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Brooke
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Brooke
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Brooke
Hey, welcome to your Saturday show. It's Brooke and Jeffrey in the morning and I was just looking at our stats. Not to start with something boring like stats. Oh, wow. That'll get people's attention. But I thought it was so crazy that this Saturday double classics episode that we're about to start right now out of the last three months has been five of the top ten most downloaded.
Yeah, the classics.
Do you guys like the longer format? Like, what do you like so much?
I think it's people are just discovering us and then got to go find the old stuff.
Let us know. Are you here because the length is so great for you?
Are you just binging and catching up?
Yeah. Or. Or is it on mute and you don't even realize it's plain? That's why. Yeah. Or is it a Saturday and you have nothing else and you're like, I guess this is what I'll do? You know, we'll take all the truth.
Jeffrey
Really?
Brooke
We're happy.
Let us know in the comment section because we love to read those. What do you see, Alexa? Yeah, one comment says my primary care physician recently ghosted me after I asked him to inject this podcast into my veins. Love you all.
Not even eye drops?
No, no.
Claire
Straight in.
Brooke
Straight in. It goes hard. You know, we're injecting it right now. Yep. Enjoy your back to back classics.
Jeffrey
I heard something the other day where having a little bit of drama or mystery or danger, even when you first meet someone isn't necessarily a bad thing.
Brooke
Oh, okay.
Jeffrey
Like Alexis's past two boyfriends who are both on the no fly list.
Brooke
I think one got deported.
Conversation starter.
Jeffrey
Is that an aerosol can, liquid or gel in a container over 3 ounces in your pocket? Or are you just happy to see me?
Brooke
What a bad boy. Wow.
Jeffrey
Well, one of our listeners says she met a guy the other night who almost got her arrested.
Brooke
What?
Jeffrey
And her response to that? I need to date that man. You're going to find out what happened in your second date update, right after this second date update. Brooke, how many times have you been in a concert and thought, forget the band. I want to get backstage with that security guard, show him how to really use that flashlight.
Brooke
I did have a security guard usher me into a concert for free once. What?
Jeffrey
What did you have to do to get back?
Brooke
Yeah, he, like, let me jump in the van and go into the back.
Whoa. That's.
I just had to look really pathetic in the parking lot because my boyfriend left me there because he had a ticket and I didn't.
Jeffrey
Oh.
Brooke
So he's like, you can hop in my van if you're by yourself.
Jeffrey
So you just had to be yourself?
Brooke
Basically, yeah.
Jeffrey
That's what one of our listeners says. Happened to her the other night. Her name is Claire, and apparently she met a concert security guard. Oh. So, Claire, it's an honor and a privilege to have you on this morning's show. Welcome.
Brooke
Yeah.
Claire
Hi. Good morning, Claire.
Brooke
Did he have a van for you to hop in as well?
Every good security guard should have a van, you know.
Jeffrey
Tell us about the security guard. Who is he?
Claire
His name's Kevin.
Brooke
Okay.
Jeffrey
Okay.
Brooke
Did you meet him at a concert, or is this just what he does for work?
Claire
He was working and I was at the concert, yeah.
Jeffrey
Oh, okay. Did he catch your eye immediately, or how did that happen?
Claire
Well, he came up to me, actually, to ask me to get off a chair that I was on.
Brooke
You were in trouble to reprimand. Okay.
Jeffrey
I thought it was gonna be some romantic line.
Claire
Yeah, no, but he did catch my eye. I thought he was really cute. I was kind of tipsy and probably being a little annoying, but I was like, you know, he was like, this is a safety hazard. And I was like, I'm just trying to get a better view. I'm short.
Jeffrey
Please, You're a safety hazard, Mr. Big Biceps Jeff.
Brooke
You'd be good at flirting.
Did you say that you asked him to lift you up so you could see? Is that what you just said?
Claire
No, I should have. That would have been good. I was just like. Let me stand here so I can see.
Brooke
Put me on your shoulders.
Jeffrey
So he asked you to get down from the there?
Claire
Yeah, so he eventually got me down, but, I mean, I thought he was pretty cute. And so I actually, like, took, like, a cocktail napkin and, like, wrote my number down on it.
Brooke
Oh, my God.
Claire
And I, like, put it in a shirt pocket and was like, if you need to yell at me or, like, teach me any more about concert safety later, like, text me.
Brooke
I like them putting it in his shirt. That's like, a little bit of, like. Here you go.
Yeah, this is from.
Claire
Yeah.
Kevin
Oh, my God.
Brooke
I like it.
I can't believe he actually called you. Because I. And I don't mean, like, you're not cute or anything, but it's like, how many drunk people does he come across that are.
Claire
I must be sexual.
Jeffrey
That's cool. So he reached out.
Claire
Yeah. The next day, actually, he texted me, and we were kind of laughing at it. I had saved him as concert police in my phone because that's what I was, like, calling him all night.
Brooke
Wait, you were drunk dialing him that night?
Claire
No, just, like, at the show. I was like, okay. Concert police.
Jeffrey
It's your cute pet name for him.
Brooke
Yeah, I get it, I get it.
And what did he call you? Annoying short girl. Leave me alone.
Claire
But, you know, I apologize for whatever. Being drunk and how I acted. You know, we had a good laugh about it, and then we. Yeah. And so we eventually, like, decided to meet up for dinner and have, like, an official date.
Brooke
Oh, my gosh. Were you nervous? Are you, like, ah. Is he gonna be as cute as I remember?
