Brooke and Jeffrey: Second Date Update - Textual Healing: Proposal Predicament

Episode Date: August 6, 2026

One of our listeners has a delicate situation on her hands involving STOPPING her best friends proposal. She needs our help so she hit us up for some Textual Healing!See omnystudio.com/listener for privacy information.

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If you found out your best friend is about to get proposed to, what's the first thing you do? What do you do? I don't know. Can you congratulate them? No. Before they get proposed to. Don't don't get it.

I don't know. Don't tell Jose. Yeah. That's a good rule just in general. Don't tell Jose anything. Sorry. I'm just so happy. Well, one of our listeners doesn't want to ruin this.

surprise. In fact, she wants to stop the proposal from happening altogether. And she has a pretty valid reason for it, but needs our help. Oh my gosh. Don't worry. She's not in love with the guy, too. It's not that, but it is a delicate situation. Can we assist without destroying their friendship in the process? We're going to try in uptextual healing. Next. Textual healing, textual. You know, a lot of the times on this show, we try to help people improve their dating lives. Yeah, I love that.

Well, today is a little bit different. Okay. Brooke's wishes have finally come true. What are you going to say? We're actually going to try and block love today. No. Because that's what one of our listeners, Emily, wants us to do. I love love.

Yeah. I do. Why do you always say that about me? Well, you're always trying to stop people from going out. Oh, my God. Emily, welcome to the show. Hi. Hi, Emily.

I think Brooke, like all of us, tries to help, but we don't end up being very successful. Sometimes that's all you. Okay. Speak for yourself. Emily. Doesn't that sound so sweet and helpful? For yourself, what do you need? Emily, thank you for emailing this show.

Tell us a little bit about your love situation and how we can help destroy it for you. What's going on? Well, I have a really close friend. Her name is Kaylee. I've known her for a long time. I love her like a sister. Oh, that's so great to have those type of friendships. Yeah.

She's like, yeah. That didn't sound like a yes. I know I love Kaylee. She's my best friend and she's been in a relationship with a guy for almost two years now. Oh, okay. She loves how it's going. I mean, she likes the guy who's very handsome. He treats her right. The only thing is she's not in a place where she wants to settle down with him yet. Okay. That's fine. Why is that an issue? Well, it wouldn't be, but like the problem is I heard a rumor that her boyfriend was going to be proposing to her.

Tonight. Oh. Wait, tonight? Oh, no. Wow. This is the team. Oh, they haven't talked about that. Yeah, normally on the same page.

Well, if you're dating for two years, you think it would have come up. Yeah. Who'd you hear the rumor from? It's from a mutual friend, and I'm in such an awkward situation right now because I've asked Haley before. Like, I've said, you know, if Thomas proposed to you, what would you say? And she's not about it. She's not into that. She told me she's not ready.

Just not yet. Like someday maybe, but just not right now, you're saying. My mom told my dad, no, I think four times before she actually, they actually agreed to get married. So what's the problem? You're worried that what? She's going to turn him down. Like, he's going to make a fool of himself. Oh, no.

So is there an event happening tonight? Like, are your friends all getting together or something? Is that how you think it's going to go down? Well, I just know that they're going to go out on a date tonight. and I wanted to warn her boyfriend just like without being very direct about the situation. Wait, you want to tell, wait, hold on, you want to tell him?

Why wouldn't you want to tell her? Give her a heads up. I don't want to ruin it. Wait, she doesn't want it. She shouldn't do it. There's no. I know my friend. Like, this is so much right now.

I don't want to put this on her. I don't want to burden her with this. Like, I want to get rid of the situation entirely. Whoa. Behind the scenes, you're doing work, so she has zero stress. That's kind of a good friend move. I like that. Oh, I see.

Get rid of the situation. That sounds like we're going to off the guy. You're just going to come to wait maybe? Yeah. So you want to text Kaylee's boyfriend and stop him from proposing without alerting him that you know that he's going to propose. Oh, yeah. That's hard to do.

