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

Episode Date: June 16, 2021

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.

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.

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.

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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. 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'm gonna play the long game on this one that's hard that's exactly what's

happening with jose and alexis right now but we're not here to talk about them today you know the protest too much yeah protest too much you guys can pretend all you want i'm not pretending alexis 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. 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. 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. Yeah, there's not much I was originally into it for like a meaningless hookup. Which is it? Oh, okay.

That's like 99%. You don't go to Tinder to like read the bios. Yeah, there's not much that strikes you. But you still want to have like a good like chemistry on your like messages together. That's true. You know, some liked shared interests. 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. 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 flustered. 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. Set the expectations so low that it doesn't take much. Did you feel yourself, like, 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 to wanting to play the long game, you know? 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. I mean, that seems pretty deep, but yeah, I kind of was like... Oh, okay. So how do you go about doing that? The shift? When did the shift happen? How do you shift the plan? How do you not sleep right away? This is interesting to me. Doing that the shift yeah, did the shift happen?

Pivot when was your pivot so I mean we hung out at the bar for a little bit And then it's kind of early and it's really hot day Okay, so you excuse yourself to the bathroom and you go put on some real underwear now 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 Warne.

Yeah, what? I know. So I was like, you know, this guy gets power. I like Kurt Warne. 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 assume you didn't come with a swimsuit. Well, I didn't want a skinny dip, but like, I just went in my T-shirt

and my undies. It was fine. Oh, you tease! I think it's a strong move. No, it's all you got. I mean, heck, right as well, right? 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.

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 close. Not only does he have a pool, but he's got a hot tub. I can't think of a guy with a bed that's not on the ground. Alexis is trying to graduate from a futon.

There's hot tub action happening now. Not even action. It was totally just hanging out. Super good chemistry, though, but I didn't want to mess it up by just cheapening it. 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 won't say we did kiss. Where? Where? Where? What part of your body? Like where on the body or where in the house? I'm like, well, kind of like after the hot tub so it didn't get too steamy. Like, it was almost more romantic.

Like, 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. Yeah, keep him 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. 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. She said it was a romantic kiss. It depends on their vibe. 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?

I mean, did he, like, you know, meet somebody who was out of town? That's my first thought. I mean, 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 okay how was it what was the vibe it was kind of flirty it was it was nice so 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. Moving 92.5 a second date update, okay, Sydney? Sounds great. Thank you, guys. Moving 92.5. Second date update. This is a challenge that we've never had before on this morning's show. Okay.

The challenge is find the only catch on Tinder and then reel them 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, Sydney still turned down the invitation to spend the night just to try to play the long game with this guy. Wrong move. I feel likeney's having regrets after hearing about the dolphins apparently he literally was like hey i have millions of dollars if you'd like it and he was like no i'm good 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 you feeling right now sydney i'm nervous as heck i really am yeah we're calling like this perfect guy pretty much yeah 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 don't seem very cool on the phone tides have kind of turned she's, now I'm having a panic attack? Yeah. 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. No.

We better hurry up and just make this call before this gets any worse than it already is. Yeah. Okay. Plus, we're broke. We might have to pay the phone bill. Let's just check and make sure it works. But I think if we've learned anything from Sydney, it's start with low expectations. Okay.

So then it can only go up from there. Yep, that's good. All right. So I'm going to 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 is why was that awkward i don't know it was it was awkward though i'm sorry for my awkwardness kurt hi kurt hi what 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 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 the date well kind of 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. I apologize for her. Don't say cool again, I promise. 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 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. Like, I made this comment, and then I went away for a couple weeks for business, and then I found out when I was away that she used the pool multiple times with her friends. Wait, what? 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? Well, I have security, you know, like security footage, yeah. I thought you were going to say like security guards. I'd be like, those are the worst security guards ever. Yeah, my security dog, 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 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, 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 had been using the pool. And then it was her over and over.

Like it was like the YMCA. OK, 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 on.

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? Hi. It's not like it's 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. 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 just so excited about like the time we had i just kind of was like showing off your place to my friends. I don't know. What? 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, I 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. 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. There was just like, oh, my God, it was just a disaster. I 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 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. 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. I know, I know. She literally used his pool. But she liked you. That's like the definition. But she liked you for you before she knew about the pool. Yeah, that was just a plus. She seemed sincere when she told us about it. Yeah. I mean, 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 i've seen the video already all right we'll just visualize it and then let us know what do you think one more shot with 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. 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. Sorry, Sydney. Snooze, you lose.

Oh, man. We've moved on. 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. 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.

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.