Claire
So true. I mean, a little bit. You never know how it's gonna be after.
Brooke
And it's, like, dark, the music's loud, you've been drinking, beer goggles. And he's in a uniform.
Claire
Y.
Jeffrey
So where did you guys end up going for a date?
Claire
We got. We got Italian, which is, like, my favorite. So perfect.
Brooke
What'd you think when you saw him?
Claire
Yeah, I thought. I still thought he was cute, but I was like, I. Well, I wish you're wearing your security uniform because you look so cute. And I, like. You look good in that. And I mean, he laughed.
Kevin
Whatever.
Claire
Like, it was fine. We had. It was a good. We started off well.
Brooke
You sound like a really good flirter, so at least it sounds like you put the vibe out on your end for.
Claire
Yeah, yeah, I try. So we ended up, like, we decided we just wanted to try a bunch of stuff, so we just split. Put a bunch of food on the menu, which is fun.
Brooke
Yeah.
Claire
And, like. Yeah, and the food was good. We were having a good time. Like, we were having fun.
Jeffrey
It's an Italian restaurant, so did you try the lady in the tramp move? Did you try to set it up at least?
Claire
We did it. We actually did not do that.
Brooke
Yeah, they got maybe the tour. Italy.
Jeffrey
Smart.
Brooke
Yeah. Three different things on, but, I mean, besides the food and sharing the food. Like, what were some of the highlights for you with him?
Claire
I don't know. We just joked around. He told me about other drunk girls he's met at concerts. Made me feel better about myself. I would not be worse.
Brooke
Oh, I bet he has some good stories.
Claire
Yeah.
Jeffrey
You didn't make the top five worst girls, so we're in the clear.
Claire
Thank goodness. And it was going really well, but everything kind of changed at the end when the bill came.
Brooke
Why?
Claire
So Kevin noticed on it there were, like, some discrepancies, like, some stuff on the bill, like, didn't seem right. Yeah, we, like split a salad, but then they charged us for two salads instead. So, I mean, it was justified. Like, he wasn't being like a total Karen, but, you know, he has to talk to a manager and stuff about it.
Brooke
And they took care of it, I assume.
Claire
Yeah. So he had to go into the back and, like, talk to someone. And it did take, like a little while. Like, it was, you know, it's good, like 10 or 15 minutes or so.
Brooke
That's kind of weird.
I feel like you went back, beat somebody up now.
I mean, typically your server would just be like, oh, my God, I'm so sorry. Let me change it. Yeah, yeah.
Claire
And so after that, like, his mood just kind of changed for the rest of the night. He just kind of fell off.
Brooke
Like it ruined his whole night.
Claire
It kind of felt like it did. Like, he just didn't seem the same after that. He hasn't really been talking to me. At first I was like, maybe he just felt like that was a weird ending, so he just wanted to give me a couple days or he just felt weird about it. But now it's been like over a week. And so I'm like, was there something else? Was there another issue I didn't know about?
Brooke
And, Jeffrey, you've been in a lot of back rooms at Italian restaurants. What goes down back there?
Jeffrey
Well, usually I'm paying extra for what happens.
Brooke
Okay, that's the off menu.
At least we can pinpoint the moment that everything changed.
But it doesn't sound like it's your fault. Whatever it is.
Exactly.
I mean, awkward on a date. Yeah. So maybe it just left him with a bad taste and that's why he hasn't.
Claire
Maybe.
Lindsay
Yeah.
Jeffrey
Were there any other weird moments from the date besides the bill?
Claire
Not that I can think of. Everything else was pretty normal. You know, I was having fun. I didn't really clock anything. Like, he didn't seem weird to me, but I don't know. His mood just totally changed after the bill problem.
Jeffrey
Okay, we're going to come back, we're going to call Kevin for you, and we're going to try and get you a second date update right after this, all right?
Brooke
Yeah.
Claire
Hey, awesome. Thank you.
Jeffrey
Second date update. Whenever we do these calls and there's a problem with the bill, usually that's an issue over who should pay, right? Does the guy handle it? Should the girl offer which exit door should we dine and dash out of? Those are the types of things that go through your mind. But with Claire and her date Kevin, they had a different problem. They noticed that they were getting overcharged on their bill, and that's why Kevin went to the back to talk to a manager about it for a while, a few minutes. And while Claire thought that was totally justified, kind of ruined his mood for the rest of the night. And that could be why he hasn't reached out yet for another date.
Brooke
Maybe he's mad that they didn't give him a free dessert. I mean, usually when they mess up the bill, you get a free dessert.
He's like, we're an Italian restaurant. Where's my tiramisu?
You know what I'm saying?
Jeffrey
Is that right, Claire? No. No free dessert at the Italian place.
Claire
No free dessert.
Brooke
We don't even need to call him.
Jeffrey
Or maybe he found an even smaller, even more obnoxious girl at another concert that he was doing. Security, and that's his type. He wants his Thumbelina.
Brooke
Who has a stand on the tallest chair to see anything. Yeah, I mean, I feel you, though.
Jeffrey
Yeah.
Brooke
Concerts suck for short people. Thank you.
Yeah.
Jeffrey
There's got to be some sort of logical explanation for this. We're going to call him right now. You ready to do this?
Claire
Yeah, I'm ready.
Jeffrey
All right, here we go.
Kevin
Hello?
Jeffrey
Hey, is this Kevin?
Kevin
Yeah, this is Kevin. Who's this?
