Brooke and Jeffrey: Second Date Update - Say Yes To The Ex: Podcast Problems

Episode Date: May 11, 2025

We've got a special new episode you this weekend! One of our listeners got dumped a few months ago during an argument about TOENAILS... But now, he swears he's changed and can PROVE IT. We've got his ex- girlfriend on the phone in hopes to get him another chance in a brand new Say Yes to the Ex!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. This week on Dear Chelsea with me, Chelsea Handler, Connie Britton is here. I think you should encourage your friend to go ahead

and not be holding out for any man to have her babies. She could be waiting another 10 years before she finds the right guy. Connie didn't meet her right guy until you were what, 50 Connie? 52, 52. 52. I kept thinking, oh, I'm gonna meet the guy,

I'm gonna meet the guy, I'm gonna meet the guy. I finally was like, what am I waiting for? And I did it, and I'm just so glad that I did. Listen to Dear Chelsea on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. I found out I was related to the guy that I was dating. I don't feel emotions correctly. I collect my roommates' toenails and fingernails.

Those were some callers from my call-in podcast, Therapy Gecko. It's a show where I take phone calls from anonymous strangers as a fake gecko therapist and try to learn a little bit about their lives. I know that's a weird concept, but I promise it's very interesting. Check it out for yourself by searching for Therapy Gecko

on the iHeartRadio 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. Yo, K-Pop fans, are you ready? It's your boy, Bom Han, and I'm bringing you the K-Factor, the podcast that takes you straight into the heart of K-Pop. We're talking music, idols, exclusive interviews, and even the real behind the scenes K-Pop stories. Plus, you're the fans, you're part of the show. And you can get a chance to jump in,

share your opinions, and be part of the conversation like never before. And trust me, you never know where we might pop up next. So listen to the K-Factor starting on April 16th on iHeartRadio app, Apple Podcast, or wherever you get your podcasts. This isn't just a podcast, it's a K-pop experience. Are you in?

Let's go. Hey, no such thing as a Sunday scary is when you got a new podcast, right? Yay! Hey, it's Brooke and Jeffree in the morning. You found the second date update podcast and every Sunday we do a little something special that we do on the show.

This time it's a brand new Say Yes to the X. And we do already have some comments because it was up on YouTube already. What are people saying about this episode? Someone named Rooster said, not everyone should be able to buy a mic. It's not about us, okay? This is about the Say Yes to the X segment. You should have to pass some sort of test to be able to own a microphone. Yeah. You're going to understand why they said that starting right now with your brand new Say Yes to the X here with Brooke and Jeffrey

in the morning. Everyone knows when it comes to relationships the biggest fights always start over the dumbest most trivial things. Brooks told us that her marriage almost ended four different times over how to properly load the dishwasher. No lie told there. I mean he like why would you put the bowls like that? I just don't understand. Okay, he's not here right now, bro. Yeah. God. You can have that fight later when you go home. But naturally, that's why one of our listeners

has reached out. He got dumped months ago by his ex-girlfriend during an argument about toenails. Oh. Oh, wow. Not only has he changed his ways since then, he's brought receipts to prove it Hoping he can get one more chance with her We'll see if it works out in a brand new say yes to the X right after this

It's Brooke and Jeffrey in the morning back with a brand new edition of say yes to the X Yeah, if you haven't heard it before it's where we try to connect to Yeah, if you haven't heard it before it's where we try to connect to Mostly sane people who've been broken up with each other for whatever reason and one of them wants another chance Yeah, and it's interesting because in the past week We've received a lot of submissions from people who want to reconnect with an old flame Oh, is it like the season for it or something? What's going on? Can I ask if we can get out of the way any of us any of our exes Jeff? Thank you for bringing this up because Brooke I wanted to say this directly to you. Oh my gosh no way. Please stop submitting. We have received

14 different email requests from Brooke with different guys on each one and well we Brooke we appreciate you not only being a host but but also a listener to the show. We're gonna ask you to pause your thirst, try to quench it for a little bit, and maybe help out someone else who's not working on the show. Think of your family too, Brooke. Devery, A, I am happily married.

