Brooke and Jeffrey: Second Date Update - Second Date Update Classic: Home Free

Episode Date: November 25, 2023

One of our listeners met a wealthy, attractive man who gave her one of the best nights ever, but she’s skeptical that it was TOO GOOD to be true, we’re on the case in another Second Date!See omnystudio.com/listener for privacy information.

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Seven questions, limitless answers. Second date update. Friends, we have another mystery on our hands we love those because normally when we do these calls the other person has completely ghosted our listener and is avoiding any contact right that's not the case here in this one the guy has moved in with her and is paying her entire rent. What? I don't get it. That's not a date. I'm kidding. I'm kidding. They're not that close at all.

Megan, our listener, wants our help because the guy is asking her out. She's just not interested in the type of date that he has in mind. Oh, interesting. So she wants our help. Megan, welcome to the show. Hi, guys. How are you? Good.

How are you doing? All right. I'm really curious about this conundrum you're in. Yeah. Yeah. Well, so I met this guy online. We were chatting for several weeks. Okay.

What's his name? His name is Finn. Finn. Okay. Yeah, I don't know any Finn, so was kind of drawn to him by a unique name. And then, you know, we're getting to know each other over a course of several weeks chatting online. And one of the things he mentioned

was that he had younger sisters and that he's protective over them. So I felt like this is a guy that knows how to be respectful of women. But he's an older brother, so it's still questionable. Yeah. I mean, the younger brother always, because he's been beaten down. The older brother, it's really a crap shoe.

Could be a little controlling. Exactly. Or he could just be a jerk to us. I mean, who knows, right? Yeah, but I thought that maybe he had more of that alpha big brother presence. I'm attracted to that. Oh, you like that? Okay.

Okay. Yeah. So anyways, for our first date he actually invited me over to his house which is not something typically you do with somebody that you've met online well not what beta men do but alpha men they invite you right over it's actually a den i believe they call it a den yes so you felt comfortable doing that you felt okay with it i did i did they felt like i got to know him you know well doing that? You felt okay with it? I did. I did. So I felt like I got to know him, you know, well enough online that I felt fairly comfortable going over.

Yeah, that's good. It was interesting. You know, he gave me an address to go meet him. And I'm driving into the neighborhood. It's a really beautiful neighborhood. Pull up to the house. And I wasn't really sure, like, am I at the right destination? It was a beautiful house.

It was a house. It's not an apartment, huh? No, it was like a huge, it was like, I guess it could be considered a mansion. Whoa. Like a nice house. Okay. Like it was a serious house. I mean, it turns out that his family is very well off.

Oh my God. And his parents allowed him to rent the house from them. Oh, so it's mom and dad's house. We use rent, I'm sure, in quotes, right? You owe me 50 kisses this month. That's right. You know that's right. No, meet me in the West Wing.

If you get to reap the benefits of that, then go for it, I say. I mean, it was awesome. So you're impressed walking up to the door. Yeah, I mean, he had a whole game room. I mean, there's like a billiards table, like a shuffleboard. We played all these things. There was a bar, like a full stock bar with beer on tap in it. What was he like?

Like, it's great that he's rich, but what was your vibe with him? No one honestly cares. Tell us more about the house. Did you ride cartwheels in the living room? Do you take hoverboards between all the rooms? No rooms i want to know if you guys got along yeah he's casual he wasn't like stuck up or snobby about it he's like oh let me show you around and that's good nice making small talk what was the most romantic part of the night that's what brooke wants to know yeah sure i would take dinner um he ordered in from a really, really nice steakhouse.

Oh. Wow, he ordered delivery. That's cool. From a steakhouse? Dang. Two filet mignons and lobster tails. Big flex. But he had set it up in Al Dorpato,

and he laid out the table and everything, and we had, like, a beautiful view. So that was, like, the most romantic part of it. That's better. I was going to say it sounds lazy he wouldn't take you to a steakhouse, but that's pretty nice. And this man wants to go out with you again. Why are you talking to us? This sounds amazing.