Jeffrey
Sorry, did I catch you in the bathroom or something? It's a little bit echoey.
Kevin
No, I was actually cooking something, but that's fine.
Brooke
Oh, interesting.
Hi, Kevin.
Jeffrey
What you cooking?
Kevin
I'm making some pasta. Okay.
Jeffrey
Some nice morning pasta.
Kevin
I love Italian. It's to prep for work, so.
Brooke
You are so friendly. I don't know that we've ever just launched into a full conversation with somebody.
Jeffrey
You haven't even asked who we are yet. You know, we're a radio station.
Brooke
I feel like he's gonna invite us over.
Kevin
Okay.
Jeffrey
We're doing a segment called A Second Date Update where we're trying to help out one of our listeners. You took out to actually an Italian place the other night named Claire Clear.
Kevin
Rings a bell. Yeah, I think so.
Brooke
Didn't you have a really nice night with her? Because her description sound like you guys really connected.
Kevin
Well, if I'm not mistaken, is this the girl that I met at the concert? Because I work as a security at some concerts and I do.
Jeffrey
Yeah, yeah, yeah, that's right. Sounds like you're going out with a lot of different women. If you can't tell, which is fine.
Kevin
Not. I'm not gonna lie. I'm. I'm single, so I'm dating.
Brooke
Yeah. Claire's the one that kept calling you concert police. Like, apparently that was her, like, funny nickname for you.
Kevin
I mean, it is my job.
Jeffrey
Okay, well, our job is to call people like you and try to figure out why you're not going out with some of our listeners.
Brooke
Open up.
Jeffrey
That's what Claire is wondering.
Kevin
Well, okay, so if I'm not mistaken, I remember we went out to dinner. We went and had Italian and.
Jeffrey
Yeah, no, you don't have to run us through the whole story. We've actually heard it before.
Brooke
Yeah, perfect.
Then I think we just need the part where, like, you're not calling her back anymore and she's confused because it seems like you guys had a good connection.
Kevin
Okay, yeah, I'm trying to recap a little bit. So I remember that when the bill came, I went to the back to talk to the manager. And then when I'm coming back, I see something weird. You know how they put this olive oil kind of dishes there?
Jeffrey
Yeah, for your bread.
Kevin
So she was putting her fingers in inside the bowl and rubbing the olive oil on her.
Brooke
On her body?
Kevin
Yeah. Okay, so she was dipping her fingers in it and then rubbing it against her shirt, and then a little bit on, like, on her belly and then.
Brooke
Wait, are you talking about you saw Claire or just some random woman in the restaurant rubbing olive oil all over herself?
Kevin
I saw Claire. I mean, I saw her from afar. Right. I saw her from afar.
Brooke
That would stain her shirt. No one would say that. That's the worst.
Yeah, unless she was going inside her shirt.
I mean, honestly, the only thing I could see is, like, if you have, like, dry skin with a cracked knuckles.
Jeffrey
I'm sorry, Kim. You're saying that a girl rubbing oil all over herself is a bad thing? Because I think most guys would be into that.
Kevin
No, no, I didn't say it was bad. I thought it was weird. I don't know what she thought that was gonna happen afterwards. I don't know if she thought that was like an aphrodisiac or something.
Brooke
No.
Jeffrey
Why wouldn't you ask her if you think you saw that?
Brooke
She deserves the right to explain.
Kevin
Now, let me ask you, how do you bring that up to a girl? You know, sit down and act like, why are you rubbing oil by taking.
Jeffrey
Your shirt off and being like, apply right here, ma'.
Kevin
Am.
Brooke
Or you just go to kiss her neck and go, ooh, is that a little bit of balsamic vinaigrette?
Kevin
I didn't want to sound like a creep because you know how girls are always.
Brooke
You know that's true.
Kevin
Okay.
Brooke
Hey, I was watching you from across the restaurant. Was that oil?
I think, like, what were you doing with the oil? Is a fair question.
Jeffrey
And I could understand if you were uncomfortable asking her in the moment, but now that it's been a while, you can ask her over the phone because she's actually been listening on the other line this entire time wanting to talk to you.
Brooke
Yeah.
Kevin
Are you serious?
Brooke
Yeah.
Jeffrey
Possibly rubbing herself down. Claire, you there?
Claire
Hi, Kevin.
Kevin
Oh, God. Hey.
Jeffrey
In all seriousness, I doubt she was even doing that, but Claire, I don't know.
Brooke
Oil slick Claire, over here, maybe?
Yeah, clever.
Jeffrey
What's going on?
Kevin
Okay, what was going on? What were you. Were you actually rubbing the oil?
Claire
First of all, I had no idea you saw that.
Brooke
Oh, so you do know what he's talking about.
Jeffrey
Yeah. Claire, please explain in very, very detailed, what's the thing?
Brooke
There's no olive oil.
Claire
Like, you rub it on your chest. That helps keep everything perky. Like, I don't want saggy breasts when I'm older. Like, admittedly, like, it's a TikTok hack I've adopted, but I mean, like, it's a thing. Like, it gets the blood flowing. It keeps you moist.
Brooke
Never knew that.
Not in public, in a restaurant. No, it's not like, don't you do.
Kevin
That in the restaurant.
Claire
It's totally normal.
Brooke
Privacy.
He wasn't there.
You're at a restaurant, girl, you're not putting your hand down. Was your bread in the oil before your fingers?
Claire
It wasn't like I was pouring the bottle on me. I just.
