Brooke and Jeffrey: Second Date Update - Awkward Tuesday: Un-Dump My Ex

Episode Date: June 30, 2026

One of our listeners admits she might have taken things too far with her boyfriend, and now she wants our help to UN-dump him.See omnystudio.com/listener for privacy information.

Joy is essential and it's also elusive, but now there's a new and exciting way to start your journey toward a more joyful existence, Joy 101. It's a new podcast hosted by me, Hoda Kotby. If you're craving inspiration to maximize your joy, tune into these candid, uplifting, and moving on-air chats. Open your free IHeart Radio app. Search Joy 101 and listen now. Joy 101 with Hoda Kotby is presented by CVS. This Black Music Month, the Questlove show celebrates the visionaries, shaping culture, through sound, from country trailblazer Mickey Guyton to hip-hop icon Fat 5 Freddie, the sonic genius of Thundercat, and the revolutionary voice of Chuck Dean.

I want it loud. So the timing might be off, the sound might be muffled, but what's going to come out of there is something that you can feel. Celebrate Black Music Month with special episodes of the Questlove show. Listen on the I-Heart radio app, Apple Podcast, or wherever you get your. podcast. I'm Mungesh Chitigula and I'm back with a new season of my podcast, Skyline Drive. This time I talk to scientists, biopunks, kermudgins, blues owners, super seniors, and Goa's top cryotherapy lab to try to understand this obsession with living forever and what it means

for all of us. And I get into a bit of trouble along the way. I'd say probably start bone smashing. That doesn't work. To make it look more defined. They say it works. I don't know. Listen to Skyline Drive, How to Live Forever on the IHeart Radio app, Apple Podcast. or wherever you get your podcast. Betrayal Weekly is back with brand new stories from threatening text messages disturbing a small Midwestern town.

It was from an unknown number. Who else is getting these messages? Why did it start with us? To long cons and stolen identities. Who lies about being this sick? This was the last time I ever believed a word she said. Listen to Betrayal Weekly on the IHeart Radio app, Apple Podcasts,

wherever you get your podcasts. This is Michael Rappaport, and my podcast, the I Am Rappaport Stereo podcast, is unlike anyone you've ever heard. If you're looking for strong opinions about sports, entertainment, politics, pop culture, and whatever else catches my attention, then subscribe now.

This kid Jafar Jackson should absolutely positively get nominated for his portrayal as Michael Jackson. Listen to I Am Rappaport on the IHeart Radio app, Apple Podcast. or wherever you get your podcast. Hey, it's Brooke and Jeffrey, and you have found the official second date podcast. If you didn't realize,

maybe you're new to this podcast feed every Tuesday, we actually do something a little different called our awkward Tuesday phone call. Yeah, it's way cooler than put together Friday. Yeah. We're just perfectly spot on, you know? Totally. Totally.

And that's anytime you have an awkward situation, you call us for help. And then we just, you know, air all your dirty laundry. So you get to enjoy that episode in just a second, but first comments. Yes. C. Giorano said, I literally found you guys again recently for a second time. I used to listen when I was younger probably 15 years ago.

Then I found the podcast and forgot that I remembered it and now I'm obsessed. Okay. Wow. I hope you're obsessed with this episode too. And just by chance, if you are the Giorado, the heir to the Giorado pizza empire in Chicago, please send us some pizzas. Okay. Yeah, there we go.

Just in case. All right. You never know. If not just listen, it starts down. One of the biggest milestones in every relationship is the first major fight over something really, really dumb. Yeah, and it has to be something dumb. Like when Brooke almost left Michael, all because he insisted the soy sauce had to be stored in the fridge. I can see that being an argument.

It doesn't make sense. Then why do they leave it out at all the restaurants, Michael? Thank you, Jeffrey. A good point, Brooke. Never been poisoned ever by soy sauce, all right? won that argument for sure. Well, one of our listeners is going through something similar and she admits she may

have gotten overly emotional during a text exchange with her ex-boyfriend. Uh-oh. The question is, can we work our magic and answer the soy sauce question before things get really ugly? You're going to find out your brand new awkward Tuesday phone call right after this.

It's awkward. It's Tuesday. It's awkward Tuesday phone call. When you're in love, sometimes you do crazy, irrational, emotionally charged things. God, like have kids. Is that what you're saying? No, no. Maybe that's your life story. But later on, you come to regret those things.

Like for me on Valentine's Day. And I know some of you in this room, I've heard this before. But when I was in college, I basically destroyed my own fraternity house. After I invited two women to the Valentine's Day party, both said yes. and once they arrived, neither hung out with me the entire evening. Oh, that's right. So, yes, the ceiling above my bed had to be kicked in. Thank you, Bacardi-O.

It's not fair, Jeff. I'm glad I don't see angry, Jeffrey, because that sounds like weird. That's in love, Jeffrey. But today, one of our listeners, they're dealing with a regret that was also spawned out of love, not sure if Bacardi was involved in their misfortunes, but let's talk to Jennifer about it. Jennifer, how you doing? I'm good. Hi, hi, guys.

Just one red flag talking to another possible red flag. Even you talking about Bacardi. Bacardi orange flavor. Oh, Jeff. I made all the good decisions back then. Even college kids wouldn't want that. Jennifer, please tell us that you're making smarter choices than Jeffrey. That's my girl.

All right. Tell us about your situation. How has love come back to bite you? So I was dating a guy for four months. His name is Jason. And we met when my... car got declined at a bar and he offered to pay for it. Oh.

Oh, opportunist. Yeah. That's cute. Yeah. We started hanging out. And I was very clear with him that I like it when he pays attention to me. Like, for example, when I say that, I mean, like, if I'm on the couch with you, look at me, listen to me, respond to me. Well, that's three whole things that you're asking a man to do while he's sitting on a couch.

So you're telling. This is a big ask. You just, you don't want your boyfriend to ignore you? Is that what you're saying? No watching the movie. Only look at me. But also, like, don't be checking the sports scores constantly. Like, know that I'm there and be present with me as well.

Be present. Okay. I kind of see that. Okay. I mean, is this something like, how soon into the relationship did you lay this down there? The first week. The first week. Okay.

Yeah, it's pretty clear. That's what I like, and that's how I like to be dated, you know? It's good to establish rules early on in the courtship. Sometimes. And it works for four months. Yeah. So he was into it. He was fine with it.

I mean, he agreed because he had no other choice, but then one day kind of just threw me off and he stopped. Wait, wait. What happened? He stopped paying attention to you? So one day he just didn't respond to me for an entire 24 hours. He didn't respond to my text. I get upset. Like, clearly he doesn't respect me enough to answer one text.

I don't care how busy you are. I'll give you three hours max. Oh, okay. So you're not even together in the same space right now. You're texting him. He's not responding. Right. Okay.

Are you guys in the same city or is he traveling for work? Nope. We're in the same city. So I dumped him over tech. Oh. Oh. Wow. That seems a little rash.

Was he in a surgery or something? Like, you don't know what he was doing? Well, you know, the next morning he's like, are you joking? I was just busy. We literally talk every day. Do you want to be with me? And I was like, you didn't even respond for 24 hours. So, no, thanks.

What? Look, okay, in the weirdest defense of my life, listen here, if you're used to texting someone every single day, morning, noon, and night, and then one day, four months later, with no explanation, that does seem out of the blue. I don't know if you break up, but that's very weird. Yeah, but you don't even have a talk about it. You just dump them via text. That's a different story.

Are you, like, are you regretting it now? Is that why you're calling our show? Well, you know, when I dumped him over text, I kind of got me thinking about the other stuff that annoys me. Like, he never posts on social media ever. I like, I like when guys I'm dating, sends me Instagram funny memes. You don't want them on their phones. You want them looking at it. That's not true. She wants them on the phone

talking to her only and not looking at anything else. Oh my, sorry, honey, I'm trying to pose a picture of you. Get off your phone. Okay. So you started snowballing with all these reasons that you were right to dump him. Yeah, so then I get worked up. I block him from every social media text. As one does.

Such a reasonable thing. It's been a few weeks and I regret it and I realize I probably got a little overly emotional about it. Huh. Oh, that's good. This is matured man. There's maybe some growth there. So did you reach out to him and apologize? No.

Well, that's why I'm asking you guys. I don't know how to ask him to go back with me and give me a chance. Yeah. Oh, this is the first time we're going to be reaching out to your ex-boyfriend after you dumped him over text. Because he didn't respond to you. 24 hours. Yeah, I mean, I overreacted. Yes, I know this now, you know, and I regret it, and

I probably should have thought about it or taken a couple deep breaths, but it really picked me off. Okay. I think, honestly, a lot of what you just said right there to us would be great to put somewhere in the conversation when we reach out to him for your awkward call. What's funny is I was thinking the opposite.

I was thinking that that all sounds like an excuse is why it's okay that she did that. Like, that's not an apology. An apology is just, I'm sorry. Like not, but you really ticked me off. Hold on. What's our goal here? Are we spelling it out you want him back?

Or are we trying to subtly convince him that he's missing out on you? Whatever works, guys. I want to date him again. So can you help me? Okay. We'll try. We're going to come back. Give you a little bit of advice, whether it's a sincere apology or a subtle threat.

And we'll try and make you make your awkward Tuesday phone call right after this. Hold on. It's awkward. It's Tuesday. It's awkward. Tuesday phone call. Brooke, I have a question. How hard is it to admit

when you're wrong? It's actually pretty easy. Hmm. Yeah. I do it all the time. Asked my husband. Asked my husband. That's how she's easy. Are you kidding me? I admit I'm wrong all the time. Well, we took an informal poll

around the office recently. And it had to be a secret poll, obviously, because some people here are afraid of you and quote what you might do to their careers and families. You mean everyone. But I will say your name was up there as one of the people that gets the most votes for someone who can't admit openly when they're wrong. But I say it all the time.

Maybe that's just happening in your head. You should try it out loud every once in a while. Maybe your listening skills aren't very good. Oh, right. You know. Spoken like a true humble person. You're constantly apologizing. It's our fault for not to listen.

We have a similar mindset on the phone with us right now named Jennifer who regrets breaking up with her boyfriend. Because he didn't text her back one. day into their four-month-long relationship. So, Brooke, since you and her think alike, why don't you talk to work? Give her some advice on what you would do in this situation. Everyone knows that's the type of person I am, Jennifer, and I am here for you. But I actually do have a good plan for you, okay? Jennifer, you told us about a story when you first met where he rescued you after your credit

card got declined, remember? Yeah. You guys remember that? Yeah. He is the guy who wants to be the night in shining armor. So guess what? You're another damsel in distress right now. Hey.

You need to call him. You need to tell him something's broken at your house, and he is the manliest man is the only one that can fix it. And I guarantee he'll come rushing back. Actually, you're probably right. What do you think about that, Jennifer? Make up some sort of scenario he can save you from. Yeah, and then you're like cute and sexy when he shows up.

Just by chance. Do you think he'll fall for it? Yes. Yeah, we're guys, we're dumb. Yeah, it could be like, I don't know how handy he is, Maybe like a broken outlet or a... Well, if the guys are saying yes, then I'll try it. Okay.

One of the guys is saying yes. It could be worth a shot, though. That's true. Jose, what's your advice for Jennifer? Well, you seem like a very passionate person, like very intense person, which isn't a bad thing. But sometimes intense people can be more, you know, ranty. So I think you just need to convince him that you were ranting when you sent that breakup text. You didn't really mean it.

You weren't serious. You were just mad. I think that's gaslighting. I think that's like the definition of gasoline. Well, whatever works to get him back. That's her. Her mission is to get him back and I think that'll work. Okay.

A little bit of make yourself a damsel in distress, a little bit of gaslight him for causing all of your problems. Look, we've been dating for four months. You just don't know how I am. Yeah, it's your fault. Yeah. Yeah. How does that sound, Jennifer?

You feel ready now to make this call? I think so. Oh, right. Good. And if anything doesn't go according to our plan, Brooke is more than willing to admit that she is wrong. She has said it out loud. You're right.

I could see nothing going wrong with this at all. Exactly. I feel like he's going to be so open to dating again. We're ready. Here we go. I'm dialing your ex-boyfriend, Jason, right now. We'll step in if we feel like you need a little help. Okay.

This is awkward. What's going on? Why are you calling? I just, how have you been? Um, fine. How about you? Good. I actually went to the bar where we first met, and I just thought of you.

Okay. How's work going? Yeah, no, it's been good, but can I help you with something or why you're calling? Well, you probably want to say something to me, so I'm ready when you are? You're calling me, and you want me to say something? I'm confused. Yeah, okay, fine. I'll go first.

I just hate how everything went down with us. I mean, we definitely should have talked on the phone. I also want a little crazy and, like, may have overreacting a little, but... A little? A little, yes, a little. I wouldn't need that word to describe it, but... But I'm willing to forgive you for what you did. You're willing to forgive me?

Are you serious? Like, you're calling me? out of the blue asking me to apologize to you when you're the one who just like went that crazy pretty much. Jason, I think you're interrupting me. I really hope you're not. I just wanted to give you a fair chance to apologize. Unfortunately, I'm sorry, but you're not going to get an apology from me because you are

the one who put us in this predicament. So, yeah, I'm not really sure what you're expecting from me. Let me just make it really easy for you. like, I, I, what you need to do is just apologize to me because, you know, and say, sorry, Jennifer, you know, I know you wanted to see me and I know that a day shouldn't go by where you, like, don't text me back. Thank you for making it so easy for me. Really, really, really just made my day here. Okay. I get this is hard for you, maybe, and you're adding sarcasm on top of that, but just so I'll help you start off. I'm very, very sorry for not responsible.

responding to you and making you feel neglected. I'll, you know, I'll make it up to y'all. I'll even let you get my groceries or buy me dinner or pay me rent, like whatever gesture you want to show, you know? Are you actually being serious right now? Like, I... Yes, I am. And also, I actually have something that's broken at my house

and is hoping you can fix it. It's an outlet. I've never heard of what outlet say sell sex alone. Oh, my God. What the hell? is actually going on. Like, who are all these people on the phone? Jason, we're a radio show called Brooke and Jeffrey in the morning.

Oh, I'm so uncomfortable right now. You bought me on the radio. Yeah, we're doing something called an awkward Tuesday phone call trying to help out our friend, Jennifer, here, with an issue. And I will say, just to take her side, I didn't hear any apology whatsoever. She gave you a lot of chances there. Jeff is being sarcastic. Well, I'm actually, I'm very thankful that you guys.

just witnessed that because this has been my life. Isn't this ridiculous? What is happening? Can you actually believe this is real? Jennifer, you told us that you wanted to like see him again because you were sorry. Remember you were like- I do, but he needs to apologize. Yeah, everybody knows a sincere apology is always better when you force somebody to give it to.

Makes total sense. That's right, Jeff. That is right. Either way, however you want to look at this, there were some hurt feelings on both sides. And I think what would really help is to get an apology out there from both of you at the same time. So I'll count to three and you guys can both say I'm sorry to each other. Ready?

One, two, three. I'm sorry you didn't text me back. Oh, yeah. Jason's still saying awkwardly silent over there. Yeah, I think Jason's made up his mind, Jeffrey. I don't think he's going to go over and fix the outlet. No, he wants to go over and give her an in-person apology because an in-phone apology wasn't enough.

Is that what you're thinking, Jason? You hit it right on the head. Yeah. See? I just know these things. He finally gets you. Yeah. He does.

He finally heard you right. And you know what? Jennifer, I've actually moved on and I have a date tonight. So I just don't know. Like, there's really no purpose in these kind of calls moving forward. Oh. Okay. You go your way.

I go my mom. Well, good luck. I'm sure she likes to be texted back as well. Oh, okay. I don't think they should probably throw a fit about it. I don't think you're reading in between the lines. What he's saying is he wants you to show up to the date. No.

No. And prove your love. Who's. Can you do that, Jennifer? Text me a time and place, Jason. Wow, you really are crazy. And fun. Oh, my God.

Man, talk about being nervous for your first date. Not because you want to impress the new girl, because Jennifer might show up out of nowhere dressed up as one of the waiters. No, Jeffrey, don't even say that and put that in her head. No, it just means that she loves him. No, it does not. It means that somebody needs a restraining order. Either way.

Brooke and Jeffrey in the morning. Listen, and you're there for heart-wrenching knockouts. The world's biggest stage! And breathtaking triumph. In 2026 FIFA World Cup, the knockout stage. Every match, every moment. Listen on TSN Radio. Join the globe.

On the road to the July 19th final. 2026 FIFA World Cup. Stream it all live on TSN Radio. Available on IHeart Radio. My first guest is Paris Hilton, Shakira, Luke and Yerrin, Samira, and Gracie. I'm so excited on the bouncy bed. You have surprises, many surprises. Welcome to Sweet 305, where the group chat comes to life.

What a f***! It's like a way to say like, Oh, my name, oh, my best friend, hello, her, oh my brother, what a . Look, never I've ever had to have to be about with nobody. Except with my kids, my

kids are so my amante. Uff! Oof! That's incredible! Yeah, the telenovela!

You're the only person I know that loves a yellow starburst. It's lemonade! And no, there's someone like, I'd like to

collaborate with this person. This is Sweet 305. Listen to Sweet 305 with Lele Pons as part of my Culture Podcast Network on the IHartRadio app, Apple Podcast,

or wherever you get your podcasts. Well, a lot of people have a lot of opinions on her right now. Hey, it's Brooke and Jeffrey in the morning. Thanks for sticking around to part three. And there is just a lot to cover right now because I mean, we were shocked. Yeah. We didn't expect her to come off like that. No, no.

You know, I thought she was going to be the one apologizing. Man was, I incorrect. Oh, and it is triggering all the key words in the comments here. Oh, we got narcissists, crazy, nuts, run. suffocating, toxic, immature. Check for a tracker. There's a therapist listening, hearing a gold mine right now. Like, oh, my gosh, please give them my number.

Or that could be someone's type. Yeah. There's someone who's like, ooh, give up my number. Yeah, you're right. Now I want to scroll. There is a lot of comments, but let me try to find. Maybe there will be the one person who wants her. I'll give you a second.

I'm not seeing it yet, though. I think what she really is actually destined for is a reality show. Oh, yes. That is perfect reality show behavior. Oh, my God, you're right. I hate that, but it's so true. It is. So, true.

So hopefully there's a producer listening that she gets her shot. She'll be famous and make more money than all of us someday. There's got to be the villain on every reality show. That's right. Could be her. We've got her. All right, thanks for leaving your comments.

And for sticking here, it's Brooke and Jeffrey in the morning. Joy is essential, and it's also elusive. But now, there's a new and exciting way to start your journey toward a more joy. existence, Joy 101. It's a new podcast hosted by me, Hoda Kotbe. If you're craving inspiration to maximize your joy,

tune into these candid, uplifting, and moving on-air chats. Open your free I-Heart Radio app. Search Joy 101, and listen now. Joy 101 with Hoda Kotby is presented by CVS. This Black Music Month,

The Questlove show celebrates the visionaries, shaping culture, through sound, from country trailblazer Mickey Gaiman It's a hip-hop icon Fat 5 Freddie, the sonic genius of Thundercat and the revolutionary voice of Chuck D. I want it loud.

Look, so the timing might be off, the sound might be muffled, but what's going to come out of there is something that you can feel. Celebrate Black Music Month with special episodes of the Questlove show. Listen on the IHeart Radio app,

Apple Podcast, or wherever you get your podcast. I'm Munga Shatigula, and I'm back with a new season of my podcast, Skyline Drive. This time I talked to scientists, Biotrunk's Kermudgens, blues owners, super seniors, and Goa's top cryotherapy lab to try to understand this obsession with living forever

and what it means for all of us. And I get into a bit of trouble along the way. I'd say probably start bone smashing. That doesn't work. To make it look more defined. They say it works. I don't know. Listen to Skyline Drive, How to Live Forever, on the IHeartRadio app, Apple Podcasts,

or wherever you get your podcast. Betrayal Weekly is back with brand new stories from threatening text messages disturbing a small Midwestern town. It was from an unknown number. Who else is getting these messages? Why did it start with us? To long cons and stolen identities.

Who lies about being this sick? This was the last time I ever believed a word she said. Listen to Betrayal Weekly on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. This is Michael Rappaport and my podcast, the I Am Rapaport Stereo podcast is unlike anyone you've ever heard. If you're looking for strong opinions about sports, entertainment, politics, pop culture, and whatever else catches my attention, then subscribe now.

This kid Jafar Jackson should absolutely positively get nominated for his portrayal as Michael Jackson. Listen to I Am Rap Report on the I Heart Radio app, Apple Podcasts, or wherever you get your podcast.