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Jeffrey
This is Troy Millings from Earn your leisure. When you think about discovering small brands, what store pops in your mind? Well, it should be Walmart. Seriously, Walmart has thousands of small brands and they're all in one place. Just go online or in store, discover and shop. It could not be easier. Every one of these brands has a real story and real people behind it. They're true American success stories and you can find them all at Walmart. Discover thousands of small brands@walmart.com today.
Brooke
The breakup no one saw coming has hit the freezer aisle. Cherry, Orange and Grape Popsicle Ice Pops are going solo. Now fans must pick a side and help crown the Flavor Feud champion with a chance to earn a long term solo spot on freezer shelves. Pick up the Cherry, Orange and Grape Popsicle Ice Pop variety pack to experience all three iconic flavors and decide where your loyalty lies. And then vote by shouting out your favorite on Social and don't forget to follow the flavorfood drama all summer long on Instagram at Popsicle. Hey Portlandia fans, Kerry Brownstein and Fred Armisen here.
Jeffrey
The dream of the 90s is alive in podcast form.
Brooke
We're launching Podlandia AO 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.
Jeffrey
And we'll also be joined by the people who helped bring it all to life, guest stars, collaborators and friends, including director Jonathan Krisel, the mayor himself, Kyle McLaughlin, legendary musician Amy Mann, and many more.
Brooke
Kyle is going for it. Here you fully improvised, not just words, but a song.
Jeffrey
Well, I thought you were all going
Pete
to write a song.
Brooke
I remember you thinking that. Listen to Podlandia AO rewatch on the iHeartRadio app, Apple Podcasts or wherever you get your podcasts. This is Chelsea Handler from Dear Chelsea. Every week the news gets worse, the
Jess
world gets crazier, and Yamanika is here
Jeffrey
to tell whoever's responsible, you're the do you know, I just found out who Sydney Sweeney was.
Brooke
If he got a bunch of women,
Jeffrey
then I should have a bunch of men do better or do less so I don't have to do so much.
Brooke
I'm Yamanika and I'm out. Listen to youo're the Problem with Yamanika on the iHeartRadio app, Apple Podcasts or wherever you get your podcasts.
Jeffrey
I'm Nick Turturro. You probably know me from NYPD Blue, the Longest Yard, or Spike Lee's blackkklansman And on my new podcast, delivering happiness with Nick Turturro, I deliver pizza to a new guest. I've share slice with everyone from Seth Rollins. What are you doing?
Pete
My belt.
Jeffrey
To Bill Burr.
Brooke
I don't think I've ever met somebody
Jeffrey
so exactly out of their mind as I am. And now we even have more great guests coming up, including the great John Turturro. It's called happiness, Delivering happiness and many, many more. Open your free iHeartradio app search delivering happiness with Nick Turturro and listen.
Brooke
Now, do we have to do today's podcast? We do, Brooke. We do. And you know, I'm gonna cut you off and say who's gonna be happy about it? Brooke is named Montanasaurus.
Pete
Okay. Wow.
Brooke
They said this was the world cup of segments. Never stop breaking people up.
Jess
Brooke.
Brooke
Oh, my God. 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, extra twist that got added into this one. God, why did he just dump her on his own? Okay, you're gonna hear it. It starts right now.
Jeffrey
For most people, your old high school drama should end once you grad.
Brooke
Well, yeah, yeah, it should.
Jeffrey
Unless you're me and you're still furious at the drama teacher for casting you as bear number five in the Nutcracker.
Brooke
I'm sorry, I didn't even know that's what I'm saying.
Jeffrey
Are there bears in that place?
Brooke
Especially about five of them?
Jeffrey
I didn't think so. But one of our listeners has some old high school drama that's bubbling back up to the surface 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.
Brooke
Bear number five.
Jeffrey
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. Yeah, it's Brooke and Jeffrey in the morning. So you're in luck if you're listening because it's time for Brooke breaks you up.
Mandy Woodruff Santos
Yeah.
Jeffrey
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.
Brooke
So I would Have Brooke do it for me.
Jeffrey
That's right. Can you unleash Brooke's fury onto my significant other and tell them that it's over?
Brooke
I took that off, Okay? I just had a moment there. I'm back in.
Jeffrey
No, keep channeling that energy. That's exactly, 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.