Brooke
Stabbing a little, like, okay, I have face olive oil before, but like, it's from a beauty brand. It's not.
I don't meant for that. Yeah, it's not just.
It's like, refined. I would assume the different way. Or at least I paid for it.
Claire
As if it's refined.
Jeffrey
Claire, you're Going to have to excuse Brooke. This is the part of the show where she tells our listeners how to live their lives.
Brooke
So you think it's normal for her to stick her hands down?
Jeffrey
I don't. I don't know what's normal. People do their own things, their own different ways. They try beauty hacks. They do. And don't work. Okay.
Kevin
Can I ask a question?
Jeffrey
Yeah. Yeah, of course.
Kevin
I mean, now that you explained it, I actually really liked you, and I'm sorry for not calling back. Would you go out with me again? On a second.
Brooke
She said perky, and now the guy's.
Jeffrey
Like, yeah, let's go. Claire, did this whole experience change your mind with him not communicating with you earlier?
Claire
I mean, maybe. Yeah, a little. Like, I thought we were having a good time. I'm an open person, obviously. Like, obviously.
Jeffrey
Yeah.
Claire
I would have talked to him about it if he had asked me about it.
Kevin
Moment.
Claire
Like, I'm not embarrassed about it. But now I think it's a little weird. He's coming around.
Brooke
Come on, Claire. If the tables were turned and you. You're walking to the table and you see some dude putting oil on his body, you would be.
We use butter. Okay.
Claire
I would have said something, though. Like, he didn't do that. Like, I would have confronted. I would have asked a. I can see that.
Brooke
I could see that.
Claire
I wouldn't just stop communicating.
Kevin
It was the first date, and I don't know if you would have been okay with that or not. So now I know. Maybe on a second date we could fix it. Oh.
Jeffrey
Oh. He wants to be the one to apply the oil onto you.
Brooke
Hey, is that.
Kevin
What?
Brooke
Is that the meeting you took?
Jeffrey
Well, that's what I'm visualizing.
Claire
All right, now it's getting weird. You're making it weird. It's just olive oil. It's TikTok hacks.
Brooke
Okay.
Jeffrey
All right, well, at this point, Claire, Kevin has already said yes to another day. He's apologized for not being more communicative. And third, you don't even have to pay for this next one because it's on us.
Kevin
Even better.
Claire
I mean, I can get from the visuals, I get that it was kind of weird and how some people might not want to approach that. Yeah, I. Yeah, I'll give you a second chance. Let's go.
Brooke
What are we doing Italian, then?
I don't know.
Jeffrey
He did say that there's a lot of concert girls, so you just gotta get in line first, Claire. But if you oil yourself up, you can slide faster to the front. Of the line.
Brooke
Security's not tackling you.
Jeffrey
Then.
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Jeffrey
And that usually never happens where even before I offer to pay for the date, the guy is jumping in, ready to go out.
Brooke
Yeah, you're right.
It was almost like a light bulb went off in his head and he's like, what am I thinking? Yeah, he's rubbing oil on her body to make it perky. I hate it.
Jeffrey
Those two words in combination, oil and perky put together, that's an instant.
Brooke
Like, yes, it makes me oily and perky.
Oh yeah. I just hope that nobody ate any more bread. This is so unsanitary.
Jeffrey
Oh yeah, from that same container. They change them out in between people, right?
Brooke
Like her and her date had been like eating bread and dipping it with their mouth crumbs on her body.
Jeffrey
I was curious if my co hosts are going to be adopting that beauty hat. Coming up here.
Kevin
Here.
Brooke
I mean, Brooke said she's trying special.
Jeffrey
No, not you, Brooke. I don't care about you, Jose.
Brooke
Motor oil. I'll rub it everywhere.
I feel like he's just gonna come to her greasy.
Jeffrey
Yeah, I'm glad we were able to get him to go out.
Brooke
Yes, there we go.
Greasy and perky.
Jeffrey
By the way, remember, if you want to get greasy and perky, try listening to our second date updates. That'll do the trick. You can find all of them up on our podcast wherever you get yours. BrookeandJeffrey.
Commercial Announcer
Brooke and Jeffrey. In the morning.
Jeffrey
When you hear somebody got kicked out of a bar, you would assume it's for fighting or disorderly conduct or passive aggressive licking or.
Brooke
Wait.
Licking?
I was gonna say just go in with Alexis. Yeah, so what? I puked a few times on the floor. She's 86 for most parts of the city.
Jeffrey
Well, one of our listeners says both her and her date were out asked to leave a bar trivia night over the most ridiculous reason, and it only bonded them closer.
Brooke
Did they bring their own booze?
Jeffrey
Question is, how did she end up here asking for our help? You're gonna find out in a second date update right after this second date update. Brooke, out of all the men that you've lured and seduced, how many of them have gotten up and walked away mid hookup?
Brooke
Oh, my God.
Jeffrey
Or did they all suffer through it to the bitter end?
Brooke
No, they all suffered through it. One did dump me right after midnight on New Year's Eve. Oh, that one hurt because I was too drunk to drive home, so I had to sleep on the couch until the next morning. Which was embarrassing cuz he lived also with his brother. It was just. It wasn't embarrassing, but responsible it was.
And I'm sure you hooked up again when you woke up up.
Jeffrey
It's a little.
Brooke
No, we didn't.
