Brooke and Jeffrey: Second Date Update - Say Yes to the Ex: Unlucky Number 13

Episode Date: June 1, 2025

We've got a special new episode you this weekend! It’s easy to say yes to some things, but saying YES to your EX is another story… After today’s call you’re never gonna look at ESCAPE ROOMS the same again. It’s SAY YES TO THE EX!See omnystudio.com/listener for privacy information.

This is an iHeart Podcast. 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. Go! Amy Robach and T.J. Holmes here. Diddy's former protege, television personality, Denity King alum Aubrey O'Day joins us

to provide a unique perspective on the trial that has captivated the attention of the nation. It wasn't all bad, but I has captivated the attention of the nation. It wasn't all bad, but I don't know that any of the good was real. I went through things there. Listen to Amy and TJ Presents, Aubrey O'Day, covering the Diddy Trial on the iHeart Radio app,

Apple Podcasts, or wherever you get your podcasts. 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. The Made for This Mountain podcast exists to empower listeners to rise above their inner struggles and face the mountain in front of them.

So during Mental Health Awareness Month, tune into the podcast, focus on your emotional wellbeing, and then climb that mountain. You will never be able to change or grow through the thing that you refuse to identify, the thing that you refuse to say, hey, this is my mountain, this is the struggle. Listen to Made for This Mountain

on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Have you ever thought about going voiceover? I'm Hope Woodard, a comedian, creator, and seeker of male validation. I'm also the girl behind voiceover, the movement that exploded in 2024. You might hear that term and think it's about celibacy, but to me, voiceover, the movement that exploded in 2024. You might hear that term and think it's about celibacy, but to me, voiceover is about understanding yourself outside of sex and relationships.

It's flexible, it's customizable, and it's a personal process. Singleness is not a waiting room. You are actually at the party right now. Let me hear it. Yes. Listen to voiceover on the iHeartRadio app, Apple podcasts, or wherever you get your podcasts.

All right, you are in for a Sunday treat, my friends. You have found the second date update podcast. It's Brooke and Jeffrey in the morning. And Sunday is where we introduce you to something new. Yay. Something different that we do on our show. Cause we do do a full hour podcast over on our main feed. And this one is a segment called Say Yes to the Ex.

Alexis, have we run this in the second day feed? I think so, you guys might have heard it once or twice. Okay, yeah, it's where, I mean, it's pretty obvious, right? You wanna get back together with your ex and we help facilitate that. This one's gonna be a big discussion about cheating. And if once a cheater, always a cheater, I think it's gonna be the comment section for sure

But before we start the podcast Alexis, let's highlight some of the great comments that people are leaving I saw one from Keegan Barnett who said that point when you wake up from a tonsillectomy Go to the recovery room and the first thing you ask for is your phone and headphones to listen to your daily Brooke and Jeffrey episode I think I have a problem I think we're better after any sort of anesthesia. A lot of funnier. Yeah. Surgery.

Totally. Well, thanks for being with us. And hey, if you got a great comment, please leave it. We love to highlight them. Like, subscribe, and sit back and enjoy. Yes. There's a lot of things that you'd happily say yes to without even thinking about it. Oh okay. Yeah. Like yes to free Costco samples. Yes. Yes to

concert tickets for a band I don't even like. Yeah yes. I'd even say yes to a free trip to Mexico with the stipulation I'd have to hide balloons somewhere on my body But it's much harder to say yes to your ex What one of our listeners is hoping for today and all I know is this after today's call I will never look at escape rooms in the same way ever again never look at escape rooms in the same way ever again. You're gonna understand why when you hear it in a brand new Say Yes to the X right after this. It's Brooke and Jeffrey in the morning and it's time for another charming edition of Say Yes to the X. Oh my gosh this is what we're doing. Where we try to help a listener reconnect with an old fling to see if there's any chemistry or desire lingering there hoping to be explored

And you know what it's worked once A success rate is there and today's caller has actually been on the show with us before You might remember one of the more disturbing second date calls we did last year involving two people going to a red envelope party where after midnight the party turns from nice to super naughty. Yes. Again. I do remember red envelope.

Why? Did they end up dating? So Natalie was the woman that we called that day. She said yes to our offer of a second date, but now she's back this time for say yes to the ex. Or, okay. I think not the same guy that we hooked her up with that time on the show.

But first Natalie, we wanna welcome you back. Thanks for being on again. Thanks for having me. Okay. So you're not saying yes to this relationship that just happened like a month or two ago. Oh you mean Alvin? Yeah, what happened with that guy in the red envelope party? You're not gonna believe this but he turned out to be kind of a freak Thing that you could have said

You're right I probably should have known but it really sunk in when he started referring to his bedroom as the arena. Like he had an actual neon sign above his bed that says the arena. Okay, well hold on, now he's starting to sound like he's kind of a good guy. Are you sure that you should have ditched him?

A neon sign? Oh my God, welcome to the arena. Oh my God. That's so cringe. Which is worse, that he's single, which means he's bringing new ladies into that place. a neon sign? oh my god welcome to the arena oh my god which is worse that he's single which means he's bringing new ladies into that place oh my god apparently this isn't about alvin and his arena we're focused on a new old guy yeah

tell us about your new old fling okay so we dated like 3 years ago and we dated for like six to seven months. Okay, what's his name? His name's Caleb. Okay, and what made you start thinking about him again? Is it just by comparison to Alvin, everybody's, he's the only one that seems normal?

No neon signs. Yeah, that's part of it. This guy was so sweet and I just I have like really good memories of him and I was the one who sort of messed it up. And that is something people say. It's all about timing. Can we know how you messed it up? Uh yeah I mean I was unfaithful and I got caught. Yeah.

Do you say you don't? You you got caught? Yeah and I totally deserved them breaking up with me But the thing is I'm I'm not that person anymore And I just know he's a solid person that doesn't have neon signs and giant arrows in his bedroom. Oh, there's arrows, too Yeah, okay, I like a map to follow Yeah, okay. I like a map to follow. I mean, you cheated. Like, why would he want to take you back?

I know that you know you're a changed person, but... Why do you deserve a second chance? I mean, I've done the work to improve myself and, like, be a better partner for him. And I just know that if you do get him on the phone, I'm sure the questions of trust will definitely come up because that was kind of a big thing. I mean, that is a good question.

What do you guys think? Can you come back from a cheating scandal? It depends on the person. I would never, but there's some people that- Like how hot they are, you mean? Yeah. If you're already cheating six months into a relationship, it doesn't feel like you're fully-

You're a cheater. I mean, I don't think, you know, I don't think once a cheater, always a cheater, it just doesn't sound like you were fully into him. Yeah, and if it's like a marriage, you can maybe try to work it out, but you're just dating. Like, just break up and find someone else. Like, it doesn't sound like you're really into the relationship to begin with. I mean, I was. I just think that I've changed and I've done a lot of work on myself and I'm just a better person than I was when we were dating

A lot of the grass is greener on the other side type of thinking but in the last three years since you broke up Have you had any contact with your ex like at all? I tried, you know, I tried in that first year I reached out more than a few times and he made it clear He needed more time and space and he's gotten that now it's been three years Yeah, you can't get over cheating in three years Oh, man, do you know do you know is Caleb single right now? I Don't know honestly and I and I I like I don't expect them to be like jumping at the chance to get back with me But I would like to just grab a coffee and see if we have that same like comfortable fun vibe between us And invite him back into your arena

It's a bigger arena with people watching What? I don't know. Coming up with a new name. It's a bigger arena with people watching. Sure. It's like Madison Square Garden. That's right. Yeah. So obviously, Natalie, you know how this works. We had our producer reach out to your ex, Caleb, and was able to get him on the phone.

He is waiting on hold right now. Just doesn't know who he's about to be talking to. Oh my gosh. Okay. Are you ready to talk to your ex from three years ago and see if he's willing to say yes to the ex? I think I'm ready. I'm ready. I can do this.

If he hangs up, I mean, it's a tough one. It's understandable. Yeah, that's what I'm saying. But at least say, oh yeah, you know why I'm hanging up. Yeah. Maybe he's up into it though. Maybe we're wrong. I mean, she claims that she's changed a lot in that time.

So we'll find out if that's enough when we come back and put them together for Say Yes to the X right after this. Thank you so much. Hold on. If you're just joining us, we're in the middle of Say Yes to the X with Natalie. Spicy one too. She's attempting to reconnect with a guy that she dated three years ago. She told us that they had a fun casual vibe together but admits the

biggest issue in their relationship was her unfaithfulness. Yeah, a little bit of an issue. A little problem. She was caught, admitted it to the guy, regrets it, and since then has taken accountability for her actions, chose to move on and work on herself, and would like to know if there's any chance at a second go around with this guy. Yeah. You make that sound great because most cheaters won't admit it and fall on the sword and be the bigger person. I mean, I guess you're right.

Well, it's because personally, I believe in forgiveness. And in certain situations, maybe this is one of them. I'm hoping that enough time has passed that Caleb could find it in his heart to at least sit down and have a cup of coffee with her. Jeff, you've never been cheated on, have you? I have not been cheated on. And I believe that there is goodness I mean I mean I do think that people can grow and change and make different choices But doesn't mean that's not on Caleb though. Yeah

Have fun with your new life. It doesn't seem like too much to ask for him to come sit down for coffee right Natalie You're right about that Natalie you would agree. Yeah, that's all I'm asking for like just a coffee But he should pay for the coffee Last time you talked to him on a scale of one to like super angry being ten where was he at? Oh I would probably say 10. Okay, that's good. Yeah, because she said that she tried texting him but he was like, I don't want to talk to you,

I need more time. Yeah, but that's not. Three years should be enough time. My 10 sounds a lot more vulgar than that. Well, let's see what number he's at, because he is, remember, waiting on hold, has not heard this segment happen up to this point, does not know the reason that he has been called by a radio

I don't know. I feel like he might not be a full ten. Let's find out. I'm gonna punch him up Let's producer Boyd really riled him up before putting him on the phone You know boy can really get under your skin sometimes he does that but here We're gonna talk to him a little bit and then we'll tell him that you're there. Okay, Natalie Okay. Thank you. Okay. So here we go Hello Caleb you there Yellow hey, hey, welcome to the show Caleb. Good morning Hey, good morning. How are you guys?

Thanks for being on the show with us. I know you don't know the reason why you're here yet. Yeah, yeah it's all mysterious what's going on. Yeah, that's us. It could be really fun, the reason. It could be. What is it? It's a segment we do it's called Say Yes to the Ex where somebody from your past who you've dated before wants to know if there is any shot of a second chance with you and I know we don't even know like what your situation is if you're single or what you've got going on in your life right now yeah if you are taking we're not trying to Yeah, yeah, I am single okay I'm not sure if I want to talk to this person unless I know who it is Yeah, that's a valid request. Oh really okay? Well normally okay normally I wouldn't do this normally I just put you on the phone with them But I can tell you it's somebody you dated for about half a year and her name is Natalie Are you kidding me? I'm not

That's this isn't gonna be a thing I don't I don't want to talk to her She did come with a lot of regret for her actions and you may just want to hear her out Yeah, cuz I'm assuming you're hesitant because of the whole infidelity thing You're gonna have to make that plural my guy infidelity Yeah, it wasn't once she cheated with 13 people with 13 people. What? 13! Oh my gosh!

That is some work. But it sounds important. You guys only dated for six months. Yeah, that's what she told me when the truth came out, when I caught her. Wait, she told you? Yeah. Oh my god. You caught her 13 people? Hi, Caleb. Caleb, hi. We don't need to tell them all that.

Oh, that is happening. Yeah, we do. You told me 13 different dudes. the landlord, the propane guy, and my brother? Oh! OK. His brother? No, no, no, no, no, no, no.

Your frat brother. It's not like you're related. No, wait, what brother? His frat brother. Oh, fraternity brother. Oh, frat brother. Oh, whatever. That doesn't count.

No. Yeah. They're not even real people, right's not fair! It doesn't count. They're not even real people, right Brooke? Yeah, that's right! I mean it counts, it just doesn't count as a bro. There was a lot of people and I knew most of them. We knew most of them. Listen, no here's the difference. Back then I was unhappy with myself

and that had nothing to do with you. Except that we were together. And you were cheating on him. No, but she's... and that had nothing to do with you except that we were together right but I was honest with you about it I didn't hide it I told you a while until I found out with guy number 13 eventually and that's my karma and something I dealt with and I'm over it now. I'm so much better. Oh, sorry, I'm not over it. Yeah.

Yes. Natalie, did you really think, like you didn't tell us, I had just assumed that it was one time, you know? I said that I was unfaithful. You didn't ask for like a specific number. Okay, you know what? I feel like we specific number Her cheating

We need to be better at asking questions when we're doing these segments. Let's keep that in mind Did you cheat in any relationships after him? Well that doesn't matter about that She's grown and changed, but we're not worried about her other relationships. We're worried about this relationship with Caleb Caleb she's done the work, she's moved past it. Are you ready to move past it yet? That was well done, but wild question. Yeah. Like, yeah.

Here's the deal. It's like, I still live in the same building and I still have the same landlord who occasionally looks at me in that weird way. Whoa. Maybe the work is that- It's pretty messed up that you didn't get a rent discount. Oh, yeah. It's not just the landlord.

I mean, she slept with the freaking escape room instructor. What? Okay, okay. That was not my fault. Wait. I need to hear this. It just kind of happened. We were locked in separate rooms.

He was a team leader. You do what the team leader says. Oh my God. You are insane, Madeline. We have to get out of this god. You are insane, Adam. We have to get out of this room. Everyone take their pants off. Is there an escape room employee that isn't a 20 year old like acrobatic D&D guy? Okay.

You guys can see why we're not together now, right? Yeah. She slept with a guy in the middle of your date. Of course you're not together. Also I don't want to say anything but I think her and Jeff were fooling around a little when she was on hold. Yeah, by the way, team leader. You have to listen to the team leader. So Brooke, don't appreciate that. You guys are not helping. Why would you ever think that he would move past this?

Like why would you ask this question? You just need to move on and give up. Brooke, what you're forgetting is this is all past stuff. That's great! I'm glad she changed. We're talking three years ago, and I would hope that Caleb, you could find it somewhere in your heart to say yes, because this girl deserves a 14th chance. As of today, she hasn't cheated on me. You know the saying is, fool me once, shame on you. Fool me 14 times. Shame on the landlord. Okay, you guys are making such a big deal about the number of people and the truth is like I've changed and I just want a cup of coffee

Okay, I think that's fine, but just maybe do it with a new guy. Or sleep with a barista. Then you get free coffee. That's before we even do that we need to ask the whole purpose of this segment is Caleb. We she wants it broke. She's begging us for the coffee with Caleb. So Caleb, we have like that team leader in that escape room. Caleb, would you be willing to say yes to the X and meet up with Natalie for coffee? You know what? I think I actually have a thing or two of yours still at this apartment. So yeah, I can mew up the coffee. But just so you know, there is zero chance of me ever trusting you again or being in any kind of relationship.

Okay, so you're gonna hook up over coffee. Yeah, cause he's set the boundaries. I hear there's a coffee themed escape room that they just started downtown. I am truly a new woman, so you'll see the new me. It's gonna be great. Well, go, let yourself shine. Let him see this new woman.

And we're proud of you for that. Just go to coffee, bring your landlord, and let's squash old qualms. You know what, bring all 13 of those other guys back, and we'll hash this out. What is this, the bachelor? I don't know. 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. Amy Robach and TJ Holmes here. Diddy's former protege, television personality, Danity King alum Aubrey O'Day joins us to provide a unique perspective on the trial that has captivated the attention of the nation.

It wasn't all bad, but I don't know that any of the good was real. I went through things there. Listen to Amy and TJ Presents, Aubrey O'Day covering the Diddy Trial on the iHeart Radio app, Apple Podcasts, or wherever you get your podcasts. The Made for This Mountain podcast exists to empower listeners to rise above their inner struggles and face the mountain in front of them. So during Mental Health Awareness Month, tune into the podcast, focus on your emotional well-being and then climb that mountain.

You will never be able to change or grow through the thing that you refuse to identify, the thing that you refuse to say, hey, this is my mountain, this is the struggle. Listen to Made For This Mountain on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Have you ever thought about going voiceover? I'm Hope Woodard, a comedian, creator, and seeker of male validation. I'm also the girl behind voiceover, the movement that exploded in 2024. You might hear that term and think it's about celibacy, but to me, voiceover is about understanding yourself outside of sex and relationships. It's flexible, it's customizable, and it's a personal process.

Singleness is not a waiting room. You are actually at the party right now. Let me hear it. Listen to voiceover on the iHeartRadio app, Apple podcasts, or wherever you get your podcasts. I've seen a lot of stuff over 30 years, some very despicable crime and things that are tough to wrap your head around.

This ranks right up there in the pantheon of Rhode Island fraudsters. I've always been told I'm a really good listener, right? And I maximized that while I was lying. Listen to Deep Cover, The Truth About Sarah on the iHeart Radio app, Apple podcasts, or wherever you get your podcasts. This is an iHeart podcast.