Well, so after I left and we had a great time, he invited me over again for a second date. But I have actually suggested us going out somewhere and like having fun and, you know, maybe dancing a little bit. But he was really adamant about going back to his house is it like sending you red flags that he's like trying to keep things secret or something is he like famous where he like literally is like I don't want to draw attention

I was thinking married but yeah not famous enough if she doesn't know who he is you don't want to hang out back at his house? I mean, it's not that I've minded, but it just seems weird that he was, I mean,

just his tone, he was very specific about just staying in at his place. Yeah, not a good sign. Well, maybe he has a second

parent's house that he wants to show you that's even better than the first one. That's true. Oh, man. Are you worried that it's like too good

to be true? Well, I can't tell like, is he hiding me? Or is he trying to just get in my pants and he just wants to get there quicker? I have no idea. Well, Alexis will tell you that's not the worst thing in the world. Yeah. Especially if it's a rich guy.

At least it's a nice house. Yeah. Okay, so even though he is reaching out and asking for a date, you want a different type of date out in public. Yeah, I want like a social date. And honestly, you just want to find out why, why he's so adamant about the house. We have a mystery and we're putting on our Sherlock Holmes costumes as we speak. I'm not going to do that. I'm Dr. Watson.

I'm not doing it this time. Brooke said this time. The whole detective attire is coming out. And then when we come back, we're going to try and get you your second date update right after this. We're on the phone with one of our listeners named Megan, who went out on an interesting first date with a guy named Finn. And Megan, there's something that you mentioned when you wrote your email to us that you didn't talk about in the first part. What's that? You mentioned when you wrote your email to us that you didn't talk about in the first part. What's that?

Because you said that you had your first date at his place, which turned out to be this really big mansion that his parents owned. You got steak dinner ordered in. But in your email, you said that Finn cut your steak for you. Aww. Is that a sweet thing or is that a creepy thing? I love doing that for girls. What? I think it depends if you ask. I hate cutting my own. No, I'd rather someone else cut it.

Well, that's probably because you order it super well done and you have to use a chainsaw to get into it. Why would you do that? What was your read on that, Megan? I mean, at the moment, I thought it was kind of endearing because the food is actually delivered with plastic flatware. And he took out actual steak knives, so I thought he was doing it to be courteous and nice and serving. So he was like, here comes the

airplane. Which also I would love. Jose just wants to be a giant man child. I really just want to take care of a girl. But did your mind change about it? It sounds like you were going to say but. I mean, when you say it out loud, yeah, it sounds, like, kind of creepy, but in the moment, it wasn't that way. It felt fine in the time, in retrospect.

Right. You probably should have just handed the knife to you and let you cut it yourself. Well, I think Alexis is right. You ask. Like, some girls, like Brooke, are like, ew, I can cut my own steak, man. Well, it's just I'm not a child. I don't want my whole meal. But then Alexis is like, ew, I can cut my own steak, man. It's just I'm not a child. I don't want my whole meal. But then Alexis is like, I love it.

I feel like it could have been a chivalrous move and let's call this chivalrous man and find out for sure because the weird part is he is asking her out. He's just not willing to go away from his house. He wants to keep it kind of secret. This is going to be a weird call. Can I dial the phone number for you, Jeff? You know what? Thank you for asking.

I thought you just did it. You go ahead and dial the numbers. No, you do ask. That's what I was saying. That was really sweet, Jose. Dial the numbers for me, and we're going to call Finn and talk to him. Here we go. Hello?

Hey, is this Finn? Yes, who's speaking? Hey, sorry. I hope this isn't a bad time. You're on the radio right now with Brooke and Jeffrey in the morning. Excuse me, who is this? We're a morning radio show. It's called Brooke and Jeffrey.