That's why I turn to you guys. Like, this is so tough to navigate. Like, I need your help. And I've already started a text message with him. Oh, you did. Good. Wait, no. That's unusual for us.

I don't know if it's good. What did you say? Well, it's good because we don't have to do as much work. What's you say? What did you say? Okay, I'm going to try to read this. So I sent him, hey Thomas, how's it going? He goes, stop M, doing great.

Thanks for asking. How about you? Put, oh, you know, just trying to save Kaylee from a lifetime of misery. Wait, what? What? What the heck? She put ha-ha. It's okay.

Like, you're coming out of... Like, this is why I needed your help, because I thought it was funny to kind of do this, you know? It sounds like you're saying that being with him would be a lifetime of misery. I mean, maybe he doesn't even know that. There's not enough, like, context there even. I mean, marriage is a lifetime of misery. Everybody knows that. What did he say?

Yeah. Well, then I tried to play it off cool. I was like, but seriously, how's your day going? Oh, that's the serious part. I'm going to get she knows that you know now. Yeah. What did he say? Yeah, he goes, my day's going pretty well.

Why do you ask? Yeah. I put, oh, no reason. I was just wondering if you had any big plans tonight. Oh, my God. You are so awesome. So we're kind of like doing more like restoration. We're fixing right now more than helping.

How did he respond? He goes, actually, I do, but it's a big secret. Oh, yeah. No, it's not. Shut your mouth. That's what he's telling you to do. Keep your mouth shut. Or maybe he's kind of a dummy.

and doesn't know that she's on to him yet. Yeah. I don't think so. What have you written back to that? Did you say anything? No, I didn't. Because I'm really stuck, and I don't know what to say, so I just need help at this point. Okay.

We need to neutralize a situation, I think immediately for the third time, how is your day going? No. Explain more. Big day with no plan. I think one common theme that we go to with these is using humor to try and get people to open up a little bit more. True, true. Because even though our goal is a little bit serious trying to get him to stop proposing, we need to get him to lighten up a little bit in order to make it there.

Yeah, I mean, we didn't start well with that whole like saving her from a lifetime of misery thing. So, I mean, he's already admitted like there is something I've planned, but it's a big secret. What if we throw out some horribly wrong guesses to make him laugh? Oh, like, oh, let me guess. Is it a big casino heist tonight? Oh, that's better. Are you? That's funny.

photographing Spider-Man around the city. Like, just obviously wrong funny guests. I like casino heist. Go with that one. Yeah. What do you? I'll make him laugh. What do you think, Emily?

I think that's good. Like, I just want to, like, not come off to crazy right now. Like, I'm prying into his life, but. You know, I think we're a little late for coming off crazy. I like casino heist, and then you followed up with, because Kaylee's really not ready for that type of commitment. Yeah. I think so. I mean, why don't you start tight.

that out like ooh let me guess we're doing a casino heist tonight and with the money bag emoji yeah that's good are you typing emily yeah okay I'm putting ooh is it gonna be a casino heist tonight I guess don't get caught or something no am I close am I close question mark we just want them to open up and start talking with us and if you end it with a set you have to end it with a question else he'll never respond to you okay am I close question mark yeah that's that make, okay, I got it. And are you sure your best friend isn't like telling you one thing about her commitment level and telling her boyfriend something else? No, I swear to God.

She does not want to get married right now. Okay, that's good to know. Is that what you were doing with your husband, Brooke? You were telling everybody else like, there's no way I'm going to marry this loser. Are you kidding me? I was begging him to propose. I'm like, what are you doing? Well, get on it.

I remember that because every weekend you'd go away. We're like, this is the weekend. Yeah, he's going to ask. Oh, not yet. I would fake drop down on the knee and I'm like, get up, get up. It's embarrassing. So, Emily, you sent that, right? Yeah, I did.

Okay, well, we're running out of time for this first part. We're going to play a song, come back, and we'll see if Kaylee's boyfriend has responded and then we'll try and stop him from proposing. Oh, my gosh. When we continue textual healing next. How do you stop a guy from proposing to your best friend? Oh, my God. It's usually the opposite. How do you get a guy to do it?

