I don't know that we're doing that. I don't think you're doing that.

[Jose]

Well, that's what Seth is looking at.

[Lola]

I'll tell you what, everybody get this, okay? Because he has prolonged giving back and I'm doing little quotation marks in my in the air stuff to his ex for a year. So, like, we're trickling this along with this act. I'm not even mad anymore. Dude, please. I will let you into the apartment to pick up your stuff, but with one condition. And I want it on the air. I want you to pick up, oh, your stuff. Like, if you ever put a scent that you might possibly in the foreseeable future, say that might be mine and I'm attached to it. So if I have to return it to you, you will take that with you seriously drawing out, handing your stuff back to your ex girlfriend for a year. Because what you're randomly picking one thing like, oh, she really loved this pen. I have to go call her and give her back the pen.

[Jose]

Seth, what I'm hearing is you are allowed back into the apartment and we achieved what we came to get. We did it, Seth. You're back in. And it's going to take a year for you to finally move it all out.

[Brooke]

I think she is very clear. If you don't get your stuff set that it's going to be garbage.

[Lola]

Yeah. Thank you.

[Brooke]

Okay.

[Seth]

Okay. I mean, I just. When I come over, I just want to sit down and talk about this because I really like you.

[Lola]

I can't.

[Jeffrey]

Is it starting from the beginning?

[Jose]

Seth, you're back in. You did it.

[Brooke]

Do you guys have lived together and you're only. I really like you.

[Lola]

Bye.

[Jeffrey]

Feelings for you.

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[Brooke]

Oh, my God. And I think I have a girl crush on Lola.

[Lola]

Brooke and Jeffrey in the morning.

[Brooke]

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[Jose]

He said he was totally finished with his ex. Now Lola's totally finished with him. The only shoulder Seth has left to cry on is the big chested robot girl from his AI picture. And she's not even real.

[Brooke]

Yeah. I think she'll get annoyed with them too, though.

[Jose]

Yeah, she'll probably be over it. It was funny. At one point, Lola was even defending the AI woman like she's a person. She has feelings.

[Cat Treat Ad Host]

Yeah.

[Jose]

Give her a chance.

[Brooke]

She didn't know it sounded bad. I thought it was good that she had another woman's back. Yeah. Nice. Even if the woman was fake, it

[Jose]

was a wholesome moment.

[Odoo Ad Host]

Yeah.

[Jeffrey]

A fake escort in her eyes. Yeah.

[Jose]

I don't think anybody's surprised that the call ended the way that it it did. Probably the way it should have.

[Brooke]

Yeah. I think he's got some stuff to work out before he starts another relationship. You know, that probably won't happen.

[Jose]

Yeah.

[Jeffrey]

Yeah.

[Jose]

But hey, don't let our failure as a morning show to help him stop you from reaching out to us for help.

[Brooke]

Yeah.

[Jeffrey]

All right.

[Jose]

We can always try and step in and intervene in your personal life. Just email us, tell you your issue, and we'll give the world's best advice.

[Lola]

Wow.

[Brooke]

I promise. Yeah. There's a lie.

[Jose]

You can try it.

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Yeah.

[Jose]

It's Brooke and Jeffrey in the morning.

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