Brooke and Jeffrey: Second Date Update - Second Date Update: The Long Game

Episode Date: November 29, 2024

The woman in today’s Second Date was in shock once she ended up back at a guy’s place. There was no question she wants to see him again, but the real question is why doesn’t he want to see her?See omnystudio.com/listener for privacy information.

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If you want us to invade more of your life, we're on YouTube. Yeah, we are. You got that with Brooke and Jeffrey. Text in your address. I can show up. Jose will come to your house and give you hugs. And food, or you give me food. And also, there's 45 more minutes of this dumb content that apparently you like,

which we're really grateful for. You can go over the main feed for the full show, Brooke and Jeffrey. But right now, let's get into this relationship stuff. Yeah. Second date update. I think a lot of us have gone out on a first date with low expectations. And before you know it, things happen and you end up spending the night. Oh, yeah.

Yeah, you're lucky. I know. But not very often does it happen the opposite way, where your whole plan is to stay the night, but you decide, actually, you know what? I'm going to play the long game on this one. That's hard. That's exactly what's happening with Jose and Alexis right now.

Whoa. But we're not here to talk about them today. Listen, listen. You gross. I'm the grossest thing You know the protest too much. You guys can pretend all you want.

We know what's really happening. I am not pretending. Alexis is cute. We're not here to talk about the situation happening between you two. We're here for one of our listeners, Sydney, who needs our help today. Welcome to the show, Sydney. Thanks, guys. Oh, man.

Thank God you're on the phone. You cut the tension in this one. Yeah, sounds steamy. So tell us about the guy that you went out with recently. What's his name? His name is Kurt, and I met him on Tinder. Okay. Okay.

I mean, what struck him about you on Tinder? On Tinder he was just cute. I was originally into it for a meaningless hookup. Which is it? 99%. You don't go to Tinder to read the bios. There's not much that strikes you. But you still want to have

a good chemistry on your messages together. Some liked shared interest i'll give you that i'll give you that so how did things play out with you and kurt oh my gosh so it turned out he was pretty amazing like i met him at this bar and he was just so put together and had this beautiful smile wow well hello kurt i mean i'm getting yes is that all it takes just a little smile you're like wow this guy really knows what he's doing when you have your expectations so low it doesn't take much right that should be tinder's catchphrase expectations so low that it doesn't

take much did you feel yourself, growing more nervous during the date because you're realizing this? I wouldn't say nervous, but just shifting, like, away from wanting to hook up to, like, wanting to play, like, the long game, you know? Oh, okay. Oh, that's cool. You suddenly felt like this was going to be

more than just a one-night thing. You wanted to actually maybe start a relationship. Like, date this guy. I mean, that seems pretty deep, but yeah, kind of. Wow. Okay, so how do you go about doing that? The shift?

Yeah. When did the shift happen? How do you shift the plan? How do you not sleep right away? This is interesting to me. Pivot. When was your pivot? So, I mean, we hung out at the bar for a little bit,

and then it was kind of early, and it was a really hot day. Okay, so you excuse yourself to the bathroom, and you go put on some real underwear now. Because you feel like this could be a relationship situation. Get rid of the edible stuff. Plus, it was a hot day. It was melting. It's getting sticky down here. I'll be right back. I see where you're at, Sydney. Keep going.

Yeah, so anyway, it was super hot out, and he said that he had a pool at his house. Oh, this guy gets hot. I like Kurt Warner. Yeah, what? I know. So I was like, you know, this could be shady, but the fact is I've been hanging out with him for a while,

and he's just so easy, and we just get along, you know? So I was like, why not? That's good. So wait, was your plan then to skinny dip because i i assume you didn't come with a swimsuit well i didn't want to see it but like i just went my t-shirt and my undies it was fine oh you tease okay i think it's a strong move no it's all you got i mean heck right as well yeah but it's also like i didn't want to hook up with him i'm just gonna go get naked and wet at his house.

That's the long game, bro. Okay. Sydney clearly is an expert in the art of seduction. So did it work? I mean, I think so. Like, first of all, let me just tell you, his house, holy moly. Oh, really? Oh, this guy's rich?

