Brooke and Jeffrey: Second Date Update - Second Date Update: High Flyer Liar

Episode Date: January 15, 2024

The woman in today’s Second Date has such a COOL job, it stopped us all in our tracks. We wanted to know every single detail, and you will too!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.

Joel, the holidays are a blast, but the financial hangover, that can be a huge bummer. If you are out there and you're dreading the new statement email that reveals the massive balance that you may have racked up, well, you could use our help. That's right. I'm Joel. And I am Matt. And we're from the How To Money podcast. Our show is all about helping you make sense of your personal finances so you can ditch your pesky credit card debt once and for all, make real progress on other crucial financial goals that you've got, and just feel more in control of your money in general. You know it. For money advice without the judgment and jargon, Listen to How to Money on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

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 plus you'll get special content just for podcast listeners like in-depth interviews and a roundup of the week's top headlines listen on the iheart radio app apple podcasts or wherever you get your podcasts second date update now occasionally we check back in with callers months after they come on the show to see how their relationship is going.

I love when we do that. We call it a Second Date Update Update. Yeah. But today, we're doing something kind of new. We have a Second Date Update Update Update. Okay, wait a minute. That's right. A triple update.

I feel like now we're getting clingy. You know what I mean? Like, can't we just let people live their lives at some point, Jeff? It's like second date update square. No, we want to be as deeply involved in our listeners' lives as possible. We even live with them. We're too involved. We're doing a trup date today.

I've been involved in a few of those One of our listeners Anthony reached out to us again So first of all Anthony welcome back to the show Hey guys thanks for having me I'm having a hard time placing What Anthony what you were on before So last time Anthony was on

You were dating a woman named Mallory And you guys were saying that you were happy together But she was having you pay for a lot of her and her friends activities. Oh, I kind of remember this and we're like, oh, she's using you and then you're like, no, she's hot. You're like, I don't mind. Am I

remembering right? That's pretty close. Okay. Good recap. No Mallory, it's just you today, Anthony. What's going on? So with Mallory, I ran out of money. Oh. Wait, you're broke? What?

Just go get a bank loan, man. Did she? You'll also run out too eventually. Wait, did she leave you? Well, yeah. She basically dropped me after I stopped paying for everything for her and her friends. Alexis, good, right? Good for her.

I mean, I see where she's coming from. Alexis is like, you go, girl. stop paying for everything for her and her friends so alexis good right good for her i mean i see where she's coming from okay alexis like you go girl that sucks man but it sounds like you're better off without that which i think we told you so yeah i think so okay so is that it guessing you went on a date with another person that you're interested in. Yes, that has been happening. Oh, okay. Who's the new girl? I found a new woman named Lisa.

Okay. All right. And what do you like about her? Well, the first thing that stands out to me about her that I find fascinating is that she does private security detail for celebrities. Whoa. Wow. That's such an interesting job.

Brooke, one of your employees. Yeah. This is amazing. Let's get her on the phone. Was that like right there on her dating profile? No, that's just something that came out after. But she won't tell me who these clients are and that's what i'm always trying to get out of her that's she's good at her job at least yeah the privacy okay so have

you guys been on one date two dates where you at we just got out once okay okay i mean how did it go it went pretty well i mean another thing that I thought was pretty funny is one thing I did see on her profile is there's like an ad that comes up on people's profiles that says today's high flyer of the week. Like when they're getting a lot of action, I guess, on their app or something. High flyer, that's what they call it?

On the app? That's funny. Is that a good thing for you or a red flag? Jury's out on that. But I mean, I was calling her the high flyer as a joke. Is that something that she puts on her profile or is it something that the app does automatically? Sorry, I'm an idiot when it comes to apps. Yeah, I think the app does it if you're really popular on the app.

That's another interesting talking point, though, to bring up on the date. Like, how did it go? It was good. At first, I couldn't tell if she was going to be a real person or not, but she was exactly how she described herself. So she's real pretty is what you're saying. Yeah. Yeah.

