Brooke and Jeffrey: Second Date Update - Second Date Update: E-Trade Mogul

Episode Date: December 26, 2022

The woman in today’s Second Date met up with someone very rich, and arguably pretty famous too… but now he’s not calling back. Can we get her another shot at big time love?See omnystudio.com/listener for privacy information.

Ugh, we're so done with New Year, New You. This year, it's more you on Bumble. More of you shamelessly sending playlists, especially that one filled with show tunes. More of you finding Gemini's because you know you always like them. More of you dating with intention because you know what you want. And you know what? We love that for you. Someone else will too. Be more you this year and find them on Bumble.

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Seven questions, limitless answers. Second date update. You know, I honestly wasn't sure if this was a second date update or a misconnection because apparently these two have crossed paths more than once in the past oh cool which just goes to show you either one it was meant to be yes or two when you're in the single scene for a while you're going to keep running into the same desperate people over and over again until you settle. It's like a club.

The pool isn't as deep as you would hope. Still single, huh? We'll find out which one it is when we talk to Caitlin, who emailed us for some help today. Caitlin, welcome to the show. Hi. How are you? I'm 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, my gosh. His name is Chase, and we met online. Yeah, it is ironic. That's a good point. 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. Okay, so that's kind of the weird thing. He kind of threw me when we were chatting, and his, like, opening line is, Hey, remember me? We were matched and his like opening line is, Hey, remember me? We were matched like a year ago. And then you just flew me off.

Oh, I actually had those. You ghosted him? Honestly, I can't even remember, but I, I do get matched with a lot of people. And so maybe he just flipped through the cracks.

Oh yeah. Got lost in the fold of hundreds and hundreds of matches that are coming after you. It's, it almost seems like kind of passive aggressive. Like, remember me? You blew me off. Yeah.

Because I remember. Yeah. Like he's been holding on to 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 did.

I felt crappy about it. I was like, oh, my gosh. Oh, my gosh. He was hot and I blew him off. What was thinking 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 the minute we walked in like a lot of people seemed to recognize him the host seemed to like oh hey you know and greeting him and then and then 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 have sworn I heard him say something about like a Sports Illustrated shoot. What? Whoa. Who did you go out with? Yeah, is he famous? I don't think so. But he's obviously someone super important.

Is there a famous Chase? Chase Utley. I don't know. He hasn't been around in a while. Yeah, I can't think so, but he's obviously someone super important. Is there a famous Chase? Chase Utley. I don't know. He hasn't been around in a while. Yeah, I can't think. I don't know. There's a game show called The Chase. What does he do for work?

Is he a photographer? You know, he was, like, a bit vague about it. He said, like, into investments and... That means something illegal. No. Actually, that's smart, because he can say anything. If he says investments i just get confused and believe him yeah yeah yeah investments okay sounds wealthy that's great 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 anymore for some reason okay so you're right and once you got seated how did dinner go it was great we we had really fantastic food and great conversation the chef came out and kissed him on the mouth people were signing asking for autographs i mean it wasn't quite that crazy but okay he definitely got some attention and the thing is he was kind of like shy about it like i tried to ask him questions and he just he didn't seem that interested in talking about how fabulous he was. Shy or secretive? Yeah.

That's a good question, Alexis. I know. I kind of have to have this guy's back because even though we're not that cool. Because I'm famous. Let me tell you what it's like for me when I'm not. When people ask us about our jobs, you know, you're like, it's radio. It's cool. It's fun.

You know, like, we don't 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 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 is chase we know that he was an extremely generous tipper i did i don't know exactly what he left but he left cash and it looked like he was leaving like a hundred. And if he's leaving cash, you know he's like counting it in front of her. One, two, three.

He's not radio famous then. Yeah. But if he's leaving a big cash tip, then 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 does not call 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 a different area code and time zone right now. This guy is a total enigma. Like, you don't know. Like, you don't know if he's busy. You have no idea what his schedule is.

I think it's crazy. This is what I've always wondered about celebrities, and please don't be offended by this. Because he's so rich, do you think maybe on the date he realized you're not up to his richness level? No. And maybe just materialistically,

he's like, nah, she's not a Barbados traveler like I am. You think rich people only date rich people? Yeah, most of the time they do. Rich guys don't date rich women. I hope not. They just date women who like money, I think. Yeah, those are the classy ones. I mean, it did cross my mind,

like maybe I'm not up to what he's used to, like maybe he's used to celebrity. Yeah, that's what I meant. Okay, let's find out which one of those is true. We're going to play a song. We'll come back. We'll call Chase for you, and we'll try and get you your second date update.

Okay, Caitlin? I appreciate it. Thanks. All right, hold on. Second date update. 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. I forgot to get details. Does that mean he left a half hour later good, or did he leave the next morning good? Yes! Did he leave the next week good? Oh, wow.

That would have been more than good. That would have been, whoa, Caitlin. He's a squatter. How good was it? I guess, like, the next morning good. That would have been, whoa, Caitlin. He's a squatter. How good was it? I guess like the next morning good. Yeah, girl. Gave you an air high five. Sounds like a fun night.

