WEBVTT - Second Date Update: E-Trade Mogul

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<v Speaker 1>Second date up today. You know, I honestly wasn't sure

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<v Speaker 1>if this was a second date update or a misconnection,

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<v Speaker 1>because apparently these two have cross paths more than once

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<v Speaker 1>in the past. Oh cool wow. Which just goes to

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<v Speaker 1>show you either one it was meant to be yes

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<v Speaker 1>or two. When you're in the single scene for a while,

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<v Speaker 1>you're gonna keep running into the same desperate people over

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<v Speaker 1>and over until you settle. We'll find out which one

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<v Speaker 1>it is when we talk to Caitlin, who emailed us

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<v Speaker 1>for some help today. Caitlin, welcome to the show. Hi,

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<v Speaker 1>how are you doing? Okay? How are you doing good?

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<v Speaker 1>So tell us about the guy that you want us

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<v Speaker 1>to call today. What's his name? Oh gosh, his name

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<v Speaker 1>is Chase and we met online. Yeah it is ironic,

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<v Speaker 1>all right. So you met him online? And when you

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<v Speaker 1>say you met him, are you talking about the first

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<v Speaker 1>time you guys met, because Jeffrey said that you kept

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<v Speaker 1>running into each other. Wells, so okay, So that's kind

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<v Speaker 1>of a weird thing. He kind of threw me when

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<v Speaker 1>we were chatting and his like opening line is, hey

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<v Speaker 1>remember me, we were matched like a year ago, and

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<v Speaker 1>then you just blew me off. Oh, you ghosted him. Honestly,

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<v Speaker 1>I can't even remember, but I do get matched with

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<v Speaker 1>a lot of people, and so maybe he just flipped

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<v Speaker 1>through the crack. Oh yeah, I got lost in the

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<v Speaker 1>fold of hundreds and hundreds of matches that are coming

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<v Speaker 1>after you. It almost seems like kind of passive aggressive,

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<v Speaker 1>like remember me, you blew me off? Yeah you know, yeah,

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<v Speaker 1>he's been holding on just some grudge for a long time.

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<v Speaker 1>But you didn't take it that way. No, I don't know.

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<v Speaker 1>It was kind of like mysterious and everything, but I

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<v Speaker 1>but I did. I felt crappy about it. I was like,

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<v Speaker 1>oh my gosh, you know, oh my gosh, he was

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<v Speaker 1>hot and I blew him off? What was I? Thank you? Yeah?

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<v Speaker 1>So did you end up meeting up? We did. He

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<v Speaker 1>took me to like a really super fancy restaurant and

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<v Speaker 1>it was amazing. I mean, like, for a minute we

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<v Speaker 1>walked in, like a lot of people seemed to recognize him,

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<v Speaker 1>The host seemed delay, oh hey, you know, in greeting him,

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<v Speaker 1>and then and like a server came up to him

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<v Speaker 1>and I was like, I couldn't quite overhear everything, but

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<v Speaker 1>something about like Barbados, and then I could warn I

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<v Speaker 1>heard him say something about like sports illustrated, shoot what like, Yeah,

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<v Speaker 1>is he famous? I don't think so, but he's obviously

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<v Speaker 1>someone super important. Is there a famous Chase Chase? Utly?

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<v Speaker 1>I don't know. He hasn't been around in a while. Yeah,

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<v Speaker 1>I can't think. I don't know. What does he do

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<v Speaker 1>for work? Is he a photographer? You know? He was

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<v Speaker 1>like a bit vague about it. He sounds like into

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<v Speaker 1>investments and mean something illegal. Yeah. Actually that's smart because

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<v Speaker 1>he can say anything. If he says investments, I gets

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<v Speaker 1>get confused and believe him. Yeah, yeah, investments. Okay, sounds

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<v Speaker 1>wealthy exactly. It's like when I don't want to tell

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<v Speaker 1>people I'm in radio and I just say I've been marketing. Yeah,

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<v Speaker 1>nobody has any questions and some reason. So okay. So

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<v Speaker 1>and once you got seated, how did dinner go? It

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<v Speaker 1>was great. We we have really fantastic food and great conversation.

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<v Speaker 1>Checked him out and kissed him on the mouth. People

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<v Speaker 1>were signing asking for autographs. It wasn't quite that crazy,

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<v Speaker 1>but he definitely got some attention. And the thing is

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<v Speaker 1>he was kind of like cry about it. Like I

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<v Speaker 1>try to ask him questions and he just didn't seem

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<v Speaker 1>that interested in talking about how fabulous he was. I

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<v Speaker 1>are secretive because yeah, I know, I kind of I

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<v Speaker 1>have to have this guy's back because even though we're

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<v Speaker 1>not that cool because I'm famous, it's like ask us

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<v Speaker 1>about our jobs. You know, you're like, it's it's radio

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<v Speaker 1>is cool, it's fun, you know, like when I want

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<v Speaker 1>to talk about it and delve into it right because

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<v Speaker 1>people think it's oh wow, and it's really not. I

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<v Speaker 1>don't know, it just sounds like you don't really know

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<v Speaker 1>anything about this guy, you know, like what what do

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<v Speaker 1>you know? What did you learn about him? Well, um,

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<v Speaker 1>his name, that he's an extremely generous tipper. I didn't

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<v Speaker 1>I don't know exactly what he left. He left cash

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<v Speaker 1>and it looked like he's leaving like a hundred and

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<v Speaker 1>if you know he's like counting in front of well

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<v Speaker 1>you know he's not radio famous, then yeah, if he's

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<v Speaker 1>leaving a big cash too, So how did you end

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<v Speaker 1>up leaving things with him? He was a total gentleman,

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<v Speaker 1>Like he walked me home. I invited him up for

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<v Speaker 1>a nightcap and we had a great time and he

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<v Speaker 1>has not called me back. And I mean, I'm sure

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<v Speaker 1>if he is going to places like Barbados and stuff. Like,

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<v Speaker 1>maybe he's just crazy busy and like in different countries

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<v Speaker 1>and it's just hard to get back in touch. Yeah,

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<v Speaker 1>he's different area code and time zone right now. This

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<v Speaker 1>guy's a total enigma. Like you don't know, Like you

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<v Speaker 1>don't know if you're too if he's busy, you don't

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<v Speaker 1>you have no idea what his schedule is. Like, I

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<v Speaker 1>think it's crazy. This is what I've always wandered about celebrities.

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<v Speaker 1>And please don't be offended by this because he's so rich.

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<v Speaker 1>Do you think maybe on the day he realized you're

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<v Speaker 1>not up to his richness level and maybe just material

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<v Speaker 1>Basically he's like, she's not you think rich people rich people? Yeah,

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<v Speaker 1>most of the time they do. Rich guys don't date

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<v Speaker 1>rich women, I hope not. They just fight women who

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<v Speaker 1>like money. I think, uh yeah, those are the classy ones. Yeah,

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<v Speaker 1>I mean I did cross my mind, like maybe I'm

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<v Speaker 1>not up to what he used to like. Yeah, Okay,

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<v Speaker 1>let's find out which one of those is true. We're

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<v Speaker 1>gonna play a song, we'll come back, we'll call Chase

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<v Speaker 1>for you, and we'll try and get your second date update. Okay, Caitlin,

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<v Speaker 1>I appreciate it, Thank you all. Hold on, Caitlin, I'm

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<v Speaker 1>just wondering. Tell me if I'm getting too personal here.

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<v Speaker 1>But when you said at the end of the night,

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<v Speaker 1>he walked you back to your place and then you

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<v Speaker 1>invited Chase up for a nightcap and it went good?

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<v Speaker 1>Oh yeah, we forgot to get details. Does that mean

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<v Speaker 1>he left a half hour later? Good? Or did he

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<v Speaker 1>leave the next morning good? Oh? Yeah? Yeah? Did you

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<v Speaker 1>leave the next week good? Oh? Well, that would have

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<v Speaker 1>been more than good. That would have been whoa, Caitlin

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<v Speaker 1>was I guess like the next morning guy a high five?

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<v Speaker 1>That's like a fun night. Yeah, we just wanted to

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<v Speaker 1>get a little clarification. But after that, Chase is not

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<v Speaker 1>calling back at all? Is that right? Right? Okay? How

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<v Speaker 1>many days has it been? Five? Five? Well, it's interesting

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<v Speaker 1>because you guys went to a really nice restaurant and

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<v Speaker 1>at first I was like, Oh, he's wanting to impress her,

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<v Speaker 1>But then when everybody knew him, I'm like, oh, he's

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<v Speaker 1>just a rich guy and this is his place. Totally

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<v Speaker 1>Like that changes the narrative. I mean, did you get

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<v Speaker 1>a vibe that there was going to be more? I

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<v Speaker 1>mean everything seemed to like click. So I don't I

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<v Speaker 1>don't know why there wouldn't be more okay, yea, yeah, yeah, totally. Okay, Well,

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<v Speaker 1>let's call Chase and get some answers for you. I

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<v Speaker 1>mean a Dalla's number right now? You ready? Yeah, thank you? Okay,

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<v Speaker 1>here we go. Hello. Hey is this Chase? Yeah? Who's this?

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<v Speaker 1>My name's Jeff from a morning radio show called Brooke

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<v Speaker 1>and Jeffrey in the Morning. Okay, how you doing, man,

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<v Speaker 1>I'm doing good man, all right, Yeah, we're buddies. We're

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<v Speaker 1>best bros. At this point. How many people are on

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<v Speaker 1>the phone right now? There's four of us. Yeah, there's

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<v Speaker 1>four people on this call. Yeah. Well yeah, that's the loan.

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<v Speaker 1>Yeah okay, but no, it's a morning radio show. We're

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<v Speaker 1>called Brooke and Jeffrey in the Morning, and we do

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<v Speaker 1>a segment called the Second Date Update. That's where if

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<v Speaker 1>you go out with someone and afterwards, if that person

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<v Speaker 1>isn't calling you back, you can email us to call

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<v Speaker 1>them for you to help figure out the reason why.

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<v Speaker 1>Oh okay, okay, okay, See it's a good thing. That's funny. Yeah,

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<v Speaker 1>it can be Yeah, it can be good to sweet. Yeah,

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<v Speaker 1>can be a lot of things depending on what your

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<v Speaker 1>answer is. And we're calling on behalf of one of

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<v Speaker 1>our listeners named Caitlin. Uh, that's even funnier. Hey, we're

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<v Speaker 1>funny show. Yeah, why is that funny? Yeah? I don't know,

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<v Speaker 1>it's just funny. Okay, Well, Caitlin, I don't think finds

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<v Speaker 1>it that funny because it's been apparently five days since

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<v Speaker 1>you guys went out and you're not calling her anymore.

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<v Speaker 1>Is that funny? Well? I mean that was kind of

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<v Speaker 1>like a one time deal. What did you make that clear?

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<v Speaker 1>Because for her, she felt like you guys really connected.

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<v Speaker 1>She told us that, like you're the one that hit

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<v Speaker 1>her up on the dating app and we're like, yo,

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<v Speaker 1>year ago you brush me off or whatever. Yeah, I

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<v Speaker 1>mean I wasn't that invested in it, and I mean

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<v Speaker 1>it was fun, it was fine, but yeah, that's not

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<v Speaker 1>gonna happened sometimes. But why did you go hunt her

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<v Speaker 1>down after a year or I could stay the night

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<v Speaker 1>at her house? I mean, why would I spend a

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<v Speaker 1>night at her house? Why would you spend so much

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<v Speaker 1>energy finding this person that had blown you off a

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<v Speaker 1>year ago and then asking him out again if you

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<v Speaker 1>weren't invested at all, well, yeah, I mean, I don't know,

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<v Speaker 1>like we matched up after a year. Again, It's not

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<v Speaker 1>like I hunted her down, you know what I mean,

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<v Speaker 1>We just rematch, that's all. That was okay, okay, okay.

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<v Speaker 1>But she told us all about your night, and she

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<v Speaker 1>made it seem like it was a pretty great experience.

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<v Speaker 1>She told us you took her out to this really

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<v Speaker 1>nice restaurant where apparently the waiters love you, and they

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<v Speaker 1>were bringing up photoshoots and Barbadoes and Sports Illustrated and

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<v Speaker 1>about that. Is this funny again? This is hilarious? Why? Well,

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<v Speaker 1>the dating scene out there right now is just utter.

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<v Speaker 1>Can I am allowed the curse? Yeah? You did it?

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<v Speaker 1>That's okay, okay. And so you can't just like close

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<v Speaker 1>your eyes and hope for the best. You gotta have

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<v Speaker 1>to have a game plan, and you also need like

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<v Speaker 1>one of your buddies to help you out with this.

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<v Speaker 1>So I said, I said investments because I knew that

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<v Speaker 1>that would probably make her be like, ooh, investments you're

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<v Speaker 1>talking about Are you saying your job in investments? Yeah?

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<v Speaker 1>Because it was just vague enough, but it still intrigues. Wait,

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<v Speaker 1>so wait, is it is it a lie? Is that

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<v Speaker 1>what you're saying, I got an e trade account, but

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<v Speaker 1>it's not investment. But the thing is here is that

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<v Speaker 1>I asked my buddy who's a waiter at this restaurant,

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<v Speaker 1>to like help me out, build me up a little

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<v Speaker 1>bit in front of her in her eyes, he gives

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<v Speaker 1>me an employee discount. I leave him a really nice tip.

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<v Speaker 1>She's none the wiser, you know, and it builds ability

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<v Speaker 1>for me in her eye. This is just like a

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<v Speaker 1>game you're playing with all your dates so you can

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<v Speaker 1>get laid. Really, I would totally fall for this. So

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<v Speaker 1>this isn't just something that you did with Caitlin. Once

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<v Speaker 1>you do this all the time, well that's what dating is.

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<v Speaker 1>It's games. It's not outright lying about who you are

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<v Speaker 1>and pretending to be a famous person, Like you don't

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<v Speaker 1>think you could get laid on your own, like you

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<v Speaker 1>have to like make up some extravagant story about it

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<v Speaker 1>and get other people involved. I did not make up

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<v Speaker 1>an extravagant story. I made it look like something. But

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<v Speaker 1>as far as she's like, she took it the way

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<v Speaker 1>that she took it, well, she took it as like

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<v Speaker 1>you're a big, a big shot that goes to Barbados

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<v Speaker 1>and does photoshoots for sports illustration. She took it exactly

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<v Speaker 1>as you wanted her to take it, Like that is

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<v Speaker 1>exactly what you planned out. Dude, what do you really do?

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<v Speaker 1>I'm not going to tell you. I don't know who

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<v Speaker 1>you are. Maybe if you're willing to sleep with him,

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<v Speaker 1>then all right. So your whole plan was to just

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<v Speaker 1>say whatever you want to say, spend the night with Caitlyn,

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<v Speaker 1>and then never talk to her again. I mean that's

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<v Speaker 1>layman's terms. But yet I like how you say like

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<v Speaker 1>you're not interested. You're not interested in her, and that's

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<v Speaker 1>why you can't talk to her again, Like you can't

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<v Speaker 1>talk to her again because your whole life is a lie.

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<v Speaker 1>Like what you're gonna say, You'll never what if you

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<v Speaker 1>meet somebody you actually like, you'll never be actually able

0:12:22.280 --> 0:12:26.000
<v Speaker 1>to date them. Look, you sound really bitter right now,

0:12:26.320 --> 0:12:28.480
<v Speaker 1>and I'm assuming that this has happened to you in

0:12:28.520 --> 0:12:36.400
<v Speaker 1>the past. I says hate liars like Matt, You're going

0:12:36.440 --> 0:12:38.520
<v Speaker 1>to ruin your own life by doing this and you

0:12:38.559 --> 0:12:41.520
<v Speaker 1>don't even see it. I never lied. The waiter was

0:12:41.559 --> 0:12:47.360
<v Speaker 1>saying those things and I just politely smile. Is going

0:12:47.440 --> 0:12:51.640
<v Speaker 1>to be glad well, at this point, Chase, I need

0:12:51.679 --> 0:12:53.880
<v Speaker 1>to tell you something that's probably going to break your

0:12:53.880 --> 0:12:56.960
<v Speaker 1>plan of never talking to Caitlyn again. Yeah, because she's

0:12:56.960 --> 0:12:59.240
<v Speaker 1>actually on the other line listening and she wants to

0:12:59.280 --> 0:13:03.280
<v Speaker 1>talk to you. Who's sneakier now? Yeah? Oh yeah, Oh

0:13:03.360 --> 0:13:08.920
<v Speaker 1>my god, what the hell? Name? Like, people are ruining

0:13:08.920 --> 0:13:14.520
<v Speaker 1>my life? Who's just messed up? It might be messed up,

0:13:14.559 --> 0:13:16.560
<v Speaker 1>but that's the way that dating is right now. So

0:13:17.240 --> 0:13:20.240
<v Speaker 1>I mean, well, yeah, if you're gonna be that sour

0:13:20.320 --> 0:13:23.360
<v Speaker 1>about it and like have to just come up with lies,

0:13:23.640 --> 0:13:26.400
<v Speaker 1>not ever giving anyone a shot, who knows. Maybe you

0:13:26.480 --> 0:13:28.480
<v Speaker 1>were actually a nice guy, but I kind of doubt

0:13:28.520 --> 0:13:31.080
<v Speaker 1>it after hearing all this information, only kind of doubt

0:13:31.120 --> 0:13:38.200
<v Speaker 1>it's not wrong about But Kate, like, honestly, if you

0:13:38.280 --> 0:13:39.920
<v Speaker 1>ask me if that's true, then I would have I

0:13:39.920 --> 0:13:42.719
<v Speaker 1>would have told you the truth. Oh really ask him now, Kate,

0:13:44.280 --> 0:13:46.600
<v Speaker 1>you do this over and over for one night state.

0:13:46.679 --> 0:13:50.520
<v Speaker 1>I mean, that's just disgusting, ampathetic, It's just so pathetic.

0:13:50.760 --> 0:13:53.280
<v Speaker 1>I just I know that I did what was best

0:13:53.320 --> 0:13:56.360
<v Speaker 1>for me. I have to put the playing field in

0:13:56.400 --> 0:13:59.559
<v Speaker 1>the way that would best suit me. Who wouldn't do that?

0:13:59.760 --> 0:14:02.600
<v Speaker 1>You know what? I mean who you could have think

0:14:02.600 --> 0:14:07.000
<v Speaker 1>your two Benjamin's on just getting what you wanted. I mean, well,

0:14:07.120 --> 0:14:10.920
<v Speaker 1>jokes on UK because my buddy actually gave me back

0:14:11.200 --> 0:14:16.240
<v Speaker 1>some of the tip that I gave him. It turns

0:14:16.280 --> 0:14:23.600
<v Speaker 1>out he's not so rich. Well in that case, Yeah,

0:14:23.640 --> 0:14:27.000
<v Speaker 1>you showed her, didn't you, Chase. If you're not that

0:14:27.160 --> 0:14:29.840
<v Speaker 1>well off, then we need to help pay for your

0:14:29.840 --> 0:14:34.240
<v Speaker 1>second days bad we're offering to do. Yeah, Brooke has

0:14:34.240 --> 0:14:37.560
<v Speaker 1>actually gonna fund it fully. I'm always standing up for

0:14:37.560 --> 0:14:40.480
<v Speaker 1>the under Chase. What do you say you want to

0:14:40.480 --> 0:14:42.600
<v Speaker 1>give it another shot? Yeah, I don't have to take

0:14:42.600 --> 0:14:47.360
<v Speaker 1>any of it. Oh, I'm sick of being ridiculed by

0:14:47.400 --> 0:14:52.040
<v Speaker 1>you losers. Oh did he hang up? Yeah? That was

0:14:52.080 --> 0:14:54.120
<v Speaker 1>the best part of the whole call for me just

0:14:54.200 --> 0:14:56.520
<v Speaker 1>to hang up. Which one of us was he calling

0:14:56.520 --> 0:15:06.880
<v Speaker 1>a loser? Definitely you got to ruin that first yea. Yeah, Caitlin,

0:15:06.960 --> 0:15:09.320
<v Speaker 1>I'm sorry that it played out that way. I just

0:15:09.360 --> 0:15:13.800
<v Speaker 1>want to throw up. I'm so sorry. You know, they

0:15:13.840 --> 0:15:16.400
<v Speaker 1>get what they want. Yeah, they're not all like that

0:15:16.440 --> 0:15:20.600
<v Speaker 1>out there, Caitlin, Maybe ask for a real profession next

0:15:20.600 --> 0:15:22.280
<v Speaker 1>time when you ask him what they do for were

0:15:22.480 --> 0:15:24.280
<v Speaker 1>no way, I think you need to go back to

0:15:24.320 --> 0:15:26.920
<v Speaker 1>that restaurant every day this week and just blow up

0:15:26.920 --> 0:15:31.520
<v Speaker 1>his spot. Oh, oh my god, I'm doing that. I

0:15:31.560 --> 0:15:38.280
<v Speaker 1>am totally doing that. Thank you. Please. Suggestion, Yeah, take

0:15:38.280 --> 0:15:40.520
<v Speaker 1>a video and send it to us please. Finally, a

0:15:40.560 --> 0:15:44.880
<v Speaker 1>successful second date up Broke and Jeffrey in the morning.