Brooke and Jeffrey: Second Date Update - Second Date Update: High School Holiday Hangout

Episode Date: December 11, 2023

One of our listeners thought inviting a guy over might save her from spending time with her parents while home for the holidays… but you need to hear how badly it backfired in a Second Date!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.

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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. Second date update. Going back home for the holidays can be really fun.

Yay! Yeah, I'm so excited. It can be great to reconnect with your siblings again, your grandparents, relatives you haven't seen in a while. And if you're really lucky, you might even see someone from your past and have a little holiday hookup session. Wait, we're at a family? Not your family member.

It's like when everybody goes out. Like, you know, to the one bar. Totally. Exactly. Like, Brooke, didn't you and your old PE coach reconnect one year and get to second base or something? No, he married, I think, one of my other friends. Oh, you almost had him. He was off the table.

Oh, too bad for you, Brooke, Mr. Chance. But one of our listeners, Simone, reconnected with someone recently. Not an ex-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, was this a fellow student or a faculty member? Oh, my God. It was not a faculty member.

Also 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 dorky in high school. Nobody wanted to. All the girls get hot later. I tried. It's not that I didn't try.

I just didn't have the takers. Some are late to skank and some skanker. That's what we call late bloomers. As long as you get it done. So Simone, who is 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 for the holidays.

And I was trying to kind of give everybody a heads up that I went to school with so we could try to plan something and all catch up. Yeah, it's 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 that this is a guy that we've never dated. We were always kind of floating around in neighboring circles, but we were never super close.

Okay. Got it. He was one of the first people to comment on this post. Oh, like, oh, this would be great. Would love to catch up. And I was like, catch up. Like, what do we have to talk about? Like we didn't, you know.

You know, some people who stay in the hometown that you're from. Yes. Maybe need some outside influence every once in a while. Yeah. Leave the city is what she's saying. Let me tell you, I will not miss an opportunity to show off my glow up. Okay. I love that.

Good. 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 two. 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 fit. 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 have to do this, but he was very

cool and came in and we all were just hanging. It was really sweet. Like we 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 high pressure situation. Yeah, I know that happened to me. That's a high pressure situation. Yeah. I know. If that happened to me, I would absolutely not want to go inside.

I do not want to spend my precious free time during the holidays meeting some other person's family. I love meeting families and moms. Yeah. I like other families. But not people meeting mine. And parents always love me. It's so fun. You can charm parents

so easily. Okay, we get it, Brooke. You're amazing. Everybody thinks that you're the best person in the world, and everyone wants to hook up with you. Usually their kids don't like me, but they like me. Oh, okay. Well, so what happened with Jack? Well, so we're all talking, and we ended up playing some games, and everybody was having a good time. So the hangout.

Oh, this is full-on holiday family time. Yeah. Yeah, I mean, I didn't mean for that to happen. It just kind of did. Playing the piano, singing carols together. Yeah. He was into it, though. Yeah, and I will say this.

My dad was a little tipsy, which around the holidays is not a surprise. That's everybody. Yeah, and he was kind of ribbing him a little bit. Like, what are your intentions with my daughter? That type of thing. I know. I know. Well, let me go to the laundry room, and then was kind of ribbing him a little bit, like, what are your intentions with my daughter type of thing. I know, I know. Well, let me go into the laundry room, and then I'll show you. Is that not how your guys' family holidays go?

I've never had a date take my dad into the laundry room. Just the P.E. teacher, I know. How did Jack handle the ribbing? He just kind of laughed it off. And finally, I kind of pulled him aside. And I 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 one of my friends.

And they really need me. So I actually, I have to get going. And he's like, well, 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? No, probably not. 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 and we'll figure it out, and then just never heard back from him. Oh, man. A complete ghost. It's not like he's stalling?

No, no. Like, he just went radio silent. And so I don't know what happened. Are you crushing on him still? Like, you still like him? Yeah. I mean, especially, too, like like seeing how cool he was with hanging out with my family for a little bit that's impressive you know 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 aunts that maybe like could have swooped in now we're talking no i i'm the only girl i have two brothers maybe that's an option for him though yeah i mean there's a chance that someone could have swooped in? No, I'm the only girl. I have 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. That is some messed up family dynamics, if that's the case. It's called the holidays, Brooke. Things happen. Now he's dating her mom.

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, and get your second date update, alright? Thank you. Alright, hold on. Second date update. 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. Until you're 100% sure they won't be scared off. Wow, that's a long time. I would say probably even pop out a few kids with them before they meet the fam 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. They should have heard your advice first. Are we blaming the drunk dad? Is that what we're blaming or no? We don't know who to blame. That's where I'm leaning. I think that the dad even though it's a joke, it's still very

intimidating to know that that's like your dad is even thinking those things. And it's such an old cliche joke like what are your intentions? I'm going to polish my gun. See, Simone dad is even thinking it's such an old cliche joke like what are your intentions really i'm gonna polish my gun yeah see simone do you wish that you hadn't let him come inside that house that night i mean yeah we know where this ended up it's absolutely true easy answer oh my god i mean or do you wish that your dad was funnier i mean he thinks he's funny, which is way worse.

Typical dad. Yeah, we know. Yeah, well, we're going to try and get you a second chance here. We're going to call Jack and find out which member of your family is the one to blame. Or maybe it was something that was totally unrelated. I love how we think it has to be the family. I mean, come on. Yeah.

It's like the holiday edition of Clue. Oh, yeah. All right. Is it the mom in the kitchen with the butcher knife? Or Colonel Father. Yeah. Let's get to the bottom of this. I'm going to dial his number right now. Here we go.

Hello? I know it's brushed the microphone. Hello? Hey, is this brushed the microphone. Hello? Hey, is this Jack? Yes, this is he. You are awake and ready. I like Jack. I know.

You seem alert, Jack. You're on the radio right now with Brooke and Jeffrey in the morning. Yeah, I seem alert because I answered a business call. This is kind of a business call. It's about your business. Yeah. Your personal business. Yeah. With an old friend of a business call. It's about your business. Yeah. Your personal business. Yeah.

With an old friend of yours named 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 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. You answered a phone number that you didn't recognize.

That is old person behavior. Joy's still out on that. It's so true. 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, man. He's got jokes, too.

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 to interrupt you, but I just—no, I don't think I want to do this. Okay, is it because it wasn't supposed to be a date with Simone? Was it supposed to just be more like of a friend hangout? No, no, no, no, no, no. I'm definitely interested in Simone. Oh, that's good.

Still? 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, that wasn't the plan, bro.

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.

We're like date detectives. Yeah, it's kind of weird. Well, we talked to Simone. 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 an uncomfortable situation. Oh, she feels bad for that.

Yeah, but just not going in and talking to her family. Her family was great. Oh. Nice. So great that maybe you hooked up with one of them? Talk to that. What? Okay.

That was a theory that I had, and I'm glad that we can squash it right now. Yeah, we can definitely. Was the text that you got, the emergency text, was that real or was that fake? Be honest. No, no, it was not real. I did not get the 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 another guy and they're both like snuggled up together and it it was like a it looked like a you know couple had sent a 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, how early do you send Christmas cards? I know, but 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 just, you know. You just wanted to jump to conclusions. I see. If it is the ex, you just took pictures recently. Yeah, but who cares? She obviously didn't take pictures recently.

I know you don't want to have that awkward conversation with her, but I kind of do right now. She's on the other line listening and wants to be asked an awkward, escalating question. What? Simone? 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 somebody? Are you in a relationship? Okay. Hold on, Jack. You're asking like five different questions. Let's do one question at a time. Who's the guy? Oh, I was going to start.

What kind of sweater are you wearing right now? Because that might ease his tension a little bit. No, who's the guy? First of all, I can't believe you even saw that card. I'm so mad at my mom right now. Uh-oh. Why? Are you dating that guy?

Not technically. Oh. That means. Dude, what? Your parents are wingmanning your side piece? No. So, listen. Okay.

I'll be honest. That guy is a guy that I dated for a while. Okay. 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 together. But you promise you're not exclusive with him? Oh, 100%.

You're not exclusive and you send Christmas cards out together. Yeah. That seems. Yeah. That's a strange combo. 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 hassling us at the holidays for being single. So we were like, we should just do a Christmas card anyway. And that backfired. So. Funny.

So I just, I'm actually, I mean, Simone, I'm 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 not 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 this guy. 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.

What? 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? Oh, you don't want that answer? Don't ask.

I wouldn't know that. Exactly. Be honest here, Simone. Did it happen, and what sweater were you wearing at the time? Jeffrey! It didn't happen over the holidays but it has happened recently jack i need an answer from you what do you think one more date with simone we'll pay for it i don't think so and here's why it's a healthy here's why. It's a healthy decision. Here's why. I feel like you could have told me that you were getting out of a relationship, and I just, I can't.

We get it, Jack. We get it. It's the holidays. Everybody's sad. We understand. Okay. Thank you. Brooke and Jeffrey in the morning.

I was thinking, does that ever work on our show? What? 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, hey, what if I get a butt lift? Yeah.

Or, hey, what if I put my dog down because you're allergic? Oh god. Will you go out with me then? It's always no. You made the boyfriend sound like the best option. I mean, honestly. Would you go with me then? Oh, my God. See, I can't just not. It's always no. You made the boyfriend sound like the best option. I mean, honestly. I just can't think of a time where that strategy's ever worked. And she definitely gave it a try.

Oh, God. I just have this feeling that the guy on the card, Sweater Boy, doesn't know that they're not exclusive. Yeah. Does anyone else feel that? It's always like that. The other one is always like, what? Wait, I thought you were my girlfriend. Yeah. We sent out Christmas cards for God's sakes. Yeah. How does it feel bad? The other one is always like, what? Wait, I thought you were my girlfriend. Yeah.

We sent out Christmas cards for God's sakes. Yeah. How does it get more intimate than that? I don't know. 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 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. 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 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 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.