Brooke and Jeffrey: Second Date Update - Awkward Tuesday: My Ex Can't Let You Go

Episode Date: August 5, 2025

One of our listeners hadn’t thought about her ex-boyfriend in years until she got a random DM from a complete stranger… and what it said left us all shocked!See omnystudio.com/listener for privacy information.

In 1920, a magazine article announced something incredible. Two young girls had photographed real fairies. But even more incredible, that article was written by Sir Arthur Conan Doyle, the man who invented Sherlock Holmes. How did he fall for that? Hoax is a new podcast for me, Dana Schwartz, the host of Noble Blood. And me, Lizzie Logan. Every episode, we'll explore one of the most audacious and ambitious tricks in history

and try to answer the question why we believe, what we believe. Listen to hoax on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. The Stuff You Should Know guys have made their own summer playlist of their must listen podcasts on movies. It's me, Josh, and I'd like to welcome you to the Stuff You Should Know Summer Movie Playlists. What Screams Summer?

More than a nice, darkened, air-conditioned theater, and a great movie playing right in front of you. Episodes on James Bond, special effects, stuntmen, and women, Women, disaster films, even movies that change filmmaking, and many more. Listen to the stuff you should know summer movie playlist on the IHeart Radio app, Apple Podcasts, or wherever you listen to podcasts. I'm Bob Crawford, host of American History Hotline, a different type of podcast. You, the listener, ask the questions. Did George Washington really cut down a cherry?

Were JFK and Marilyn Monroe having an affair? And I find the answers. I'm so glad you asked me this question. This is such a ridiculous story. worry. You can listen to American History Hotline on the IHeart Radio app, Apple Podcasts, or wherever you get your

podcasts. I'm Noah, and I'm 13, and I started this podcast because honestly, adults don't ask the right questions. Now you know with Noah DeBaroso is a show about influence. Who's got it, how they use it, and what it means for the rest of you. It's not the news. It's what the news

should be if someone Gen Z or Gen Alpha made it. Politics is wild, And I'm definitely not here to payment, but I'm here to make sense of it. Listen to Now You Know with Noah de Barroso on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. Get fired up, y'all. Season two of Good Game with Sarah Spain is underway. We just welcomed one of my favorite people, an incomparable soccer icon, Megan Rapino, to the show. And we had a blast.

Take a listen. Sue and I were like riding the lime bikes the other day. And we're like, we're like, people write bikes because it's fun. We got more incredible guests like Megan in store, plus news of the day and more. So make sure you listen to Good Game with Sarah Spain on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Brought to you by Novartis, founding partner of IHeart Women's Sports Network. All right, we got some drama for you today. It's Brooke and Jeffrey in the morning on the second date podcast.

Yeah, we do. Because it's awkward Tuesday. Awkward. We should just call it drama Tuesday. I mean, honestly, today. is a lot. This poor girl and the DM she received from a complete stranger.

Yeah. So we'll get to that in just a second. But first, we need to rewind. We need to go back to yesterday and talk air friars. Oh, yeah, we do. Because you guys were talking airfriars in the comments. Dude, that lit up our comments section yesterday's second date update. We live in an air friar world. And I like it. Wow, you're on her side then.

I'm definitely on her side. Okay. Okay. Okay. What do you see it, Alexa? Honestly, it was funny. It was really like 50-50. There was a lot of like, you know, She doesn't have emotional maturity, blah, blah, blah. But then these ones were my favorite. I don't usually comment, but I felt compelled to on this one. Air Friars are awesome. And as you guys were recording this, I'm making myself a four-course meal in both of my air friars.

Two. And finally, Air Friars Rock. He should be in the hospital, SMH. Oh, my God. I don't have one still. Maybe I should get one. They are pretty cool. They're nice.

They take up so much space. on your counter. It's true. They're not like aesthetically pleasing. Yeah. Okay. All right. We can talk about air friars for another 10 minutes.

We really could, but. We won't. Let's get into the new Awkward Tuesday phone call happening right now. Don't you hate it when a random thing pops up that instantly reminds you of your ex? Oh, yeah. It could be like a certain song or a funny meme or the smell of an old dumpster. What? That's what reminds Brooke of all of her exes.

Oh. But one of our listeners says she literally hadn't thought about her old boyfriend in years till she got a random DM from a complete stranger. And what it said left all of us shocked. So she sent us an urgent email asking for help. You're going to hear why in your awkward Tuesday phone call. Next. It's awkward.