Oh, lucky. Oh, my God. Like, brand new, like, all the finishing touches, like a floaty staircase. Whoa. That's cool. Not only does he have a pool, but he's got a hot tub. So we just got... Come on.

I can't even get a guy with a bed that has, like, not on the ground. Alexis is trying to graduate from a futon. Yeah. So there's hot tub action happening now. Well, not yet. Yeah, but not even like action. It was totally just like hanging out. I mean, super good chemistry, though.

But I didn't want to like mess it up by just cheapening it, you know? Girl, it is not cheapening it. I mean, he's inviting you at his house. You're in his hot tub. Like, you're telling me nothing happened? No, I will say we did kiss. Where? Where? Where? What part of your body? Like, where on the body or where in the house? I know, hot tub like you're telling me nothing happened no i won't say we did kiss where where where what part of your body or where i'm like well um kind of like after the hot tub so it didn't get too steamy like it was almost more romantic let me get you a towel and then he pulled you in and then what happened after after the nice kiss he asked for one to hang out

a little more but i thought maybe you know it's time to call it just to keep it super high point. Yeah. Keep them wanting more. Oh my gosh. If I was him, I would be like, oh my God. Right, because you have the kiss, you have the moment, you have your heart racing. And I'd be thinking about you every day after that. I don't know. If I was him, I'd feel like

I just blew it. She just left. Really? I don't think so. She said it was a romantic kiss. It depends on their vibe, right? Yeah. Okay. On paper, yeah, I can see that. She just left. I don't think so. She said it was a romantic kiss. It depends on their vibe, right? Yeah. Okay. On paper, yeah, I can see that. So what happened?

So when I left, he said that he was going to be out of town for about two weeks or so. Whoa, okay. But then, like, he got back, and it's just been, like, he texted me one time that he wanted to hang out, but now he keeps saying that he's, like, busy. So I'm like, oh no, what happened? Did he meet somebody who was out of town? That's my first thought. Two weeks is a long time to go between seeing someone in the dating world.

Were you able to keep a conversation going with him while he was away? Yeah, we did text a little bit. How was it? What was the vibe? It was kind of flirty. It was nice. Oh, good. You know, it makes it even weirder when he gets back, like the texts aren't as flirty.

Okay. From experience, I mean, I think anybody can say. The momentum, yeah. You go a week without even talking to somebody or a lot. I mean, it definitely changes the momentum. Well, maybe we can change it again. Maybe. Oh, maybe.

Okay, let's give this a shot. We're going to play a song. We'll come back. We're going to call Kurt for you, and we'll try and get you a second date update. Okay, Sydney? Sounds great. Thank you, guys. Okay.

Second date update. This is a challenge that we've never had before on this morning show. Okay. That challenge is find the only catch on Tinder and then reel him in without any favors. Uh-oh. And the reason that he's a catch is because Kurt

not only has good hair and a nice smile, and he's put together, on top of all that he owns a great house with a swimming pool, a floaty staircase, an expensive hot tub, and they even shared a passionate kiss during sunset as a pod of dolphins swam by and did a synchronized water dance to a BTS song. Wow.

Wow, they're in the shoes of a heart. And after all that, Sidney still turned down the invitation to spend the night just to try to play the long game with this guy. Wrong move. I feel like Sidney's having regrets after hearing about the Dolphins. It sounds like he literally was like, hey, I have millions of dollars if you'd like it. And she was like, no, I'm good. Not today. The reason why she might have some regrets is because it's been two weeks

and now their conversation has cooled off a lot. So she's hoping that we can turn the heat back up with this second date update. How are you feeling right now, Sydney? I'm nervous as heck. I really am. We're calling like we're the perfect guy, pretty much. I mean, it's interesting because you wanted to play the long I'm cool game and now you have a radio station calling for you So they seem very cool Kind of turned she's like now I'm having a panic attack

Thank you for that I Think we can do it though. I mean, you know, we're like rich powerful people too what speak for yourself any of those words define us i just think we'll impress him no we better hurry up and just make this call before this gets any worse than it already is yeah okay so we're broke we might have to pay the phone bill yeah let's just check make sure it works but i think if we've learned anything from sydney it's start with low expectations so then it can only go up from there yep that's good all right so i'm gonna i'm gonna dial kurt's phone number right now, and we're going to try and get you your second date update.

You ready, Sydney? Okay, I'm ready. We'll try not to screw it up. No promises, though. Here we go. Hello? Hey, is this Kurt? It's Kurt.

Hey, Kurt. How you doing? My name's Jeff. Why was that awkward? Why was that awkward? I don't know. It was awkward, though. I'm sorry for my awkwardness, Kurt.

Hi, Kurt. Hi. What's going on? This is a morning radio show called Brooke and Jeffrey in the Morning, and this is the morning radio show team that apparently doesn't like the job I'm doing you're not very good at small talk including just saying your name all I said was hi I'm Jeff what's up you said it wrong I'm a Jeff Kurt we have a great reason for calling you though am I in the air right now yeah is that okay okay yeah it's just

weird cool yeah cool did I win something or what happened well the reason that we're calling you i know both of you is because one of our listeners has been trying to get a hold of you and she's been having a hard time lately her name's sydney oh yeah yeah okay you remember sydney yeah i do remember her so she had you guys call me yeah yeah she was just so excited about your date i mean now you guys want to talk about. Yeah. She was just so excited about your date. I mean. Now you guys want to talk about the date? Well, yeah, sort of, because we know that a date happened two weeks ago over at your house. And she had a lot of great things to say about you and your place. And she's a little bit confused why now, two weeks later, things have cooled off between you.

This is really awkward. Is it Brooke again? Brooke. It is Brooke. things have cooled off between you this is really awkward uh is it is it brooke again i apologize for her i mean the thing is kurt like she really felt like there was a true connection between you two and it was something that she wasn't expecting at all and it really surprised her i I agree. I did think there was potential, to be honest with you. Okay, that's good.

I just, I feel like I honestly, I think I kind of screwed up a little bit. Wait, you think you screwed up? Why do you say that? Okay, so you're like, she really liked the pool. Yeah. People enjoy it when they come to visit.

I get that. But I kind of messed up. I was like, well, you know, you're welcome to use it anytime. I made this comment, and then I went away for a couple weeks for business. Then I found out when I was away that she used the pool multiple times with her friends. Wait, what? Oh, no. Wait a minute.

While you weren't there? Yeah, she just kept over and over, kept coming over with her friends. How would you know that? I have security. Cameras? Security footage, yeah. I thought you were going to say security guards. with her friend how would you know that well i have security you know like my security footage yeah yeah i thought you're gonna say like security guards i'd be like those are the worst security guards yeah my security dog my security dog yeah okay but you told her she could use it whenever no wait hold up she didn't ask you no she didn't mention it and then like the motion sensor

triggers like i know people were in there so i I, you know, multiple times I got an alert, you know, people were in the backyard or whatever. And I, when I checked the footage, it was like, yeah, there's apps now where you can see what's going on. Yeah. We have one. That's the same. You can see it from your phone. Honestly, my brother uses my pool all the time. So I kind of figured it was him. And then when I got back, I was curious to see like who, who had been using the pool. And then it was her over and over. Like over like it was like the YMCA.

Okay. That is crazy. So you come home and you check your security cams and you see that it's actually Sydney and her friends using your pool. And that's why you've kind of cooled off towards her. Yeah. I mean, I just feel like she took advantage. Absolutely. Did you warn her that you have security cameras outside your pool?

