Second Date Update: High School Holiday Hangout

I think one of my other friends. Too bad for you, Brooke, mister Chance. But one of our listeners, Simone, reconnected with someone recently. Not a next boyfriend. It was just a guy from her high school. And I'm curious about how it went down because she's on the phone right now, Simone. So what was this a fellow student or a faculty member? Oh my god, it was not a faculty member. Was a student? Okay? Honestly I hooked up with more guys from my high school way post high school than I

did in high school. I was too darky in high school. Nobody wanted to I try. It's not that I didn't try. Some are late linked to skank and some bloomers. Yeah all right, Yeah, as long as you get it done. So someone who's this guy that you met up with?

So his name is Jack and we reconnected over Facebook because I had posted that I was coming home and I was really excited to spend time with my family and friends like the holidays, and I was trying to kind of give everybody heads up that I went to school with so we could try to plan something and all catch up. Yeah, it's like like a mini informal reunion almost. Yeah. Yeah, And did you know that you wanted to hook up with him immediately or did you want to wait and see how it went? Well? So

that's the thing, is it? Like, this is a guy that we've never dated. We were always kind of floating around in like neighboring circles, but we were never super close. Okay, and got it. He was one of the first people to comment on this post. I was like, Oh, this would be great. We'd love to catch up. And I was like catch up, Like what do we have to talk about? What's like we didn't you know, you know

some people who stay in the hometown that you're from. Yes, maybe needs some outside influence everyone to watch ye let me tell you, I will not miss an opportunity to show off my glow up. So okay, so what did you and Jack do when you met up? Well, this is the thing. So we were texting for a while until I got back and trying to make plans, and I was staying with my family, so I was like, why don't we just make it easy. You can come pick me up from my family's place and we'll go

wherever you want to go. Oh, so this feels more like a date than a hangout if it's just you too, Yeah, I guess so I think maybe I don't know if that was the intention, but things kind of ended up taking a slight turn and it wasn't really anybody's fault.

But he came to pick me up when I was I just finished dinner with my family, and my family was like, oh, you know, why don't you come in for a second, which I kind of gave him the look of like you don't know how to do this, But he was very cool and came in and we all were just hanging. It was really sweet, like they were all hanging out for a while, and like, because like, it's not like he knew your family in high school. You guys weren't even really fair, high pressure situation. Yeah,

I know. If that happened to me, I would absolutely not want to go inside there. I do not want to spend my precious free time during the holidays meeting some other person's family. Would I love meeting families, Yeah, but not people meeting mine? And parents always love me. Okay, we get it, Brook, You're amazing. Everybody think the best person in the world, and everyone wants to their kids

don't like me, but they like me. Okay, So what happened with Jack, Well, so we're all talking and we ended up like playing some games and everybody good time. So the time. Yeah, yeah, I mean I didn't mean for that to happen, and it just kind of did. Playing the piano, singing carols together. He was into it though, Yeah, he was. And I will say this, my dad was a little tipsy, which around the holidays is not a surprise. Yeah. He was kind of ribbing them a little bit, like,

what are your intentions with my daughter? I know, I know, let me go to the laundry room and then I'll show you. Is that not how your guys family holidays? Yeah? I never had to take take my dad into the laundering room. Yeah, just a pe teacher. I know how to jack handle the ribbing. He just kind of laughed it off, and finally I kind of pulled him aside and it was like, hey, listen, we can get out of here whenever you need to, Like we already were

here a lot longer than I thought. And he was like, oh, I just got a text from more my friends and they really need me, so I actually I have to get going. Yeah, and he's like, well, we'll we'll catch up in a few days. And of course, in my head, I'm like, did he really get a text from his friend or I think that maybe he didn't. I don't know, like maybe he thought you guys were just going out as friends, and then your dad is assuming that you're a couple. Like it just it feels like a lot

of weirdness. Yeah, I agree. And the way we left it was we'll make more plans, we'll text him, we'll figure it out, and then just never heard back from him. Oh, complete ghost. It's not like he's stalling, no, no, Like I just he just went radio silent and I don't know what happened. Are you crushing on him still? Like you still like him began. I mean, especially to like seeing how cool he was with hanging out with my