It's Tuesday. It's awkward Tuesday phone call. Do you ever have someone from your past suddenly pop up again? out of nowhere, like a giant Zit right before your wedding day. Oh. And now you got a dilemma where it's like, do I just ignore this thing and let it hopefully go away on its own? No, don't do that.

Or do I bust out the tweezers in hydrogen peroxide and attack this Zit head on? I mean, you're not supposed to be. You probably are going to attack it. Probably has you something. Well, one of our listeners is dealing with that issue where somebody from her past has suddenly resurfaced in her life. and she's decided she needs help popping that zit. Gross.

He's got to break out. So gross. Jose is the only one that likes that stuff. It's gross. It's only analogy I could think of, but let's talk to Amanda about it. Amanda, welcome to the show. Hey, thanks so much for having me. I appreciate it.

Can't wait to hear who the pus-filled person is in your life. We're like Dr. Pimple Popper right now, guys. Yeah, we'll try to help you. Tell us who from your past is suddenly back to haunt you. So I dated this guy a while back, but we'd broken up. So it's an ex. Well, I get a DM from a random woman, and she asks me, hey, are you dating this guy? She's asking if you're dating your ex-boyfriend now?

She said if I had dated this guy. Oh, she's asking it in past tense. Okay, so maybe she's doing some research or something, you know? Right, which, I mean, it's weird, but I had no reason to laugh, so I said yes. And, on a hold, she tells me that she's dating him now okay cool okay great awesome is that the one sentence response

she said because that's awkward he's mine now you should know that okay thumbs up I left him for a reason but yeah objectively that's weird we agree well and that's kind of where I thought I would stop but she starts asking me all of these personal questions about myself

like what Just kind of things I like, style questions, and I'm sort of like... Oh, like personal stuff, not like questions about you and your relationship with your ex. Exactly. Huh. Which, I don't know. I don't know this person at all, so I said, why are you asking me this? What's going on?

Maybe she's just a really bad stalker, like too up front about getting all the information. She's like, save me the time from scrolling and just tell me now. I'm going to find out this information one way or the other. so just out with it. What does she say to you? Well, she tells me that he still has my picture up in his place. Oh. So she's wondering, there's something going on between us still.

Are we hooking up? Oh, texting, what's the deal? Oh, God. He still has your photo? When did you guys break up? Have we asked that? It's been a few years. And that's what I told her.

I was like, look, I haven't spoken to that guy and thought about him. I'm like 100% moved on. Were you, like, freaked out or what is your reaction to him still having your photo up? That is so bizarre. Yeah, freaked out or flattered. I was a little shocking. I mean, again, like, I'm totally done.

I've moved on. It's been years. So why is this still bothering you? Like, shouldn't you just be like, oh, weird, move on? I mean, I thought that would be the end of it. I told her nothing's going on. Yeah. And then a few weeks later, I get another message from her saying that

she's at a bar right by my place and wants to know if I can meet her to chat. What? Oh, God. What is she doing? Wait. Well, hold on. Like, is this a girl thing? Like, because guys don't do this. Not your problem. No, that's not. This would be, it's weird of her, the ex. Did you go to drinks with her? Well, I was pretty hesitant, but she promised me it was going to be quick,

and she said she really needed to talk to me. I mean, I'd be intrigued to. If it's quick, if you're paying, let's go in and out. What the heck is going? And you want to see what she looks like in real life. I mean, I was pretty much. secure. At this point, I'm just curious, right? Yeah, it's curiosity for sure. This is a great

story. So how to go? What happened? So I went down there. She's already sitting down, having a drink by herself at the bar. I walk over, stay hi. I'm a little nervous. And she just jumps up and gives me this weird hug. Oh. Oh, hi, bestie. I mean, maybe

like sometimes when I feel uncomfortable, I will hug people. Oh, she'll kiss people. Do you know what I mean? Hugging is better than a handshake. Yeah. For sure. Or like a punch to the chin Or whatever Okay, that's obviously a weird start But not the worst thing, I guess

Yeah, it's sort of like What does she want? Does she want to know more about This guy? Like is she And turns out We just have this incredibly awkward Conversation where she's asking me about my skin care And my hair routine

What kind of music I like? Oh no, is she like trying to be More like you? Yeah You said this brook Because I was thinking that It just seemed like maybe she doesn't have a ton of friends. Go to Bumble BFF, girlfriend. Thank you.

Why you? Because they have a common interest. The ex. I guess. That's something that they share. No. It's funny, but. Yeah.

Not exactly healthy. I mean, you left that meeting feeling what? It was so weird. I mean, she was nice, but I finally kind of got myself out of there by saying I had to leave for work. And she's messaging me again now. Oh. I know. Now what's she messaging you about?

She just wants to hang out, it sounds like. I'm to hang out, yes. So I'm curious, what made you email the show for help today with your awkward Tuesday phone call? What are you looking to do here? Well, at this point, I feel like I just need to tell her. It's not that I have any ill will towards her or towards my ex, but I just don't want to be friends. And I feel like I've tried to deliver this message. And I just want to be polite so that she doesn't think that we're enemies.

Right, totally. I don't know what to do at this point. Oh, my gosh. This is so awkward. Extremely awkward, which makes me happy for the segment of the show. But, like, for you, Amanda, I'm not sure how I would feel if I was in your shoes right now. I'd be extremely nervous to make this call. And for her, she could possibly get her feelings certain.

You don't want that. Like, she's not a bad person, it sounds like. Exactly. So that's why I've reached out to you. I just don't know what to do. Okay. Oh, man. Well, we're going to try and think of some advice.

for you and come back, let you make your awkward Tuesday phone call to your ex-boyfriend's new girlfriend. Who you... A little premature on that, but we'll tell her I don't want to be friends with you politely right after this. Hold on.

It's awkward. It's Tuesday. It's awkward Tuesday phone call. It's one thing to have to tell your ex-boyfriend. Hey, stop texting me. Yeah, that's easy. It's a whole not. situation to tell your ex-boyfriend's new lady to leave you alone.

Dang, everybody likes you. Who seems lonely and needs friends. Like, that's the hardest part of it. Yeah, that's what brought our listener Amanda to the show today because she's been broken up with a dude for years. But recently, she's been getting text messages from the new woman, her ex is seeing. And this woman is asking Amanda very personal questions. She's wanting to grab drinks.

No, they did grab drinks, which is wild. She wants to hang out more. and get matching Brazilians with her together or whatever it is that girls like to do. I don't know how the girl hangouts go, but it's just getting super awkward. So she needs advice on how to deliver the message. I don't want to hang out with the clingy new girlfriend

of my crazy ex-boyfriend, but how does she say that more gently? Yeah, let's not let you say it. Yeah, because like Brooke was saying, there's a chance this woman is just super lonely and is looking for a friend in her life. So, Jose, what's your advice to a? Amanda before she makes her awkward call here.

So you don't sound so harsh. Like what we think is right, she really just needs friends and she's lonely. You just blame the situation. What do you mean? No one should be friends with the person dating their ex. Just like ever, like anyone. So you don't dislike her. It's just the situation you're in.

I'm sorry. You don't make it personal about her. It's just any situation involving crossover between exes and the new relationships is a bad idea. seem like she's not over the X then. Well, he's saying like, don't do with the X either, too. Yeah. What do you think, bro? I think you need to blame somebody else. Yeah. And you need

to say that you've got a new man who's super jealous and just doesn't want you to have anything to do with the ex or the girlfriend, any of it. Yeah, he's really rich boyfriend, too, by the way. I mean, he totally sucks, but I'm dating him. What do you think of that, Amanda?

I think these are both great ideas. I'm hopeful she'll be receptive to something. Just be gentle. Because you're not trying to crush her with this message. You're just trying to politely back away from any interaction with her or your ex-boy friend. Some boundaries. Exactly.

And it seems like it needs to be a really specific boundary with her. Boundaries are a good word. Maybe you can throw that in there. But I'm going to dial this other woman. Her name is Courtney, you said. Mm-hmm. Okay. Oh, God.

You're so nervous. You've got this. It's okay. Okay. It's okay. Yeah, we're going to be waiting to jump in if we feel like you need a little bit of help, but this is all you. Good luck.

We dial her number right now. Here we go. Hello. Hey, Courtney. I was just going to text you later. That's so funny. Oh, okay. What's up?

What's going on? Yeah, because I have an extra ticket to the Sean Paul concert next weekend. So I want to see if you could go with me. Shut up all. Um, you know, I probably shouldn't, but thank you. I appreciate it. Oh, why not? It'll be fun.

We can grab drinks before. We could get our pre-funk. On, you know, hang out. That does sound fun, but I am going to have to pass. Aw. Stop. And I don't know that we should spend more time together. Wait, what do you mean?

I'm going to be, like, completely honest with you. It just feels really weird for me that my ex-s current girlfriend wants to hang out with me. Oh. Why? I don't know. I mean, it's not weird for you? No.