Jeffrey
Okay, this is way too much information and too deep of a dive into Brooke's sad past. So I only was asking because our listener today, Lindsay, said in her email she's feeling confused after her date ended awkwardly, just as things were starting to heat up romantically.
Claire
See?
Brooke
And I bet she feels better after hearing my pathetic story.
Jeffrey
Yeah, probably. Lindsay, welcome to the show.
Lindsay
Hi.
Claire
I do feel better, but also like, oh, gosh, this is.
Lindsay
This is so weird and embarrassing and confusing.
Jeffrey
Well, don't feel bad about it.
Brooke
All the words people love to use in dating these days.
Jeffrey
After we hear your story, I'm sure Brooke will share some of her real life advice. Then probably even have some video evidence of guys sprinting away from her house, so that way you'll feel really good about yourself. Now tell us about this guy that you hung out with the other day.
Lindsay
Okay, so I met this guy on a dating app. His name is Damon, and we totally hit it off on our banter. He had a great sense of humor and I was really happy because we didn't text for like A crazy amount of time. It was just like, okay, why don't we meet up? And we ended up meeting at a bar. Just a simple, like, a drink at a bar. It was great.
Brooke
Yeah, this all sounds fantastic. What was it like when you first saw him?
Lindsay
It was good. He looked like his pictures. And then it was actually kind of fun because literally, like, 15 minutes after we get to this bar, staff starts handing us us whiteboards and dry erasers. And it turns out that it was trivia night.
Brooke
Oh. Oh, my God. I haven't done that one.
I actually had that happen to me once. Me and my buddies were at a bar, and all of a sudden, like, people kind of coming with pencils, and.
We'Re like, oh, I feel like that's how I've ended up at every trivia night I've ever been in. The bar is always really busy. Yeah.
Lindsay
Yeah. Well, we decided to stay. I mean, I. In my mind, I was like, oh, this is kind of a nice little, like, icebreaker. Something fun to do. And then it turned out that the questions were very hard.
Brooke
Oh, they always are. Yeah, they.
Lindsay
Where we drew the line. It was like the square root of 16. And both of us were like, we're so horrible at math, we don't even remember.
Brooke
It's pretty basic. I mean, not did math shame you, but at least you guys are on the same page.
Jeffrey
I said, yeah, just stick to relationship shaming her. So keep going.
Lindsay
We did stick. We were on the same page because neither of us knew it. So instead, we just threw a square around the number.
Jeffrey
Oh, square. Well, did they accept that as a correct answer?
Brooke
That's funny.
No.
Lindsay
Not only did they not accept it, they took our whiteboards away because they thought we weren't taking it seriously.
Brooke
Dude, you got trivia shamed.
But you guys were being silly. You were having fun with it, and you got kicked out.
It's way better than ending up on a date with someone who takes trivia too serious. Yeah. Yeah.
Kevin
Okay.
Brooke
That's fine.
Yeah. So where'd you guys go after that?
Lindsay
Well, yeah, Then obviously, we had to pivot a little bit, and he very casually basically said, well, look, I live really close to here. If you want, you can just come to my place, and maybe we can just watch a movie or something.
Brooke
Did he wink when he said movie?
Lindsay
Oh, no, but I hope not.
Jeffrey
Would that have worked on you, Brooke?
Brooke
No, but everybody knows what movie means. Okay, let's be honest. Brooke, more questions. Nobody's watching anything.
Kevin
That was on me.
Jeffrey
Okay?
Lindsay
So, yeah, we get to his place. We watch a movie. It was some action movie that. I don't even remember the name. I don't know. I had a couple drinks, and then I was really feeling it, so I actually initiated things.
Jeffrey
Okay, what's your move? To go in for it.
Lindsay
Oh, gosh.
Jeffrey
I mean, just throw yourself at him.
Kevin
Good old.
Brooke
Good old yawning stretch. Oh, man, it's getting late.
7:00Pm I think she probably just kissed him. Jeff, I think that that's all.
Jeffrey
Women don't really need a move. Okay.
Brooke
Yes.
Lindsay
I was just. We were just.
Claire
Okay.
Lindsay
We were just kissing. Okay.
Jeffrey
All right.
Brooke
Yeah. Nobody here's judging you, no matter what. You're in the right space.
Jeffrey
We're looking for advice is also. Okay, so how.
Lindsay
Well, anyway, things did start heating up, and then the second that they got a little hotter, his mood completely changed and things just sort of stopped.
Brooke
Interesting.
Do you know why at all?
Lindsay
No idea. So much so that I asked him.
Claire
Like, hey, are you okay?
Lindsay
Is everything okay? He's like, yeah, yeah, everything's fine.
Jeffrey
And then he started crying.
Brooke
That's just what you do, Jeff.
Jeffrey
Was that just me post hookup? No.
Brooke
Honestly, the first thing that comes to my mind is that he's cheating.
Jeffrey
Honestly, like you're saying, Brooke, that he felt guilty. Yeah, mid act.
Brooke
Yes.
Jeffrey
And had some remorse. So do you give him credit for at least stopping?
Brooke
No. Oh, absolutely.
Jeffrey
Well, he should have gone through with it.
Brooke
See, I was thinking he wasn't ready. Like, if I don't shave my legs and then, like, something, you know, maybe he didn't, that stops you. No, but I think about it.
Jeffrey
Okay, Lindsay, did you get that vibe from Damon that maybe he felt guilty about another woman?
Lindsay
To be honest, I didn't even think about that. His place didn't give me the vibe that there was someone else, like, living there with him, so.
Brooke
Yeah, but he could still be dating.
Lindsay
I don't know. At that point, I could tell something shifted. I don't know. He's like, oh, it's fine. I'm thinking in my head, like, fine what? I mean, you have a girl making out with you, and things are going so great.
Jeffrey
Okay, so that was. Was that the end of the night then?
Claire
Yeah.
Lindsay
I basically just finished my drink and I left. And now ever since then, I haven't heard from him, and I don't. I don't want to seem like the needy one to be texting him.
Jeffrey
No, let us be the needy ones that are calling him on the radio.
Claire
Thank you.
Jeffrey
We'll take all the blame for you when we come back, we'll call Damon and try and get you a second date update and finish what you two started on the couch that night right here on the radio.
Claire
Thanks.
Lindsay
I mean, it sounds kind of weird the way you say it, but.
Claire
Okay.
Jeffrey
Okay. We promise not to listen. Hold on.
Brooke
What?
Jeffrey
Second date update? Two dummies walk into a bar on trivia night. Sounds like the setup to a joke, but it's what actually happened. And I'm not the one calling them dummies. Lindsay said herself the trivia that night was just way too hard. So hard that they decided to ditch the bar and went back to Damon's place instead.
Brooke
There's definitely some math teachers listening that are shaming you on the text board.
Jeffrey
The square root of 16. That is a hard one, I think. But just when things were about to get hot in hell heavy, Damon put the brakes on, and that's where things kind of ended. Awkwardly.
Brooke
Yeah.
Jeffrey
Which is the big mystery. We still don't know why he did that. It's been floated around that maybe he could be a cheater and felt really.
Brooke
Guilty halfway through because they're starting the kissing.
Jeffrey
And maybe he forgot to hit record on the camera and decided it wasn't worth going through with it. I'm just saying, it's happened to me before. But our goal today is figure this out. Why did he stop it? So that she can either get another day or at least get closure on what happened that night.
Brooke
Yeah.
And the thing is, Lindsay, you sound really hopeful about this guy.
Lindsay
Yeah, I really, really liked him. We had a great time on it. To be honest with you, before that happened, that was probably one of the best first dates I've had.
Brooke
Like, truly, we got to get. We got to fix it. That's all.
Lindsay
I really kind of running it through my mind about what you said about him.
Brooke
Sure. Whatever. The real reason is, is 10 times worse than whatever you're thinking.
Jeffrey
Yeah, it's always good to overthink it. Definitely.
Brooke
This poor girl's anxiety. I know you're joking, but it's still.
Jeffrey
Well, let's get an answer or put you out of your misery, whatever it is. I'm going to dial his phone number right now, so hopefully he picks up. Here we go.
Claire
All right.
Kevin
Hello?
Jeffrey
Hey, we're looking to talk with Damon.
Kevin
Yeah, who is this? Hey.
Brooke
Hey, David.
Jeffrey
We're a radio show. We're called Brooke and Jeffrey in the Morning.
Brooke
Welcome to the show, man.
Kevin
What y' all calling me for? Radio show. What's up?
Jeffrey
Yeah, we're. We do A segment on our show. It's called a second date Update. And that's where we try to help out listeners who've gone out with someone recently. They had a really good time. Time, but they aren't getting that second meetup. And this woman is trying to figure out why that happened.
Brooke
Do you have any ideas? Who are you referring to?
Kevin
I don't really play games with the radio or nothing like that, but I have no clue who you're talking about.
Brooke
It's not a game.
Jeffrey
We do have. We do have segments where we do games and we can have you on for that later if you'd like.
Brooke
No, I don't think he's good at trivia. Remember square root of 16?
Jeffrey
Yeah, we heard that trivia is in your strong thing, but this is more just about helping out our listener, Lindsay.
Kevin
Okay.
Jeffrey
Yeah. So she called us and she told us about your guys's hangout the other night and.
Brooke
Sounds awesome. It sounds like it was a great night.
You guys got kicked out of a bar together. That's like a bonding experience.
Kevin
Yeah. Okay. Yeah. I mean, we. We hung out. I mean, I don't know everything that she told you, but I mean, we.
Jeffrey
Heard about the bar trivia. She said that you were one of the funniest, funniest guys that she's been out with in a long time.
Brooke
Yeah.
Jeffrey
But afterwards she left your place having kind of more questions in her mind than answers.
Kevin
Oh, really? I got questions too, right?
Brooke
Oh, you do? Oh, that's interesting.
We don't normally hear that.
Jeffrey
Okay.
Brooke
She was really into you.
Kevin
Well, we had fun playing trivia and all that, but she started kissing me. You know, we were watching a movie and she started kissing on me, like doing one of the best scenes. Bad boys.
Brooke
The original bad boys.
The Will Smith.
Kevin
The original. The original bad boys. Okay. It was the first movie. It was the first movie where there were two black lead actors and Hollywood thought it would never work. And it was one of the best.
Brooke
It's a great film, but you weren't watching a movie to actually watch the movie. You were watching a movie to lead to the kissing part. Right? Like that's what you do.
Kevin
Listen, it was the good part of the movie. It was a really good part of the movie.
Brooke
That you've seen a million times. If you don't care about, you know.
A pause button exists if you really want.
That's true too.
Wait, that's why you stopped the makeout session.
Kevin
This action packed movie, and here she is trying to get action with me.
Brooke
You are the first man that I think I've ever heard has been upset about something like that.