And B, I have- And why do you put air quotes up? Don't do that every time. I have way more than 14 exes. I mean, that number would be vastly higher. But only 14 that you really pine for still, apparently. You still go through your head. Anyway, I'm sure we could discuss your dating history for years and years on this show, but let's try and help out somebody who needs our help right now.

His name is Gavin. Thanks for being here, dude. Tell us about this ex that you want to reconnect with. Yeah, so Michelle, we dated for a while, a few months, I guess, and it was going really well. I was super into her. Yeah, first few months normally go really well, right? You would hope.

Yeah. And if it starts off bad, then it's usually a red flag. Why did you guys break up? Okay, so I've been doing this podcast where I would tell personal stories from my life You were the host you were telling your own stuff on the podcast. You're our competition People think this is so simple, but it gets messy real quick What so you told stories about your own life on this podcast? Yeah, it would just be embarrassing stories from my life or if I had a crazy night out

with my buddies. Yeah, we do that. But then part of it was telling stories about my dating life. Yeah. And so that would include details about my new girlfriend. Yeah. Okay. See, that's so tricky because they're not there to defend themselves.

I'll say I've done this for decades now, shared my own personal life and like the rule that I always try to follow is I always try to tell my own story, not somebody else's. And I always try to make myself look the worst. Yeah, totally. Which is super easy for you.

It's also funny, it's safe to make fun of yourself. Right. Because you're making fun of other people that aren't in the room, that's mean. But hey, in the beginning I messed up all the time too. Super easy for you In the beginning I messed up all the time too I heard some people's feelings I'm guessing that's what happened to you Yeah, so anytime somebody did something strange or out of pocket We just talked about like is this weird is it a red flag like I did it with all the girls I had dated it was yeah, and it's okay with Michelle though What was she was she on the podcast talking about it with you, or was it just you talking about it by yourself?

No, she was not a guest, it was just me talking about it. Okay, okay. What incident did you share that upset her? Let's share it again, huh? Yeah! Yeah! At least we know beforehand this is not the okay story. It's not his current girlfriend, so he's allowed to talk.

Oh, I guess. At least not yet. store. It's not his current girlfriend. He's allowed to talk At least not yet. I don't even remember the specific details But it was like there was one time where she threw a tantrum. It was like about where we clipped our toenail Oh, yeah Like what room you clip them in you do it in a gross place. That's a reason It's not like I was doing it like a dinner table or while cooking or anything on her bed pillow Okay, so wait when you're telling this story on the podcast, I'm guessing you're not making fun of yourself You're telling it about how she's getting upset for no reason I guess I'm realizing more and also from y'all's reaction that it's people are kind of sensitive about it more than I think about

I got your back. I chew my fingernails all the time and I put them in a little pile in front of me And every once in a while, I forget to throw them away after the break. I can see why that's gross I mean that doesn't matter. It's that you're talking about it at the podcast, right? Like what yeah, what's her response? Well, how first of all if she wasn't on the podcast How did she learn about it? Like did you tell her about it? Yeah, she probably supported it. There's a lot of stuff that I don't tell people that I date. You have a full show and you wouldn't tell the person you're dating?

Never. Are you kidding? That is so weird. This is so embarrassing. She knew about the podcast, right? Yeah, she knew about the podcast, but she didn't like listen to it all the time. But one of her friends found it and forwarded the audio to her. That's even worse. Oh, God.

Because that means somebody else is upset about it for her. And she wasn't thrilled that you were talking about her? No, she got really pissed off and confronted me about it and we got into it and she was like, you have no right to broadcast my life. And I'm like, what's my life I'm broadcasting? I mean, is that what you guys broke up over then? Yeah, yeah. She said she felt that she was like totally betrayed

and I'm an a-hole for talking about it and she dumped me. Okay. Okay. And where are you at with that now? Are you regretful? I'm absolutely regretful. I mean, I don't even do the podcast anymore and I took down all of it and I feel like I'm matured and I have a different perspective on

things now so wait a minute I mean does she know that you quit the whole podcast because of this that's kind of endearing like is it cuz of this really feel bad is it cuz you didn't have any listeners when you couldn't talk about your dates yeah I mean I didn't have any delusions of grandeur it was always just a fun thing and okay it ran its course And now you moved on to whatever well, she might be happy to hear that Yeah, I was thinking you don't have a podcast to talk about her on anymore and that seemed to be the biggest issue that she had Yeah, I mean I have different opinions now about sharing my things for all the public to know but like I learned lessons by doing that

Hopefully you could share a little bit more about yourself personally. We call the person who hates to be in the public to know, but I learned lessons by doing that. Well, hopefully you could share a little bit more about yourself personally. Why don't we call the person who hates to be in the public? I know what you're talking about. Actually, Brooke, she's already on the line right now, waiting on hold. She just doesn't know why yet. Okay, so she knows she's about to be on the radio.

Yes. Okay, good. She does not know that it's her ex-boyfriend, Gavin, on the other line Hoping to get another chance with her do not tell her I have four fingernails in front of me right now, okay We're leaving all the nail clippings out of the conversation We're just gonna focus on Gavin and Michelle and the possibility of reconciling when we come back and continue Say yes to the X right after this

When we come back and continue, Say Yes to the Ex, right after this. If you're just joining us, we're in the middle of Say Yes to the Ex with our listener Gavin. Yeah, we are. Who's been thinking a lot about his ex-girlfriend Michelle lately. Because they split up months ago, when Gavin was doing his own podcast at the time, telling stories about his personal life. And naturally that included details of his dating life with Michelle.

Well, I mean, he did describe her being upset as a tantrum even to us. Even if it was, it's a bad description. Right, right. Like, you don't say that stuff. Yeah, he gets it now though. Unless you really don't wanna talk to someone again. But here we are.

And when she found that out, she obviously didn't like being talked about on his show. It led to her breaking things off with him. But the good news is things are different now. Gavin, you're not doing your podcast anymore. You took it down. You say you've matured. You're reconsidering.

Alexis, can you not do that in the middle of our show? It's very distracting. Oh, am I throwing a tantrum for you, Jess? Oh, it's a cost tantrum. I think she's trying to interrupt you, actually. No, she's not. I'm saying get on with it. Extremely rude to do that, but Gavin,

you're hoping for another chance now that that chapter is behind you. Are you feeling nervous before we bring her on? Absolutely. And you know what we didn't ask? What was the last conversation you had with her like? I think it was the breakup conversation. I don't remember having any contact after that.

Oh. Was it heated or was it like sad? Yeah, I mean, it started heated, but by the end, I was pretty sad. I don't know, I regret the whole thing. Oh yeah, that's kind of difficult. I'm sure we could have heard it on your podcast exactly what the breakup was like

if you didn't take it down. Could you repeat that? I didn't hear it down, could you repeat that I didn't hear a corner anyway, so Again, we've moved on from that from your old podcast and now Michelle is on the phone She hasn't heard any of the previous segment that we did with her We've just had her on hold this whole time and she knows she's been selected to be on the radio Just doesn't know why yet Disappointing when she doesn't get concert tickets

Maybe not maybe she's gonna be really excited to learn how much Gavin has changed The things that he's naturally done deleting everything and quitting podcasting altogether I think is a huge gesture, but I don't think you did it for her No, he just did it cuz he's like I don't need this anymore like he learned he said he's changed he's grown yeah exactly yeah I mean it was a it was a combination of things but I definitely knew that it had to come down before I could do something like this okay good point well yeah I think we're in a good spot we're gonna bring on Michelle we'll just talk to her first Gavin and then we'll tell her that you're on the line but um let's talk to her real quick So let's punch her up here

Hello, is this Michelle? Hello, hey Good morning. Thank you so much for being on with us today. I'm sorry to keep you on hold for so long. Oh good Yeah, we usually actually put people on hold for longer. So. Yeah. That means we like you. That usually means Jose forgot someone was on the phone and wandered into the break room

for coffee. Oh my god, that person that won that prize is still on the phone, guys. It's been two days, Jose. Tell them. But no, we are having you on today. I know you don't know why yet, but it's a segment that we do called Say Yes to the Ex. I don't know why yet, but it's a segment that we do called Say Yes to the Ex. I don't know if I like the sound of this. Okay, okay, here Jeff out. Yeah, because there is a certain guy that you used to date

and basically you've been on his mind a lot lately. He isn't sure if you're dating anybody else right now or if you're single or anything like that but the whole point of this is he's open to the idea of maybe re-exploring things with you. That's a good way to put it. Okay but yeah, who is it that you are talking about? Well before I tell you, do you need to cough again? No, we need to tell her who! Sorry, before I tell you, do you need to cough again, Alexis?

No, we need to tell her who. Oh, OK, sorry. Say anticipation. Before I say it, I just want to know, are you dating anybody right now? Are you single? I am currently single, but I am dating. I'm dating around.

OK. You're going on dates. OK, well, that's good to know, because there is a certain ex who says that you guys broke up not too long ago, just a few months back, and you had a fight with him about podcasting Oh, she's gonna jump right in huh Jeff? Bring up the bad part. Oh, it's Gavin. Yeah. Yeah You're good at guessing good job. Yeah, I remember how could I forget? Yeah, he was talking about me a lot

All our friends are listening. I didn't like it. It was really embarrassing. It's a huge turn off for me at the time. And so I don't know. It's just, it was weird for me. Okay, but the podcast never existed. Would the relationship have continued? That's hard to say.

Maybe. Okay. Okay. There's a possibility there. And we would like to give you the chance to talk directly to Gavin about it But I will say Gavin is on the other line right now waiting to talk to you. Oh God. Yeah.

It's a good thing. I think. I'm not sure. Well, let's find out. Gavin, are you there? I'm here. Gavin, what are you doing? What is this?

Why are we here? Look, the way I remember it is that when we were together, we had a good time and we broke up over something stupid. Like I stopped doing the podcast. It's not that important to me. It was just something I did for fun. I apologize for airing your dirty laundry. It's not something that I would do again.

And I don't know. I heard you said that you're dating. Like, are you dating like a lot of people or? I I am dating. I'm I'm exploring. Okay. I mean that's cool. Obviously like I wouldn't be like, oh no You're dating people. I won't i'm not interested like you're a single person, but like if you want to hang out i'd be into that I could have just said that yeah, yeah, I mean, I don't know. I don't know about that, but I, I, I don't know if I want to, I want to tell you this because it's going to sound a little hypocritical. What?

What is it? I recently started my own. HODCAST. I seriously have never seen that coming. That is fine. Oh my God. I seriously have never seen that coming. That is fine. Oh my gosh. It's her telling her own story.

I can see her like, I'm engaged before saying I have a podcast. Okay. So you're comfortable talking about yourself. You just don't like to hear other people talk about you. It's different because at the time we were in a committed relationship and he was talking about me and I'm not in that right now. I'm dating You're just talking about random guys you go out on single dates with yes Gavin How does this make you feel hearing?

I mean it's kind of crazy to me because I never would have thought that you would so like you're talking about basically the same Stuff though right like the people you date. No, it's different. I'm not banging would. So like you're talking about basically the same stuff though, right? Like the people you date. No, it's different. I'm not banging on my partner like you did. Just banging on random guys. Yeah, randoms. But hey, if it's anonymous and random, I mean, that's a way to go on our show. That's like every podcast ever.

If you don't know, if you can't pinpoint the person, that's the good stuff. I can't tell Gavin, are you upset with her? Are you are you flattered that she's kind of following in your footsteps? Like, where's your head? I'm a little shocked and surprised by it, for sure. It's not something I would have expected, given her reaction to what happened.

I can't believe you have an ex that you still like and you didn't find her podcast. Yeah. Yeah. Exactly. Yeah, do you not stalk her pages, bro? Yeah. Sounds like he's been so traumatized by his podcasting experience.

He probably doesn't go to any podcast. Or she blocked him on everything. Yeah, that's true. Okay, I'm sensing some common ground between the two of you though. Is there? I mean, I guess that's cool. It doesn't bother me. I mean, obviously I have some experience doing it, so I understand why someone would do it. Gavin, do you want to listen to her podcast?

Hold on though if you guys hang out are you gonna talk about him? Could be your guest I wouldn't hang out with him if he wouldn't let me talk about I feel that that is juicy content to be like, I went on a date with my ex and now I'm gonna dish. Oh, yeah, we have to talk about it. Okay. Okay, Gavin, looks like the tables have turned my friend. I feel like you guys are gonna go on dates now

and then go report back on your own podcast on how good or bad the date was. Well, Michelle seems open to giving him one more chance for a date as long as Gavin agrees to being talked about on her podcast Gavin doesn't have a podcast. Will you say yes to your ex now Gavin? I mean I would take the chances that that if I did anything Embarrassing and stupid that I guess I would deserve to be exposed for it It's funny that you use the word if but let's uh, oh so you guys are gonna go out again

Yeah, cuz she's thinking of all the content she's gonna be My mind just started like swirling I am down. I am ready Is this the first time that we've ever had a positive ending to this segment? Yeah, I mean, I haven't been doing tally marks, but I'm going to go with yes. I think so. Instinct says yes. I swear if Michelle's podcast becomes bigger than ours though, we're coming after you, Michelle.

Yeah, look out. I'm coming right at you. Oh wow, this collab is done. It's on. Brooke and Jeffrey in the morning. This week on Dear Chelsea with me, Chelsea Handler, Connie Britton is here. I think you should encourage your friend to go ahead and not be holding out for any man to have her babies.

She could be waiting another 10 years before she finds the right guy. Connie didn't meet her right guy until you were what, 50 Connie? 52. 52. 52. I kept thinking, oh, I'm going to meet the guy I'm gonna meet the guy, I'm gonna meet the guy. I finally was like, what am I waiting for? And I did it, and I'm just so glad that I did.

Listen to Dear Chelsea on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. I found out I was related to the guy that I was dating. I don't feel emotions correctly. I collect my roommates' toenails and fingernails. Those were some callers from my call in podcast, Therapy Gecko. It's a show where I take phone calls

from anonymous strangers as a fake gecko therapist and try to learn a little bit about their lives. I know that's a weird concept, but I promise it's very interesting. Check it out for yourself by searching for Therapy Gecko on the iHeartRadio 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. Yo, K-Pop fans, are you ready? It's your boy, Bumhunt, and I'm bringing you the K-PAC. The podcast that takes you straight into the heart of K-Pop fans, are you ready? It's your boy Bom Han and I'm bringing you the K-Factor,

the podcast that takes you straight into the heart of K-Pop. We're talking music, idols, exclusive interviews, and even the real behind the scenes K-Pop stories. Plus, you're the fans, you're part of the show! And you can get a chance to jump in, share your opinions, and be part of the conversation like never before. And trust me, you never know where we might pop up next. So listen to the K-Factor starting on April 16th on iHeartRadio Apple podcast or wherever you get your podcasts. This isn't just a podcast, it's a K-pop experience.

Are you in? Let's go. I want you to ask yourself right now, how am I actually doing? Because it's a question that we rarely ask ourselves. All of May is actually Mental Health Awareness Month and on the psychology of your 20s, we are taking a vulnerable look at why mental health is so hard to talk about. Prepare for our conversations to go deep. I spent the majority of my teenage years, my twenties just feeling absolutely terrified. I had a panic attack

on a conference call. Knowing that she had six months to live, I was no longer pretending that this was my best friend. So this Mental Health Awareness Month, take that extra bit of care of your wellbeing. Listen to the psychology of your 20s on the iHeart Radio app, Apple Podcasts, or wherever you get your podcasts. You're listening to an iHeart Podcast.