That's funny. I know there must be a cosmo. article about this, but we must have thrown that issue away. So we're kind of on our own here, helping out one of our listeners, Emily, because she knows her friend is about to get proposed to by her boyfriend tonight. I mean, he confirmed it via text. He said he had a huge surprise. The thing is, Emily's friend isn't ready to get married.

Even told her if he proposes, I'd probably say no. Oh, man. So to prevent all that drama, Emily wants to get ahead of it and tell the boyfriend, and please don't do it without letting him know that she knows. Yeah, that's tricky. There's been a whole conversation in the lead-up, and our suggestion was let's throw out some wrong guesses. About what the secret is.

But what the secret is, and we guess big casino heist, am I close? And has he responded to that, Emily? Yes, he has. Okay. What do you say? So he put, OMG, no casino he heist. Oh. What I've planned is kind of bigger than that.

there will be cameras and maybe some roses. Oh, no. This guy is the worst at secrets ever, by the way. Like, could you give away more clues? I'm probably got a camera person, though, honestly. Yeah. It's a good planner. Guys, if you're listening, look that if you're going to propose.

All right. Well, now he's really confirming that something romantic is about to go down. I think we need to, like, deter it right now. I don't think we need to do any more back and forth. Like, is there any way... I don't know. Like, is there any way, like, your friend Kaylee's like going through like other life changes and maybe we could be like you know

Kaylee's going through so much she just really needs a steady non-changing relationship with you that's not a bad idea like is she going through like a changing careers that she get a new pet like something really stressful she got she got a hamster she just really is got in a head space to propose the hamster was pregnant and so now she's got 20 hamsters ever since she got buttons it's been rough for her. Is anything going on like that? Well, her wax person quit pretty recently and she's been looking for a new

one. Like the person who does her bikini life? Oh. It's hard to find someone. Is that taking a big toll on her mentally? Exactly. She loved before she'd been going to her for years and she just doesn't need more stress.

Okay. She's really sad about wax lady. Well, let's go with that, I think. Okay. Or you just say I hope Kaylee not involved in the surprise. She's not in the right head space since her wax woman left. Yeah. She really can't handle more stress on her plate. Okay.

So Kaylee can't handle more stress on her plate. Yeah, just say I hope she's not involved in the surprise. That's good, work, yeah. Because Kaylee's not in the right head space. Right. Because we're still trying to play dumb like we don't know the proposal's about to happen. Yeah. Okay.

So I put, I hope Kaylee is not involved in this. She doesn't need more stress. She's already stressed out about. finding a new wax person. It just sounds funny. It sounds so dumb. But to be fair, you want to get a wax before you're proposed to. So this is stressful.

You want to look your best. Come on. Look, that's not stressful to us, but for her friend. Clearly, it's causing some mental anguish. And that should be enough. And no wonder Kaylee's not ready for a proposal or an engagement. If she's that fragile. Yeah.

Okay. So we've sent that text, right, Emily? Okay. And now he's... Do you think he's free? Speaking out. Thinking about her unwaxed body. If you got that text saying the person you're about to propose to is like super freaked out,

would you be like, oh my God, I should do it another night? As a guy, to be honest, I would be like, wax lady, that's nothing compared to what I'm about to, you know. I don't know if it's going to stop him. He thinks he's doing a good thing. Yeah, like maybe I'll get her mind off of it. But that makes it about you tonight the proposal is all about her. That's true. That's true.

So you want her to be in the best headspace that she possibly can be to guarantee a yes. I like... Well, especially because it sounds like they haven't even talked about it. If he's proposing tonight and Kaylee is so not on board, the communication in this relationship is terrible. Yeah, he's probably super nervous flying blind on this. Anything, Emily? Yeah, something just came in. Okay.

It's as if you think I'm proposing tonight, that's 100% not true. Oh, right! Wait, what? That's awesome. Oh, so he finally clicked in his head. I thought you confirmed with the rumor. Yeah, wait. And what's all the roses and cameras about?