We're doing a segment called The Second Date Update. We're reaching out for one of our listeners who you went out with the other, well, I guess't go out with you stayed in with at your house you guys had a date her name was megan um okay i don't i don't understand why is she reaching out to you why are you calling me well apparently there's a little bit of a miscommunication because you are asking her out on another date you just don't want to go out-out in public with her. Yeah. That's just sending up some weird vibes, maybe. Is there a reason? No, it's just I'm just trying to get to know her more.

That's all. Okay. And why your house every time? We heard your house is beautiful. Yeah, dude. No, yeah, it's? We heard your house is beautiful. I mean... Yeah, dude. No, yeah, it's great. It's a great, yeah, it's a great place. So, you know, what's the problem, right? Well, it just seems counterintuitive because normally people want to get to know someone before they invite them over, but you want to get to know her before you go out in public. Yeah, but we've talked a long time online. We really got to know each other.

Yeah. That's good. She mentioned that, and she said she really likes you, but one of the theories that has been circulating around here is that maybe you're trying to hide her, that you don't. Hide her? No. Yeah, you don't want anybody to see that you're out with her. No, not at all.

That's good to hear. Okay, so post a picture of you two right now. She's great. Prove it. That's cute. You said she's great? a picture of you two right now. She's great. Prove it. That's cute. You said she's great? Yes, absolutely. I mean, she's beautiful.

So what's the problem? Just a misunderstanding there. Why won't you take her out? Like, that's what she would really like. Well, I mean, I... Are you, like... You sound like something is there. You know what's going on.

You just don't want to tell us. Are you married or something? Is that what it is? What is it then? Look at we're assuming the worst of you. Just if it's something that simple, just clear it up. Well, it's not simple, but it's just stupid. It's stupid.

And I just that's great. We love stupid. Yeah, we're experts in stupid on this show. I'm so stupid, bro. Make it feel comfortable. No, I just made That's great. We love stupid. We're experts in stupid on this show. I'm so stupid, bro. I'm trying to make you feel comfortable, guys. It made me feel good. You laugh, Brooke. You don't laugh at all. Well, essentially,

for the next six months, I'm not allowed to leave the house. Ooh, strict rules from your parents? Why? Is it why we think? It's I'm under house arrest. Ah.

That's what I figured. Okay. What did you do? Is it for something really bad or just like kind of? Well, it could be too bad or he'd be like in jail, right? It's stupid. What'd you do, Ray? I don't even know if I could say this, though.

You've already been sentenced. You're good, dude. You can't get more house arrests for just telling people what happened. True. Basically, me and my buddies, we got together to pretend like we were the village people. Wait, what? I like this. I work in TV and film, and so I had a police uniform, and my buddy has a construction worker uniform.

We all got together we pretended like we were the village people to play at this casino so we show up and they're like uh no you're not the village people right because the village people are super old you guys are dead. I don't know. Probably at least one of them is dead. So let me see if I understand what you're saying. You and your friends impersonated a famous band to get money from a casino, and you got caught. Oh, no. Well, I mean, yeah.

So what is that? That's like defrauding a company? Yeah, that's it. How do you know, Jeff? It doesn't matter what the charges are, really, because I'm on house arrest and I can't go anywhere. Okay. She was going to notice if you ever got intimate, because that ankle bracelet is...

Well... Oh, yeah, I didn't think about that. Can't hide that one. Here's the good news. I know you didn't want to come out with the truth to Megan, but you kind of did. Yeah, it's true. What do you mean? I didn't tell you this before.

She's on the other line listening. What? Surprise. Hi, Ben. Hi, Megan. How are you? I mean, I wasn't really expecting that as a reason why we couldn't go out. If I'm relieved that you're not married or have a girlfriend or...

