Brooke and Jeffrey: Second Date Update - 2nd Date Update PODCAST: Rich Guy Problems

Episode Date: May 10, 2019

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Moving 92.5. Brooke and Jubal in the Morning's Second Date Update. You know who I feel bad for? The super rich. What? Why would you feel bad for them? I feel terrible for super rich people. What, because they're jerks? That's why today's Second Date update is interesting, because we got an email, and I'll just read a little bit of the email from the dude that wants to do a second date update today.

It says, I just sold my startup company. I'm super rich, and I don't have to work a day in my life. I have nice cars, I go to the gym three times a week, but I still have trouble meeting quality women, and I can't figure out what's wrong. And recently, I had a date not call me back, and I need your help. Poor guy. So, once again, another poor rich person is on the phone, and we need to help him. What's up, Sean?

How are you? Hey, guys. How are you? Not as good as you, I don't think. I'm imagining he's on a gold phone right now. Guys, I feel like I could tell you right now what's wrong with this dating life. Did you hear your email being read out loud? You're just bragging.

I didn't know you guys were going to read it out loud. I was just telling you guys so you would know the whole truth because I try not to let that out when I'm meeting people. I'm having a hard time believing it,

but okay. Sure, Sean. I mean, I'm serious. I try not to talk about it on dates. Like, not bring it up at all. I can kind of see that. I mean, I read it.

It sounded less like you were bragging, more just like, I have everything else I could need, but I can't get a date. It's not that I can't get a date. It's just I can't meet people that are real or just seemingly like true. And if I told him how I live, I certainly I find like gold diggers. Oh, yeah. Okay. So you're concerned that people only kind of want you for your money or want to be friends with you or date you for your money? Yeah, for like my money, my houses, you know, my cars.

Okay, again, you just— By the way— That's bragging again. If you're free this Saturday and want to hang out, dude, I could use a new friend. And it's just because I like you, Sean. Just the sound of you is cool. Has nothing to do with all that stuff you have. We'll see.

Let's see how this second date goes first. Okay. Well, tell us about the girl you want to call today what's her name her name's tracy tracy all right and is she broke no i have comparatively i currently i have no idea about her financial status and i don't want to know okay where'd you meet her i hope it wasn't like date rich people dot com no no no i mean it's through a matchmaking service for professionals. Okay. So you met her on this matchmaking service, and how was the date with her? The date was good. We went to, like, a nice, like, new, trendy restaurant.

I was trying to be cool. Like, I didn't, like, take my Maserati. Like, just drove, like, my Beamer. Oh, my God. Just drove my Beamer. And you drove it yourself. You didn't have somebody drive for you. You didn't have your butler drive it for you that day.

I'm having a hard time relate with anything that you're saying right now, Sean. How cool. Look, I'm just painting the whole picture for you so you can understand the conscious effort I made going into this. Okay. Okay. All right. So you tried to not show her how rich you are by just taking your Beamer to the date. Only the Beamer.

So what was the meeting like the date who cares about your cars at this point the date was good we had normal conversation like avoided anything about my lifestyle and i've been to a few recent celebrity weddings recently and like i just try to avoid conversations like that that make it feel weird right because how would that normally come up in a conversation anyway? So, with just Serena Williams' wedding. Like, that's not going to ever come up naturally.

Well, I mean, it would come up like, oh, well, what have you done? Anything fun lately? Or, like, you've gone out of town? Or just any of that sort of stuff. I mean, my lifestyle is different. Okay. Yeah.

Flew to France. But, okay, on the other side of that, by you trying to avoid all the details did you think you came off sounding boring because maybe there was just so little details that you sounded like bland no no i mean i know what you mean but we end up talking about how we're both from out of town as well about our families and okay the date didn't last super long it was like an hour oh wow that wow, that's short. It's really short. How did it end?

Well, I paid for the bill. Obviously. Then I was offered to see if she wanted to go to this party that I had been invited to, and she politely declined. You thought it was Beyonce's party. She told her that. She might have said yes.

It's funny you say that, because it actually was a celebrity who was throwing the party. But I wasn't like trying to tell her all that. Well, good for you for not being a name dropper and just say she wants to hang out with you. You want to meet Leo? Yeah. Yeah. I mean, that's what I was trying.

I was trying to be cool and play it off. But the thing is, now she's not getting back to me. And she doesn't even know that I have a surprise for her. Oh, what's a surprise? So we were talking, and we were talking about her family and how she was from out of town. I got her a plane ticket to go home to visit her family. Oh, that's super nice. Ooh, I don't know.

She's not answering you, and you bought her a plane ticket? Oh, man. Well, she doesn't know about it. I feel like that's too much. Really? Yes's too much. Really? Yes, so much. You literally hung out for an hour, and you're buying her a plane ticket to go visit her family. I would feel like you're a stalker.

That's over the top. Does she know that, though? No, she has no idea. When we were talking, it was clear how much she missed her family and how she hadn't been back to see him in a while. It's not like I'm going no i know so it sounds like you're saying if she agreed to go out with you again you were gonna like surprise her with that on your date yeah no i thought it'd be a nice gesture and i have the means to do it so yeah that's what i was gonna do i'm thinking about what brooke was saying though if he's just a normal guy that might be a little much i mean she's not calling me back so

it's not like the normal guy routine's working either. Yeah, none of it's working for you. How many times have you tried to get a hold of her? I mean, I reached out to her just a couple times, but I wasn't going to, like, go nuts trying to stalk her. So we do the second date update, and she doesn't want to

go out on a second date with you. Are you still going to give her that plane ticket? You have to. Even if she doesn't want to go out, I'm happy to give her the ticket and let her go visit her family. That better be a first-class ticket, are you still going to give her that plane ticket? You have to. Even if she doesn't want to go out, I'm happy to give her the ticket and let her go visit her family. That better be a first class ticket, I just hope you know. Yeah, it better be first class. All right, well, play a song

and then come back and call her and get your second date update, okay? All right, man. All right, hang on. Moving 92.5. Brooke and Jubal in the Morning's Second Date Update. Today's second date update is like a mashup of a second date update and that old TV show Secret Millionaire

Missed the first part Sean is on the phone for a second date update. He wants to call this girl named Tracy Sean is very rich. Apparently he had a startup company sold it doesn't ever need to work again. But he has trouble finding women who are into him for just being Sean and not being ultra rich Sean. And he finally met a girl named Tracy that he really liked, but now she's not calling him back. On the date, he tried to appear as broke as possible, even though his like bad car is a BMW. He didn't take the Maserati or any of his other cars, but he took the BMW to the date. Didn't talk a whole lot about money or like the fancy friends

and the fancy parties that he goes to all the time and just tried to downplay it, but now she's not calling him back. And on top of that, he actually bought her a plane ticket to go visit her family

that he was wanting to give her on their second date. And she hasn't got back to him. So we're about to get her on the phone and find out the reason why. Sean, are you ready? Yeah.

I mean, I just want to say, like, I didn't know you guys were going to, like, talk about all that stuff. You know, I'm just trying to meet, like, a normal girl. Yeah, but it's, I mean, from your description, it sounds like normal Sean didn't work. So you're willing to be rich, Sean, and just if she likes you for your money, you're okay with that now? Yeah. I mean, just at the beginning, like, there's no need to just, like, flaunt my wealth. Well, then maybe you shouldn't have bought her a surprise plane ticket. I don't know, like, if that's your game plan for the second date, that probably wouldn't, isn't a very good

strategy. It's like I said, it's not a big deal to me, like, it's just a plane ticket. Yeah. But, like, to her, it should be, like, a great time, and, like, I'd rather just be able to make people happy with my money than them just be happy because I have money. Yo can you send some money to the station? Because I would be happy. I mean let's see how this goes. Yeah if it works out we'll present you with a bill. It's fine. Alright well I'm gonna dial her phone number right now okay? Alright I appreciate it. Yep here we go. Hello? Hi, may I speak to Tracy? This is Tracy.

Hey, Tracy, how are you? This is Jubal from the radio show Brooke and Jubal in the Morning. Um, hi. Hi. Hi, Tracy. How are you? Hey.

Uh, good. Have you heard the show before? Um, I've heard of the show. I can't say that I really listen heard the show before? I've heard of the show. I can't say that I really listen to the show. When are you guys on? Well, the show's called Brooke and Jewel in the Morning. I'll let you draw your own conclusion there.

Get it? Yeah, okay. So, in the morning. Good morning. And we do a segment on our show called The Second Date Update. That's where if you go out on a date with somebody and they don't call you back, you can email us to get them on the phone and find out what happened. So we got an email about you. Okay.

All right. It's from a dude named Sean. Oh. Yeah. So why aren't you calling Sean back? I can't. Um, I don't really want to embarrass him on the radio. What if I told you we were an afternoon show?

Would you be cool with it then? Embarrass him in the afternoon? I don't know if I should say. Did he do something embarrassing on the date? Not embarrassing like in the way that you think. Oh my gosh, where do I start? Because he has no idea. How well do you know Sean?

He and I are great friends. We go back minutes. We don't know him that well. He emailed the show and we talked to him about your date. He told us about it and that's about as far as it goes.

But he said it seemed like you guys had a really good time. He also said that you guys only hug out an hour so how well could you even know sean yeah well that's the thing so before i went on the date i googled him okay so i knew who he was and i knew who he was, and I knew that he was pretty well off. Okay. So since that's out in the open, he did tell us that he tried to downplay how much money he has because he's trying to find someone that just likes him for him.

Right. He said he took his Beamer instead of the Maserati. Well, so that wasn't really the problem. After I Googled him, like, I mean, I was a little bit excited, but I wasn't really expecting anything. But after being with him, he's so stingy. Stingy? Yes, about everything. What do you mean? Bill came. He had an intense conversation, let's say that, with the waiter about the amount of the bill because he ordered a Caesar salad without croutons, but he was charged the full price. Oh, my God.

And all this is going on and you know he's rich, but he doesn't know you know he's rich. Right. all this is going on and you know he's rich but he doesn't know you know he's rich right you guys though i'm gonna come to his defense i mean wouldn't it be refreshing like the last thing you want is to go out with a rich guy who flaunts it in your face all the time no i'd love that what about going out with a cheap rich guy that is like that's a good thing there's a difference between frugal and stingy in my mind like that was kind of the whole mentality like it seemed like he just was nickeling and diming everything and so like when we were leaving the place that we went had valet parking but he just like breezed right by it like he was walking down the street for the free parking. And I just thought, really? You didn't even valet your car?

I think that's smart. Come on. He brought the beamer. I don't know. It felt stingy to me. Like the whole vibe. Right. So not just like being frugal, but I mean, arguing over croutons, it seems a little bit extreme.

Right. Well, Tracy, you know what? What? Sean is actually on the phone and wants to talk to you. What? He's on the phone and wants to talk to you. What? He's on the phone? Yeah. Unless he's out of free minutes, he might have hung up.

Sean, are you still there? Yeah, I'm here. Tracy, just to be clear, as far as, like, the croutons go, I ordered the salad. It was supposed to come with croutons. I didn't get croutons. And, like, I'm just not okay with being told I'm going to get one thing and not get the other. So, I mean, maybe other people let it go. But, like, that's how I'm successful in business, by not letting people get away with things.

Don't get away with the croutons. But croutons? I mean, you're going to argue about croutons? Like, it seems petty is what it seems. No, I mean, it's none of that of that i mean it's just being responsible i ordered something i didn't get it and i shouldn't pay the full price for it yeah but what about the valet parking like there was parking right there i mean you know how parking is where we live like why didn't you valet park your car you had to walk a mile to get back i mean i can only imagine well i mean i don't mind walking it doesn't bother me i'm in great shape it's like fine by me

and as far as being stingy i got you a ticket to go home and visit your family whoa so like how stingy is that you did what yeah you might want to ease her in to that new sean yeah that was a bomb tracy when we were talking about how much you missed your family, how you hadn't been home in a while, I thought to myself, wow, like, let me get you a ticket so you can go home and visit your family when you get a chance. So I don't really know how that's, like, stingy, as you call it. Well, thank you, I think. is it an economy ticket what you are not asking that what do you

want to go see your family or not like it doesn't matter yeah i'm just trying to prove a point is it an economy ticket that's true are you no it's not you think he should have bought you a first class ticket wait he's rich what are you talking about think he should have bought you a first class ticket? Wait, he's rich. What are you talking about? Of course he should buy me a first class ticket. I mean, that's the point I'm trying to make. If he's not stingy, then he would have bought me a first class ticket. He has plenty of money.

