Brooke and Jeffrey: Second Date Update - Second Date Update PODCAST: Marriage Pact

Episode Date: September 30, 2020

David made a PACT  with a girl in high school that if they're both single at 30 they HAVE to get married....Well the time has come... He's single, 30, and ready to see if the deal still holds true!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. racing event. Tune into my new podcast, Throttle Therapy, with Katherine Legg, an iHeart Women's Sports production in partnership with Deep Blue Sports and Entertainment. You can find us on the iHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Presented by Elf Beauty, founding partner of iHeart Women's Sports. I'm Dr. Laurie Santos, and to welcome the new year, my podcast, The Happiness Lab, is releasing a series of happiness how-to guides to help you in 2025.

I'll distill the wisdom of world-class experts into easy-to-digest, actionable tips. Struggling with tough emotions? We have a how-to guide. Worried that you're not enough? We got you. Self-obsessed and want to get over yourself? There's a guide for that, too. The Happiness Lab's how-to season starts January 1st. Listen on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Bread and butter wines pair with the life moments

you love. Offering a rich and jammy Cabernet Sauvignon, a silky smooth Pinot Noir, and a buttery Chardonnay. Bread and butter wines are delicious. Find bread and butter wines in your favorite store. Moving 92.5. Second date update. We've seen it happen on pretty much every cheesy sitcom since the 1980s.

Maybe that's why it became so popular in real life. What? Where two lonely singles make a pact saying, you know what, if we're both still single by age whatever, then how about you and I get married? Yeah, I did that in kindergarten. I did it too. And I was like, we're single at 21. Let's get married.

Yeah, when our lives are almost over. I thought at 14 that 21 was really old. Yeah. I mean, it's kind of the ultimate diss because it says, you know, I'm really desperate right now, but I'm not that desperate. It does say that. At least not yet. Give me 20 more years and maybe I'll sink to this level. I mean, will you be my last resort?

I have a shot, but you, we all know you're sinking to life. So today we have a guy on the phone who made that pact with a woman way back in the day. His name is David. What's up, David? Hey, how are you guys? David. This is cute, but you're really taking this pact seriously? I just wanted to see if she's serious about it.

Okay. I see how it is. We'll get to the pact in just a second, but first, how long has it been since you last spoke with your future wife? Oh, don't say that yet. Well, okay, I'm jumping to conclusions. How long has it been since you spoke to her? Well, it's actually been almost like 12 years. Whoa. Wait, wait, wait. Before we go further, what's her name?

Well, her name is Libby, but she goes by Liv. Liv? Okay. And I mean, did you guys make this pact in high school? Is that 12 years ago for you? Yeah, actually, we were really, really good friends, but I was super shy and I don't know, I was really insecure. So I never asked her out, but we kind of always like had a thing between us. At least on your end, you had a thing between you and her and she probably didn't even know. That's not true.

She actually wrote it in my yearbook. So she's the one who wrote it. Oh, she wrote the marriage pact down. Did you guys like prick your thumbs and then sign it with blood? Oh, Brooke. Jesus. What school did you go to? Cutting fingers? I see what Brooke's saying. She's saying, did you get it notarized?

Yeah. Otherwise, it's not binding. Oh, come on. It's actually really cute. It is. So this was her idea, and now it's been since high school, since you last spoke to her, and how did she come back into your life?

Well, we always were Facebook friends, so whatever. We just kind of were peripheral with each other, but then I realized about a month ago that she was single because she was in a long relationship for a while i realized it i mean i wasn't stalking her page or anything refreshing it every couple weeks three hours ago yeah okay so did you reach out to her or did she

reach out to you i like dm'd her and then we were just talking and then i got the courage to ask her out like i straight up just was like hey this could be a thing that's so nice oh my god where'd you guys go what'd you do tell us everything so we just went to this like little divey bar and we had drinks and it was so cool like we both were just smiling like we were really good friends for six years so cute and it's so nice to like be out with somebody on a date that you still feel that comfort with. Right. Like, like you didn't skip a beat.

No. And you can just be yourself. I mean, I'm assuming that's how you felt. Yeah, it was really, really, really nice. And so anyway, we we ordered apps and stuff. And I actually bought our yearbook, our senior yearbook. Oh, OK. You brought it. Bold move. To, okay. Oh, you brought it.

Bold move. It's a reminder. Was she into that? Well, yeah, she really liked the yearbook. It was fun to reminisce. She was really popular, so she was in a lot of pictures. Was there romance on the date, though, too, or was it just nostalgia?

Yeah, I think so. We were, like, laughing, you know, and I feel like there were some old sparks, definitely, that popped up for me. The only thing that I'm confused about about because I just couldn't read her is like we got to the page where the pact was because she was a gymnast so it was on her gymnastics team page so there was like a lot of memories for her but she also wrote there if we're both 30 and not married that we would get married so oh man when we got to that page, it got a little confusing. Really?

Why confusing? Yeah. Well, she was smiling and laughing, like, extra on that page. And so then part of me was like, is it because these are some of her best friends and there's, like, goofy pictures of them, or is it because she was reading the pack? Oh.

Okay. So, I mean, it was a positive. Like, she was putting out positive vibes Oh. Okay. So, I mean, it was a positive, like she was putting out positive vibes no matter what. Well, laughing. Well, she was definitely smiling and kind of laughing, but I didn't want to bring up the pact because I didn't want it to be like, this is the reason I brought you here,

the reason I brought the yearbook. Yeah, because that'd be creepy. Yeah. So anyway, how old are you? I'm just kidding. I know you yearbook. Yeah, because that'd be creepy. So anyway, how old are you? Just kidding. I know you're 30. Yeah. So did it come up?

Did she see it? I mean, she definitely saw it. It didn't come up because we kind of just like flipped the page. But then like later she had mentioned something about gymnastics, her uniform. So then I pulled out the yearbook later, and we opened it up to that page again. Oh, no.

Now we're getting into the weird stuff. I feel like that was planned. Was that planned? It was bookmarked. Well, she's the one who was talking about her uniform, and we were going back for reference. You're weird. There's a picture of it right here next to this sentence.

Marriage or something. Yeah, what does that say? I can't read it. Look how good your calligraphy was back in the day. So it never came up then? It never came up, and obviously I wasn't going to bring it up because I wasn't, you know. Well, right, and you gave her enough opportunity for her to say something. I mean, what did the night end like?

Well, it ended with a hug, which is fine. I'm cool with that. I'm cool with it. You're not. I'm fine. I'm fine. Have you guys ever kissed in the past or would that have been

your first kiss ever? Her photo in the yearbook doesn't count. Just saying. Well, technically, we were both in a play in 10th grade and we kissed then.

Oh, that odd drama kisses that are so awkward. This is interesting. This is very weird. So what's happened since that night ended? Have you reached out to her again? I mean, I have, and I haven't heard from her. So I don't know, because she travels a lot for work. So I don't know if she got weirded out, she's ghosting me or she's truly just busy.

All right. Okay. I can't read this one. This is an exciting one. It is exciting. There's a lot on the line. This is so cute. So let's play a song.

We'll come back and we'll call Lib for you and try and get you your second date update, all right? Thank you. All right, hold on, man. If you're just tuning in, we've got David on the phone. And David made a pact with a girl named Lib back in high school that if they were both single by age 30, they'd get married. Yes.

And fast forward about a decade, they're 30. Uh-oh. And the other day, they reconnected and went out on a date. David even brought along the school yearbook with the signed agreement inside but he's not sure if libs saw the pact in there so i think she did of course he did he showed it to her twice but it never came up in the conversation because it was on her gymnastics page and it's been kind of weird ever since then now dav, I know a lot's on the line here, but how about this, okay? If by the end

of this phone call, you don't get another date, how about you and Brooke make a pact? Aww, that's cute. I'm already married. If she's still married by age 50, she will sleep with you. How does that sound?

We all know that's very likely. No, that is not. David, don't take me up on that, okay? I don't cheat on my husband. Yeah, not today. Yeah, sure. Not yet. David's scared.

Are you scared, David? Yeah, I'm just listening. Okay. It's a good move. Don't say anything, David. He's writing up a whole new agreement into his yearbook now for you to sign. But, okay, we're going to call Lib here in just a second. But just so you guys know, I don't think I'm going to bring up the pact.

I don't think you should. I really don't. Why? That's the whole point. Well, David should be the one that brings it up. I don't want to ruin the mood and spoil this for everyone. Is that okay, David? Okay, I get it.

Yeah, yeah, totally. We'll see what she says. Okay. This is it. Shooting star. All right. All right. Let's find out David? Yeah, yeah, totally. We'll see what she says. Okay. Alright. Let's find out. Let's call your future wife. Here we go. When you get her on the phone, just please don't call her that, though.

I can't make any promises. We have to sign a pact before I can do that. Alright, fine. Let's just call her. Hello? Hi, can I speak to Lib, please? This is she. Hey, Lib. My name's Jeffrey from the radio show Brooke and Jeffrey in the Morning.

How are you doing? Oh, um, hi, good. How are you? I'm wonderful. Oh, my God, I'm so nervous right now. Hi, Lib. How are you? I'm wonderful. Oh my God, I'm so nervous right now. Hi, Lib. You're nervous. Hi.

Brooke's intimidated by another female presence. That is not true. Don't let it get you down. She sounds so pretty. We just have the cutest reason for calling you, I think. Yeah, we do. Oh, okay. What's going on?

So we're doing something called a second date update. That's where if you go out with someone and afterwards, if they're not getting in touch with you, you can reach out to our show and we'll call them to try and figure out the reason why. Wow. Okay. So somebody reached out to us about you. His name's David. Wait, so he reached out to you guys? Yeah. He emailed our show because he told us the whole story about

how you guys reconnected on Facebook and then you guys went out together. You went to a bar and hadn't seen each other in something like 12 years. We really did have a good time. It was a lovely night. Lovely. I mean, I'm sure looking at the yearbook brought back a lot of great memories.

Was there anything that you saw in there that, like, stood out to you? Did he bring that up to you guys? I mean, maybe. Was there, like, anything about the yearbook that stood out to you? Well, I saw all of these pictures of an old crush of mine, one of the male gymnasts on my team. What? I was kind of looking male gymnasts on my team. What? I was kind of looking at those pictures a little bit, and I hope he didn't notice.

Oh, my God. Oh, there was a dude in the gym pictures. When you were looking at your gymnastic pictures, you weren't looking at, like, your funny outfits. You were looking at some dude that you liked? The outfits are so funny. But, yeah, I mean, there was this this really really sweet guy on the team and you know he was like our our star those pretty boy gymnasts always get all the girls back in high school

but uh yeah no david didn't mention anything about your gymnast crush but uh he is interested in hanging out with you again is that something that you would be open to? I mean, I don't know, you guys. I think I might need some space, I think, before I see him again. Oh, man. Why? Why do you need space? Well, even though it was great seeing him and super fun

reconnecting, over the last three days, he has DM'd me over a hundred times. What? Oh. In three days? No, no, no. Dang. He has DM'd me over a hundred times. What? Whoa. In three days? No, no, no, no, no. Dang.

Oh, yeah. It was like a new message every hour. Yeah, David did not mention that to us. And we also forgot to tell you that he's been on the other line listening and wants to talk to you. So I guess we both made oopsies over the last few days. Oh, my God. Oh, my God. Oh, my God. Are you serious? Yeah, it's okay.

He needs to hear this. David, you there? Yeah. Hey, Lib. Hi, David. David, 100 DMs, dude, in three days? Yeah, you're supposed to slide in her DMs, not surge into it. Well, it was not

100 messages. It was maybe like 80, maybe 90. But, I mean, a lot of them were just pictures. They were scanned pictures from high school. So, if I'm sending like 20 pictures, that is counting as 20 messages. That's not fair. Okay, it's

just been really overwhelming. Yeah. I mean, it's so fun to go down memory lane and to be nostalgic. I really did have a great time seeing you again. Well, that's good. I mean, I felt that same way. And I mean, I know you're saying that. Yeah, obviously, David. I think your message is loud and clear, bro.