Well, she's pretty casual. She showed up in Gucci sweats and a Tupac hoodie. Okay. She doesn't have a sense of style. She can do a matching set. I think it's kind of cute. I thought it was pretty cool. And we did have fun.

She talks a lot about this charity work she does. So she's really big on giving back to the community. And I was able to relate because I was just involved with the charity with my ex-girlfriend and her friends. I hope you didn't say that. Yeah, is that how you brought it up? No, no. i made that joke and then failed to go into further detail about it with their book okay okay okay so you kind of ended up being the chair we didn't even ask what were you guys doing were you drinking eating what was the date about yeah we got a couple drinks we went to a happy hour okay so it's chill so that's why she could wear the sweatshirt and the sweatpants happy hour i see you budgeting that was her idea i think she wanted

to meet me in the daylight did you feel like you had a good connection with her though i did but yeah i could definitely tell why she is the high flyer because her phone keeps buzzing the whole time we're together and i have a suspicion that she's definitely talking to more guys than just me yeah probably i mean jose if you were out on a date with someone who was a high flyer is that a red flag to you uh no i would just be happy to i'm on a date you're buying a ticket onto that maybe she wants to take step off the fast plane move on to the slow plane with him oh and i'm definitely a slow flyer overall though how do you think the first date went good bad i think it went good okay i was hoping that we're gonna go on another date but her responses are a little spotty i don't, and I don't know if you did this or not,

but did you ever point out, hey, your phone is buzzing a lot, are you getting a lot of dudes trying to hit you up right now? Oh, like come across as weirdly jealous? No, I didn't think that would be a good style on my part. Yeah, so that's causative. I played it cool. I played it cool.

It was just slightly eating me up inside. All right. Okay. You seem to have answers. Let's find out what Lisa has to say for herself. We right. Okay. You seem to have answers. Let's find out what Lisa has to say for herself. We're going to call the high flyer directly. Maybe she charted it as well.

Maybe. I hope she answers. We'll read off what's on her chart when we do your second date update right after this. Second date update. Imagine being out with someone you're very interested in and finding out that they do security detail for the rich and famous. Cool. But they won't tell you who. And not only that, they're a verified high flyer on the dating app where you met them.

Which means that they get a lot of action. Yeah, they're like on the front page. Yeah, or someone just paid to feature them or something like that. Yeah, that's what I'm assuming. And they wear Gucci sweats with Tupac hoodies to first dates like it's no big deal. Yeah. I mean, they're cool. For me, personally, this is a very interesting second date call. Because like Jose said before, I really hope that she actually answers us. Because we don't get to talk to people like this very often.

Because we cannot be the one that also pries into who the celebrities are she works for. You could just ask once. I know. He already did that on the date. She didn't want to answer. What if she's like standing next to Kim Kardashian right now and is like I can't talk. I mean, we do want a lot of answers from her, but the main thing

we want to know is why she's not going out with Anthony. That's true. Because this is a very unique type of woman. And Anthony, best part is she hasn't made you pay for anything yet either. But you are willing to, yes? Wait. Oh, yeah. Wait, you paid for the date though, right, Anthony? You paid for happy hour?

Yeah, I paid for the date at the bar. But it wasn't like with Mallory. I wasn't paying for her parking. Right. The last girl that you were on the show with. Okay. Exactly. But you'll pay for her parking on the second date, at least.

Let's let's call her and try and figure out where that's going to be. If she'll go out with you. Here we go. Hello. Hey, is this Lisa? Yes, it is. Hey, Lisa, what's up? You're on the radio right now with Brooke and Jeffrey in the morning. Welcome to the show, Lisa. Oh, um, hi? I guess.

Hi, can you protect us? If you haven't heard us before, we're low-key bougie. The lowest key. I feel like Jeff just learned those words. We're low-key bougie. The lowest key. I feel like Jeff just learned those words. I mean, we're low key bougie. He's wearing a free show shirt that he's got. Yeah, he is.