I think you're actually, like, really cool and, like, I kind of want to be like you. Wait. You want, what? Yeah, like, Sean stated a lot of girls. You and I both know that. And out of all of them, he only talks about you. And, like, he still has your photo up in his room and everything. weird Courtney

I don't think so I mean you know like sometimes at night like we'll stay up and he tells me stories about you so yeah like he just says that you were like really special

and like I don't know maybe if we hang out enough I could be more like you you know I no I'm sorry I don't like that at all I'm so sorry

like I did not mean for it to sound rude it is 100% of compliment no it's it's not that And I don't want to, like, give you advice, especially because I don't know you very well, but I'll be know each other. Well, to me, any guy that's keeping old photos up or can't get over an X, I mean, isn't that just kind of a red flag? Yes. Wait a second. Why would you say that?

Well, because it's true. I mean, nobody should want to be around someone who can't let go of an X. It's, I mean, I don't think that's called me. Hold on a second. Hold. Oh, my God. Are you saying that? because you're trying to break us up?

No. No, no, no, no, no, no, no, not at all. I'm just saying this whole thing. Oh, my God, you're, like, totally still, I knew it. You're still in love with him. Oh, my God, I knew it. You want to hook up with him. That's what a thing.

Okay. Let's not let us go on anymore. You don't want me to be like you because you want to just keep being you and keep hooking up with him. No, Courtney. She can't even hear us. Courtney, hello? What? What? Yes. Who is this?

Hey, Courtney. Oh, man. There's actually a whole bunch of... Hey, you. Who's this? Okay. Hi, Courtney. Hold on and let him talk and he'll tell you. There's a whole radio show that's on this phone call right now because you're on Brooke and Jeffrey in the morning. What? Why? Why? We want to date your boyfriend.

No, stop it. Nobody wants to date your boyfriend except for you, Courtney. Yeah, we're helping. We all support your relationship with Sean. Amanda included, this is something called an awkward Tuesday phone call. I don't, an awkward, what does that even mean? Amanda reached out to our show because she was telling us about the situation going on with you and her and the ex-Shahn. Oh my God, why couldn't it? We know we're like friends. She could have just confronted in her. Well, I think.

Courtney, I think there's some boundaries that have been crossed that you just need to listen to Amanda a little bit on. The only boundaries being crossed is from Amanda trying to break up. and Sean. No. Amanda, talk to Courtney and explain the situation. Just be honest with her.

Courtney, I just, it's been years since Sean and I were together. I just don't have any interest in revisiting this part of my life

and I just think it's such a strange situation. Whatever you say. Are you not listening to her, Courtney? She's saying it doesn't matter

because it's not real. What? What? Look, at this point, it's shocking to me that you could possibly think that I would want to be with Sean. I mean, you're the one that initiated this entire friendship.

Yeah. Well, I don't want to be friends with you anymore. So I'll tell you that right now, because I don't like to be friends with homewreckers. Oh, my God. Problem solved. Honestly, Courtney, she's got your best interest in mind. Like, you're going to bed at night with your boyfriend, having him tell stories of his ex-girlfriend to you.

I don't think if she wanted him back, she could get him. That is not healthy. It's research. No. No. What? No. Do not become Courtney. Be yourself. And whoever you're with. I am Courtney. What? What? She is Courtney. I mean, I'm sorry. Don't be Amanda. Sorry. I got the names mixed up between you, too. You were saying to her earlier, Courtney, that you think you want to change stuff about yourself to be more like Amanda so that your boyfriend feels the same way. But he must like you if he's dating you right now. You don't have to change yourself. We're talking about all this. And what we should be talking about is Amanda. coming for my man

Sean You think that's what If we're going to go that route Amanda you stay away from Courtney's man If Courtney don't talk to her You terrible woman you You know what that's fine with me Okay

Okay you're willing to break off all communication With Sean which you've already done But you're going to keep doing that Yeah Okay Courtney is that cool with you Stay away from him but we can still be friends No.

No. No. Courtney, there's no friendship between you and Sean's ex. You just go your separate ways and raise each other luck. Yep. Cut the cord here. You're not in charge of my friendship with Amanda. Are you trying to break us up now?

Oh, my God. Oh, my God. You just let people live. Girl. Amanda, you need to block her. I'm sorry. I've tried. Brooke and Jeffrey in the morning.

Have you ever looked at a piece of abstract art or music or poetry and thought, that's just a bunch of pretentious nonsense? Well, that's exactly what two bored Australian soldiers set out to prove during World War II. When they pulled off what was either a bold literary hoax or a grand poetic experiment, publishing over a dozen intentionally bad but highly acclaimed works of expressionist poetry under the name Earn Malley in an incident that caused a media firestorm and even a criminal trial. The Earn Malley episode made fools of believers and critics alike and still fascinates poetry, lovers to this day. We break down the truth, the lies, and the poetry in between on hoax,

a new podcast hosted by me, Lizzie Logan, and me, Dana Schwartz. Every episode, hoax explores an audacious fraud or ruse from history from forged artworks to the original fake news to try and answer why we believe. Listen to hoax on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. The stuff you should know guys have made their own summer playlist of their must listen podcasts on movies. It's me, Josh, and I'd like to welcome you to the stuff you should know summer movie playlist. What screams summer? More than a nice, darkened, air-conditioned theater and a great movie playing right in front of you. Episodes on James Bond, special effects, stunt men and women, disaster films, even movies that change filmmaking, and many more. Listen to the stuff you

should know summer movie playlist on the IHeart Radio app, Apple Podcasts, or wherever you listen to podcasts. I don't know what it is, but there's some people who, if there's just not enough drama happening in their lives at the moment, they'll manufacture it on their own, just so that they have something to be angry and upset about. Some might call them crazy. We try not to say

that word out loud. I said some people not me. If you say some people, it makes it okay. I like it. For Courtney to go from I want to be exactly like you to clearly you're trying to break me and my boyfriend up. Oh, man. I mean, Alexis, this is some Love Islands level

drama that we're dealing with, and I don't even watch that show. Yeah, it gets much crazier than this, Jeff. Oh, does it? If anything, it sounds like Amanda's ex really leveled up. Yeah, right. I'm not being sarcastic at all. Yeah, they're probably great for each other. That was wild. I can't believe it got

there, and I'm not trying to start any drama right now, but if you're listening to this on podcast and you're not hitting subscribe, are you trying to cancel us? You are, aren't you? God, I knew it's snakey snakes listening to us. Not subscribing. I hate you.

Whoa. Unless you hit subscribe. But the likes is calling people crazy. You're telling people you hate them. Can I just say we actually like our listeners? It wasn't me. I said some people. Yeah.

Some people aren't a fan of our listeners. Just some of us. Just some people. Anyway, we do like you. If you can want to subscribe, go ahead and do it. It's Brooke and Jeffrey in the morning. In 1920, a magazine article announced something incredible. Two young girls had photographed real fairies.

But even more incredible, that article was written by Sir Arthur Conan Doyle, the man who invented Sherlock Holmes. How did he fall for that? Hoax is a new podcast for me, Dana Schwartz, the host of Noble Blood. And me, Lizzie Logan. Every episode, we'll explore one of the most audacious and ambitious tricks in history and try to answer the question, why we believe, what we believe. Listen to Hoax on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. The Stuff You Should Know guys have made their own summer playlist of their must listen podcasts on movies.

It's me, Josh, and I'd like to welcome you to the Stuff You Should Know Summer movie playlist. What Screams Summer? More than a nice, darkened, air-conditioned theater, and a great movie playing right in front of you. Episodes on James Bond, special effects, stunt men and women, disaster films, even movies that change filmmaking, and many more. Listen to the Stuff You Should Know Summer Movie playlist on the IHeart Radio app, Apple Podcasts, or wherever you listen to podcast. I'm Bob Crawford, host of American History Hotline, a different type of podcast. You, the listener, ask the questions. Did George Washington really cut down a cherry?

Were J.F.K. and Marilyn Monroe having an affair? And I find the answers. I'm so glad you asked me this question. This is such a ridiculous story. You can listen to American History Hotline on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Get fired up, y'all. Season two of Good Game with Sarah Spain is underway. We just welcomed one of my favorite people, an incomparable soccer icon, Megan Rapino, to the show.

And we had a blast. Take a listen. Sue and I were, like, riding the lime bikes the other day. And we're like, we're like, people ride bikes because it's fun. We got more incredible guests like Megan in store, plus news of the day and more. So make sure you listen to Good Game with Sarah Spain on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Brought to you by Novartis, founding partner of IHeart Women's Sports Network.

I'm Noah, and I'm 13, and I started this podcast because, honestly, adults don't ask the right questions. Now you know with Noah de Barroso is a show about influence. Who's got it, how they use it, and what it means for the rest of you. It's not the news. It's what the news should be if someone Gen Z or Gen Alpha made it. Politics is wild, and I'm definitely not here to payment, but I'm here to make sense of it. Listen to Now You Know with Noah de Barroso on the IHeartRadio app, Apple Podcasts, or wherever you get your podcast.