Brooke and Jeffrey: Second Date Update - Say Yes To The Ex: College Crush

Episode Date: August 7, 2025

The woman on the phone today is hoping that someone from her college days still has the same feelings for her that she’s held onto since they graduated. We're going to see if we can get him to say YES to the Ex!See omnystudio.com/listener for privacy information.

What would you do if one bad decision forced you to choose between a maximum security prison or the most brutal boot camp designed to be hell on earth? Unfortunately for Mark Lombardo, this was the choice he faced. He said, you are a number, a New York State number, and we own you. Listen to shock incarceration on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Everyone thinks they'd never join a cult. But it happens all the time to people just like you. And people just like us.

I'm Lola Blanc. And I'm Megan Elizabeth. We're the host of Trust Me, a podcast about cults, manipulation, and the psychology of belief. Each week we talk to fellow survivors, former believers, and experts to understand why people get pulled in and how they get out. Trust me. New episodes every Wednesday on Exactly Right. Listen wherever you get your podcasts. I'm Bob Crawford, host of American History Hotline, a different type of podcast.

You, the listener, ask the questions. Did George Washington really cut down a cherry? Were JFK and Maryland Monroe having an affair? And I find the answers. I'm so glad you asked me this question. This is such a ridiculous story. You can listen to American History Hotline on the I Heart Radio app, Apple Podcasts, or wherever you get your podcasts.

I'm Jeff Perlman. And I'm Rick Jervis. We're a journalist and hosts of the podcast, Finding Sexy Sweat. At an internship in 1993, we roomed with Reggie Payne, aspiring reporter and rapper who went by Sexy Sweat. A couple years ago, we set out to find him. But in 2020, Reggie fell into a coma after police pinned him down, and he never woke up. But then I see, my son's not moving. So we started digging and uncovered city officials bent on protecting their own.

Listen to Finding Sexy Sweat on the iHeart Radio app, Apple Podcasts, or wherever you get your podcast. Every case that is a cold case that has DNA right now in a backlog will be identified in our lifetime. On the new podcast, America's Crime Lab, every case has a story to tell, and the DNA holds the truth. He never thought he was going to get caught, and I just looked at my computer screen. I was just like, ah, gotcha. This technology's already solving so many cases. Listen to America's Crime Lab on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. It's Brooke and Jeffrey in the morning

and this is your second date podcast. Thanks for being here. Today we got to say yes to the X. That's when someone writes our show and maybe wants to give an old relationship another try. We give them a helping hand to try to make that happen.

We do not believe it's called a breakup because it's broken. Okay, we don't believe that. Oh, I love that, bro. That was like an old book from the early 2000s or something. So you can quote anything and I'll think you're smart. Yeah, he was like a big self-help guy. Anyway, I'm on a tangent.

But we still have comments from yesterday's second date, the motivational speaker. Yes. And Shiny Candy said Brooke wasn't that nice in this one. Oh, M.G. I did not mean to be mean. I just don't think you could call yourself a professional if you're only paying yourself.

All right? That's just my only caveat. I was telling Ash and our technical director as comedians, we can have nobody come to our comedy shows. And I can still say one person showed up. Because you were there. That's me. Yeah.

Basically, we can be pros at anything and we want. If we're there. Okay. Brooke on a gymnast. Yeah. Sure you are. I like it, Jose. All right, let's start this episode right now.

It's say yes to the X. Do you think people change after college? I think so. I hope so. Yeah? I think they do. Mature. I mean, just look at us.

Alexis drinks way more than she did back in her school. I think I have a higher tolerance. Yeah. Slightly. Jose doesn't drink at all. Yeah. It rules. I mean, those four months that he wins.

You technically didn't go to college. It was community. No, he went for a little bit. Like, I think a semester. One semester. And I passed three classes. That's right. Out of six.

I'm sure that counts. I didn't go to those other three. And me, I'm way more peppy and energetic than I ever was back in my college days. What, Jeff? What were you just like the most depressing person on campus? Yeah, what? This is you energetic? Well, one of our listeners.

That was the most. laughing years guys. One of our listeners has reached out to us because she's been hoping and praying that someone from her college days still has the same feelings for her that she's been holding on to ever since they

graduated. It's a brand new edition of say yes to the X and we're going to do it right after this. I know in the movies and on TV shows they always have that sappy storyline of the one that got away. Because everybody has

one, right? Pretty much. I got mine. Got secured it. Well, not me. Yep. Okay. If I'm being totally honest, producer Boyd asked me that the other day, and I thought

through high school and college and even after that, like the closest thing I could remember to the one that got away was back in 2013 here at the station. Really? Do you guys remember Jana? Yeah? You do? I love Jana. Yeah.