So, Sean, what is it? Oh my gosh. It's not a first class ticket. Oh, dude. No, no, you're missing the point. The point is you should be thankful for any ticket at all, and if you expect a first class ticket, And Tracy, no, no, you're missing the point. The point is you should be thankful for any ticket at all and if you expect a first class ticket, then you come off as a gold digger. Exactly.

He is a billionaire. Obviously you don't know much about him. He's a billionaire. So a first class ticket to him is nothing. And so that's totally proving my point. His whole mentality is stingy and i cannot be with someone who is stingy would you like to go on a second date with somebody who's stingy we'll pay

for it clearly she wants someone else to pay for it okay so here's the deal sean if you will upgrade that ticket and email it to me to first class, then I will go on a second date with you. You will have proved to me that you are not stingy. Do not go out with her. Do not do it, Sean. Are you going to upgrade that ticket to a first class ticket so you can get a date with Tracy? No, I think I'm going to cancel that ticket, actually.

Yeah. But there's charges. There's usually charges associated with that. I don't know if you can handle a date with Tracy. No, I think I'm going to cancel that ticket, actually. Yeah. But there's charges. There's usually charges associated with that. I don't know if you can handle that, Sean. I'm more than happy to pay for those charges. Oh. Wow. That's what I figured.

I knew you couldn't handle it. You are so going to regret this, Tracy. Oh, your family misses you. You're the worst gold digger ever. You don't even know. Like, you had a chance with a billionaire. Oh, my God. He's a billionaire that spends, like, $3 a day.

No, thank you. He will die rich and alone. Sean, at least you found somebody who doesn't want you for your money. Oh, yeah, for sure. For sure. Well, how about this, Sean? Text in at 78592 if you have any interest in going out with Sean. Oh, really?

By the way, every single person is going to text in and want to go out with you, Sean. So we'll find you another date, all right? Let's do it. Line them up. Oh, wow. Broken Jubal in the morning. Everybody texting in at 78592 right now wants a date with Sean. We already knew that was going to happen, though.

I mean, I want a date with him. Yeah. Sean is very rich. He wanted to call a girl named Tracy, so he tried to keep his newfound wealth a secret from her

during his date and thought he might have played it too cool and that's the reason he wasn't getting a call back. But when we got Tracy on the phone, she said she already knew

about Sean being basically a billionaire. Yeah. But during their date, he was super stingy, like arguing over the bill and not using valet parking. Croutons!

Yeah. And she argued just because he's rich doesn't mean that he needs to throw his money away. But he should also be generous to the people that he cares about and not argue with waiters over if he should pay for croutons on a salad or not. And he actually bought her a plane ticket to go visit her family and was going to give it to her on her second date. And then he offered it to her and she wasn't impressed because the ticket was economy class. I'm just so confused. Like she's like a gold digger who's super picky. Does she have like other billionaire options?

I don't know. And if she does, how? She said if he bumped it up to first class, she'd go on a second date and he didn't do it. So no second date for Sean, although he's got a lot of options. Trust me. If you want a second date, remember, just email the show, and we will call the person who didn't call you back. Young Jeffrey's Song of the Week is coming up at 8.10.

It's Brick and Jewel in the morning. Catch Jon Stewart back in action on The Daily Show and in your ears with The Daily Show Ears Edition podcast. From his hilarious satirical takes on today's politics and entertainment to the unique voices of correspondents and contributors, it's your perfect companion to stay on top of what's happening now. Thanks for listening to the iHeartRadio Podcast. Apple Podcasts, or wherever you get your podcasts. business story that matters. You'll hear from Bloomberg journalists like Matt Levine. A lot of this meme stock stuff is, I think, embarrassing to the SEC. Follow the Big Take podcast on the iHeartRadio app, Apple Podcasts, or wherever you listen.

People, my people, what's up? This is Questlove. Man, I cannot believe we're already wrapping up another season of Questlove Supreme. Man, we've got some amazing guests lined up to close out the season. But, you know, I don't want any of you guys to miss all the incredible conversations we've had so far. I mean, we talked to A. Marie, Johnny Marr, E., Jonathan Sheckner, Billy Porter, and so many more. Look, if you haven't heard these episodes yet, hey, now's your chance. You gotta check them out. Listen to Questlove Supreme on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.