We just had this conversation like not too long ago where you said if anybody comes over to your house, you need to warn them that you have cameras. If you invite someone to your home, she was never invited. Like, that's the thing. Like, when you give an open invitation to somebody saying oh use the pool you know everyone knows that you ask before you do it you don't just show up it sounded to me like he told her you can come over at any time and i don't know if that's true maybe we should ask sydney sydney is that what he said um hi it's not look at you're on the call yeah sorry i should have let you know kurt that sydney's

been on the other line listening this entire time she wants to talk to you after all that now you didn't let me know yes well i guess my co-workers are right i'm not very good at this job so i apologize but go ahead sydney oh my gosh i can barely even stand i'm so horrified right now i feel so bad maybe i was was just so excited about the time we had. I just kind of was like showing off your place to my friends. I don't know. But now I just feel like

I messed up so bad and that's not respectful on my part and I'm so sorry. I feel really bad. I mean, yeah, I appreciate that. I just don't know. It's just a little weird. Sydney, how did you even get into his pool? Like, did you have to scale a fence or something?

Yeah. No, there's like a door that isn't kept. One of those ones you just reach over and unlock. Oh, my parents have that too. I'm like, why do you have a door then? Everybody can come in. Sydney, what were you thinking? What do you mean, what was she thinking, Brooke?

Pool party! But why wouldn't you ask him? Why wouldn't you say, hey, do you mind if my friends and I come over while you're out? I bet she thought she'd get away with it. I'm asking her. I mean, if you want me to be completely honest here, you're right. I didn't think he would actually know. And I was so excited to show my friends where he lived.

See? I mean, it sounds to me, Kurt, like Sydney realizes that she made a mistake and she's really sorry about what she did. It was just like everything was just thrown around, too. She didn't even clean up after. It was just like, it was just a disaster. Really? Well, she just figured that she would come back the next day.

I don't recall that part. And if that's true, I'm super horrified in every way right now. I mean, honestly, this seems unforgivable, but I really hope that you'll just take my word that I'm not a tool and that, like, I'm so sorry. And I hope we can give it a second chance is all I'm saying. At least she's impressed by you, bro. She's trying to show off your pad to her friends. Yeah. And with that being said, we want to send you out on another date.

And we'll pay for it, Kurt, if you're willing to give Sydney one more chance. Public pool. I mean, to be fair, Kurt, she didn't, I don't think she's like a gold digger. I don't think she's trying to use you. I mean, it is hard to find a guy with a pool. She literally used his pool.

But she liked you for you before she knew with a pool. I know. She literally used his pool. But she liked you for you before she knew about the pool. Yeah, that was just a pause. She seemed sincere when she told us about it. Yeah. Yeah. I mean, before you answer,

just think about Sydney in her shirt and her no pants. Swimming around in your pool. Okay. That's not helpful. Did that not help? I don't have to think about it.

I've seen the video already. All right. Well, just visualize it and then let us know. What do you think? One more shot with Sydney on our bill. I'm sorry. I don't think so. I feel like.

Oh, she blew it. She had a hot ridge guy and she blew it. I blew it. Oh. Oh. This is why you hook up the first night. Hurry. Everybody swipe right on Kurt.

Hurry. The one good Tinder guy. The rest of you guys, you're all welcome to use the pool anytime you want. Oh. Okay. Sorry, Sydney. Snooze, you lose. Oh, man.

We've moved on. Brooke and Jeffrey in the morning. Oh, man. 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. 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. Snakes, zombies, sharks, heights, speaking in public. The list of fears is endless. But while you're clutching your blanket in the dark,

wondering if that sound in the hall was actually a footstep, the real danger is in your hand when you're behind the wheel. And while you might think a great white shark is scary, what's really terrifying and even deadly is distracted driving. Eyes forward, don't drive distracted. Brought to you by NHTSA and the Ad Council. Hey, I'm Jay Shetty and my latest interview is with Mel Robbins. Work has been seen as the number one cause of stress. How can the let them theory help? As you notice the stress come up, Jay, you're simply going to say, let them. You have no idea right now how much time and energy is being wasted because of other people's behavior.

It's like a death by a thousand cuts. Listen to On Purpose with Jay Shetty on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. The forces shaping markets and the economy are often hiding behind a blur of numbers. So that's why we created The Big Take from Bloomberg Podcasts, to give you the context you need to make sense of it all. Every day in just 15 minutes, we dive into one global 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.