Yeah, Jana. She was in front of me and took the last chocolate muffin in the break room. And I missed my chance with that muffin forever. I was going to say she was married. Yeah. I know. I was wondering where that was going. I have never gotten over it to this day.

I still think about where that muffin went. It's the same brand that they still are stocking. But it wasn't the muffin. The one. And that's the closest it's ever been for me. Your heart is so deep. Thank you for understanding my pain. One of our listeners apparently has a more romantic version of that story with

actual human not a piece of food for our latest edition of say yes to the ex yes oh my god i am loving this segment i think it's so fun yeah i mean it's fun if it works out if it doesn't it's you already broke up with them once that's true you got to give it you okay well let's talk to her because her name is jessica so jessica welcome to the show hi guys hey cheerful jessica i'm so excited to hear about who we're talking about Man, so basically, let me just start off by saying I have been dating. I just haven't met anybody that really, like, sparked anything. You know what I mean?

Okay. So you haven't been putting all your energy into your ex? No, no. But the thing is, is that every time anything starts to get serious or I think I really like someone, I just can't stop thinking about my ex. And everybody compares to him. Does he have a name? Does your ex have a name?

Oh, yeah. His name's Kent. Oh, that's a strong name. I feel like it's a rich name. Yeah. I feel like he's a TV broadcaster. Yeah, I thought of like superhero, like Clark Kent. Yeah, yeah, I mean, I just, no matter what, he's wearing an ascot to me.

We're all already in love with him, Jessica. So we're on board. We get it. I mean, we dated in college for like three years. Oh, that's a long time. He was the guy, right? Yeah. I don't know, he was popular.

He's good at sports. Like, so charming. Solid keg stand? Mm-hmm. She said he was athletic, obviously. Okay, he really is the one. Wow. So why did you guys break up?

I mean, after three years, what happened? So basically, like, at graduation time, I started getting more serious, not partying anymore, and he didn't want to settle down at all or stop partying or, you know. Yeah. I can see that leading to a lot of fights. Yeah. Right. I mean, not to take his.

side on this. I'm not on his side, but I could understand as a guy who, where everything is going great for you in college and you're the most popular guy and everybody loves you, why would you want to leave that situation? And in hindsight, I definitely rushed it, right? Like, I should have given him more time. Well, you've been together for three years. Well, yeah. I think every man should be allowed like 10 to 15 years time to mature fully into what they want to be. At the time, you'll just be single. Take it by yourself. That is a very good point.

So you guys went your separate ways, and it sounds like it probably was a pretty sad breakup, right? You were a pretty heartbroken. How did that go down? I was devastated, like sobbing all the time. I mean, I really thought he was the one. Yeah. Do you know anything about him now? Well, it's taken me a while to get to this point, but I talked to a mutual friend a couple weeks ago,

and they said that he's actually single now, and I'm single now. And? I was kind of hoping that maybe you guys could help me out, reach out to him. Hey, that's not about it. They say sometimes it's all about timing, right? He's single, but is he, like, still living in his parents' basement?

Like, I mean, seriously, like, going to old college parties. You remember, there's always, like, those old people that would show up, and you'd be like, why are you here? Yeah, we're the cool ones, bro. Yeah, still goes. Does he's got his life in order? Yeah, like, have you seen him on social media or anything? Can you tell anything?

Like, does he look the same? Does he have a better job? I mean, he's still super good-looking. I have not friend of him again because, like, I'm embarrassed. Yeah, but you've creeped. It's fine. Like, have you stalked his LinkedIn. Does he have a job?

I mean, okay, I didn't go all the way. Okay. But I just kind of fished around a little bit, and I know that he's single, and I just, I don't know. I want to ease into this, you know, guys. Okay. So this is going to be the first time that you've reached. reached out to him since your breakup. What is easing about that?

Oh, my goodness. I mean, girl. I'm sorry, but like, that's a lot. You haven't, even if he still likes you, that's a lot. Yeah, you haven't DM'd him. You haven't liked a picture, nothing? No, I have been, like, crickets on this guy.

Oh, my God. Okay. I mean, I'm not. That's exciting for us. I'm not sure if we've ever had a female reach out to us for say yes to the X before. Mostly it's dudes who have failed. So we really need a success today. Yeah.

I mean, I am very hopeful. I want this to happen. What would you say if you, okay, if your girlfriend contacted you from college years and years later, totally out of the blue, would you be excited? Oh, you're asking me? Yes. I didn't date anybody in college. Thanks for bringing that up again. Now, if the muffin reached out to me, oh my God, I would melt.

Did you not date anyone in college? Okay, sorry. Not seriously. Anyway, so we're going to call Kent here and try and get him to give you another show. Maybe meet up with you once more. Oh my God. Say yes to the X. Wow.

Interesting. You know, I've heard you guys do this before and it's just then back in my mind. So to be honest, I'm a little nervous here. That's what we're here for. I am too, but I'm excited, nervous. Like, it's good. It's good energy nervous. We all are nervous now.

We're going to come back. We'll call Kent for you and we'll see if he says yes to the X and do it right after this. If you're just tuning into this segment, we're doing something that we don't often do. on the show called Say Yes to the X. Oh, my God. We've gotten such good response, though, when we have done it, people love this segment. Even us, we love it. Very relatable for a lot of people where if a guy or a girl is years later still pining

after a former flame of theirs, they are brave enough to reach out to us and say, you know what, let's reconnect with that person over the radio. I mean, it is kind of a grand romantic gesture. It's bold. You take offs out of it, anyway. You can ignore a DM, but you can't ignore this call. We are kind of the sad version of this. But our listener, Jessica, is one of those courageous few individuals who has called us about her old college boyfriend of three years, Kent.

Oh, my gosh. I bet they were just Jess and Kent all over the place in college. They had a great relationship back then, but he afterwards really just wasn't ready to move on from his college days. And mature. So now it's been over a decade since their breakup. Has it been that long? We forgot to ask before. That's what she told us off the air.

They've done a little digging, found him on socials, learned that Kent is still cute. Yeah. And I know I'm going to date myself when I say this, but he's just got that Riz. Oh, yeah, baby. You know what I mean? We do know.

You did make it uncool. I don't think that's how it works. If I do it with jazz hands, he's got that Riz. No, that's worth. I think it's just he's got Riz, not that Riz. We don't even know if he has words. We haven't talked to him. That's true.

According to Jessica. Well, the most important part is she heard that he's currently single. So this is her opportunity to reach out and see if maybe they can reconnect. This is her shot. And since a friend told you he was single, maybe he's been putting a little word out there, too, that he's been wondering about you. You know what I mean? Oh, man, that would be a dream. Oh, that's so cute.

I hope that's the end of an all of us cry and sing you goodbye. They're off on your wedding. And I forget, Jeff, do we stay on the phone with them? Do they talk? Yes, this is a little bit different than the other segments that we do. We already have him on hold right now on the other line. He cannot hear us. Okay.

Okay, so we are going to do the segment. We've already. Sometimes the point. This is happening. Okay. And so the producer has talked to him. All that he knows is that someone is on the phone for him right now. He does not know what it's for.

Oh, my God. But, dude, his, when he realizes it's going to say so much. It's like opening a mystery door and seeing your ex. Oh, my gosh. This should be on Netflix. Yeah. So, but before we put you on with him,

is it okay if I talk to him just for a little bit? Yes, please. Okay. We'll talk her up. We'll just ease him in slightly to what this is, but let's punch him up right now. Be my hype man. Okay.

Yeah, don't steal her man. All right, here we go. Hey, Kent. Yeah, what's up? Hey, man, my name is Jeff from the radio show Brooke and Jeffrey. morning, the one that you're on right now, and I want to introduce you to somebody. Reintroduce, maybe is a better way to say. Hi, I'm Jose.

Nice to meet you. Welcome to Brooke and Jeffrey in the morning. Yeah. I'm a little confused about what's going on, but all right. It makes feel better. A lot of the listeners that come on this show feel the exact same way as you do. And I know this might sound a little bit awkward, but Brooke was right. I do want to reintroduce you to somebody.

from your past. Okay. I think it's somebody you might... This is going to be exciting for you. Yeah. We hope. Yeah, exactly. Do you remember a girl from your college days

named Jessica? Jessica, really? Wait, what? Yeah. Do you remember your girlfriend of three years from college? Hold on. You guys, why do you know that?

Oh, my God. Jessica has reached out to us because she says she still thinks about you sometimes and wants to know a little bit about how you're doing. Oh, my goodness. So she's on the phone right now. Why don't you go ahead and talk to her?

We're going to step away so you two can talk. Hi. Hi. Oh. Kent. Yeah, so, hi. Hi. I know this might be like a little bit of a surprise

and I'm sure it feels like it's coming out of nowhere for you but I guess basically the thing is is that even though it's been a while I still like think about you and I was just kind of wondering if like maybe there was any chance that maybe you still think about me from time and time deep breath maybe we should ask like a little small talkier question

like how's life how you been Yeah, you have a job. Remember how conversation works? Okay, Ken, I'm really sorry. I'm so nervous right now. I should have asked you how you are. How are you? There we go.

Everything's fine now. Well, I mean, I'm doing all right. Sure. Sure. I guess I think about you sometimes. Oh. Okay. That's good.

Okay. And never. And all you wanted to know? Oh. Um, I mean, that's awesome. But, uh, I, that's awesome. Cool, cool. Cool.

I was curious if maybe you'd want to catch up for real sometimes. I mean, is it just to catch up or maybe a bit more? What are you thinking? Well, I mean, we definitely have a lot to catch up on. But to be honest, like, I mean, I heard from a friend that now you're single, and I know you had been dating someone for a long time. So I thought maybe the timing right now might be, I don't know. Wow.

Good? Wow, I didn't really expect that when I woke up this morning. It's supposed to be a weird day. Happy surprises. For sure. I can get that. I mean, I think what she's asking for here, Kent, is just like a very casual meetup. She's not looking for anything.

Yeah, nothing. I don't want to, like, put too much pressure on it. I just want to. It's like, who knows? It's been over a decade for you, too. Maybe, maybe there's nothing there anymore, you know? Why are you assuming that? But, I mean, you know, like, you know I'm an optimist here.

Oh. And I got to tell you, like, I am getting pretty good vibes. And. Right now? He's like, sure, coffee. She's confident and direct. See? I mean, yeah, exactly.

It wouldn't hurt to hang out. Yeah. Hey, oh, my God. Okay, you want to hang out. Okay, cool. I'm actually going to have to break up with the guy that I'm dating. What? Wait, what?

Jessica, you didn't tell us when you called us that you were dating someone else. I mean, it's not like super serious. No. He's just a placeholder. Oh, God. Wait, you have a relationship by ending another one. You have a boyfriend? Okay, he's not a boyfriend, boyfriend.

He's more of like a... He's enough that you have to break up with him. Did we ask him that he didn't say this in the first part if she was like currently attached? It's an assumption, Jeff, that someone is going to be single. Future contestants, be single when you get on the show. Oh, my God, Kent. So you're dating someone and now you want to break up with them

and hang out with me. Oh, gosh. Maybe this is coming out wrong. I think it is. I just, I've always really liked you. And the way things ended, has never, like, really sat well with me. No, no, I totally get all of that. But what about this boyfriend that you're breaking up with?

I mean, he'll understand. He'll understand. He has heard all about you, Ken. I've actually said, every single night for, like, the last three years. I bet that's true, Jeffrey. She's like, yeah, you mean Kent, too? Yeah. Look, you guys are making it sound way worse than it is.

It really is more like a situation-smanship. Okay. All right. Now it's all right. Well, I guess congratulations. Yeah, I mean. It would be good, though. It would be good if we could do the breakup live on our show and get some extra content. No, Jeff.

Awkward Tuesday. Is that what you're thinking? Or say no to the current. Is that the new segment? I already text them, so we're good. Oh, wow. You didn't over text? Ouch. You were on the phone with us. You were quickly.

He really wasn't important. We don't even know that Kent doesn't still go to college parties. Oh, my gosh, he's right. I mean, it doesn't matter. He's got that Riz, remember? Yeah, we heard him now. We know. Okay.

I have a point. Yeah. Don't worry about it. You got it. Yeah. I'll explain it to you later. Yeah. Okay.

All right. So, we haven't even said what the name of the segment was, but officially, Kent, are you saying yes to the X? Oh, that's right. I feel like I'm saying yes to an ambulance. It's just as good. Congratulations, you two. Probably over quickly. I'll take it.

Oh, yeah. Well, we'll take it. this off there so you guys can organize when you want to meet up. Brooke and Jeffrey in the morning. American history is full of wise people. What women said something like, you know, 99.99% of war is diarrhea and 1% is gory. Those founding fathers were gossipy A.F. And they love to cut each other down. I'm Bob Crawford, host of American History Hotline, the show where you send us your questions

about American history, and I find the answers, including the nuggets of wisdom our history has to offer. Hamilton pauses, and then he says, the greatest man that ever lived was Julius Caesar. And Jefferson writes in his diary, this proves that Hamilton is for a dictator based on corruption. My favorite line was what Neil Armstrong said. It would have been harder to fake it than to do it. Listen to American History Hotline on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Imagine that you're on an airplane and all of a sudden you hear this.

Attention passengers. The pilot is having an emergency and we need someone, anyone, to land this plane. Think you could do it? It turns out that nearly 50% of men think that they could land the plane with the help of air traffic control. And they're saying like, okay, pull this.

Do this, pull that. turn this. It's just... I can do my eyes close. I'm Mani. I'm Noah. This is Devin. And on our new show, No Such Thing, we get to the bottom of questions like these. Join us as we talk to the leading expert on overconfidence. Those who lack expertise lack the expertise they need to recognize that they lack expertise. And then, as we try the whole thing out for real. Wait, what? Oh, that's the run right. I'm looking at this thing. See? Listen to No Such Thing on the I heart. radio app, Apple Podcasts, or wherever you get your podcasts. Well, I don't know how, but that just works.

Yeah. So funny. Do you guys, is Vine swinging still a term that people use? Yeah. I mean, I've heard it. I've never heard that ever. Oh, it's where you don't let go of one relationship until you have another in your hand, as if you're swinging from Vine to Vine.

People that have to be in relationships and can't be alone. Got it. Yeah. Vine swinging. You know, swinging. Yeah, you always keep one in your hand. I like it. official. Thanks, thanks. They'll be added, okay, and I'll be so Gen Z cool eventually.

Oh, no. What do people say on the comment board for this say yes to the ex? Oh, not a lot of fans of Jessica here. Oh, I'm shocked. Yeah, people like this girl are why relationships are so hard these days. Oh, no, big red flag. She literally broke up with a man on the radio. Poor Kent. Now he has the red flag. You can't get out of it. She's a nightmare, blah, blah, blah. Okay. But they sound happy. So, you know, on the phone. He was into it. Yeah, he was. I guess. Is there like an orange. orange flag she has or is it all red? Oh, I see. Like a middle ground.

Is there any other shade in there? I don't know. I think it's all red. All red from our fans anyway. Hey, thank you so much always for participating in this show. It means a world to us. And we'll be back tomorrow with a brand new second date update right here on Brick and Jeffrey in the morning. Every case that is a cold case that has DNA right now in a backlog will be identified in our lifetime. On the new podcast, America's Crime Lab, every case has a story to tell. The DNA holds the truth.

He never thought he was going to get caught. And I just looked at my computer screen. I was just like, ah, gotcha. This technology's already solving so many cases. Listen to America's Crime Lab on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Everyone thinks they'd never join a cult. But it happens all the time to people just like you. And people just like us.

I'm Lola Blanc and I'm Megan Elizabeth. We're the hosts of Trust Me, a podcast. about cults, manipulation, and the psychology of belief. Each week we talk to fellow survivors, former believers, and experts to understand why people get pulled in and how they get out. Trust me, new episodes every Wednesday on exactly right. Listen wherever you get your podcasts. What would you do if one bad decision forced you to choose between a maximum security

prison or the most brutal boot camp designed to be hell on earth? Unfortunately for Mark Lombardo, this was the choice he faced. He said, you are a number, a New York State number, and we own you. Listen to shock incarceration on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. I'm Jeff Perlman. And I'm Rick Jervis. We're journalists and hosts of the podcast Finding Sexy Sweat.

At an internship in 1993, we roomed with Reggie Payne, aspiring reporter and rapper who went by Sexy Sweat. A couple years ago, we set out to find him. But in 2020, Reggie fell into a coma after police pinned him down, and he never woke up. But then I see, my son's not moving. So we started digging and uncovered city officials bent on protecting their own. Listen to finding sexy sweat on the I-heart radio app, Apple Podcasts, or wherever you get your podcast. I'm Bob Crawford, host of American History Hotline, a different type of podcast. You, the listener, ask the questions.

Did George Washington really cut down a charity? Were JFK and Marilyn Monroe having an affair? And I find the answers. I'm so glad you asked me this question. This is such a ridiculous story. You can listen to American History Hotline on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts.