Brooke and Jeffrey: Second Date Update - Awkward Tuesday: Flowers For Who?

Episode Date: August 25, 2026

Imagine getting a text from your ex you haven’t seen in a year and she’s ECSTATIC about the WORST NEWS POSSIBLE… It happened to one of our listeners and he needs our advice in an Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.

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I'm upset. Listen to pro society on the Iheart radio app, Apple Podcasts, or wherever you get your podcasts. Hey, welcome to the second date podcast. It's Brooke and Jeffrey in the morning. Thanks, Brooke. You welcome to you as well. Alexis, welcome in. Thanks, Jose.

That's so nice. You're welcome. I feel seen. And it's Tuesday, which means it's going to get awkward. We always love our awkward Tuesday phone call on Tuesdays. That's why we need a label that. We are so smart. We are so good at naming things.

All right, let's get this awkward Tuesday phone call started. Imagine you're dating a woman for a few years and eventually break up. Okay. But then a year later, you receive a text from her, and she is over the moon ecstatic. Wow, this is a dream for me, Jeff? No. Because for you, it's the worst news possible. Oh.

Uh-oh. Whatever you're thinking is in that text message from her, I promise you you're wrong. It is the most uncomfortable and awkward. situation to ever be in if you're this dude who is on the phone with us right now, begging for help to get out of it. You're going to hear the story in your awkward Tuesday phone call right after this. It's awkward. It's Tuesday.

It's awkward Tuesday phone call. We got an emergency email from a listener who says he just went out on a great first date that was so good. It actually got him into a little bit. bit of trouble. Wait, what? Wait, that's a good thing? Well, we're going to talk to him about it here so we understand why. And this is probably going to sound kind of like a second date update,

but remember, it's not. So just keep that in mind. Just because we say so. Yeah. And we are in charge of the rules here. Let's get Charlie up in here to talk to him about it. Charlie, how you doing, man? Not too well, man. I'm in a real rough situation. Did we call him or did he call us collect from somewhere?

I don't know all the details, Charlie. Just tell us what happened? What went on with this date? I will say I would rather be locked up and have to go through what I'm going through right now. Oh, no. Now I think you're being dramatic. We need the tea. We got a tea, Charlie. Now, I did go on a great date recently with a woman, and it was amazing.

I mean, it was just one of those dates where you don't want the night to end. That sounds nice. What's his lady's name? You know what? I would rather not tell you, and it don't make sense when I get to the end. Okay. It's getting real bad. This is kind of juicy.

Can protect her? Oh, my God. I feel like she stole something from you. No, no, no. No, she didn't. Okay. It's kind of my fault. Now, I'll explain.

Uh-oh. Tell us more. It was late in the date. I mean, even though we both were tired, we were just walking around the city, and it had to be past midnight. We just kept talking. Oh, that's sweet. Yeah. Yeah.

It was nice. I mean, we ended up at her place, like, right outside. It wasn't inside or anything like that. I gave her a kiss good night, but I did not spend the night. Okay. Okay. Why? Look at you, gentlemen.

Why? Because he's a gentleman. It doesn't need to do that stuff. I'm surprised Brooke is supportive of this. That's true. Brooke would be like, oh, come on, give it to her. Scale the side of the building and get in there. Oh, my God.

He didn't say she wasn't waiting in his closet. Yeah. Later. All right. But it's a very gentlemanly move. Yes. That all sounds amazing. And it sounds like you planned on seeing this woman again.

I do. I definitely like her. Oh, you still do. Okay. Absolutely. And speaking of being a gentleman, I don't know why I said that. this, but as I was walking away, I just turned around and I said, hey, what's your favorite kind of flower?

And she kind of just looks at me. And she's like, roses, why? And I tell her, I'm going to send you the biggest bouquet of roses next week. Oh, that is so cute. Her eyes got big and she seemed really excited. How romantic. And I was happy about it, too. I mean, come on.

I was trying to do something nice for. I know. It's the best to spoil something. So you actually followed through? Yes, I went home immediately. I mean, I got right on my phone. It was like 2 o'clock in the morning. And I ordered a huge bouquet of roses.

Like 30-fix roses. Outta boy. Waste no time. Get right on that gift. You liked this girl. Okay. I do. I even put a little sappy message on it.

I said, you have no idea how much I'm missing you right now. I'm counting down the days until I can be with you again. Wait, was this after our first date? It was that good. Dang. None of us in this room have ever felt a love connection quite like that. And Brooke is married for 10 years.

We're all jealous. I felt that way. It's a lot with roses. So you went online and ordered her roses at 2 in the morning. I did. I'm not seeing what the problem is, though. Well, after I ordered the roses, it was late, I just went to bed. But I do remember that it said when I ordered them that it be delivered in two days.

Okay. So, of course, on the second day, I wake up. I'm on waiting for a text, you know, to say, oh, my God, I love them, just waiting, waiting. And then I start wondering, is she at work? And maybe she didn't see him. And then finally, at around 6 o'clock in the evening, I get a text. Oh. Not from her.

Oh. From my ex. Oh, no. Saying Charlie, you never cease to amaze and surprise me. No. You're the sweetest person ever. You sent them to your ex on accident? Yes.

I must have auto-filled it. Oh, my God. Oh, it's not your first time you do that website. Oh, you dummy. Clearly flowers are a go-to move for Charlie. Which is a sweet go-to move. I mean, I think girls would be honored to be auto-saved in the set of flowers. Now your ex thinks you want to hook back up with her.

The note said you're the sweetest person ever. I've been missing you like crazy. Oh, my God. She thinks you're putting the vibe out to reopen your love connection. Yes. And then she put on there, can we see each other Friday or if not sooner? Oh, my gosh. She's like back.

And you don't want to be with your ex? No, not at all. I mean, just making sure it's not an option, because maybe it's the only option you have to know do you feel like maybe fate intervened and that's the reason that her address went in there not one bit I got nothing against her

we were still on good terms but I know I like this new girl but I just don't know what to do because when I got the text all I could do is just heart it and say hey I'll text you later and let you know you hearted it? Well you still made her day why didn't you give it a thumbs up at least or the eyes wide emoji like oops

I don't know. I panicked. I didn't know what to do. This is right. It's good to have an Android phone. You can't even heart anything. I wish. Now you do.

You don't have a woman problem if you're using an Android phone. How long ago did this happen? When was this? It was just the other day. And when it happened, I emailed you guys right away because I don't know what to do. It's going to be the most awkward conversation I've ever been in in my life. The flowers wasn't for her. Yikes.

I might have to tell her and I know she's going to be hurt. Yes. I don't know what to say. I don't know how to do this. Oh, my God. Okay, so you want us to call your ex here and let her know the truth of what happened that night? He has to tell her. All right.

Well, this is, this is, yikes. That's all I can say. I'm understanding the jail time thing now. Yes. I understand why you don't want to make this. I do have to ask, though, what about that girl that you went on the great date with? Well, okay, good news of that. I did reorder her 36 roses.

I even text her and let her know there's a problem. problem with the delivery, but these will be there soon. Oh, good. Okay. Okay. So she's still on her mind. You didn't say what the problem was. It's a smart man. All right. Well, we're going to try and come back and give you some smart advice when we let you make your awkward Tuesday phone call to your ex-girlfriend saying, I didn't really mean to send a bouquet of romantic flowers to you. Those were for my new girl. We're going to do it coming up right after this. Hold on, man. It's awkward. It's Tuesday. It's awkward Tuesday. It's phone call.

We got a text at 78592 from a listener named Sam who says, man, this guy's completely screwed. I wouldn't know what to do either. I'd probably just go out with her for a few weeks and then break up again. That sounds easier than making this phone call. Start a fake relationship with her. No, that's even more mean. If you missed it, this really is one of the most awkward situations that we've had on

our show in a while. Our listener Charlie emailed us for help. because he had an amazing date with a woman the other night. He went home right afterwards and at two in the morning, while exhausted and still high on love, ordered three dozen roses to send to her. Only to find out a couple days later, the website auto-filled the delivery address

to his ex-girlfriend instead. Oh, darn it. The ex got the bouquet and was thrilled, thinking, oh, my stars, he wants me back. Yes, which needless to say puts Charlie in a tough spot. So now we need to give him some advice on what to say to let his ex down easy in your awkward Tuesday phone call. Yikes. Brooke, I would love to hear your advice for Charlie.

Here's my idea. Does your ex have a buddy of yours that she already hates? That who hates? That she hates, yeah. Every girlfriend has someone they hate that their boyfriend's friends with. Yeah, yeah. Okay, we're going to blame it on that guy. What you're going to do is you're going to tell.

that your dumb buddy was drunk and thought it would be a funny prank to send her flowers with your name, right? And you're so embarrassed. It wasn't funny. You're so sorry. What do you think? Make one of your buddies take the bullet for you? It kind of feels like I'm being slimy if I do that. Yeah.

You're already being slimy. No, he's not. No, I'm not. It was an honest mistake. It was an accident, Brooke. What's better than telling her that you meant to send those to somebody else? Jose, what do you think? My advice is to tell her you meant to send it to somebody else.

No. Think about it. Look, nothing is worse than false hope and embarrassment. So you want to be honest because she's your ex. No. You just say, look, bottom of my heart, I'm glad I made your day. I'm glad I made you smile. But those were honestly not for you and I'm so sorry.

Oh, God, that hurts. That hurts worse than the breakup. How do you feel about brutal honesty, Charlie? You know what? After hearing that, let's go back to that first option. Damn. Told you. No matter what way you decided to go with this,

we're going to be on the call with you. If you need a little bit of help, a little bit of support. I'm going to dial your ex-girlfriend though, Kendra right now. Oh, my God. Good luck, okay? Oh, Kendra is her name. I never even think we heard that. Okay.

Here we go. Kendra, hey. Wait, Charlie? My God, you are so sweet. I just got the second bouquet of flowers you sent. Wait, wait, wait, wait. What, what did you say? Say that again?

You're a persistent little sugar bear, aren't you? I sent you. Yeah, two bouquets of roses? I can't believe you're spoiling me like this. Where is this coming from? Um, I really don't know. my heart I guess Oh my god

I can't wait to see you and kiss you I'm gonna give you a special thank you for those flowers Oh Really Can I see you on Friday maybe Friday Um

Yeah I'm not sure I want to see you as soon as I can I mean I want to see you to But here's the thing. My work is sending me away. Like, I'm going to Ecuador. Whoa, whoa, what?

What? Yeah, I'm going away for like three, maybe nine months. I mean, what? What? You work at a grocery store, I thought? Yeah, I do. I do. But we're expanding.

That's why I'm going. They're expanding. to Ecuador? Yeah. Yeah, it's this whole thing. And Argentina, Madagascar, and, you know, all the southern places.

So, you know. Oh, my God. Yeah, I'm so sorry. I mean, I'm not going to be around for a while, as you can, you know, you could tell. I mean, and the flowers,

they were kind of like a little farewell, you know, a way for me to say, you'll always be in my heart. Oh. Oh, that breaks my heart. What? I know, I know, but hey, I don't know what to say, other than, you know, Ari Verderchi.

What? Oh, my God. Ari Verderci, huh? Oh, my gosh. It got worse, that's for sure, right? What was that noise? Hi, Kendra. That noise is a whole radio show jumping in on the call

because you're on the radio right now with Brooke and Jeffrey in the morning. Hey, what? Yeah. A going away party. What is going on? Yeah. I don't know quite how to explain it to you. So maybe I'm just going to let Charlie take the lead here.

Charlie, why don't you tell Kendra what's happening? He's doing such a good job already. I told her. I'm going away. And I just wanted to let you know that you, you know, you're a good person. and I just, you'll always be in my heart. Okay. And the reason that we're on the call is because he, it was a tough thing to say to you about how special you were to him.

So he wanted some moral support. That's what we're doing. He's happy for what was. And it won't be anymore. But I don't know if you can tell. He's in deep, deep pain, just the thought of leaving you. Okay. And all the way to Ecuador.

It's not too all of that. I mean, Charlie, I would wait for you. No, no. No. Oh, that's what I'm not. No. Don't ever wait for a man, Kendra. Don't ever wait for a man.

It would be selfish for me to ask you to do that. I can't do that. That's right. Yep, that's right. That must have hurt to say. After all this, are you kidding? People told me you'd never change. I mean, you'd always be selfish, but this shows them.

Nope, I think the other people were right, Kendra. Yep, yep, I've changed. I mean. What, you've changed? I have. I mean, there's no real way to stay in touch either because, you know, on this trip, it's such a big deal. They're taking my cell phone.

It's like if Survivor were to do grocery stores. Yeah. Like, you're taking your phone? Yeah. How can they do that? Well, because it's business, and they really want me to focus on my job in this expansion. So it might look like I'm ignoring you or blocking you, but that's not the case. I'm just, you know, working.

Yeah. Plus the international fees are wild. We're really sorry about that, Ken, Joe. We all feel really bad about it. So I think he's saying, don't wait for him. I mean, I'm more sorry than you know. Yeah. Can I write to you at least?

Like, are you going to have an address? I think this is going to be too painful, Kendra. I think you should just move on. Yeah. I think you should move on. I don't know if Charlie would be okay with that. I think he would be fine with it. I want her to be happy.

I want to define happiness. But is happy being with him? That's really big of you, dude. But he loves me and he misses me. Oh, I know it hurts. Did the note say love? I don't know if it did. Charlie, you love me, right?

Oh. There is love in my heart. That's such a good answer. It's one of those. Charlie, I love you too. Oh, my God. This feels bad. This feels real bad, Jeff.

Well, I don't know. It feels kind of warm inside now. No, no. This is awful. Well, this is the farewell. Goodbye Charlie. Is there anything that you want to say to him before he goes to Ecuador and changes the world? Charlie, just the flowers and you doing this radio thing? I mean, like, that's so thoughtful and special. I think I really do love you. He's a very, very thoughtful man, very detail-oriented.

Is he? Because he said a Rivadirche and he's moving to a Spanish-speaking country. He's working on it, Brooke. I don't know how detail-oriented Charlie is. He's going to get one of those language apps and he's going to come back in three to nine months, a total. totally changed man. Wow. Maybe years. Don't wait for him.

We wish you all the best. Okay, Kendra. Okay. Yeah. Okay. Bye. He's dead to you. Just move on.

Arivadarchi, as they would say, in Ecuador. Or Nebraska. Brooke and Jeffrey in the morning. Today's episode is brought to you by Vinted. And if you guys are anything like me, my style changes with every season. I love keeping up with trends, but I'll go from loving one style to suddenly wanting a completely different wardrobe just a few weeks later. And I definitely don't want to spend a ton of money every few months. And that's why I've started using Vinted. Vinted is a

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Factor, Canada's number one meal delivery service. Well, there's another prime example of someone who's definitely not over their ex. So true. Dude. And you just get so clouded when you like someone. Yeah. Like you just want to believe everything that they say that the Ecuador move was real. Yeah.

Oh, God. I know. That was a rough one. What do we see? How are people responding to this one? We got it just kept escalating. Yeah. This must definitely be the most awkward one ever.

Oh. I can't believe it. I didn't know someone could dig themselves so deep. WTF. How do you make the same stupid? mistake twice. Okay. Yeah, a lot of people just eye rolls, but maybe we'll get an update. That's what I would love. But what is the update going to be? I mean, we can't make

international calls, so how would we reach him in Ecuador? I think the update is he's going to be backpacking around the world until future notice. Yeah, I'm going to be awkward when he runs into her at a grocery store. Oh, no. Like, oh, I was just hoping for the weekend. Yeah. That's it. Oh, this isn't Ecuador? Yeah. This isn't Ecuador. That is so right. Oh, man. Well, we love when you disowning discuss, you know, what happened and what's going on with these. So definitely continue to leave those comments in here. We do read them all, even if we don't read them all on air. And we don't, you know,

we try to respond to as many as we can. So thank you so much for being here. Please subscribe. It makes all the difference in the world. And hey, we'll be back tomorrow with another classic. It's Brooke and Jeffrey in the morning. I survived nine months in captivity. And I've spent my life exploring how other people survive what should have destroyed them. I'm Elizabeth Smith. And these are the Survivor Files. Every week, I'm with survivors who live through the unthinkable, abducted, stalked, controlled, and nearly silenced.

These are stories about what it takes to make it out alive. Listen to The Survivor Files with Elizabeth Smart on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Did you hear the new episode of the Hey Jonas Podcast? We are at D23. So we'll see who stopped by. The cast of Frozen stopped by, Kristen Bell, Josh Gad, and Adina Manzell. I auditioned for Frozen.

What? For Christoph. They said, okay, what are you going to be singing today? I said, I don't know. That must have been why you didn't get it. Oh, you probably won. Plus, John Stamos, Hayden Christensen from Star Wars and more. And I guess I can share that...

No way. Listen to the latest episode of Hey Jonas on the I-Heart Radio app, Apple Podcast, or wherever you get your podcast. Hey, this is Hayes, Davenport. And Sean Clements. We host the podcast, Hollywood Handbook. Each week, we talk to someone in show business and try to help them with their careers and see what they have to offer us. Everyone has a good time and no one gets mad at their publicists for letting them do our show. We've had a lot of great guests like Sarah Sherman, Adam Scott, Danny McBride, Ben Stillard, and a lot of other big shots that wouldn't be where they are without us.

Listen to Hollywood Handbook on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. If your bookshelf and your For You page are equally important to your personality, welcome home. Pro Society is a weekly podcast that's part book club, part group chat for anyone who thinks Pride and Prejudice and Love Island to serve the same level of discourse. Each week, we're connecting the dots between books, the internet, and pop culture with your favorite writers, book talk creators, and plenty of overthought opinions. Yeah, I'm obsessed. I'm obsessed. Listen to Pro Society on the Iheart Radio app, Apple Podcasts, or wherever you get your podcasts. On the new podcast, Solita, we share the messy reality of truth. traveling alone as a woman. I can wait four hours for the next bus or this random dude is offering

me a ride on his motorcycle. I chose option B. I'm Julie Pinero and I travel by myself because it's a rare space where I can say yes without asking anyone else first. I'm on a mission to reclaim the word Solita, trading the pity for possibility. Listen to Solita on the Iheart radio app, Apple Podcasts, or wherever you get your podcasts.