Brooke and Jeffrey: Second Date Update - Second Date Update: Hometown Surprise

Episode Date: December 28, 2021

One listener reunited with his high school crush and spent HUNDREDS of dollars to make sure he didn't lose her AGAIN... But did his expensive idea backfire?!See omnystudio.com/listener for privacy information.

Jon Stewart is back in the host chair at The Daily Show, which means he's also back in our ears on The Daily Show Ears Edition podcast. Join late night legend Jon Stewart and the best news team for today's biggest headlines, exclusive extended interviews and more. Now this is a second term we can all get behind. Listen to The Daily Show Ears Edition on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. In 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. People, my people, what's up? This is Questlove. Man, I cannot believe we're already wrapping up another season of Questlove Supreme.

Man, we've got some amazing guests lined up to close out the season. But, you know, I don't want any of you guys to miss all the incredible conversations we've had so far. I mean, we talked to A. Marie, Johnny Marr, E., Jonathan Schechter, Billy Porter, and so many more. Look, if you haven't heard these episodes yet, hey, now's your chance. You've got to check them out. Listen to Questlove Supreme on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Second Date Update We've done so many second dates.

I would say each one tends to fall into a certain category. Okay, yeah. Like there's the drunken one-night stands. Oh, for sure. A lot of those. There's the blind date that was set up through friends. Always a disaster. It's more rare, but we do a lot of those.

Sometimes we get a lick date. Lick? Where a couple licks each other's faces for hours. No, I've never heard of that. Sorry. No, that was just a dog video I just watched. Oh. What?

A really good one on YouTube. It must have still been in my head. Huh? But no, back to the second date update. One of my favorites is the old school high school crush date. Oh. It's kind of like redemption after having a crush for so many years and then you finally get to

go out. You're just like lucky they're not married yet. That's what's happening today with one of our listeners named Noah. He's been looking to reunite with an old classmate. Noah, you found me. I am ready for you.

Are you calling about Jeffrey Noah? Hey guys, no you. Are you calling about Jeffrey, Noah? Hey, guys. No, I'm not calling about Jeffrey. Not this time. Okay. He went to a rich private school. I don't want you either, Noah. Okay. Forget you. Jeffrey gets all mad. Okay, whatever. Who are you calling

about, Noah? Yeah, who's this person that's so much better? It's not Jeffrey. Okay, so there's this girl that I've known forever, and we went to high school together. Can I interrupt? Noah, does she have a name? Her name's Anna. Okay.

All right, Anna. So you went to high school with Anna. Anna, Noah. I like the flow. Uh-huh. The flow-a. So how did you end up reconnecting with Anna? Well, I mean, we dated in high school, and she moved away.

She went to school. Oh. Oh, you guys actually dated in high school and she moved away. She went to school. Oh. Oh, you guys actually dated in high school. It wasn't just a crush. I guess what I mean by date was more in my mind. Oh. That's not weird at all. Well, it does count. No, it doesn't. In case I'm dating Sofia Vergara right now. Hey, for us lonely guys

in high school, it counts. Okay, in high school. Don't you dare discredit us. In high school, maybe. No way, dude. I was a lonely girl in high school, it counts. Don't you dare discredit us. No way, dude. I was a lonely girl in high school. I was trying to get anybody to make out with me, and it didn't count. Okay? It didn't count at all. All right.

Well, so you didn't actually date in high school, but you were able to reconnect years later. How did that happen? So she would come home. Like I said, she's in college pretty far away. She would come home for the holidays. And while she was home, you know, we would hang out. And so one of the places that we actually met up one night was this local bar that a bunch of friends would always hang out at. Okay. I mean, this all sounds typical. I think we've all lived this story, right? But is this your date that you're talking about, or is this just how you reconnected?

So this was the moment that we actually spent a lot of time together to reconnect, was that time at the bar. Okay. Right. And so did you, like, ask her out on a date, and you went on a date later, or you just made out that night? So there was a lot of flirting and a lot of hanging out, and, yeah, I did kiss her. Oh. Finally got the kiss after all these years. I go to hometown bars and make out with guys from high school, though.

It doesn't mean anything. But that was like two years ago. Two? Sometimes. Of course she does. She's like 22. It's kind of fun. That's what you do when you're 22.

And she just hit the bar scene. But wait, hold on. Back to you, Noah. The girls were not like that when I went back home. I just think it wasn't for you, honey. It was for everybody else. But Noah, was this the first kiss you guys have ever shared?

This was the first kiss, yeah. Oh, man. How was it? This was like a big moment for you then. This was a huge moment for me. I mean, it just rocked my world. But unfortunately, the next morning, she had to fly out.

Oh, no. And there's where the airport scene comes in in every rock song. No, don't leave. Yes, stay here. Give up on all of your education just for me. So what happened next? She didn't invite me to the airport, which kind of sucked. Okay, yeah.

But about three weeks later, I came to visit her. Oh. Whoa. She invited you out later, I came to visit her. Oh. Whoa. She invited you out? An invitation or just you showed up? It was kind of a little bit of both. She didn't really invite me, but she said the door kind of was open. Oh.

Okay. Huh. I know what that's like. It's like, yeah, we should totally hang out sometime. Yeah. And you take that as, oh, I i'm gonna book my ticket now she's like we're so far away yeah when i said there's like the one percent chance they might come i mean that's a big deal though because that's like inviting her old high school whatever into

her new world yeah right i guess the best gauge is how did she react when you showed up i guess it was a little a little weird because it was more surprise. And so she didn't really know how to handle it. But she was still excited to see me for sure. And unfortunately, she had to work a lot of the time that I was there. Well, you didn't tell her you were coming. Right. Totally.

That makes sense. Yeah, yeah. We spent time together during the day. But then she had to work nights. She worked for our catering business. Okay. So I kind of hung out with her roommate while she was working, but I don't know.

There are a couple of things that just kind of make me feel like there might be another guy in the picture with her. Why do you think there's another guy? Just the way her roommate was talking. It's just like she was dropping some hints, but like she wouldn't actually talk about it. This isn't really a second date update though this is like you were in a one-sided relationship and we need to figure out how she feels is that what you want i don't know i disagree with you i think that

it is more of a second date update because when i was there we walked around and held hands and talked about the past in our lives and kind of like our relationship we've had over the years. Oh, okay. Okay. And you did get that kiss. I mean, you can't put that aside. That's huge. I don't know.

She wouldn't hold hands in public on campus if she had another boyfriend. Unless her hands were cold. Well. But I don't know. Let's figure this out, okay? We're going to play a song. We'll come back. We'll call Anna for you, let's figure this out, okay? We're going to play a song, we'll come back, we'll call Anna for you,

and we'll ask her, do you have a crush on Noah? Circle yes or no, or kind of. All right. All right, hold on. If you're just tuning in, today's second date update is the kind of thing that movies are made of. Oh, yeah, for sure. High school boy meets high school girl.

Girl goes off to college. Years later, she comes back to visit and makes out with boy at a dive bar. Boy follows girl back to college uninvited. Girl's busy and has to work a catering job, so boy mostly hangs out with girl's roommate. Boy leaves and calls a radio station because now he has more questions than answers. Yeah. All classic. Starring Zac Efron he has more questions than answers. Yeah. Oh, classic. Starring Zac Efron and Meryl Streep.

Yeah. That's an interesting mix. Meryl Streep is a co-ed, huh? She could pull off a college student. But, yes, one of our listeners, Noah, reconnected with an old high school crush named Anna. They had a little bit of a fling. And when he went and visited her at her college, she had to work a lot. Yeah. And, you know, he didn't tell her that she was coming. Yeah. Yeah. That's the first mistake of many that I think he made. But he got the vibe that maybe

something else was going on with Anna. Maybe it's another guy. Right. He's not really sure. So we're going to call in and try and figure out what's going on. That's right. I just don't want her to slip away. Okay. So, Noah, I have a question. The one thing we didn't ask is after you got back, have you and Anna still been talking, or is she just not answering any of your phone calls? So this has been all of her texts, and any time I actually call her on the phone, she doesn't pick up. Okay.

Not a good sign. A lot of questions that you want to ask. What's the number one question that you have for her? I just want to know if she feels the same way I do after all this time. Do you have maybe a better question that is more likely to get a yes? I don't know if you're going to want to ask the answer to that. Or if you just give me a chance to make this work, and I'll make it work with all this distance. Okay.

We're getting closer to something that might turn out well. But let's give this a shot. Young love, Noah. Let's do it. We're going to dial Anna's phone number right now, and we're going to ask her the question. You ready? Well, a question. Hopefully.

Yeah, I'm nervous. Can you call him, please? Okay. All right, you're going to be fine. Here we go. Hello? Hi, I'm looking to speak with Anna. This is Anna.

Hi, Anna. My name's Jeffrey from the radio show Brooke and Jeffrey in the Morning. I was hoping you'd have a second to talk. From the radio? Mm-hmm. I know it's kind of an antiquated device. It's usually in cars. It's like Spotify in your whip.

Yeah. Music comes out of it sometimes, and sometimes people talk. She's not an idiot. Hi, Anna. You sounded really confused. Yeah, what's going on? Well, we're a radio show called Brooke and Jeffrey in the Morning. We do a segment called a second date update.

That's where if you go out with someone, and afterwards, if they're not calling you back, you can reach out to us, and we'll call that person for you to try and figure out the reason why. Okay. So one of our listeners reached out and wanted to ask about you. The guy's name is Noah. Oh my God. Do you know a Noah? Yeah, of course she knows a Noah.

I mean, it's not really a first date you guys went on. It was like a whole weekend thing. We talked to Noah. He seems like a really nice guy. Yeah, he's, Noah is nice. Okay. I don't, I don't know what you want me to tell you. Well, how about we tell you what we know and then you can go off of our story?

I mean, I don't think it'll matter, but sure. Okay, well, let's give it a shot. What do you say? Okay. So Noah said that he knew you from high school. You guys reconnected when you came back to visit at a bar. You had a little bit of a fling at the bar, a little kiss. He went to visit you at your college, but you weren't able to spend a lot of time with him because you had to work.

I don't know why he's telling you all this. Why is he reaching out to you all? I never gave him permission to talk to somebody about this situation. That's really weird. I mean, it's pretty generic information. Yeah. If you don't like him, just say that. never gave him permission to talk to somebody about this situation that's really weird i mean it's pretty generic information yeah if you don't like him just say that hey i don't like him i'm not attracted that's it like we just want to know no judgment on you yeah i mean i am engaged oh yeah that's why you're so secret that's not good wait hold up wait no why are you

before i got engaged recently it was kind of like unsure about what the status was with my fiance and i we weren't like official at that point and i guess i was just feeling like if i'm soon to be a married person like kind of having some doubts. And Noah and I connected and we kissed at the bar. So wait, Noah didn't know that you were engaged? No, he did not. You didn't tell him? So I wasn't engaged when we kissed at the bar.

And then he just randomly showed up at my doorstep at school. We didn't talk about it. He just like appeared. So, okay. I get it. Don't ask, don't tell.

No, that's from, there's so many red flags with your engagement right now. Like one, you weren't committed to the person right before you got engaged, which seems like all over the place to me to a guy shows up to your door and you don't even have the courage right before you got engaged, which seems like all over the place to me. Two, a guy shows up to your door and you don't even have the courage to tell him, hey, I'm engaged. I mean, he's a friend.

I didn't want to hurt his feelings. Yeah, but you being engaged isn't going to hurt his feelings. It doesn't have anything to do with him. Well, he really likes her. Well, I know, but like he shouldn't have showed up. It didn't give her time to plan a lie. And that's on him. Why lie?

Why not just say I'm engaged? Shouldn't you be celebrating? Shouldn't you be excited to tell everybody? I mean, it's a legit reason why you can't date somebody. Brooke, you don't know whether or not his feelings would be hurt finding out that she's engaged unless we ask Noah directly. Okay, well, this is going to get weird. I need to tell you, Anna, that Noah's actually been on the other line listening this entire time, and he wants to talk to you. Oh, my God.

It's okay. Anna, hey. Oh, man. So, this is it. Oh, my God. I wish you could have told me. Right. It didn't really feel like there was an opening to Noah.

What do you mean I mean even even when we were in like you know when you came in town for the holidays like we walked around and I don't know I I've always really really liked you you've always been my dream girl I didn't want to tell you that because that makes it weird I know but I'm sorry I have to tell you that now. And it destroys me to hear that you're engaged. Oh, see, Brooke. Well, of course it does, but it also destroys him that you weren't honest with him, Anna. Why is it so hard to be honest these days? I don't understand. Because of that. It's college, Brooke. But then you shouldn't be engaged if you were walking around campus. I didn't know what to do.

Everything kind of happened really quickly. It took me by surprise, and I'm sorry. I'm sorry, Noah. I mean, Noah, do you want me to send you back the pillow? What pillow? Can you not? Don't talk about that on the radio, please. What pillow?

You're the one who called the radio. We know nothing about a pillow. Now this is insanely embarrassing. Noah sent me a pillow of his fate. Sweet Noah.

No, I didn't. I kind of love it. It's kind of funny. Kind of sweet. Noah, you're a catch. I think you're a catch, Noah. No. If that's your girlfriend, yes.

Whatever. Don't bag on this guy. He's having a hard moment right now. What was going on in your mind when you sent her a pillow of your face? I mean, I can't be there for her physically because of the distance. And so I thought it was something that she could at least, like, have, remember with me, and maybe even cuddle with. Aw, see, if you're dating, that's cute. Maybe she's drunk, she'll kiss it a little bit.

Maybe do a little more with it. What are you doing with the pillow right now, Anna? Like, you have a pillow of some dude's face at your house when your fiancé comes over? It's just in my closet, and I just don't know what to do with it. So I didn't, it felt wrong to just throw it away. I need to ask a question, but before I do, I want to know, how serious is this fiancé, Anna?

I'm actually with Jeffrey on this one. I mean, it sounds like the switch is turning on and off. It is. And like, I feel like you're holding on to things like his pillow or letting him stay without telling him because you actually do really like Noah still. I love my fiance and I've been honest with him about the situation with Noah. Yes, I should have told Noah I was engaged up front.

I wasn't engaged when I was home for the holidays and like it was kind of freaking out a bit. So what are you saying? Is this guy pre-med? Is he rich? Is he like an athlete? Is he a frat boy? No, I'm not talking to you guys about this. It's just, it's not going to happen.

He's not. I don't think the marriage is going to happen. I need to ask at this point, Anna, would you like to go out on another date with Noah? We'll pay for it. We'll fly him out. Or we'll at least pay for the postage for you to send his pillow back to him. There you go. That is nice. I like that. Good deal. I'm going to send the pillow

back, but I don't need you guys to pay for it. Thank you, though, for the very kind offer. We feel you. Noah, I think you're going to be just fine. You're going to bounce back. Yeah. I just wish I knew. I just feel like an idiot. That's alright, buddy. It's not on you, man. You know, Noah, I feel bad.

Why don't you, when you get the pillow back, why don't you send it over to me? Okay? I'll try it out. I'll use it the right way. You'll use it the right way. You did not just say that. I'll do what you want me to do. No, thank you.

Brooke and Jeffrey in the morning. Jon Stewart is back in the host chair at The Daily Show, which means he's also back in our ears on The Daily Show Ears Edition podcast. Join late night legend John Stewart and the best news team for today's biggest headlines, exclusive extended interviews and more. Now this is a second term we can all get behind. Listen to The Daily Show Ears edition 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. People, my people, what's up? This is Questlove. Man, I cannot believe we're already wrapping up another season of Questlove Supreme. Man, we've got some amazing guests lined up to close out the season. But, you know, I don't want any of you guys to miss all the incredible conversations we've had so far. I mean, we talked to A. Marie, Johnny Marr, E., Jonathan Schechter, Billy Porter, and so many more. Look, if you haven't heard these episodes yet,

hey, now's your chance. You gotta check them out. Listen to Questlove Supreme on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.