Brooke and Jeffrey: Second Date Update - Brooke Breaks You Up: High School Drama

Episode Date: July 23, 2026

For most people, high school drama ends when you graduate. But one of our listeners has a problem with his upcoming 20 year reunion and there’s only one person on this show who can save him! It's another edition of Brooke Breaks You Up!See omnystudio.com/listener for privacy information.

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On Raiders of the Lost podcast, we explore cinema like no one else, including huge interviews with stars like Ryan Gosling on Project Hail Mary. It was like the Jaws shark. Didn't always work, came with its own problems. That's what made it great. The cast of obsession.

On set, there was so much magic happening with each scene we were putting together. Deep dives into classics like 2001 of Space Odyssey or Fight Club, plus weekly episodes on all industry news. Listen to Raiders of the Lost podcast on the Iheart radio app, Apple Podcasts, or wherever you get your podcasts. And for more, follow at Raiders of the Lost podcast and at TikTok podcast network on TikTok. Hey, Portlandia fans. Carrie Brownstein and Fred Armisen here.

The Dream of the 90s is alive in podcast form. We're launching Podlandia, AEO rewatch, our brand new podcast where we revisit every episode of Portlandia together, breaking down sketches, going deep on our iconic characters, and pulling back the curtain on how it all got made. And we'll also be joined by the people who helped bring it all to life. Guest stars, collaborators, and friends, including director Jonathan Chrysall, the mayor himself, Kyle McLaughlin, legendary musician Amy Mann, and many more. Kyle is going for it here. You fully improvised, not just words, but a song about it.

Well, I thought you were all going to write a song. I remember you thinking that. Listen to Podlandia. A.O. Rewatch on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. What's up, fam? I'm sports journalist Ari Chambers. Hey, what's up, y'all? It's your girl, Sam J. And we're the host of Everyone Watches Women's Sports, a new podcast from Together and IHeart Women's Sports. We're breaking down the biggest headlines.

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across women's sports. Because everyone watches women's sports. Listen to everyone watches women's sports. On the IHeart Radio app. Apple Podcasts or wherever you get your podcast. Do we have to do today's podcast? We do, Brooke. We do.

And you know, I'm going to cut you off and say who's going to be happy about it, Brooke. It's someone who commented named Montanosaurus. Okay, why? Because they said this was the world. cup of segments never stop breaking people up, Brooke. Oh my God. Hey! Yeah. It's another Brooke breaks you up.

It's brand new and I was definitely not prepared for what I needed to do today. Yeah. A little extra twist that got added into this one. Oh, God. Why did he just dump her on his own? Okay. You're going to hear it. It starts right now. For most

people, your old high school drama should end once you graduate. Yeah, yeah. Unless you're me, and you're still furious at the drama teacher for casting you as bear number five in the nutcracker. I'm sorry. I didn't even know. That's what I'm saying. Are there bears in that plane?

Especially not five of them. I didn't think so. But one of our listeners has some old high school drama that's bubbling back up to the surface. Uh-oh. Because his 20-year reunion is about to happen. And there's only one person on this show who he thinks can come to his rescue. Bear number five? It's not bear number five.

It's somebody else, and you're going to find out right after this. Every time we do this segment, Brooke says those famous three words. Oh, God, no. Yes. My favorite. It's Brooke and Jeffrey in the morning, so you're in luck if you're listening. I don't want to today. Because it's time for Brooke breaks you up.

Yeah. Brooke is smiling with joy because it's a fun little thing that we do from time to time. here when we receive emails from listeners and they say, hey, I've got some dead weight in my apartment. It's the person I'm dating. And I don't want to be with them anymore. But I also don't feel like telling them that myself. Because I'm not brave enough.

So I would have Brooke do it for me. That's right. Can you unleash Brooke's fury onto my significant other and tell them that it's over? I shook that off. Okay, I just had a moment there. I'm back in. No, keep channeling that energy. That's exactly what we need here, Brooke.

Because while on the outside, she has said that she despises doing this, I've heard from good sources that when Brooke goes home at night, she high-fives her children and kisses her husband right on the mouth, saying, another great day in radio. I just ended a relationship. And Brooke, I know you might think I think less of you for it. Oh, I don't really care what you think of me. But, yeah?

I don't, Brooke. I appreciate you. I appreciate all the people who get down into the gutters and do the dirty work for us. And today we have a listener named Pete who's requesting Brooks' expertise. Pete, welcome to the show, my man. Hey, thank you for having me. Can you please tell me it's a boyfriend I'm dumping because I'm really much better at dumping men than I am at women. I'm just saying I have more experience doing it.

I've been there. They cry less, which is helpful. I mean, not healthy, but helpful. I could tell you that, but I'd be lying. Oh, so who do you want to break up with today? So I think I should break up with my girlfriend, Jess. Why do you only think? You're not sure?

We need to know going into this, P. Well, can I give you just some backstory? Brooke, do you want any backstory? Just want to get right to the dumping. No, I want backstory. Of course. What's wrong with Jess? What's going on?

Okay, so a few years ago, her and I were both with other people. Okay. Okay, in relationships. Yeah, you're in. Yeah. And then it had been a very long time since I'd seen her. Oh.

How did you know her? from before? We used a date in high school. Oh, you're an old high school boyfriend. So it wasn't just your friend in high school. You actually kissed. Yeah. Brooke, why did you scoff at old high school relationship, though? Just because my old high school boyfriend makes me me, you know? I agree on that. But sometimes that's a good thing. Well, obviously not

if he wants a dumper. Okay, well, I'm sure Pete is not the same as your exes back in high school, Pete. What was your high school relationship like? Oh, it was great. Like we, I mean, we broke up because we went to college, you know. It's like, we just moved away. Yeah. But we reconnected on Facebook. I think I, like, sent her a happy birthday message.

She was like, oh, my God, I haven't seen you in all these years. How are you? I didn't hear once you hit a certain age. Everybody messages everybody happy birthday on Facebook. No. I heard that thing. I don't think they're that that age yet. I think that's more my mom.

You just misinteracting with people in general. So anybody, okay. But at this point, you two are still in relationships when you're messaging on Facebook, right? Correct. Okay. Okay. But next thing I know, we're having coffee. Oh, goodness. Oh, my. Are we telling our significant

other that we're meeting up with our ex-girlfriend from high school to have coffee? No. Oh, no, this feels a little off. Yes. But it's just coffee. Well, at that point, it was just coffee. But then we're saying like, wow, this is way more fun than hanging out with our boring relationship.

Oh, chemistry. Okay. Okay. The sparks rekindling. We started like sneaking out to meet each other. Oh, I thought you were going to say, so we broke up with our significant others and started dating. Yes, that is the responsible thing to do. This is the fun thing to do. Yeah. And, you know, I got a new apartment.

She moved in. What? Whoa, hold on, hold on, hold on. Wait, are you still moved in? Just did. She moved in. While you were still in a relationship with someone else? Well, I mean, like.

Oh, okay. Oh, my gosh. So you had an affair. It was just, it was really good for a while. It was like new and exciting. And, you know, we were back together after like 15 years. It was like just really, it was exciting. Are you saying you want Brooke to break up with your current girlfriend?

Which girlfriend, Jeff? And tell her that you're going to be moving in with your ex from high school? You mean the ex that's already living with him? That was a long time ago. That was years ago. Oh. Okay. So that breakup already happened.

So you're just establishing that the relationship you started with Jess was, not clean. Yeah. But very hot and romantic. I bet. Thank you. Yeah. That was just the back story.

Okay. That's how you and Jess came to be. And now we're only dating Jess. Is that true? That is correct. Okay. Until his middle school girlfriend showed up. Oh, man.

I mean, which is pretty boring to Pete, right? Okay. So that already happened. Where are you now? This is the thing. Fast forward, just like a few months ago. We both got messages saying that there was going to be our 20th high school reunion. Oh.

And I'm thinking, how cool is that? Like, everyone's going to see us and say, like, my God, those two are still together? Yeah. Yeah, that's true. And we'd say, like, we were always meant to be with each other. Oh, okay. So you really love Jess. Well, then why do you want to break up with her?

What is happening? I'm assuming you do. Now I'm not sure what's going on. Well, okay, because of this reunion, they started this new Facebook group for it. And now she's been talking to another guy she used to date in high school. Oh, yeah. You know, every relation ends like it begins, my friend. That's what they say. Did you know this other guy that she dated?

Oh, yeah. I have a nickname for him. D'S dhastani. Okay, we'll have to bleep that one. I'm not going to use that nickname, my man. Okay. You weren't a fan. No. Like, sometimes I'll come home from work and she'll be chatting with him on Facebook.

It's like it's open on her iPad. Yeah. Oh, okay. So she doesn't even care that you see. Yeah. What's their conversations like? He's being really flirty, and she's not, like, shutting it down. Yeah, not so f***less now.

Well, and then this is the other thing. It turns out she had coffee with him recently, just like we eat it. Yeah. Oh, my, we know that's her game. The story's just repeating itself with another guy now. It always does. Oh, my God. That thinks that this could still be, like, his intent at first.