Okay. What is this all about? I don't get it. Well, we're one of those weird shows that helps listeners with their dating lives. When they go out with someone and they're not getting a return call back. We reach out and try and they're not getting a return call back we reach out and try and help figure out the reason why uh okay i know pretty pathetic on our part but people get paid to do it thanks jeff i kind of like this segment i like it too my parents are really

ashamed of it so but that's not it's not about. We're trying to ask about you and your relationship with a guy named Anthony. Oh, okay. You guys went to happy hour? Yeah, we did. Okay. Pretty great guy, huh? I mean, yeah, he's a nice guy. Good looking.

Oh, yeah. He is. What was your, like, thoughts on the date? Um, I mean, it was really chill we just had a couple drinks at happy hour and it was just a date oh okay nothing to write home about okay i mean was there any like big red flags to you for why you're not going out with him again because he said he's been trying to organize a second meetup and it's not quite happening i mean no there weren't any red flags when we were sitting there talking i mean he was very interesting he was interested in me asked me a lot of questions okay can i offer something up that he told us because he said

he was worried he may have offended you by prying too much into your job because he found out you help organize security for big-time celebrities? Oh, my gosh. Yeah. I just made that up to sound interesting. Wait. What? What do you mean you made it up? Oh, man.

I was interested even. All of us were. We were prepared with all these questions to try and get you to reveal who you do security for. And usually when somebody lies on a date, there's like shame and stuff. You're laughing. Is it like just a joke to you? Well, I couldn't tell him what my real job is. Why? Can you tell us your real job?

I guess at this point, if I'm not going to see him again, sure. I'll tell you what my real job is. What do you do? So I am actually part owner of the dating site. Wait, what? Whoa, wait a minute. The one where you met Anthony? Yeah.

Oh my God. Some friends had the idea and we were just talking about stuff and it's just an idea. Well, they moved forward and they asked if I wanted to be an early investor. And so I was like, sure, let's do it. And it just kind of blew up. So when it says high flyer on your dating app, that just means like CEO or something? Or you get free modeling pretty much. I mean, we were looking for trying to like do a feature like on the app. And I just said, I'll do it. I I'm single I don't care about the attention whatever wow market research apparently it makes an impact yeah I guess so

okay so wait hold on so wait why did you just tell him that you were the app owner well to be honest I go on a lot of dates and I mean, essentially I would tell people what the deal is, but also it would be a little creepy. I would think in the beginning, we're trying to help him figure out what's the reason that you're not going out again. That's what he's confused about. Okay. Okay.

Is it so many men? Just so many men. You can't choose one. No, that is not the reason. So as an admin, I can tell that he's been messaging other women. And when we were on a date and talking, he told me in conversation that it was just him and I talking.

That feels like invasion of privacy. Listen, when you check off on the agreement, I mean, it says any co-founder or manager can monitor your account and your activities. So I am well within my right to do that. That's crazy. And it just proves that men are pigs. Oh. Are you one of one team? I think it's weirder that he's, yeah, what?

Anthony, what do you think about hearing all that? Wow. Hi, Lisa. Oh, yeah, I forgot to tell you, Lisa, it's down way, way deep in our agreement when you come on the phone that he's secretly on the other line listening. Okay, I never thought.

Oh, wow, you're super chill. I'm a little shocked, but I totally understand why you had to put that in your profile. Anthony, this feels like the last time you were on the show. You just agree with women no matter what they do to you. This woman's been lying. She invaded your privacy and you're just chill still.

Stand up for yourself, brother. So wait a second. You could actually go into my app and see all the messages, like everything that I've ever written on there? Yes, I can. Oh. I know Anthony's thinking of like three things he said. Hope you keep a PG on there, buddy.

That's how you know she cares. You can't see pictures, right? No. Yes, I can. Oh, no. Hopefully you can zoom in on them, too. What? I don't know if you'll have to zoom in.