Brooke
Oh, I don't really care what you think of me. Yes.
Jeffrey
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.
Pete
Hey, thank you for having me.
Brooke
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. Not healthy, but helpful.
Pete
I could tell you that, but I'd be l. Oh.
Jeffrey
So who do you want to break up with today?
Pete
So I think I should break up with my girlfriend Jess.
Brooke
Why do you only think you're not sure? We need to know going into this, Pete.
Pete
Well, can I give you just some
Jeffrey
backstory, Brooke, do you want any backstory? Just want to get right to the dumping.
Brooke
No, I want backstory. Of course. What's wrong with Jess? What's going on?
Pete
Okay, so two years ago, her and I were both with other people.
Brooke
Okay.
Jeffrey
Okay. In relationships?
Brooke
Yeah. You're in.
Pete
Yeah. And then it had been a very long time since I'd seen her.
Brooke
How did you know her from before?
Pete
We used to date in high school.
Brooke
Oh, you're an old high school boyfriend.
Jeffrey
So it wasn't just your friend in high school you actually, like, kissed? Yeah.
Pete
Yeah.
Jeffrey
Brooke, why did you scoff at old high school relationship?
Brooke
Just because my old high school boyfriend makes me, you know, I agree on that, but sure. Well, obviously not if he wants to dump her.
Jeffrey
Okay, well, I'm sure Pete is not the same as your exes back in high school.
Brooke
Maybe.
Jeffrey
What was your high school relationship relationship like?
Pete
Oh, it was great. Like, we. I mean, we broke up because we went to college, you know, 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?
Brooke
I do hear once you hit a certain age, everybody messages everybody. Happy birthday on Facebook. No, I don't think they're that bad. I think that's more my mom.
Jeffrey
You just miss interacting with people in general. So, anybody.
Brooke
Okay, at this point, you two are still in relationships when you're messaging on Facebook, right?
Pete
Correct. Yeah.
Jeffrey
Okay.
Jess
Okay.
Pete
But next thing I know, we're having coffee.
Brooke
Oh, good.
Jeffrey
My.
Brooke
Are we telling our significant other that we're meeting up with our ex girlfriend from high school to have coffee?
Pete
No.
Jeffrey
No, but it feels a little.
Brooke
Yeah.
Jeffrey
Yes, but it's just coffee.
Pete
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 chemistry.
Jeffrey
Okay, okay. The sparks rekindling.
Pete
Yeah. We start, like, sneaking out to meet each other.
Brooke
Oh, I thought you were gonna say. So we broke up with our significant others and started dating.
Jeffrey
Yes. That is the responsible thing to do. This is the fun thing to do.
Pete
Yeah. And, you know, I got a new apartment. She moved in.
Jeffrey
Hold on, hold on, hold on.
Brooke
Wait. Are you still moved in?
Pete
Just did.
Brooke
She moved in while you were still in a relationship with someone else?
Pete
Well, I mean, like.
Jeffrey
Oh, my God. So you had an affair?
Pete
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.
Jeffrey
Are you saying you want Brooke to break up with your current girlfriend? Which.
Brooke
Which girlfriend? Jeff.
Jeffrey
And tell her that you're going to be moving in with your ex from high school?
Brooke
You mean the ex that's already living with him?
Pete
That was a long time ago. That was years ago.
Jeffrey
Oh, okay, so that breakup already happened.
Brooke
Okay, so you're just establishing that the relationship you started with Jess. Not clean.
Jess
Yeah.
Jeffrey
But very hot. Romantic. I bet.
Pete
Thank you. Yeah. That was just the backstory.
Jeffrey
Okay.
Brooke
Okay.
Jeffrey
That's how you and Jess came to be.
Brooke
And now we're only dating Jess. Is that true?
Pete
That is correct.
Jeffrey
Okay.
Brooke
Okay. Until his middle school girlfriend showed up. I mean, which is pretty boring to Pete.
Jess
Right?
Jeffrey
Okay, so that already happened. Where are you now?
Pete
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.
Brooke
Oh.
Pete
And I'm thinking how cool is, like, everyone's gonna see us and say, like, my God, those two are still together.
Brooke
Yeah.
Jeffrey
Yeah, that's true.
Pete
And we'd say, like, we were always meant to be with each other.
Brooke
Okay, you really love Jess.
Jeffrey
Well, then why do you want to break up with her? What is happening? Well, I'm assuming you do now. I'm not sure what's going on.
Pete
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.
Brooke
Oh, yeah. You know, every relation ends like it begins. My knows what they say.
Jeffrey
Did you know this other guy that she dated?
Pete
Oh, yeah. I have a nickname for him was Donnie.
Jeffrey
Okay, we'll have to bleep that one.
Brooke
I'm not going to use that nickname, my man.
Jeffrey
Okay, you weren't a fan.
Pete
No. Like, sometimes I'll come home from work and she'll be chatting with him on Facebook like it's open on her iPad.
Brooke
Yeah. Okay, so she doesn't even care that you see. Yeah.
Jeffrey
Yeah. What's their conversations like?
Pete
He's being really flirty and she's not, like, shutting it down.
Brooke
Yeah, not so now.
Pete
Well, and then this is the other thing. It turns out she had coffee with him recently just like we did.
Jeffrey
Oh, my God.
Brooke
That's her game.
Jeffrey
The story's just repeating itself with another guy now.
Brooke
It always does that.
Jeffrey
This could still be, like, his intent at first. It's an old high school friend. What if that's her mindset? Jose, I can't reach you, but I would pat you on the head right now and say, oh, you poor boy. I don't think someone's gotta say it. What if, like.
Brooke
But he read the method messages. That's what's hard.
Jeffrey
And it's hard.
Brooke
Why haven't you just talked to her about this? Why are you wanting to just immediately go to breaking up with her?
Pete
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 just played off like it's a prank call. I don't know, information. Then it's okay.
Brooke
So I'll end it with, this is Brooke. We're doing a phone tap on you.
Jeffrey
Your boyfriend thought it'd be really funny to accuse you of cheating.
Brooke
Yeah.
Jeffrey
Brooke and Jeffrey in the morning.
Brooke
I can't wait to see what your magic is Brooke that he's talking about.
Jeffrey
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.
Pete
It's the coffee and the flirty, and that is just making me nervous.
Brooke
And it's the coffee and the flirty and the history.
Jeffrey
Yeah. You know, we'll take a break, we'll let Brooke compose herself, and then when we come back, Brooke is gonna call your current but former ex girlfriend now current again.
Brooke
Don't make it so messy, Jeff.
Jeffrey
Jess. And break you up.
Brooke
That is. That is if she's cheating.
Jeffrey
Unless she's not cheating and she'll call it a prank.
Brooke
Yeah, this is a good title. I like this title.
Jeffrey
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.
Brooke
Because this is messy is cuz. That's the messy part.
Jeffrey
It's. 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.
Brooke
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.
Jeffrey
There was some hiccups. Yes. They were both technically in 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.
Brooke
Oh, she already did meet up with coffee. I thought it was coming up. Okay.
Pete
Yeah, coffee happens. Okay.
Brooke
If she didn't tell you about it, you only know from the mess messages that you saw.
Jeffrey
Yeah. 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.
Brooke
It's an old guy.
Jeffrey
You make him sound like he's Asian.
Brooke
If we find out that Jess is cheating or just what is our percentage here? We're 90 sure that Jess is cheating
Jeffrey
or thinking about it.
Brooke
Yeah. You want me to break up with her?
Pete
Yeah, I mean, I'm pushing more like 60, 40%. Also, I forgot to tell you that she loves you. Brooke. She loves the show.
Jeffrey
Oh, she listens.
Pete
Yeah, she listens. So that might be good for me.
Jeffrey
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, sit on the tea.
Brooke
As soon as I do this, this will be great. Then I'll be back to my only fan being my mom.
Jeffrey
All right, so we're gonna dial your girlfriend, Jess. Brooke's gonna do her magic. Are you ready?
Pete
No, thank you.
Jeffrey
I was not asking you, Brooke. I was asking you.
Brooke
But I'm still gonna answer the question.
Pete
Jeff, thank you so much. I appreciate you.
Jeffrey
All right, you got this. I'm dialing Jess's number right now. Here we go.
Jess
Hello?
Brooke
Hey, is this Jesse?
Jess
Yes, who's this?
Brooke
Okay. Hi, Jess, this is Brooke from Brooke and Jeffrey in the Morning. First we wanted to call and say thank you for listening.
Jess
I'm sorry, what did you just say? Brooke?
Brooke
Yeah, yeah, it's me.
Jeffrey
No.
Pete
What?
Brooke
Oh, Jess.
Jess
No, no, no, no, no. This is. Wait, why am I on the. Am I on the radio right now?
Brooke
Yeah, yeah, yeah. Welcome to the show. Jess, I'm so glad you're here with us.
Jess
This is crazy. This is. I've always wanted this to happen.
Brooke
Okay. What you wish for. Yeah. So, Jess, it gets a little bit crazier because we did have someone email us about you.
Jess
Okay.
Brooke
Yeah.
Jess
What did they say?
Brooke
Well, they said that you are very excited about your 20 year high school reunion coming up. Right?
Jess
Oh, yeah. How. Why did they say that? Okay, first.
Brooke
Okay, wait, just tell me, how are you feeling about it? Who are you you excited to see?
Jess
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,
Brooke
Okay, 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?
Jess
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. I don't take it too seriously.
Brooke
Ok. I mean, Facebook's a great way for people to reconnect. Is there anybody you've been talking to? Like, pre reunion?
Jeffrey
Nice.
Jess
No, I. I mean, I talk to a lot of people on Facebook. It's. I mean, everyone does, right?
Brooke
Like, how much you like coffee? Do you like coffee a lot?
Jess
I go out for coffee. Yeah. I mean, cool. Everyone goes out for coffee.
Jeffrey
Are you asking her out for coffee, bro?
Brooke
No, not really.
Jeffrey
Oh, okay. Are you asking her to be friends on Facebook?
Brooke
You guys, I've never figured out how to figure this stuff out.
Jeffrey
What about her boyfriend?
Brooke
Hey, how about Your boyfriend?
Pete
Huh?
Brooke
No, Jazz, honestly, his name. Are you going to the reunion with your boyfriend?
Jess
Oh, well, I mean, I guess I'm going to have to talk with Pete before the reunion, and I don't know. Yeah.
Brooke
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?
Jess
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.
Brooke
Yeah.
Pete
Hey, babe. Surprise, it's me. I'm on the phone.
Brooke
Oh. Yet Because I'm terrible at this, Pete. Brooke was never gonna get there.
Jess
Why are you. What is going on? Like, are you guys joking? Like, why are you.
Pete
What are you doing?
Jeffrey
We're not joking. Yeah, we're laughing, but we're not joking. I'm not sure exactly what we're doing. Pete, why don't.
Brooke
Why don't you.
Pete
Okay.
Jeffrey
Talk to your girlfriend.
Pete
Yeah, I. I hit them up, and I got Brooke to try to find out. I know. 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.
Brooke
Oh, we're just gonna say it. You already said the nickname, like, twice, my man.
Jeffrey
Okay.
Pete
Anyway, Donnie and I didn't tell these guys this, but I. I know that you sent him pics, as well, of yourself.
Brooke
Why wouldn't you just let me break up with her?
Jeffrey
Brooke, hold on. This isn't about you. It's about them and the really hot pics that apparently she sent.
Brooke
What more proof did he need?
Jess
Yes.
Jeffrey
Wait, there. Yeah, man. Jess, there's pics.
Jess
Okay, and so
Brooke
what?
Pete
You just send pics of yourself to guys who aren't your boyfriend?
Jess
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 that big of a deal.
Jeffrey
Oh, they're topless, girl.
Jess
Okay, look, I'm proud. I'm not ashamed. Like, I look good. What's the big deal?
Pete
You show the pics to the assistant vice principal? Those as well?
Brooke
I don't think you want to ask that question.
Jess
Look, honestly, if I was friends with him on Facebook, maybe.
Brooke
Oh, okay. No, I'm.
Pete
Honestly, I just want clarification. I just need to know, are you interested in Donnie?
Jess
No. What?
Pete
You sure?
Jess
Crazy. I. Yes. Like, look, he's an old boyfriend. It's innocent flirting. Babe, we are good.
Brooke
You Just called it flirting.
Jess
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.
Jeffrey
No, that's even worse.
Brooke
No, no, no, no, no, no. We're not gonna let you get away with that.
Jeffrey
They're in a happy relationship. She just said it, Brooke. Rogue, break up with her right now. You have the power.
Mandy Woodruff Santos
Yes.
Brooke
This is how you started your relationship with Pete. This is how you're gonna start the relationship with Donnie. You're already sending him him pictures. You're already calling it flirting. Just break it off, girl. Move on to the next guy cleanly.
Pete
Honestly, I believe her. Like, if she says that she doesn't have feelings for Donnie, I believe her.
Jess
I mean, he knows me, Brooke. Like, you don't know me like that. So he. I'm. Thank you for believing me, and I'm glad that we can move on.
Pete
Thank you, babe. I got you.
Jeffrey
Look at that.
Brooke
Stayed together, broke up a happy couple.
Jeffrey
But her cold heart couldn't shatter the warmth of this loving relationship. Good luck, Jess and Pete. When you go, love wins once again.
Pete
Oh, man.
Jeffrey
Laughing right in front of you.
Brooke
Cutest couple at the reunion.
Pete
It's gonna happen.
Jess
Brooke and Jeffrey in the morning.
Mandy Woodruff Santos
This is Mandy Woodruff Santos from Brown Ambition. You probably think of Walmart as a store that carries just about everything under the sun and maybe not as the place place to discover small brands. Well, two things can be true at the same time, because Walmart is home to thousands of small brands founded by people who had an idea, took a chance, and built something of their own. Behind everyone is a real story and a lot of hard work. So why not take a little time to recognize all the people building small brands across the country and support everything they're creating? Walmart is proud to give those brands a place on its shelf. And online, it's never been easier to find and support small brands. So take a look at Walmart. You might come across something new, something unexpected, or a brand whose story speaks to you. You never know what you're missing until you look. Discover thousands of small brands@walmart.com.
Jeffrey
we've all been there. We've had seasons that have shaken everything.
Brooke
The question is, what remains when the ship shaking stops?
Jeffrey
Hi, I'm Gary Valenciano, and on my
Brooke
podcast Unshaken with Gary Vee, I sit
Jeffrey
down with amazing personalities and we talk
Brooke
about the seasons that nearly broke them, the lows that carried them to their highs. Listen to Unshaken with Gary Vee on the iHeartRadio app, Apple Podcasts or wherever you get your podcasts.
Jeffrey
Brooke, the text board's blowing up right now at 78592.
Brooke
I bet it is.
Jeffrey
One person said maybe you should check. Change the title of this from Brooke breaks you up to Brooke judges and shames you for finding true love.
Brooke
Okay, it is not true love. She's sending pics to other dudes. That's the true love you want to be in.
Jeffrey
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.
Brooke
Even if they're tough guys.
Jeffrey
Yeah, it's totally fine. It's a weight loss thing.
Brooke
Lose weight in your chest too. I mean, unfortunately.
Jeffrey
So when I lose weight, I'm going to send certain pics too.
Brooke
Cuz it's probably going to get smaller. Yeah, I mean, that's what they want is smaller pics.
Jeffrey
And when you take your clothes off, that's just more weight that you're shedding.
Brooke
That's a good point. I never weigh myself with clothes on.
Jeffrey
Yes.
Brooke
Which makes the doctor awkward.
Jeffrey
I'm happy that we have come to a happy conclusion here. That's what we've learned today.
Brooke
I don't know why divorce rates are so high. Doesn't make sense that if you need
Jeffrey
some help with your personal life life, you can always email the show if you need Brooke to break you up.
Brooke
Yeah, I'm glad you guys talked me out of this whole thing.
Jeffrey
Yeah, email us. Find us on our podcast too at Brooke and Jeffrey.
Episode Title: Brooke Breaks You Up: High School Drama
Podcast: Brooke and Jeffrey
Release Date: July 23, 2026
Main Theme:
This episode’s main theme centers on the messy entanglements of rekindled high school romances and navigating relationship anxiety before a milestone class reunion. “Brooke Breaks You Up” puts co-host Brooke in the hot seat, as listener Pete asks for help breaking up with his girlfriend Jess – unless Brooke’s “magic” can clear up suspicions of infidelity first. The episode is packed with candid, comedic commentary from the hosts and reveals just how tangled modern relationships (and breakups) can get, especially when old flames and Facebook are involved.