It's an old high school friend. What if that's her mindset, too? Jose, I can't reach you. But I would pat you on the head right now and say, oh, you poor boy. I'm like, someone's got to say it. What if? But he read the messages. That's what's hard.

I know. So, okay. It was a hard. Why haven't you just talked to her about this? Why are you wanting to just immediately go to breaking up with her? Well, I guess this is the thing. Maybe Brooke, you can get it out of her. Like, you do your magic.

And if she didn't cheat on me, then maybe he just played off like it's a prank call. I don't know. You want information and if you get confirmation, then it's over. So I'll end it with, this is Brooke. We're doing a phone tap on you. Your boyfriend thought it would be really funny to accuse you of cheating. Brooke and Jeffrey in the morning. I can't wait to see what your magic is, Brooke.

They're talking about. That's the thing. We don't actually have, do you have any actual proof that anything besides the conversations on Facebook is going on? It's the coffee and the flirty. And that is just making me nervous. And it's the conversation. And it's a copy and the flirty and the history. Yeah.

You know? We'll take a break. We'll let Brooke compose herself. And then when we come back, Brooke is going to call your current but former ex-girlfriend, now current again. Don't make it so messy, Jeff. Yes. And break you up. That is if she's cheating.

Unless she's not cheating and she'll call it a prank. This is a good title. I like this title. Best segment ever. We'll do it right after this. Hold on. History repeats itself on a special edition of Brooke breaks you up. Oh, boy.

Because you're just messy. It's because that's the messy part. Yeah, it's a little tricky because a few years ago, our listener Pete got back together with his old high school crush thanks to Facebook. Yeah. And it wasn't on the up and up. He was still dating someone. She was still dating someone.

They were secretly dating each other. There were some hiccups. Yes. They were both technically and exclusive relationships. At the time that this all happened Things did get messy But eventually worked its way out Where now they live together

Yeah At least for the moment Because what happened recently Their 20 year high school Reunion announced it was coming up And now his girlfriend is suddenly Talking to a different guy That she used to date back in high school

On Facebook again And she's already met up with him for coffee Oh she already did meet up with coffee I thought it was coming up. Okay. Yeah, copy happened. If she didn't tell you about it, you only know from the messages that you saw. Yeah.

So all of this is why Pete is asking Brooke to do a little digging and find out what's really going on between his girlfriend, Jess, and this new old guy named Donnie from high school. Old guy, you make him sound like he's 80. If we find out that Jess is cheating or just what is our percentage here, we're 90% sure that Jess is. cheating. Or thinking about it. You want me to break up with her. Yeah, I mean, I'm pushing more like 60, 40%. Oh. Also, I forgot to tell you that she loves you, Brooke. She loves the show.

Oh, she listens? Yeah, she listens. So that might be good for me. Well, it'd be good because maybe since she's familiar with you, she'd be more willing to open up and tell you about her feelings. Yeah, come on, girl. As soon as I do this, this will be great. Then I'll be back to my only fan being my mom. All right, so we're going to dial your girlfriend, Jess.

Brooke's going to do her magic. Are you ready? No. Thank you. I was not asking you, Brooke. I was asking Pete. I know, but I'm still going to answer the question, Jeff. Thank you so much, Brooke.

I appreciate you. All right, you got this. I'm dialing Jess's number right now. Here we go. Hello? Hey, is this Jess? Yes. Who is this?

Okay. Hi, Jess. This is Brooke from Brooke and Jeffrey in the morning. First, we wanted to call and say thank you for listening. I'm sorry, what? Did you just say Brooke? Yeah. Yeah, it's me.

No. What? Oh, Jess. No, no, no, no. Wait, wait, why? Am I on the radio right now? Yeah. Yeah.

Welcome to the show, Jess. I'm so glad you're here with us. This is crazy. I know. I've always wanted this to happen. Okay. I don't know what you wish for. Yeah.

Yeah. So, Jess, it gets a little bit crazier because we did have someone email us about you. Okay. Yeah. What did they say? Well, they said that you are very excited about your 20-year high school reunion coming up. Right? Oh, yeah.

Why did they say that? Okay. First, okay, wait, just tell me, how are you feeling about it? Who are you excited to see? I don't, a lot of people, I don't, like, I did have a thing for, like, the assistant principal back in the day. Yeah. I bet maybe more like your classmates.

Like, is there any anybody you haven't seen in a long time or maybe someone that you're really excited about reconnecting with? No, I mean, like, I dated a lot back then. But I was just like having fun. So it's just, I think it'll be fun to reconnect. I don't take it too seriously. Okay. I mean, Facebook's a great way for people to reconnect.

Is there anybody you've been talking about? talking to like pre-reunion? Nice. No, I mean, I talk to a lot of people on Facebook. I mean, everyone does, right? How much you like coffee? Do you like coffee a lot? I go out for coffee, yeah. I mean...

Cool. Are you asking her out for coffee, bro? No, not really. Oh, okay. Are you asking her to be friends on Facebook? You guys, I've never figured out how to figure this stuff out. Yeah, what about her boyfriend? Hey, how about your boyfriend, huh?

No, Jess, honestly, are you going to the reunion with your boyfriend? Oh, well, I mean, I guess I'm going to have to talk with Pete before the reunion and I don't know. Yeah. Okay. Are you, I mean, that would be cute, right, for you two to show up together again? How is that going to feel to announce to everybody? I mean, it'll be interesting, I'm sure, just like him seeing all the people that like we haven't seen in a long time. Yeah.

Hey, babe, surprise. It's me. I'm on the phone. Oh. We haven't found anything out yet because I'm terrible at this, Pete. Brooke was never going to get there. What is going on? Like, are you guys joking? Like, why are you, Pete, what are you doing? We're not joking. We're laughing, but we're not joking.

I'm not sure exactly what we're doing. Pete, why don't you talk to your girlfriend? Yeah, I hit them up. I got Brooke to try to find out. I know you've been talking with Donnie, and I'm not going to say my nickname for him because we're on the radio. Oh, we're just going to say it. You already said the nickname, like, twice, my man.

Okay. Anyway, Donnie, and I didn't tell these guys this, but I know that you sent him picks as well of yourself. What? Why would you just let me break up with her? Brooke, hold on. This isn't about you. It's about them and the really hot picks that apparently she's sending it. What more proof did he need?

Yes. Wait, there's. Jess, there's picks. Okay, and so? What? What? You just send picks of yourself. to guys who aren't your boyfriend?

So, okay, this is really hard out of context, but, like, I just, I told him I lost a lot of weight in the last five years, and so I just showed him my before and afters. It's not a bad big deal. The topless? Oh, they're topless. What about.

Okay. Look, I'm proud. I'm not ashamed. Like, I look good. What's the big deal? Well, the... Okay. You imagine those way around.

Can you show the picture that the assistant vice principal? Those as well? I don't think you want to ask that question. Yeah. Yeah. Yeah. Sure. Look, honestly.

if I was friends with him on Facebook, maybe. Oh, wait. Okay. No, honestly, I just want clarification. I just need to know, are you interested in Donnie? No, what? You're sure? That's crazy.

I, yes. Like, look, he's an old boyfriend. It's innocent flirting. Dave, we're good. You just called it flirting. I get that's what it sounds like, and it's hard to talk my way out of it, but I promise I have no feelings for him. I'm comfortable in my body.

No. That's even worse. No. No, no, no, no. No, no. We're not going to let you get away with that. Oh, Judge. You start taking a relationship.

She just said it. Brooke, rogue break up with her right now. You have the power. Jess, this is how you started your relationship with Pete. This is how you're going to start the relationship with Donnie. You're already sending him pictures. You're already calling it flirting. Just break it off, girl.

Move on to the next guy cleanly. Brick, Rick, honestly, I believe her. Like, if she says that she doesn't have feelings for, Johnny, I believe her. Oh, my guy. Brooke? I mean, he knows me. Brooke, like, you don't know me like that.

So, Pete, I'm, thank you for believing me. And I'm glad that we can move on. Thank you. That's right. I got you, babe. I got you. Oh, man. Look at that.

Stayed together. Brooke almost broke up a happy couple. But her cold heart couldn't shatter the warmth of this loving relationship. Oh, man. Good luck, Jess and Pete. When you go. Love wins once again. Oh, man.

Laughing right in Brooklyn. They're going to be voted cutest couple at the reunion. Oh, yeah. Yay. It's going to happen. Brooke and Jeffrey in the morning. Get Bell, Pure Fiber Internet with Crave, Netflix, and Disney Plus from $94 a month. Price guaranteed for two years on internet with a two-year term and auto pay credit.

Visit bell.com.com for details and to check availability. Bell, connection is everything. I'm Nick Tuturo. You probably know me from NYP. Pee-D-Blue, the longest yard, or Spike Lee's Black Klansman. But I'm also from Queens, which means I know pizza. And on my new podcast, delivering happiness with Nick Totoro, I deliver pizza from Prince Street Pizza to a new guest.