Well, I mean, okay, the truth is, and lib you can you can attest to this like we made a pact i mean we did we said if we were 30 and not married that we would be together the tone of that was not right so i was like you owe me yeah oh i was hoping you wouldn't bring that up that was from so long ago that was from two weeks ago like we re-looked was from two weeks ago. Like, we re-looked at it. No, no, no. When you wrote the pact, I think she's talking about David. And did you hear her? She wrote it on her gymnastics page, like, next to a picture of her actual crush.

Like, I don't know how sincere. I mean, Lib, maybe I'm wrong. I mean, can you take stuff seriously when it's written in, like, rainbow gel ink? Brooke, you were on my side. Yeah, you were, Brooke. Yeah, but, David, you DM'd her, like, 80 times, man. Like, there's a difference between, like, touching on, like, the relationship you used to have and trying to build a new one and then just living in the past. Because that's what it feels like you're doing right now, David.

Okay, I have to ask this. This is weird. But have you been waiting for this, bro? Have you been trying to date all these years at least yes i haven't been waiting i've been dating and i'm very successful in business and it's just kind of hard to find someone that doesn't want to use you and that's why reconnecting with libby okay i just had to ask lib? What are you thinking, Lib? Oh my god, so much. Oh, David, I just, I have so much going on right now. Like, I just, I'm so busy all of the time. All of the time. Every single second. I mean, here's the thing, David. I think Libby is, I mean, obviously she values you as a person

and as an old friend, and she's trying to let you down gently right now, man. Brooke, that's not what I want to hear right now, okay? You are on my side, and your job is to call her and get her to go on a second date with me. Not break up with me. We have a pact. Break up? You're not in a relationship.

Which pact are we talking about, the one with Lib or the one that he made with Brooke before we made the call? Oh, relationship. Which pact are we talking about? The one with Lib or the one that he made with Brooke before we met? Which pact are you referring to? Oh my gosh, that was a joke. Now I'm starting to worry because he's taking these pacts seriously. That was a joke, David. He's writing the date down right now.

Well, let's just focus on Lib. Okay, Lib, I need to ask you, would you be willing to go out with David one more time? We will pay for that date yeah what about this what if we change the pact can we say 40 instead of 30 10 more years another 10 years you want to make an amendment i don't know what's gonna happen wait are you saying that because you actually would think about marrying him in 10 years or because you're just trying to

be nice i don't know where life's going to take us. I mean, I never thought I'd be where I am today, you know, and David, I really did truly have a good time with you, but I'm willing to extend the pact a little bit. It's like a contract extension.

Okay. You're almost, it's like almost like she's stringing you along at this point, David, are you going to take this? Oh yeah, I'm going to take it. Okay. You's almost like she's stringing you along at this point, David. Are you going to take this? Oh, yeah. I'm going to take it. Okay.

Yay. There you go. You're good with the contract extension. All right. Well, is it a successful second date update? I don't think so. Okay. I just think it's just putting off another really awkward phone call in 10 years.

I hope we're not doing this show anymore. Okay, David, well, you didn't get a second date, but you did get a notarized marriage back. Yeah, you got 10 more years till you end up with your dream girl. Well, thank you guys. Except for Brooke, you turned on me.

I couldn't help it then. Move in 92.5. 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. Hey, you guys. I'm Katherine Legg. I'm a racing driver who's literally driven everything with four wheels across the planet. And I've got a new podcast. It's called Throttle Therapy. This season, I'm competing in some of the world's most notorious racing events. Tune into my new podcast, Throttle Therapy, with Catherine Legg, an iHeart women's sports production in partnership with Deep Blue Sports and Entertainment. You can find us on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

Presented by Elf Beauty, founding partner of iHeart Women's Sports. I'm Dr. Laurie Santos, and to welcome the new year, my podcast, The Happiness Lab, is releasing a series of happiness how-to guides to help you in 2025. I'll distill the wisdom of world-class experts into easy-to-digest, actionable tips. Struggling with tough emotions?

We have a how-to guide. Worried that you're not enough? We got you. Self-obsessed and want to get over yourself? There's a guide for that too. The Happiness Lab's How-To Season starts January 1st. Listen on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.