Kevin
I'm just saying, like, she just had an opportunity to get to know me.
Brooke
But listen, why didn't you just tell her, like, she. What do you mean? To know that, like, if you.
Is what he's saying is, is this.
Jeffrey
Something that you discussed with her before putting the movie on, that this is a really important film and that you really want her watch it.
Kevin
No. I mean, no, I didn't. I didn't say that. But, like, during the part of the movie, in the middle of the movie, I was like, yo, this is really good. You have to really pay attention to this part.
Jeffrey
See?
Brooke
Oh, you talked in the middle of the movie.
Jeffrey
No.
Kevin
No. Yeah. I mean, she was kissing up all up on me. You know what I mean? Like, and these are not regular kisses. These are French kisses. These are. You know what I mean?
Jeffrey
Okay. Some ladies just don't know that eyes need to stay on the screen during this time.
Brooke
Besides, French kisses, too. That's a bigger deal.
Jeffrey
Okay, I. I don't think it was malicious. I don't think that's. Lindsay was. Was trying to, like, shove something in your face and say, she doesn't care about your movies. She just really liked you. And you can let Lindsay tell you that because she's on the other line right now wanting to talk to you.
Brooke
Don't. The good part. Okay, just listen.
Jeffrey
No, Yeah, I mean, she is actually on the other line right now.
Lindsay
Yeah. Hi.
Claire
Hey.
Kevin
I didn't know you was listening, but, I mean, you. You get my feeling, though, you know? You know what we talked about, how I kept trying to talk to you about it?
Lindsay
I just want to make sure. So you're really, like, ghosting me? Wait, I'm just trying to figure this out. You. You. We had such a great date, and then the reason why now you've decided to leave me hanging is because I started making out with you in your favorite part of the movie.
Kevin
You know what? It's not a movie. It's Bad Boys. It's Will Smith and Martin Lawrence. It's bad boys. And here you are trying to just make out with me. Me. And not really pay attention to the movie. Like, really, like, you know, I mean.
Lindsay
Listen, I. I was really into you, and I wasn't quite focused on anything else but you.
Claire
You.
Lindsay
I thought you would be, like, over the moon with that. We can watch Bad Boys.
Kevin
Anything to me to get into me is to get into the movie.
Jeffrey
If you really liked him, you would Take an interest in the things that he is interested in.
Brooke
I mean, isn't this like a refreshing flip? You know, honestly, doesn't this feel good to have the worst problem? A man say that he really wants to share his passion with you?
Kevin
That's all I want.
Lindsay
I mean, if that's really what you wanted, you could have said so. And then we could have saved right now. Like you.
Kevin
I wasn't giving you tongue back. I was trying to watch.
Lindsay
I've never had a. A date like this ever before in my life.
Brooke
Wow.
Jeffrey
And I think you mean that in a good way. Because most guys aren't like Damon. He's one of a kind.
Brooke
That's true.
Jeffrey
He's kind of the opposite of a bad boy. He's a good one.
Brooke
He's a man.
Lindsay
But like, it was that bad that. That took precedent over how much fun we had before that.
Kevin
Listen, we had fun, but I want to get to know you too. But you need to get to know me.
Brooke
And you're not listening, Lindsay. It wasn't bad at all. It just was part of it.
Jeffrey
No matter how weird or unusual that might sound. That's from the whole heart.
Brooke
It is a great movie if you pay attention.
Kevin
It is.
Jeffrey
Lindsay, is there any way that you could see past this miscommunication that happened? Damon, he. He wants to be intimate with you. Just pause the movie or wait till it's done.
Kevin
No, no, no. You're not pausing the movie. You watch it all the way through.
Jeffrey
Okay, well, once. Once the credits roll, then the clothes can come off.
Kevin
So that's it.
Jeffrey
Okay.
Claire
Okay.
Jeffrey
Is that something that you could see yourself being open to? Lindsay. Lindsay.
Lindsay
I mean, if I haven't already offended him enough, I don't know. I just did such a bad job getting to know him.
Jeffrey
That's a fair point. That's fair.
Brooke
Sarcastic, right now, of course.
Claire
Are you kidding me?
Jeffrey
Well, sounds like that's a yes from Lindsay for another date.
Brooke
I don't think that's it. That was sarcastic.
Jeffrey
I'm just reading in between the lines of what she said. Damon, are you willing to look past all of her flaws and give her one more chance to watch Bad Boys all the way through without interruption?
Kevin
You know what? That's gonna be a no for me, cuz. She still know the name of the movie? She still don't even know the name of the movie.
Brooke
What's the name of the movie?
Kevin
What's the name of the movie? What's the movie?
Lindsay
I've heard it now. Bad boys 1, 2 and 3.
Brooke
But who's it starring?
Lindsay
Will Smith And.
Kevin
And. Yeah, exactly.
Jeffrey
Damon, you're right. Let's ditch this girl.
Brooke
We're bad boys for life.
Jeffrey
Where are the respectful women in this society?
Kevin
Bad boys, come out and play.
Jeffrey
Yeah, this goes out to to you, Damon. The best movie trilogy of all time.
Brooke
Get her out of here.
Jeffrey
Will Smith and Martin Lawrence. Remember the name Lindsay.
Claire
Oh my God.
Lindsay
I don't even know what to say.
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Jeffrey
Wow, the Internet is right. Men really are more sensitive nowadays.
Brooke
I love it. I think that it should be celebrated. Good on you all. I know because women evolving.
Jeffrey
Women just don't understand that men don't want cheap, easy hookups. Yeah, they want a lady who appreciates their Netflix action movie watch list.
Brooke
They want the hookups just there. It's timing, no?
Yeah.
Jeffrey
No, no. That's all we care about is our Netflix watch list. And if a woman isn't willing to do that and take that journey with us, then hit the bricks.
Brooke
Oh, really? What's your movie?
Jeffrey
Yeah. Okay. I don't care if you've got a perfect 10 body in the face of a Disney princess.
Brooke
If you.
Jeffrey
If you don't know who Martin Lawrence is, then you are not right with us.
Brooke
Okay? Is that for you too? Because I feel like yours is going to be more like west side Story or something.
Yeah, I'm snapping my way out of the room.
Jeffrey
Don't you dare. Musical shame me. Okay. But I will say Lindsay was right. Damon was actually really funny.
Brooke
He was.
He was great.
Jeffrey
And I hope that. I hope we talk to him again in a future secondary.
Brooke
I think it still could have worked out if she would have just been like, I'm sorry. Yeah, I'm so sorry.
Jeffrey
No, she had to double down and not appreciate bad boys for the genius that it is.
Brooke
I mean, honest. It was not knowing Martin Lawrence's name that did her end.
I love us. We're pretty disappointed there.
Jeffrey
And don't disappoint us any further. Make sure you go check out all of our second dates. They're up online. It's Brooke and Jeffrey's second date Update. Go, listen, subscribe, and show some damn respect for Martin Lawrence in the comments.
Brooke
That's right.
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Brooke, Jeffrey, and their crew tackle two classic missed connection mysteries:
The hosts dig into these real-life dating disasters, call the unresponsive parties, and deliver their signature, high-entertainment attempts at reconciliation.
Claire recounts meeting Kevin while he was working security at a concert. After being told to get off a chair for safety (06:13), she slips him her number on a cocktail napkin, placed in his pocket with a cheeky note:
“If you need to yell at me or, like, teach me any more about concert safety later, like, text me.”
— Claire (07:08)
Kevin texts her the next day. They bond over joking pet names (she saves him as "concert police") and swap stories about wild concertgoers.
Claire and Kevin meet for Italian food. Claire admits:
“I still thought he was cute, but I was like, I wish you’re wearing your security uniform because you look so cute!”
— Claire (08:37)
They share appetizers, try each other's food, and feel a solid, teasing rapport.
“His mood just totally changed after the bill problem.” — Claire (11:15)
The hosts reach out to Kevin, who is surprisingly friendly (cooking pasta at home!) and not confrontational.
When asked, Kevin reveals what really weirded him out:
“She was putting her fingers in (the olive oil bowl) and rubbing the olive oil on her… against her shirt, and then a little bit, like, on her belly.”
— Kevin (15:16)
Kevin admits the act was so odd he couldn’t bring himself to bring it up. The hosts turn this into a running joke.
Claire explains her side:
“Like, you rub it on your chest. That helps keep everything perky. Like… it’s a TikTok hack I’ve adopted. … It gets the blood flowing. It keeps you moist.”
— Claire (17:29)
“Yeah, I’ll give you a second chance. Let’s go.” — Claire (20:14)
Lindsay meets Damon via a dating app. Their bar meetup unexpectedly turns into an impromptu trivia night with whiteboards and tough questions:
“It was actually kind of fun because … staff starts handing us whiteboards and dry erasers. … The questions were very hard.”
— Lindsay (25:51)
Neither can solve the square root of 16, so they draw a square around the number “16” (26:37). Their joke gets them kicked out of trivia:
“They took our whiteboards away because they thought we weren’t taking it seriously.”
— Lindsay (27:02)
Damon invites Lindsay to his nearby apartment to “watch a movie.”
Lindsay initiates a makeout session but feels things grow awkward as soon as things escalate:
“The second that they got a little hotter, his mood completely changed and things just sort of stopped.”
— Lindsay (28:46)
She checks in, but he claims everything’s “fine” and she leaves, deeply confused and feeling rejected.
“This action packed movie, and here she is trying to get action with me.”
— Damon (35:00) “It’s not a movie. It’s Bad Boys. It’s Will Smith and Martin Lawrence.”
— Damon (36:44)
Lindsay is incredulous:
“You. We had such a great date, and then the reason why now you’ve decided to leave me hanging is because I started making out with you in your favorite part of the movie?”
— Lindsay (36:21)
Damon stands by his priorities:
“Listen, we had fun, but I want to get to know you too. But you need to get to know me.”
— Damon (38:01)
“…That’s gonna be a no for me, cuz she still don’t know the name of the movie.”
— Damon (39:09)
| Segment | Timestamps | |------------------------------------------|-----------------| | Italian Surprise – Claire Introduced | 05:41–06:50 | | Bill Discrepancy & Mood Shift | 09:43–10:27 | | Oil Incident Revelation & Explanation | 15:16–17:29 | | Resolution: Second Chance | 19:03–20:14 | | Mid Hookup – Lindsay’s Story Begins | 24:52–28:46 | | Damon's Reason: The Movie Is Sacred | 34:04–36:44 | | Second Date Attempt & Sarcastic Goodbye | 39:09–39:45 |
For listeners: If you crave more cringe, catharsis, and curveballs in the world of dating, explore more “Second Date Update” episodes — and remember, sometimes the biggest surprise is which tiny detail makes or breaks a connection.