Brooke and Jeffrey: Second Date Update - True Confessions: School Edition

Episode Date: May 25, 2025

We've got a special new episode you this weekend! Can you figure out which of these embarrassing stories from our high school days are true and which ones are lies? It’s TRUE CONFESSIONS!See omnystudio.com/listener for privacy information.

You're listening to an iHeart podcast. Ugh, we're so done with New Year, New You. This year, it's more you on Bumble. More of you shamelessly sending playlists, especially that one filled with show tunes. More of you finding Geminis because you know you always like them. More of you dating with intention

because you know what you want. And you know what? We love that for you. Someone else will too. Be more you this year and find them on Bumble. I'm Andrea Gunning, host of the podcast, Betrayal. Police Lieutenant Joel Kern used his badge to fool everyone. Most of all, his wife, Caroline.

He texted, I've ruined our lives. You're going to want to divorce me. How far would he go to cover up what he'd done? The fact that you lied is absolutely horrific and quite frankly I question how many other women are out there that may bring forward allegations in the future. Listen to Betrayal on the iHeartRadio app, Apple podcasts, or wherever you get your podcasts. Why is a soap opera western like Yellowstone so wildly successful? The American West with Dan Flores is the latest show from the Meat Eater Podcast Network. So join me starting Tuesday, May 6th, where we'll delve into stories of the West and come to understand how it helps inform the ways in which we experience the

region today. Listen to the American West with Dan Flores on the iHeartRadio app, Apple podcasts, or wherever you get your podcasts. Clayton English. I'm Greg Glott. And this is season two of the War on Drugs Podcast. Sir, last year a lot of the problems of the drug war this year, a lot of the biggest names in music and sports. This is kind of star-studded a little bit, man. We met them at their homes, we met them at their recording studios. Stories matter and it brings a face to them. It makes it real. It really does. It makes it real. Listen to new episodes of the War on Drugs podcast season two on the iHeartRadio app,

Apple podcast or wherever you get your podcast. Hi, I'm Sam Mullins and I've got a new podcast coming out called Go Boy, the gritty true story of how one man fought his way out of some of the darkest places imaginable. Roger Caron was 16 when first convicted. That spent 24 of those years in jail. Hey, it's Brooke and Jeffrey in the morning and this is the Second Date Podcast. But- On a Sunday. podcast. Hey, it's Brooke and Jeffrey in the morning and this is the Second Date podcast. But on a Sunday, but we're doing something totally different that you've never heard on this podcast before.

It's something that, I'm not going to lie, we totally ripped off of Jimmy Fallon. Oh, you know. It's a radio word. Yeah, it is. And I'm sure he ripped it off of somebody else. Let's be honest, there's no original ideas. But it's called True Confessions, and it's where we confess something embarrassing

about our own past, and then each host, we get a time to interrogate each other to see if we're lying or telling the truth. Yeah, it's I have I compared to two truths and a lie, kind of. Oh yeah. Yeah, it's like, can we convince each other? Because we know each other so well.

Are we lying or are we telling the truth? And if you've ever heard our show do any sort of like embarrassing stories about our lives, I'm going to tell you, Jeff is always the king. Yes. He has the most embarrassing moments that I've ever heard. I don't think he realizes how embarrassing his moments are.

Like, he's a little out of touch. Yeah, so you're going to get to know Jeff a little bit better as well in this segment. But before we get it started, what are our comments today, Alexis? We love to highlight those listeners who leave great ones. Yeah, Kristen Miller said, "'I'm addicted to these segments.

"'I listen to them on the way to work, on the way home. "'After I get home, when I take a shower, "'I'm a little addicted.'" Yeah. I don't know that there's any groups to help you with that yet, but I'm sure that they'll start soon. Hey, thanks for being here. Please like and subscribe, and True Confessions

on your second update podcast starts now. I get a lot of hate from other people on this show who are jealous that I went to private school going. Yes, that's it, Joe. That's why. And it's not fair. I mean, were my school uniforms designed by Christian Dior? Oh.

Sure. Did my school cafeteria have a full-time sommelier? No way! Yeah, obviously. You're drinking wine? In high schools? Was my school's equestrian team ranked number one in state? No. No, number one in the country.

Thank you, Wyoming. But hey, I suffered- Take that, Wyoming. I suffered low moments, just like the rest of you poor people did. And that's why today we're going to level the playing field as we all share true stories of our cringiest school memories in a special game of True Confessions School Edition. It's coming up right after this. It's Brooke and Jeffrey in the morning and right now kids everywhere are counting down the days and the hours to the end of the school year. Many of them are going to be donning a cap and gown moving on from middle school to high

school or high school to college or college back to mom's house forever. That's right come home babies come home. Save that rent money. But we make lifelong memories during our school years. Some of them very positive moments that we cherish forever. Others we chug tequila, hoping to forget them permanently. But they still make great stories when you're with your friends. But today we're airing out all of our schoolyard shame by playing a special little game called True Confessions School Edition. If you aren't familiar with this,

each member of the show has two envelopes in front of them with embarrassing confessions about something we did in our past during school. I'm pre-embarrassed. I'm already embarrassed. Because we all know what's true in our lives, but these could be from graduation night, could be senior pranks, detention room debaucheries with Mr. Winklehouser, and once-

We know Jeff's. No spoilers there. One statement that we say is true, one is a made-up lie. Yeah. So we'll pick one envelope, read the confession inside, and then the show only has 30 seconds to ask questions and try to figure out if that's the true story or is it the made-up lie? It's kinda like, do we know each other well enough to know if we're lying to each other?

I love the interrogation part of this. I know you do, Brooke. Well, let's get started with Brooke. Alexis, which envelope should she open first, one or two? One. OK. All right, Brooke, open envelope. Read us your true confession.

After our middle school graduation, the entire eighth grade class went on a camping trip. Fun. After I checked in, the female counselor asked my sister, what's your brother's name? Oh! Oh no! And that's when I realized she was asking about me. Oh, that's in your hair.

Do you swear on both of your children's lives that this story is true? Oh, that's easy to, yeah. You can't do that. Oh, okay. That's not cool. I'm not gonna do that even if it was true or not true, Jeff. Bad question.

How long was your hair at the time? My mom had convinced me to get a pixie cut. And it would be really cute. Did you have glasses? Oh, big ones. Yeah, she liked glasses. I know this picture of Brooke. I have seen her from this era. Oh my gosh, it was on Brooke and Jeffrey Insta recently.

And you did look like a boy. What? She's a little... Double down, Alexis. Jeez. I need to get asked if you had already hooked up with that teacher yet. Oh, yeah. No, in eighth grade no one would kiss me.

I really wanted to kiss everyone. Alexis, what do you think? Is that a true statement or did she make it up? Based off the photo I saw, I have to say it's true. Jose? I am confident it's true. We were all very confident that really happened to Brooke. Brooke, is it true or not?

Yeah, it's true. Yeah. Very true. Yeah, no surprise there. We were all very confident that really happened to Brooke Brooke is it true or not? Yeah, no surprise there now we're going over to Jose it's your turn Brooke which envelope should he open one or two Let's go to Go I Was fired as the school mascot being too lazy Let me finish. Okay. I talked to the cheerleaders too much instead of dancing. Cut. Do you swear on both of Brooks children's lives that that statement is true? Yes I do. I absolutely do. Both of them.

Hey, did you have to audition for the job? No, they's... come on, it's me. What was the mascot? We're tigers. Stadium tigers! Let's go! And your mom always thought that you would be Tigger. Like I know your mom was obsessed with that. What was one school chant that you had to do? Let's go tigers!

Oh yeah. I mean literally they were like just go dance. I have the energy. Okay. It didn't last long. I don't think it's true. You don't? I don't think Jose had the commitment even to audition I think it's true Alexis. I think the flurry with the cheerleaders is true, but not It's not true. Is it true?

Yeah, no one of my teachers didn't suggested to me though she'd be like, you'd be perfect for our mascot, but I was already JV on the football team. Oh, wow. Sorry, I'm busy. If you're just joining us, we're in the middle of a game called True Confessions School Edition where we're going around sharing cringe-worthy stories from our school years, trying to figure out if they're true or if they're made up. Alexis, it's your turn to confess

I think you should open envelope number one, okay Sorry, it's hard to fake nails to open Okay, we had a final track banquet my senior year after the awards and dinner I went to drive home and hit a car in the parking I'm not sure we need to ask any questions at this point. You got time. What kind of car were you driving? I had my first car was a gold Lexus. It was really old and the trunk didn't close. Did you report the accident? Brooke. Did you even stick around for the accident? It's been long enough I think I could say no I did not report

the accident Damage I could you lose a bumper was it a dent. I don't really look I just hear How proud of your mom was you? Are you mother? What do you think? Is that true? I actually, I want to believe it, but I think it's false. Really? Okay, Jose. I'm kinda with Brooke. I say it's false.

Old habits die hard. I say it's true. Hey! It's true! Oh, Alexis! I gotta be a swig. I'm backing in the cards. Okay, so I'm up. Jose in my opening here number two, okay My senior year highlight was being featured as a tap dancing waiter in the musical. Hello, Dolly The non highlight was all the dudes on my soccer team showed up to the performance and were like what the hell are you doing?

You're the captain of the soccer team Jeff was the team captain. No, he's bragged about it. Remember we played soccer with a pineapple He's like I was a team captain You guys can ask me a question Center mid Invited them to the show you or your mom it was probably my mom, but they may have come on their own accord, okay Proud of your performance. I was proud of my performance Embarrassed that everybody saw it. I want this to be true.

Brooke says true. Jose? I don't know. I'm going to say false. Alexis? I'm with Brooke. I want it to be true. No one actually believes it. Was I the star waiter in the musical Hello Dolly when my soccer team showed up? Of course that's true. And boo on your soccer team for not being more supportive You got fancy feet. That's why you're good at tap dancing and soccer So take that one made it to the quarterfinals in the playoffs That's right. I could just see him prancing down a soccer field What other shameful stories that we have to share but there is one of mine left that I hope I don't have to tell

We're gonna find out as we do more true confession school edition right after this We're in the middle of true confessions school edition going around the room trying to figure out who's telling the truth Who's being a nasty little lie mask? The way that it works is we all have written down confessions about embarrassing things We did back in our school years one confession is true One's a made-up lie ready for a brand new round starting fresh with two brand new envelopes in front of us Two brand new confessions and it's Brooks turn again Jose choose which envelope she's gonna open, one or two. Well, I guess I gotta go two.

Okay. All right. I was a journalism major and at the end of my senior year, I had to give a commencement speech to the class. Oh. But I stayed up all night and didn't prepare. Uh-oh. The next day with hardly any notes, I gave the worst speech in the school's 120 year history.

What was the speech about? Just, I basically said I love you all over and over again. It was supposed to be you're graduating from college and you just spent X amount of money and how life will be great for us all. But it's like, it's Montana. You could have just like spit in a cup and just kept getting it. What were you doing the night before? I was a director on our student documentary. It's Montana. You could have just like spit in a cup and

I was a director on our student documentary. So I was trying to finish it cuz we Play doing other Drinking with a boy. Yeah, okay. Jose. What do you think? You know, I just feel like Brooke is such a superwoman She would never let herself even if she's wildly hungover fail that miserably on his big speech So I'm gonna say this is false. I know Brooks like such an over planner for stuff There's no way she wouldn't do anything before the speech. It can't be true really See I think Brooke will be like I have charity event tonight oops gotta talk in five minutes So I think it's true That's not good stuff

Brooke is it true or not? It's true It was the most mortifying 15 minutes of my life Oh it was so long The guy I was dating at the time I finally got off the stage and he's like whoa Yeah Well that was a speech It wasn't good So to my professors who are still lovely people I apologize Oh! Yeah! Oh my gosh. Well that was a speech. Wow, I did not see that coming.

So to my professors who are still lovely people, I apologize. You picked the wrong person. Jose, you're up. Alexis, which envelope is he going to open? One or two? One. Okay. At one of our high school football games, I was injured and I couldn't play. So instead of sitting on the sideline with the team, I ended up spraying my entire body with cologne and sitting in the stands next to my crush Brand of cologne was it awkward to Gio?

Text in if you own a bottle of it still were you breaking a rule by leaving the team? I mean I wasn't like Varsity so like I it wasn't a big deal for me to not be on the sidelines with everybody else. What was your injury? I tore my sacroiliac right back here in my hip yeah and to this day I still have issues with sacroiliac. Why did I ask? I pushed me down and I had back spasms for months. I'm trying to pull his pants down and do more of a demonstration if you'd rather, Alexis. I kind of want that demonstration later, but just for the term sacroiliac, there's no way he could make that up.

That has to be true. It's a real joy. That's what I'm saying. It has to be true. I got true on that too. Yeah, but Brooke? I think that all of that happened except for him leaving the bench. I think he would be forced to sit on the bench and he could coach.

I think it's false Jose it is true I told him I couldn't make it cuz I was so hurt But then I snuck into the stands and I remember putting oh man it's supposed to be raised on myself And this girl would not sit next to me And I kept moving to her and eventually later her friends are like dude She said you smell really strong and yeah, oh the coach is like

Turns out to be true If you're just joining we're in the middle of a game of true Confession school edition going around sharing cringe worthy stories from our school years trying to figure out if they are real true stories Or if they're just made up. We're gonna keep it going with Alexis's turn. I think you choose envelope number one. Okay. If Alexis tore her sacroiliac, I'm gonna be so mad.

Yeah. I had to sit out from running, and I sat with my crush, okay. At the end of high school graduation, one of my teachers came up to me and said he saw me cheating on my test all Semester then gave me a fist bump. What? How old was the teacher I don't you think I know teachers

What class did they teach AP world history, how did you cheat? Well, it was a P class How am I supposed to get by that on my own? Wait, how did you get into AP if you were cheating? Wait a minute. That's what was in it. Can't anybody get into AP? They get it, you just sign up. They usually reserve it for the upper echelon, but maybe in your school, they let anybody in.

OK, so is that true or is that false? I know she's really proud of her cheating history. Yeah, that's my answer. They've talked about it multiple times. School cheating, school cheating, by the way. But I don't know that a teacher would fist bump you. That'd be terrible. I'm gonna say false. I think she's lying.

I think this is true. I've read her Instagram captions, and I could tell she's taken AP. So I'm gonna say... She takes Kylie Jenner's captions. Absolutely, it's true. Thank you, Jeff Jeff it is true Coaches a kind of chill after

There's a two-story building so we look down and see me cheating Yeah, wouldn't stop you. Yeah, you weren't even a very good. I didn't know that he was above me All right, it's my turn Brooke which envelope in my opening one or two two, please let it be the embarrassing thing Stories just really Let's see On graduation night after high school. I went to my first house party ever Where I drank vodka for the first time and attempted to ride a donkey? Oh my god Property that had a barn and in the barn was a donkey

Why were you never invited to a party before this if you were the captain of the soccer? You were the captain of the soccer team. He was busy with the tap dancing, girl. Yes. I have so many extracurriculars going on in my life. There was no time for me to be cool. No. You weren't invited for a reason. How was the vodka?

Did you handle it well? Or were you life of the party? I was life of the party for the first time. I don't know. I've been drunk with Jeff, and that's hard to believe. Yeah, that's me too. I feel like he was passed out in a corner somewhere. Oh, wow.

He was really hurtful. OK. I have partied with Jeff before. Oh wow. This is really hurtful. Okay. I have partied with Jeff before and you were the life of the party but- For how long? Not in a good way. Everyone was focused on Jeff so I'm gonna say no. This is not a roast. It is a true confession segment.

Alexis I'm not even gonna ask. Alexis please don't say it's true. I just did it again with the drunk. Also I don't see you going to a bar and a barn. After I went to any barns ever. After grad night, I went to my first house party, drank vodka for the first time, was the life of the party and tried to ride a donkey. That's true. It's true according to you. It is true. I think if we dug somebody in, it may happen to different takes.

If you went to school with Jeff, text us. Let us know what you think is cool. If you were at the barn donkey party. Okay, segment done. That was true confession school edition. Yeah, get Jeff some vodka. Now I'm going to go cry. It's Brooke and Jeffrey in the morning. See, that's what we expected.

That's what he did at the party I was at. Brooke and Jeffrey in the morning. I'm Andrea Gunning, host of the podcast, Betrayal. Police Lieutenant Joel Kern used his badge to fool everyone. Most of all, his wife, Caroline. He texted, I've ruined our lives. You're going to want to divorce me. How far would he go to cover up what he'd done?

The fact that you lied is absolutely horrific. And quite frankly, I question how many other women are out there that may bring forward allegations in the future. Listen to Betrayal on the iHeart radio app, Apple podcasts or wherever you get your podcasts. Why is a soap opera western like Yellowstone so wildly successful? The American West with Dan Flores is the latest show from the Meat Eater podcast network. So join me starting Tuesday, May 6th, where we'll delve into stories of the West and come

to understand how it helps inform the ways in which we experience the region today. Listen to The American West with Dan Flores on the iHeart Radio app, Apple Podcasts, or wherever you get your podcasts. I'm Clayton English. I'm Greg Glott. And this is season two of the War on Drugs podcast. Last year, a lot of the problems of the drug war this year, a lot of the biggest names in music and sports. This is kind of star-studded a little bit, man. We met them at their homes, We met them at their recording studios. Stories matter, and it brings a face to them. It makes it real.

It really does. It makes it real. Listen to new episodes of the War on Drugs podcast season two on the iHeartRadio app, Apple podcast, or wherever you get your podcast. Hi, I'm Sam Mullins, and I've got a new podcast coming out called Go Boy, the gritty true story of how one man fought his way out of some of the darkest places imaginable.

Roger Caron was 16 when first convicted. Has spent 24 of those years in jail. But when Roger Caron picked up a pen and paper, he went from an ex-con to a literary darling. From Campside Media and iHeart Podcasts, listen to Go Boy on the iHeart radio app, Apple podcasts, or wherever you get your podcasts. I'm Michael Kasin, founder and CEO of 3C Ventures and your guide on Good Company, the podcast where I sit down with the boldest innovators shaping what's next. In this episode, I'm joined by Anjali Sood, CEO of 2B.

We dive into the competitive world of streaming. What others dismiss as niche, we embrace as core. There's so many stories out there. And if you can find a way to curate and help the right person discover the right content, the term that we always hear from our audience is that they feel seen. Listen to Good Company on the iHeartRadio app, Apple podcasts, or wherever you get your podcasts.