Yeah, we just wanted to get a little clarification. Wow, 10 hours of sleep. 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 yeah he's a regular 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 yeah yeah yeah totally if it was awkward it'd be like duh okay well let's call chase and get some answers for you i'm gonna dial his number right now you ready yeah thank you okay 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. You should be confused. Yeah, we're buddies now, Chase. We're good. We're best bros at this point. What's up, bro?

How many people are on the phone right now? Oh, four. There's four of us. Yeah. There's four people on this call. Yes. Well, yeah. That's the low amount for this one.

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 too sweet. It 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. Ah, that's even funnier. Hey, we're a funny show. I think we have different sets of humor. Yeah, I don't know about that reaction. Why is that funny? 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, a year ago, you brushed me off or whatever. Yeah, I mean, I wasn't that invested in it. And I mean, it was fine. It was fine. But yeah, that's not going to happen. Sometimes you're just not into people. That's OK. But why did you go hunt her down after a year?

Why did you stay the night at her house? I mean... Why would I spend a night at her house? Yeah, exactly. No, no, no. 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 rematched. That's all.

That was the universe. That's not your fault. 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 photo shoots in Barbados and Sports Illustrated. Oh my God, she told you about that? Is he laughing again? Is this funny again? I can't tell what's funny. This is hilarious. Why? Well, the dating scene out there right now is just utter s***. Can I have a lot of the curse?

Yeah, you already did. So we can bleep that out. Should have asked before 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 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 a lie?

Is that what you're saying? I got an E-Trade account, but it's not investment. Okay. I own like 10 Dogecoin. 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 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 credibility for me in her eyes. This is just like a game you're playing with all your dates so you can get laid? Brilliant. I would totally fall for this. So this isn't just something that you did with Caitlyn 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. 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? Wait a minute. 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 shot that goes to Barbados and does photo shoots for Sports Illustrated. She took it exactly like you're a big a big shot that goes to barbados and does photo shoots for sports illustrated 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 gonna tell you i don't know who you are maybe if you'd be willing to sleep with him then he'll say something all right so your whole plan was to just say whatever you want to say spend the the night with Caitlin, and then never talk to her again?

I mean, that's layman's terms, but yes. 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 are you going to 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.

You do sound bitter. You wouldn't be wrong, man. She's always the rich one, so she's jealous. I just hate liars. Like, man, 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 things and i just politely smiled

well at this point chase i need to tell you something that's probably going to break your plan of never talking to caitlin again yeah because she's actually on the other line listening and she wants to talk to you who's sneakier or no? Yeah. Oh, yeah. Oh, my God. What the hell? That's even your name. You people are ruining my life. That'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 going to 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. You only kind of doubt it. That's amazing, Caitlin. He's not wrong about the bleak dating scene. You've got to take what you can.

But, Kate, like, honestly, if you asked me if that's true, then I would have told you the truth. Oh, really? Ask him now, Caitlin. You do this over and over for one night stay. I mean, that's just disgusting. Yeah, and pathetic. It's just so pathetic. 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 wouldn't try to make it the best for me? But you're not even playing. You could have spent your two Benjamins on just getting what you wanted. Well, joke's on you, Kate, because

my buddy actually gave me back some of the tip that I gave him. Oh, I didn't think of that! It turns out he's not so rich, Alexa. Give him like a thousand bucks and he gets like 900 back or something. Oh my gosh.

You showed her, didn't you, Chase? If you're not that well off, then we need to help pay for your second date. Yeah, Brooke feels really bad. We're offering to do. Yeah, Brooke is actually going to fund it fully on her own. 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 this. I'm sick of being ridiculed by you losers. Did he hang up? Yeah, that was the best part of the whole call for me. Just the hang up. Which one of us was he calling a loser? Definitely me. Yeah, I think it was me.

Way to ruin that for us. Yeah. We thought we were cool with a rich guy. Caitlin, I'm sorry that it played out that way. I just want to throw up. I'm so sorry. Some dudes just, 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 them what they do for work. No, I think you need to go back to that restaurant every day this week and just blow up his spot. Oh, that's a good idea. Oh, my God. I'm doing that. I am totally doing that. Thank you. Great suggestion.

He's going to have to find a new friend. Take a video and send it to us, please. Finally, a successful second date update. There we go. Brooke and Jeffrey in the morning. Ugh, we're so done with new year, new you. This year, it's more you on Bumble. More of you shamelessly sending playlists,

especially that one filled with show tunes. More of you finding Gemini's because you know you always like them. More of you dating with intention because you know what you want. And you know what? We love that for you. Someone else will, too. Be more you this year and find them on Bumble. Jon Stewart is back at The Daily Show,

and he's bringing his signature wit and insight straight to your ears with The Daily Show Ears Edition podcast. Dive into Jon's unique take on the biggest topics in politics, entertainment, sports, and more. Joined by the sharp voices of the show's correspondents and contributors. And with extended interviews and exclusive weekly headline roundups, this podcast gives you content you won't find anywhere else. Ready to laugh and stay informed? Listen on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

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