Are you? Is this a better option? House arrest is a six month... Yeah, well, you know, it's like, it's so stupid. I don't want that to be our first thing that we're talking about. And I'm just like, oh God, how do I do this? I mean, Megan, now you've heard the real reason that he's not calling you back because he's a secret village people impersonator who defrauds casinos. Is that a turn off to you or is that a turn on? I mean, I guess just going back to our first day, I don't know why you didn't just tell me.

Well, it's not exactly something you lead off with, you know? Hey, by the way, you know, I'm a criminal. I'm currently under house arrest. Doesn't sound good. I mean, like, with the second date, like, you're inviting me back, right? And if I did go and we kept the charade up, I'd eventually find out.

No. No, you wouldn't have found out. What? How would she have not found out? No, I'd eventually find out. No. No, you wouldn't have found out. What? How would she not have found out? No, I mean, because you would have never seen the bracelet. How? I don't want to...

He wears snow boots everywhere. Maybe they put his monitor on a different part of his body. I don't think that's how they work. Some place you'd never find. It's not a good sign if you can't find that part of the body. I'm just going to say it's not a brag. She's like, do you hear a beeping? Yeah, I mean, I just think that it's weird that you think that I wouldn't find out or

know. I think you should have just told me. Yeah, I know. It's just not something, I'm just embarrassed by it. I didn't want to tell you. Well, that makes sense, though, Megan. You can see that. He's finally, at least, it took a lot of prodding,

but he did finally admit the truth to you, Megan. He's come clean. Would you like to go out on another date with him? We will offer you a gift card to his house. No, I think we just have to get postmates. Yeah, exactly. Or we can pay for the Uber to and from. How many more months are you still on your house arrest there, Finn?

I got three left. You got three left. Okay. So bad. Just three more months of dating at his house, and then you can go out somewhere. Yeah. Go back to that casino and do the village people thing together. Yeah, no, that's off limits.

I can't come back there for a few years. Okay. Well, maybe just do it at a bar or at a senior home or something and work your way up. But we'd like to get you guys back together. Yeah, I mean, it's not like a deal breaker for me. I mean, to be full honest, I've been binge watching Animal Kingdom. So I'm all about, you know, criminal stuff right now. Hey, all right.

Animals commit crimes, too. Zebras look great in black and white. Yeah. So is this a yes for another date? Yes, that's a yes. I think they're both really mismatches. Okay. All right.

Good for each other. We'll get you back over to Finn's place. Yay. Or Finn's parents' house. Let's take a limo. Awesome. I can't think of a worse endorsement for online dating than, screw it, I'm not going to meet somebody else.

I'm just going to keep seeing the guy who's under house arrest for the next three months. He had a pool table. Oh, that's true. Brooke and Jeffrey in the morning. Man, you know, the more I think about it, the more I'm not sure if she should have said yes to another date with him. Just now. Just now you're feeling that.

Well, I wanted to be happy for them, but then now, I don't know. Okay, listen. I've dated a fella. Is this a brag or an embarrassing thing? No, but he was honest about it from the beginning. Like, that guy was just, he would have never told her. He even admitted that.

Yeah, three months left, there's no way she wouldn't have found out. Right. And the guy sounded like he was in his early 30s. So that's usually the time in your life when you stop making really stupid decisions. Like, I get the idea of him and his buddies at a bar one night being like, oh, you know what would be really funny?

Let's all dress up like the village people and try and steal money from the casino. That's where it should have ended. I don't even get that part. I don't either. It's a guy thing. Was it like a really bad Ocean's Eleven dream? Yeah. Because that's not how Brad Pitt and George Clooney did it.

Well, I mean, it's a guy thing. You kind of joke around about stuff like that, but you don't actually buy the costumes and go to the casino and actually take the money. He already had them. I mean, to be fair. Oh, okay. Because he worked in set.

Maybe there was a little legitimacy to this then. But remember, if you ever want to get a second date update, you can always reach out to us. We'll call that person who isn't calling you back. 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 is 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. 1.4 billion dollars in NFL quarterback contracts.

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