family for a little bit. That's impressive. Now, I did have a weird thought, though, like, while he was bonding with your family, do you have any um single siblings or single hot ants that maybe like could have swooped in. No, I'm the only girl of two brothers. Maybe that's an option for him though. Yeah, I mean there's a chance that someone could have like taken him from you, right from under your nose family dynamics. If that's the case, it's called the holidays. But let's find out what really

happened when we play a song. Come back, call him and try and get your second date update. All right, thank you? All right. Hold on. One of the main rules of dating, and I think everybody knows this is if you really like someone, you do not introduce them to your family for at least three to four years one hundred percent sure they won't be scared off. Wow, I would say probably even pop out a few kids with them before they meet the family, just to be safe.

Or you could end up like Simone who was supposed to go out with an old high school friend named Jack till her family invited him inside during the holidays, and look what happened. I mean, he ran away. Hasn't been heard from since that night. I should have heard your advice first year. Yeah, are we blaming the drunk dad? Is that where we're blaming? Or no, we don't know who to blame. That's where I'm leaning. Even that it's a joke, it's still very intimidating to know your dad

is even thinking that. It's such an old cliche joke, like order your intention. I'm gonna a polish my gun. Yeah, simone, do you wish that you hadn't let him come inside that house that night? I mean, yeah, we know where to send it up. Yeah, absolutely true answer. Oh my god. I mean, or do you wish that your dad was funnier? I mean he thinks it's funny, which is way worse. Yeah. Yeah, yeah, Well we're gonna try and get you a second chance. Here. We're gonna call Jack and find out which member of

your family is the one to blame. Or maybe it was something that was totally unrelated. We think it has to be the fam. I mean, come on, yeah, it's like the holiday edition of Clue. Oh yeah, is it the mom in the kitchen with the butcher knife for Colonel Father. Yea, let's get to the bottom of this. I'm in a Dallas number right now here we go Hello, And there was brushing the microphone. Hey is this Jack? Uh? Yes, this is he. You are waiting and ready? I like Jack.

I know you see Jack. You're you're on the radio right now with Brooke and Jeffrey in the morning. Uh. Yeah, I seem alert because I entered business calls are day. Uh this is kind of a business call. It's about your business. Yeah, your personal business with an old friend of yours name Simone. Wait, what is this about? What's

going on? This is about a segment we do on our show called a second Date Update, and our our listeners will reach out to us sometimes and ask us to help them reconnect with an old fling or an old date that they went out with that they haven't heard from in a while. Okay, but I'm not old. I'm not an old person. Old people. You answered a phone number that you didn't recognize. That is old. Oh, Jack,

I bet you're regretting it right now. I was just, you know, I thought maybe something was wrong with my car's extended warranty. It's okay. Yeah, Look, we all make mistakes, and your mistake was answering this call. But we do want to get some answers because Simone told us that you guys hung out the other night, and you know, I'm sorry, I'm sorry to interrupt you, but I just know I don't think I want to do this, Okay, is it because it wasn't supposed to be a date

with Simone. Is supposed to just be more like of a friend hang out like no, no, no, no, no no, no no, I'm definitely interested in Simone. Well, well I was interested was I mean, look, I know you're hesitant on talking about it, and I understand that, but can you put yourself in Simone's shoes here? Because she was really looking forward to spending time with you and reconnecting. And I mean she had no intention of the night going the way that it did, where you were invited

into her family's house. Yeah, I mean she thought you. I mean, maybe she read it wrong. The only reason you guys stayed there was because she thought you were having a good time hanging out with her family and playing board games. Whoa you guys know a lot about what happened, like like date detectives. Yeah, yeah, it's kind

of weird. What we talked. We talked. She told us about what happened that night, and we were wondering if something happened while you were in the house with her family that made you No, No, it was just well it wasn't It was just an uncomfortable such a she feels bad for that. Yeah, well no, but just no, not not going in and talking to her family. Her family was great, nice and so great that maybe you hooked up with one of them. What. Okay, that was a theory that I had, and I'm glad that we

can squash it right now. But yeah, so he can. Definitely was the text that you got the emergency text? Was that real or was that fake? Uh? No, no, no it was not real. I did not emergency, but she knew that. So don't feel bad admitting that. Like, I mean, it was pretty obvious what made you run

from the house. So what made what made me need to leave is um I was having a nice chat with her mom and as as we're talking, I look over and I see some Christmas cards and I see one from Simone with a another guy and they're both like uggled up together, and it was like a looked like a you know, a couple had sent a card and it was Simone and this dude. Well obviously, I mean, she didn't mention anything about an ex boyfriend, but obviously

the card could have been sent out long before. And then they broke up, Like, really do you send Christmas card? Who brings a guy over to your house with your family if you're dating someone else to a point where you're sending Christmas cards together, Like, why wouldn't you just ask Simone? Then? Why wouldn't you ask her? Because I just felt like, in order to not just escalate things, I wanted to I just you know, I mean, well you just wanted to jump to conclusions. I know you

just took pictures recently. She obviously probably I know you don't want to have that awkward conversation with her, but I kind of do right now because she's on the other line listening and wants to be asked an awkward, escalating question. What Simon, I'm yeah, Hi, Hi, You've been listening this whole time. This is like, this is so awkward. I know, I'm sorry. I mean, it's kind of cool. That you went to these lengths to try to get a hold of me. But I just, you know, I

just this is just really bizarre. So who is the guy? Come on, tell me? Are you seeing? Are you in a relationship? Because like, okay, well hold on, Jack, you're asking like five different questions. Let's just let's do one question at a time. Who's the guy? Oh? I was gonna start what kind of sweater are you wearing right now? Because that I might ease his tension a little bit. First of all, I can't believe you even saw that card. I I'm so mad at my mom right now? Are

you dating that guy? Not technically? Oh dude, what your parents are? Wing? Wing? Manny your side piece? No, so listen, Okay, I'll be honest. That guy's is a guy that I dated for a while, and we always did these stupid Christmas cards And we're not exclusive. We are not together. We hook up every once in a while, but we're not there. Okay, but you promise you're not exclusive with him? Oh, you're not exclusive and you send Christmas cards out together?

That seems yeah. Yeah, it was more of a joke because we would do it every year, so we kind of just kept up with the tradition because we both didn't want our families hackling us at the holidays for being single. So we were like, we should just do a Christmas card anyway, and that backfired, Sonny. So I just I'm actually, I mean, Simone, I really want to be with somebody that's emotionally available and not you know, still, even if it's not like you know, you're not exclusive,

you're still seeing him. I just I'm just comfortable being with somebody who's seeing other people. So I just, uh, well, that's the thing, is like I had a great time hanging out with you, and I really want to get to know you better. And I am not invested in the sky. Like I said, it's somebody that I dated, and it was just I didn't have anybody else I was interested in, and it was just, you know, i'll call him later today and tell him that we can't

see each other anymore. Really, Jack, is that something that you'd be into, because if you're willing to see her again, then we'll pay for that date. Yeah, I have one question. Did you hook up with him over the holidays? Would be honest here, Simone. Did it happen and what sweater were you wearing at the time. It didn't happen over the holidays, but it has happened recently a last night Jack, I need an answer from you. What do you think one more date was simoned? We'll pay for it. I

don't think so. Why it's a healthier Why? I feel like you could have told me that you were getting out of a relationship, and I just I can't get Yeah, it's the holidays. Everybody's sad. We understand, thank you and Jeffrey in the morning, I was thinking, does that ever work on our show? After the person says no, I'm not interested, and they throw out one last ditch plea like, hey, well, what if I break up with the other guy? Will you go out with me? Then it's like a hail Mary?

Or what if I get a butt lift? Yeah? Or hey what if I put my dog down because you're allergic? Oh God, it's always n You made the boyfriend sound like the best option. I just can't think of a time where that strategy has ever worked, and she definitely gave it a try. God, I just have this feeling that the guy on the cards your boy doesn't know that they're not exclusive. Yeah, does anyone else feels always like the other one is always like wide, Wait I

thought you were my girlfriend? Yeah, I'm sent out Christmas cards? Yeah? Yeah, how does it get more intimate than that? But clearly we're not going to be doing any update with that couple anytime soon. But remember you can always listen to any one of our second dates on YouTube because we've got hundreds of them, yeah up right now, so a lot of people are actually choosing to listen to our

show that way. And remember you can always reach out to us if you have a date that you want us to get a hold of Brooke and Jeffrey in the morning,