Second Date Update: E-Trade Mogul

for some help today. Caitlin, welcome to the show. Hi, how are you doing? Okay? How are you doing good? So tell us about the guy that you want us to call today. What's his name? Oh gosh, his name is Chase and we met online. Yeah it is ironic, all right. So you met him online? And when you say you met him, are you talking about the first time you guys met, because Jeffrey said that you kept running into each other. Wells, so okay, So that's kind

of a weird thing. He kind of threw me when we were chatting and his like opening line is, hey remember me, we were matched like a year ago, and then you just blew me off. Oh, you ghosted him. Honestly, I can't even remember, but I do get matched with a lot of people, and so maybe he just flipped through the crack. Oh yeah, I got lost in the fold of hundreds and hundreds of matches that are coming after you. It almost seems like kind of passive aggressive,

like remember me, you blew me off? Yeah you know, yeah, he's been holding on just some grudge for a long time. But you didn't take it that way. No, I don't know. It was kind of like mysterious and everything, but I but I did. I felt crappy about it. I was like, oh my gosh, you know, oh my gosh, he was hot and I blew him off? What was I? Thank you? Yeah? So did you end up meeting up? We did. He took me to like a really super fancy restaurant and

it was amazing. I mean, like, for a minute we walked in, like a lot of people seemed to recognize him, The host seemed delay, oh hey, you know, in greeting him, and then and like a server came up to him and I was like, I couldn't quite overhear everything, but something about like Barbados, and then I could warn I heard him say something about like sports illustrated, shoot what like, Yeah, is he famous? I don't think so, but he's obviously

someone super important. Is there a famous Chase Chase? Utly? I don't know. He hasn't been around in a while. Yeah, I can't think. I don't know. What does he do for work? Is he a photographer? You know? He was like a bit vague about it. He sounds like into investments and mean something illegal. Yeah. Actually that's smart because he can say anything. If he says investments, I gets get confused and believe him. Yeah, yeah, investments. Okay, sounds

wealthy exactly. It's like when I don't want to tell people I'm in radio and I just say I've been marketing. Yeah, nobody has any questions and some reason. So okay. So and once you got seated, how did dinner go? It was great. We we have really fantastic food and great conversation. Checked him out and kissed him on the mouth. People were signing asking for autographs. It wasn't quite that crazy, but he definitely got some attention. And the thing is

he was kind of like cry about it. Like I try to ask him questions and he just didn't seem that interested in talking about how fabulous he was. I are secretive because yeah, I know, I kind of I have to have this guy's back because even though we're not that cool because I'm famous, it's like ask us about our jobs. You know, you're like, it's it's radio is cool, it's fun, you know, like when I want to talk about it and delve into it right because

people think it's oh wow, and it's really not. I don't know, it just sounds like you don't really know anything about this guy, you know, like what what do you know? What did you learn about him? Well, um, his name, that he's an extremely generous tipper. I didn't

I don't know exactly what he left. He left cash and it looked like he's leaving like a hundred and if you know he's like counting in front of well you know he's not radio famous, then yeah, if he's leaving a big cash too, So how did you end up leaving things with him? He was a total gentleman, Like he walked me home. I invited him up for a nightcap and we had a great time and he has not called me back. And I mean, I'm sure

if he is going to places like Barbados and stuff. Like, maybe he's just crazy busy and like in different countries and it's just hard to get back in touch. Yeah, he's different area code and time zone right now. This guy's a total enigma. Like you don't know, Like you don't know if you're too if he's busy, you don't you have no idea what his schedule is. Like, I think it's crazy. This is what I've always wandered about celebrities. And please don't be offended by this because he's so rich.

Do you think maybe on the day he realized you're not up to his richness level and maybe just material Basically he's like, she's not you think rich people rich people? Yeah, most of the time they do. Rich guys don't date rich women, I hope not. They just fight women who like money. I think, uh yeah, those are the classy ones. Yeah, I mean I did cross my mind, like maybe I'm not up to what he used to like. Yeah, Okay,

let's find out which one of those is true. We're gonna play a song, we'll come back, we'll call Chase for you, and we'll try and get your second date update. Okay, Caitlin, I appreciate it, Thank you all. Hold on, Caitlin, I'm just wondering. Tell me if I'm getting too personal here. But when you said at the end of the night, he walked you back to your place and then you invited Chase up for a nightcap and it went good? Oh yeah, we forgot to get details. Does that mean

he left a half hour later? Good? Or did he leave the next morning good? Oh? Yeah? Yeah? Did you leave the next week good? Oh? Well, that would have been more than good. That would have been whoa, Caitlin was I guess like the next morning guy a high five? That's like a fun night. Yeah, we just wanted to get a little clarification. But after that, Chase is not calling back at all? Is that right? Right? Okay? How

many days has it been? Five? Five? Well, it's interesting because you guys went to a really nice restaurant and at first I was like, Oh, he's wanting to impress her, But then when everybody knew him, I'm like, oh, he's just a rich guy and this is his place. Totally Like that changes the narrative. I mean, did you get a vibe that there was going to be more? I mean everything seemed to like click. So I don't I don't know why there wouldn't be more okay, yea, yeah, yeah, totally. Okay, Well,

let's call Chase and get some answers for you. I mean a Dalla's number right now? You ready? Yeah, thank you? Okay, here we go. Hello. Hey is this Chase? Yeah? Who's this? My name's Jeff from a morning radio show called Brooke and Jeffrey in the Morning. Okay, how you doing, man, I'm doing good man, all right, Yeah, we're buddies. We're best bros. At this point. How many people are on the phone right now? There's four of us. Yeah, there's

four people on this call. Yeah. Well yeah, that's the loan. Yeah okay, but no, it's a morning radio show. We're called Brooke and Jeffrey in the Morning, and we do a segment called the Second Date Update. That's where if you go out with someone and afterwards, if that person isn't calling you back, you can email us to call them for you to help figure out the reason why. Oh okay, okay, okay, See it's a good thing. That's funny. Yeah,

it can be Yeah, it can be good to sweet. Yeah, can be a lot of things depending on what your answer is. And we're calling on behalf of one of our listeners named Caitlin. Uh, that's even funnier. Hey, we're funny show. Yeah, why is that funny? Yeah? I don't know, it's just funny. Okay, Well, Caitlin, I don't think finds it that funny because it's been apparently five days since you guys went out and you're not calling her anymore. Is that funny? Well? I mean that was kind of

like a one time deal. What did you make that clear? Because for her, she felt like you guys really connected. She told us that, like you're the one that hit her up on the dating app and we're like, yo, year ago you brush me off or whatever. Yeah, I mean I wasn't that invested in it, and I mean it was fun, it was fine, but yeah, that's not gonna happened sometimes. But why did you go hunt her down after a year or I could stay the night at her house? I mean, why would I spend a

night at her house? Why would you spend so much energy finding this person that had blown you off a year ago and then asking him out again if you weren't invested at all, well, yeah, I mean, I don't know, like we matched up after a year. Again, It's not like I hunted her down, you know what I mean, We just rematch, that's all. That was okay, okay, okay. But she told us all about your night, and she made it seem like it was a pretty great experience.

She told us you took her out to this really nice restaurant where apparently the waiters love you, and they were bringing up photoshoots and Barbadoes and Sports Illustrated and about that. Is this funny again? This is hilarious? Why? Well, the dating scene out there right now is just utter. Can I am allowed the curse? Yeah? You did it? That's okay, okay. And so you can't just like close

your eyes and hope for the best. You gotta have to have a game plan, and you also need like one of your buddies to help you out with this. So I said, I said investments because I knew that that would probably make her be like, ooh, investments you're talking about Are you saying your job in investments? Yeah? Because it was just vague enough, but it still intrigues. Wait, so wait, is it is it a lie? Is that what you're saying, I got an e trade account, but

it's not investment. But the thing is here is that I asked my buddy who's a waiter at this restaurant, to like help me out, build me up a little bit in front of her in her eyes, he gives me an employee discount. I leave him a really nice tip. She's none the wiser, you know, and it builds ability for me in her eye. This is just like a game you're playing with all your dates so you can get laid. Really, I would totally fall for this. So

this isn't just something that you did with Caitlin. Once you do this all the time, well that's what dating is. It's games. It's not outright lying about who you are and pretending to be a famous person, Like you don't think you could get laid on your own, like you have to like make up some extravagant story about it and get other people involved. I did not make up

an extravagant story. I made it look like something. But as far as she's like, she took it the way that she took it, well, she took it as like you're a big, a big shot that goes to Barbados and does photoshoots for sports illustration. She took it exactly as you wanted her to take it, Like that is exactly what you planned out. Dude, what do you really do? I'm not going to tell you. I don't know who you are. Maybe if you're willing to sleep with him,

then all right. So your whole plan was to just say whatever you want to say, spend the night with Caitlyn, and then never talk to her again. I mean that's layman's terms. But yet I like how you say like you're not interested. You're not interested in her, and that's why you can't talk to her again, Like you can't talk to her again because your whole life is a lie. Like what you're gonna say, You'll never what if you meet somebody you actually like, you'll never be actually able

to date them. Look, you sound really bitter right now, and I'm assuming that this has happened to you in the past. I says hate liars like Matt, You're going to ruin your own life by doing this and you don't even see it. I never lied. The waiter was saying those things and I just politely smile. Is going to be glad well, at this point, Chase, I need to tell you something that's probably going to break your

plan of never talking to Caitlyn again. Yeah, because she's actually on the other line listening and she wants to talk to you. Who's sneakier now? Yeah? Oh yeah, Oh my god, what the hell? Name? Like, people are ruining my life? Who's just messed up? It might be messed up, but that's the way that dating is right now. So I mean, well, yeah, if you're gonna be that sour about it and like have to just come up with lies,

not ever giving anyone a shot, who knows. Maybe you were actually a nice guy, but I kind of doubt it after hearing all this information, only kind of doubt it's not wrong about But Kate, like, honestly, if you ask me if that's true, then I would have I would have told you the truth. Oh really ask him now, Kate, you do this over and over for one night state. I mean, that's just disgusting, ampathetic, It's just so pathetic. I just I know that I did what was best

for me. I have to put the playing field in the way that would best suit me. Who wouldn't do that? You know what? I mean who you could have think your two Benjamin's on just getting what you wanted. I mean, well, jokes on UK because my buddy actually gave me back some of the tip that I gave him. It turns out he's not so rich. Well in that case, Yeah, you showed her, didn't you, Chase. If you're not that well off, then we need to help pay for your

second days bad we're offering to do. Yeah, Brooke has actually gonna fund it fully. I'm always standing up for the under Chase. What do you say you want to give it another shot? Yeah, I don't have to take any of it. Oh, I'm sick of being ridiculed by you losers. Oh did he hang up? Yeah? That was the best part of the whole call for me just to hang up. Which one of us was he calling a loser? Definitely you got to ruin that first yea. Yeah, Caitlin, I'm sorry that it played out that way. I just

want to throw up. I'm so sorry. You know, they get what they want. Yeah, they're not all like that out there, Caitlin, Maybe ask for a real profession next time when you ask him what they do for were no way, I think you need to go back to that restaurant every day this week and just blow up his spot. Oh, oh my god, I'm doing that. I am totally doing that. Thank you. Please. Suggestion, Yeah, take

a video and send it to us please. Finally, a successful second date up Broke and Jeffrey in the morning.