Hey, attaboy, Anthony. Why do I doubt that, Anthony? Let's go down a bad path. Lisa, does that mean that you weren't talking to anybody else either? I mean, yeah, I'm talking to some people. But I was honest about that on the date. He implied that I was the only person he was talking to. But you wouldn't have cared if he said that.

I see that. Why did you say that, Anthony? Well, you're the only person that I've met on the app that I actually like and respect. Oh, see? You don't respect the other women you're talking to? What? Not good?

That came out wrong, baby, but you're the only one I've really found interested, and I haven't met anybody like you, whether it was on the app or not. Well, I have your profile pulled up right now, and it looks like that you're trying to set up

something with somebody named Clarissa. That's creepy. But she doesn't respect her. Yeah. Lisa, you sound a little bit jealous of that even. I don't know about jealous, but look, I would have been totally fine if he had said, yeah, I'm talking to other people too. I get it.

It's not a big deal. I'm blocking Clarissa right now. Hey, you can't lie about it. She'll see. It just sounds like you need to be truthful about everything. And use another app. Yeah, bro. Definitely.

Something is happening here for sure. It feels good. It does feel good. And I'd like to offer to send you guys out on another date that we will pay for. Once again, can I just reiterate that I'm serious. You are the only one I've taken serious that I've met on there. And I'm really hoping that you're going to say yes. That's cute.

That's very sweet, Anthony. I appreciate that. Yeah, I there, and I'm really hoping that you're going to say yes. That's cute. That's very sweet, Anthony. I appreciate that. Yeah, I mean, I'm a yes. I would say yes. Start over. Fresh slate. Start from the beginning. Now that everything's on the table, we start over. Okay, and we also have 14 other guys who want to know if you'll go out with them to the dinner. What would

you like to say to them? Well, I mean, if I'm being honest, I am still talking to other guys. 14 is on the low side for me. But how many of those guys do you respect? All right. Well, more research with the second day on our bill. We're going to pay for it, okay? Sounds good.

Before you go, can you force matches? Because there's a couple of girls that aren't responding to me that I'm wondering if you can help me out a little bit on the year end. That's creepy. That's a hard no. You know, the thing that I'm coming to terms with is we just have to get it through our heads that people lie on dates. It can be small little

white lies or big giant ones, but people do it all the time, whether it's to make themselves look better or for whatever reason. And we don't all have the access to fact check them like she did. Yeah. I mean, and it's not so much if you lie, it's what you lie about that's

really important. She lied about what her job was out of boredom from all the dates that she goes on. He lied saying that she was the only girl that he was talking to on the dating app. And she found out that was untrue. Why would he even offer it up? I don't know.

You know like just don't offer it up. It sounds like one of those nice lies. That you tell someone that they're the only one that you like. Or it's like I never do this. When you know that that person always does it. You're really good at it. I do feel like society has really progressed because they were both totally okay

with each other's lies in the end. Well, they can't pull each other out. That's how lies work. Two lies make a right. No matter what, no lie, you can always email the show for help. We're willing to call that person who isn't calling you back.

It's Brooke and Jeffrey in the morning. Brooke and Jeffrey in the morning. 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 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. Joel, the holidays are a blast. But the financial hangover, that can be a huge bummer.

If you are out there and you're dreading the new statement email that reveals the massive balance that you may have racked up, well, you could use our help. That's right. I'm Joel. And I am Matt. And we're from the How To Money podcast. Our show is all about helping you make sense of your personal finances so you can ditch your pesky credit card debt once and for all, make real progress on other crucial financial goals that you've got, and just feel more in control of your money in general. You know it. For money advice without the judgment and jargon, listen to How to Money

on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. 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 plus you'll get special content just for podcast listeners like in-depth interviews and a roundup of the week's top headlines listen on the iheart radio app apple podcasts or wherever you get your podcasts