Are you delivering pizza now? Then we sit down for a real conversation. I've shared a slice with everyone, from Seth Rollins. What are you doing, my belt? To Alex Rodriguez. Just to let you people know, we're talking to one of the goats here. To Bill Burr. I don't think I've ever met somebody so exactly out of their mind.

Yes, I am. And now we even have more great guests coming up, including the great John Tuturo. It's called Happiness. Delivering happiness. Mariano Rivera. Oh, my God. And many, many more. Open your free high-heart radio app.

Search Delivering Happiness with Nick Totoro. And listen now. Brooke, the text board's blowing up right now. It's 7-8-5-9-2. I bet it is. One person said maybe you should change the title of this from Brooke breaks you up to Brooke judges and shames you for finding true love. Okay, it is not true love.

She's sending picks to other dudes. That's the true love you want to be in. I felt like that was the best part of this. I'm just thankful that finally someone says it's okay that if you're in a relationship, you can send photos to other people. As long as you preface it with, it's about my weight loss journey.

Yeah. Even if they're talking. Yeah. It's totally fine. It's a weight loss thing. You lose weight in your chest too. It's true. I mean, unfortunately.

Yeah. Oh, so when I lose weight, I'm going to send certain picks too because it's probably going to get smaller? Yeah. I mean, that's what they want is smaller picks. And when you take your clothes off, that's just more weight that you're shedding. That's a good point.

I never weigh myself with clothes on. Yes. Which makes the doctor awkward. I'm happy that we have come to a happy conclusion here. That's what we've learned today. You know what? I don't know why divorce rates are so high. Me either.

Doesn't make sense. But if you need some help with your personal life, you can always email the show. If you need Brooke to break you up. Yeah, I'm glad you guys talk to me out of this whole thing. Yeah. Email us. Find us on our podcast, too, at Brooke and Jeffrey. On Raiders of the Lost Podcast, we explore cinema like no one else, including huge interviews with stars like Ryan Gosling on Project Hail Mary.

It was like the Jaws Shark. Didn't always work, came with its own problems. That's what made it great. The cast of Obsession. On set, there was so much magic happening with each scene we were putting together. Deep dives into classics like 2001 of Space Odyssey or Fight Club. Plus weekly episodes on all industry news. Listen to Raiders of the Lost podcast on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts.

And for more, follow at Raiders of the Lost Podcast and at TikTok Podcast Network on TikTok. My first guest is Paris Hilton, Shakira, Luke and Yerrin. Have surprises? Many surprises. Welcome to the Sweet 305 podcast, where the group check comes to What a lot? You're the only person I know that loves a yellow starburst.

It's lemonade. This is Sweet 305. Here, oversharing is encouraged. Listen to Sweet 305 with Lele Pons on the IHeartRadio app, Apple Podcast, or wherever you get your podcasts. Hey, Portlandia fans. Carrie Brownstein and Fred Armisen here. The Dream of the 90s is alive in podcast form. We're launching Podlandia A.O. rewatch, our brand new podcast where we revisit every episode of Portlandia together.

breaking down sketches, going deep on our iconic characters, and pulling back the curtain on how it all got made. And we'll also be joined by the people who helped bring it all to life. Guestrars, collaborators and friends, including director Jonathan Chrysall, the mayor himself, Kyle McLaughlin, legendary musician Amy Mann, and many more. Kyle is going for it here. You fully improvised, not just words, but a song. Well, I thought you were all going to write a song. I remember you thinking that.

Listen to Podlandia. A.O. Rewatch on the Rewatch on the RON. IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. What's up, fam? I'm sports journalist Ari Chambers. Hey, what's up, y'all? It's your girl, Sam J. And we're the host of everyone watches women's sports, a new podcast from Together

and IHeart Women's Sports. We're breaking down the biggest headlines. Naomi Osaka, showing out. Shout out to you, Naomi. The viral moments. I've been obsessed with Kashan Rock's boxing journey. She looks good. Her combos are swift.

And the stories everyone's talking about across women's sports. Because everyone watches women's sports. Everyone everyone watches women's sports on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. I'm Nick Totoro. You probably know me from NYPD Blue, The Longest Yard, or Spike Lease Black Klansman. And on my new podcast, delivering happiness with Nick Tatoro, I deliver pizza to a new guest. I've shared a slice with everyone from Seth Rollins. What are you doing my belt?

To Bill Burr. I don't think I've ever met somebody so exactly out of their mind as I am. And now, we even have more great guests coming up, including the great John It's called Happiness. Delivering happiness. And many, many more. Open your free high heart radio app. Search Delivering Happiness with Nick Tutoro. And listen now.