Yeah, hold on, there's more? Yeah, he's sending something else. He's typing. Wait, what is going on? Oh, my God, what if he's breaking up with her? With roses. Yeah, that's a great way. A cameraman, right?

It would make a pretty devastating TikTok video that would go viral. Maybe he's helping a friend propose instead of him proposing himself. Okay, I have another message. It says, wait, do you know already? Oh, oh my gosh. Oh, no. Wait. Is this good or bad? But he said he's not proposing. So what is he...

What is going on? Do you know what? You have to text it back. Do I know what? Just maybe you fake like you do know. I totally know. Yeah. Sometimes that works because then he'll ease up and go, oh, you know, fine, I'll spill the beans. Yeah. No, say this. Tell him, I know something. Tell me what you know first.

Okay. What you know first. I don't know. He knows everything. Let's not turn into a game. Maybe it's like, you play it kind of cool. Like, I mean, I have a pretty good idea. of what's going on tonight. But he just said that he's not proposing.

Do we have a good idea anymore? Well, Brooke, we have no idea. We don't know what's going on. But we're just trying to get him to tell us. I see. Yeah, we know what's going. Like, let me know how I can help. Give me the details.

That's a good angle, Jeff. What do you think, Emily? Yeah, because I'm very confused right now. I'm just thinking just playing along, kind of telling him I. Text it. Okay. Text it. Let's send it.

Okay. I am like dying. What? Yeah. Wait, so is he mean that he's. He's not, like, was he being sarcastic when he was saying, not proposing or was he being serious? Yeah, now it's like, what is he going to do? And what does he think you know?

This is what I wrote. I put, I do have a good idea of what's happening. If there's any way that I can help, that's great. Just give me the details. Yeah. Okay. So I'm putting, please give me the details. And I put a heart emoji.

Oh, that's sweet. And now you're being a supportive friend. But that's not what she wants to be. She wants to stop it. But you see. We got no time. We got to send this. Hit send me.

Okay, I sent it. All right. Oh, boy. Now I'm really curious. What do you think it is? Maybe he's going to give her like an extra kidney or something. That would bond them. I think that her biggest life issue right now is not having a proper waxer.

So I don't know that kidney donation is on there. Kidney swap is pretty romantic, though. I got to admit, I was saying. People call you a romantic. Wait, wait, wait, what? I just got a response. Yeah? Okay, it says, L-O-L, you want to have.

help with your own proposal. Oh! What? No way! Because I don't think Shane would be cool with that. L-O-L. Just act surprised when he asked. Oh, my God.

Wait. This is about me? I'm going to go. I thought you said that your friend has plans tonight, not you. They probably- Oh, my God. Are you so excited? Like, this is crazy.

Wait, hold on. Are you, are you like your friend? Are you ready for this? Are you going to say yes? Do we need to text your boyfriend? I didn't want to know this. She just kind of said it. Well, he thought that she knew.

We acted like we knew and we shouldn't have. Whose idea was that? Well, at least you're going to look great for the video because you know there's going to be a photographer there. Get your nails done now. Hopefully you got a good waxer too. Oh, boy. Quick, practice your shocked reaction for when he asks it.

Um, okay, okay, let's see. Oh. That would be like that. I like that. All right. I think you're all set. That's awesome. Congratulations.

You're going to get married. Guys, oh my God. Let us know how it goes, Emily. Good luck. That was a shocking addition to textual healing. If you'd like some help with your text conversations, DM us on our socials at Brooke and Jeffrey. We can ruin your friend's engagement and get you married instead.

Yeah, look it on. Brooke and Jeffrey in the morning. Brooke and Jeffrey in the morning. Get Bell, pure fiber internet with craved Netflix and Disney Plus from $94 a month. Price guaranteed for two years on internet with a two-year term and auto pay credit. Visit bell.ca for details and to check availability. Bell, connection is everything. What's up, fam? I'm sports journalist Ari Chambers.

Hey, what's up y'all? It's your girl, Sam J. And we're the host of Everyone Watches Women's Sports, a new podcast from Together and I. I heart women's sports. Because let's be real. Women's sports is giving us way too much to talk about these days. So Kelsey Finler, she became the first female solo rower to go from California to Hawaii. My first thought is, like, what's up with the snacks? Like, what are we eating?

The highlights, the rivalries, the breakout stars, the moments that take over your entire timeline. And the conversations that start during the game and somehow keep going all week. Every week, we're breaking down the biggest stories across women's sports. Naomi Osaka showing out She beat Sabalinka Shout out to you Naomi You get the palm

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On the IHeart Radio app Apple podcast Or wherever you get your podcast You know It feels good to be the radio station That tried to stop one marriage proposal And also ruined the surprise of another That's what we bring to the entertainment industry.

We are the worst thing to happen to marriage since 90-day fiancé, and I am proud of that. If it makes you feel better, if it makes you feel better on our YouTube page at Brick and Jeffrey, it looks like Calvin Stue 120 is actually blaming the guy, not us. Oh, right then. He says he sucks with secrets, especially at the end. Okay. I mean, we didn't know that that was going to unfold like that. No, but we were willing to try to stop a marriage proposal. Okay, you're right.

And I love that about us. So whatever. And now we're encouraging one. Yeah. Okay. We have no more. So if you ever have issues with your personal life, if you want us to intervene, let us make it messy for you.

Yes. We'll get in there. Email the show we can help you out. And for more cringe content, don't forget to follow our socials. If you haven't already, find us at Brooke and Jeffrey in the morning. Summer Blockbusters are back. The Odyssey and Spider-Man. Brand new day have taken over cinemas,

and Raiders of the Lost podcast has all the coverage you need, including our interview with director Destin Daniel Cretton. What surprised do you about Tom Holland? He shows up to every meeting early. He's the first one on set. Aside from learning all of his lines,

is also able to memorize everybody's name on set. Download the free IHeartRadio app, search Raiders of the Lost podcast, and listen now. Hey, Portlandia fans. Carrie Brownstein and Fred Armisen here. The Dream of the 90s is alive in podcast form. We're launching Podlandia, AEO rewatch, our brand new podcast where we revisit every episode of Portlandia together, breaking down sketches, going deep on our iconic characters, and pulling back the curtain on how it all got made.

And we'll also be joined by the people who helped bring it all to life. Guest stars, collaborators and friends, including director Jonathan Chrysall, the mayor himself, Kyle McLaughlin, legendary musician Amy Mann, and many more. Kyle is going for it here. You fully improvised, not just words, but a song about it. Well, I thought you were all going to write a song. I remember you thinking that. Listen to Podlandia.

A.O. Rewatch on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. What's up, fam? I'm sports journalist Ari Chambers. Hey, what's up, y'all? It's your girl, Sam J. And we're the host of Everyone Watches Women's Sports, a new podcast from Together and IHeart Women's Sports. We're breaking down the biggest headlines. Naomi Osaka. Shout out. Shoutouts to you, Naomi. The viral moments. I've been obsessed with Kashan Rock's

boxing journey. She looks good. Her combos are swift. And the stories everyone's talking about across women's sports. Because everyone watches women's sports. Listen to everyone watches women's sports on the IHeart Radio app. Apple Podcasts or wherever you get your podcast. Hey, this is Hayes Davenport.

And Sean Clemens. We host the podcast, Hollywood Handbook. Every episode we're trying to help our guests improve their careers by mainly focusing on how they can help us improve our careers. The show's famously super accessible so you can easily jump into any of our 650 episodes and understand what's going on. We recommend some of our recent episodes with Ben Stiller, Danny McBride, Riz Ahmed, and Mary Steenberg. Listen to Hollywood Handbook on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts.

This is Chelsea Handler from Dear Chelsea. Every week, the news gets worse. The world gets crazier, and Yamanika is here to tell whoever's responsible, you're the problem. Do you know I just found out who Sidney Sweeney was? If he got a bunch of women, then I should have a bunch of men. Do better or do less so I don't have to do so much. I'm Yamanika and I'm out. Listen to you're the problem with Yamanika on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast.