Brooke and Jeffrey: Second Date Update - #5 Second Date Update of 2025: Vacation No No

Episode Date: December 24, 2025

One of our listeners planned a first date to last 5 full days with a woman he had never even met before! We’ll hear what happened in your Second Date Update podcast!See omnystudio.com/listener for privacy information.

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I mean, everybody does like a top 10 list of 2025, but none are more disastrous than ours. That's right. We have the worst of the worst. And with your number five, second date update, how long should a good first date last? Like maybe an hour, possibly two. No, wrong.

The correct answer is 120 hours. straight. Oh, wait. What? Because that's exactly how long one of our listeners planned his first date to span five full days and he did it with a woman that he'd never met in person before. Oh, no. What if the date doesn't go well? I don't know. I feel like hour or two, she's already ready to tap out. Yeah. Sounds like a recipe for success to me. But I guess we'll find out what happened in your number five second date update right now. Second date update. What do you do if you've been on the For so long, you start seeing the same people on there over and over and over. Does that happen? Yeah, or you like delete it and then two years later you get it and you're like, you again!

Oh my gosh. You start thinking like, oh, they haven't found somebody yet. Oh, that catfish account is still active? Weird. At that point, they're not potential soulmates to you anymore. They're more like coworkers, just occupying the same space as you every single day. Hey, Sarah, good to see you here again. That's where one of our listeners, Patrick, found himself recently, and he chose to do something about it. So let's find out. Patrick, welcome to the show. Hey, guys. Thanks for having me. It's funny to think that the people that you are seeing are also seeing you and thinking the same thing. Yeah.

But it sounds like you were on the dating apps for a long time. Yeah, I was, unfortunately. He's like, why bring it up, Jeff? Thanks for reminding me. But it says that you decided to do something about it to change that. What did you do? So I kept seeing the same people. Yeah.

So I expanded my location. Okay. So you're willing to drive four hours for a date now. Basically. Okay. So you expanded your search to farther away. And who did you end up matching with? Her name was Lisa.

And our first date actually ended up being a vacation. What? Wait, it's that far away that you had to take a whole weekend to get there? What the heck? Well, it was kind of more of a separate trip. Whoa. You invited her on a vacation and she said yes. Well, it happened to coincide with the work vacation.

So I just thought I would bring her. And it sounded fun and spontaneous. Wow. It's funny because sometimes I feel like when I go on a vacation and a girl always joke like, oh my God, take me with you. But like, you don't actually take them with you. That's a stranger, bro. Did she know you don't live in her city?

Yeah, I told her. I told her. I told her where I'm so confused. And you're calling this a work vacation? Aren't those two words that don't go together? It's kind of sponsored by my work. It's a five-day trip that we could take if we want. Oh, my God. You spent five days together?

Wow. Well, it was supposed to be five days. It actually lasted about a day and a half. A day and a half. Okay. That's not good. Why? Well, what happened?

Well, I'm not quite sure, actually. We were staying in the same. same room and of course we were going to restaurants we were seeing the sites doing all the stuff and having a really good time in my mind and my gosh like you're staying in the same room did she like there's just so many layers to that like you're meeting this person for the first time and you're going to be using the same bathroom is all I can think yeah to be fair we can't talk about anything without talking about the bathrooms of Brooks involved in the conversation cheese. But that's a part of a hotel

stay that like makes it super awkward, right? Oh, like you in the bathroom. And having to get ready and having, you know, your routine. And just like when you have to toot, like that, you got to hold it for like three days sometimes, right? I mean, that's Is that why she ghosted you after

a day and a half? I hope not. I mean, I didn't think all that throughout the time and I should have for sure. Okay. So was there like a moment, bro? Like, you guys got an argument? Tell us about like, tell us about the vibe of the vacation. Like, how did it go up to point well i thought it was going well you know we were having a lot of laughs she seemed to be enjoying herself i was enjoying myself and we went on this bike tour like the first day we were there and we were

on the bus coming back from it and she just said a door said hey i need to talk to you uh i don't think i could make you happy well that's what she said yeah and she got off the bus at the next stop and I don't know what happened to me, but I just started crying. Oh, man. This is so many emotions. Was it one of those so much? Was it one of those wine bike tours?

Because after I drink, sometimes I like to cry. Emotional? There was no alcohol involved, actually. Oh, okay. I don't know why I got emotional. It's probably, I imagine it's because I've been on the apps for so long and then I finally found somebody that I connected with. And we were in a beautiful place.

Yeah. It was more dramatic, I guess. No, it's not dramatic. That's just having feelings, man. That's all right. Yeah, either that or you got dust in your eye. Could be either one. Sand in my eye, I think.

What do you think she meant by I can't make you happy? That's what I would like to find out. I mean, when I got back, she was kind of packing up all her stuff and, yeah, I gave her space. And then she left, and I haven't really heard anything except she texted once that we're probably better off friends. It sounds like you planned a lot of activities for your vacation And some people when they travel They don't like to do that Bro, I'm just yeah

Like let's do one activity maybe two But like mostly do beach time No bike tours Like Jose and I could never vacation together No and maybe she realized you weren't compatible in that way Yeah I mean that could be She seemed to be into all the little things I'd planned for us though It's just so much time together

The stranger And she's adventurous enough to agree to a five-day vacation with a guy off a dating app. But maybe she just wanted the free vacation to, like, lie up by the pool the whole time, didn't want to be going to the zoo and go into the zip lines. Maybe she thought he'd be working and she was just getting a free vacation. Yeah, like maybe that's what she thought.

How long has it been since that happened? It was about a week ago. Okay. Okay. And obviously, you're upset about it. Yeah, I'm very upset. I mean, cried in front of strangers upset. Who hasn't cried in front of strangers?

You're fine. Yeah. Well, maybe she's still even there now. Maybe she's just partying it up wherever you guys went to. Maybe she moved? Let's find out when we call her. We'll come back. We'll try and get you your second date update right after this.

Hold on. Second date update. Some people like to go out to a restaurant for a first date. Others might see a concert or hit up mini golf, but not our listener Patrick. Nope. He jumps straight to a five-day vacation for his first date with leave. At least it was supposed to be five days, but she

cut things off after just a day and a half. She did it in a pretty respectful way. The last thing that she said to him was, I don't think I can make you happy. And the last thing he said to her was because he cried from that comment.

Understandably, he'd built up a lot of hope and those bike tours can make you chafe real bad too. Not only that, but he's been on the dating app for years. It's like years of pent-up frustration just coming out. And I think it's worse when you think things are going well. Right. He was like, this is great.

And then, oh, no. Got blindsided. The thing is, he still doesn't understand what prompted her to say that. Patrick, if you had to guess, what do you think it is? Maybe it was my breath. You usually have gum and I didn't have it. It can't be an ick. I'm not sure why that would prompt her to say.

I don't know why I can't make you happy. I cannot recommend a dent. She didn't have gum either, Brooke. It's the romantic tragedy of the century. No, it makes sense. I mean, maybe you guys can try to get just a single date together. Maybe that will be the key here. I like that, but we do live in different cities, so somebody's going to have to travel.

Yeah. Meeting up is a vacation in itself. Hey, that may be kind of fun. It's like once a month, someone takes a vacation. That could be. Let's start with trying to get it. Let's start with trying to get her to pick up the phone first and hopefully get an answer out of her. But I'm going to dial her number right now.

Let's see how this goes. Hello. Hey, is this Lisa? Yeah, who's this? Hey, thanks for picking up. We're a radio show. We're called Brooke and Jeffrey in the morning. Hi, Lisa.

Hey, Lisa. Good morning. Hi, good morning. Sorry to interrupt your day like this, but we're doing a segment on our show. It's called The Second Date Update. I'm not sure if you're familiar with that, but one of our listeners,

name Patrick has asked us to reach out to you. Oh, wow. Okay. Oh, wow. Like, oh, wow. No, not. Oh, wow. Okay.

Are you surprised to be hearing from Patrick? Yeah, I'm surprised. Well, I guess I'm not surprised because he seemed pretty desperate. Oh. Desperate. Oh, come on. That's a pretty harsh judgment for someone that you hung out with for, like, a Day in half.

Trust me, you'd be saying the same thing if you knew all the things that he said and did. What? Really? Okay. What? Desper it's like a different level of thirsty. That's so wild. Like we talked to him, he seems so mellow. Yeah.

Maybe he has to you because he's not in love with you. That's not fair either. I was sensing love vibes towards me personally, but. He can't be in love with you. I mean, he just sounds like he really liked you and you two finally connected. He was behaving as if he loved me. Oh. What happened to make you say that?

Because I don't think we have the full story. Like we know that he did a lot. And you agreed. You agreed to go on a five-day vacation with him, which is wild. That's the thing. It was just, it was a lot. And yes, I agreed to go on this trip. But there didn't need to be extra pressure on top of it.

And there was. Okay. How so? So our first night there, we went to dinner. and he was like, I could totally see myself proposing here. He wasn't talking about me, but it was like he was waiting for some of me to be like, oh, yeah, like, well, I'd be so lovely one day or, you know, I don't know. I was like, mm, okay.

And then the next day we go on the tour, and he introduces me to the guide as, oh, this is my future wife. Oh, no. Okay, hold on. Was he kidding? Was he like, was he like, this is my future wife? Like, how did he say? Is it funny even if he was kidding?

There was a note of kidding, but it was not enough to, like, he was like, ha, ha, ha, ha. I mean, he sounds kind of like an earnest guy who can be a little awkward. Yeah, he's. Right? When we talk to him. No, this is beyond, like, he then wanted to stop at a jewelry store, and he was like, hey, let's go check out some, like, rings. Okay.

But did you tell him ahead of time that you're against love and the idea of marrying someone in a beautiful location? I'm not. I'm not against love and marriage and all those things. It's more of it. I don't need it on my first date. Like, let's get to know each other. Yeah, that's true. Ring shopping is wild. I mean, I was almost engaged and we still never went ring. Maybe it was a local artisan shop and he was just being a tourist. Oh, yeah. He's looking for a necklace. And there happened to be rings there. Well, we don't have to speculate on like what he was thinking and where his mind is at because he's actually on the other line right now waiting to talk to him. God, no. He's on one knee, I think.

No, he is. He's sweet. Give him a chance. Patrick, are you there? Yeah, I'm kind of bummed out that I haven't heard from you. You haven't returned any of my calls or messages. Wow, like I said, it really, I didn't think it was a good fit. I didn't think we were handling the pace and everything and seeing eye to eye.

Was that hard to hear, Patrick? Yeah, of course. It's hard to hear. I mean, to be fair, I didn't actually propose. Yeah. We know. We know. For the ring shop, I feel like you're blowing it out of proportion a little bit.

I was just curious what your taste was. It's kind of fun to go into a shop. It could have been a T-shirt store, you know. Yeah, I think it was really too much. It was too much. Yeah, I know you're saying it's too much a lot, but sometimes people just know. It's like an instinctual thing and you just feel it. For my parents, I mean, it would love at first sight.

They fell in love within the first few minutes of meeting each other. They ended up having four kids very soon after that. Oh, gosh. I bet they were on the same page. I don't think that's a good timeline to lay out after what she just said. Yeah, and that reminds me of the time. Also, you said,

oh, one day, I hope we can have future kids' little uses. Wow. You got a lot done in a day and a half. Isn't that what everybody wants in life? I mean, I thought that's why we were going on a date in the first place is to find love, really. Isn't that why people do it? We should have known a guy who invited

to grow on a five-day vacation is serious. Maybe he could slow it down, though, you know? Maybe you could pump the brakes a little bit. I could pump the brakes, yeah, yeah. See? Wow. Dude, you're never playing hard to get, bro. I'm sorry, but.

Yeah, I'm skeptical if he's capable of that. If he's able to dial it back, pull back the reins on the love, and just do, like, one dinner date with him, no vacation. Would you be up for meeting Patrick one more time? Lisa, before you say anything, I just, that day you left me on the bus, and when you said you could never make me happy, I cried when you got off the bus. And I don't normally, I'm not a big cry here, especially in public, and it hit me. Not sure that's usually a romantic selling point, but yeah, sounds like your second date is definitely

going to be casual. I mean, this seems like a lot of pressure. I don't know about this. Yeah, but listen. Just on the radio? Sometimes opposites attract. He is hopeless, romantic, and you are more like Alexis, you know? I think she's going to wake up in bed with a ring on her finger.

Yeah. It's up to you, though, Lisa. We're not trying to pressure you. We're not trying to, like, force you to do anything you don't want to do. But we just think that love is the most important thing in the entire world and what the whole purpose that we're on Earth. So with that being said, would you give him one more chance? I am open to it. I need some confirmation that it'll be done.

I've already dialed their back. I've already dialed back. Oh, I can feel it right now. It's totally dialed back. I'm not sure if he likes you anymore, honestly. Yeah, honestly, did he hang up? Yeah, why don't we just talk on the phone for a while and see where things go from there? Hey.

That's reasonable. That's nice and slow. We can start there. Yes, let's start there. True love. See, Lisa, you were wrong. You can make him happy. Hey. Definitely. She just made me happy with the phone call, for sure.

Oh, I was in a smile. Okay. She's like not getting into that. This is not happening. Brooke and Jeffrey in the morning. I'm investigative journalist Melissa Jeltson. My new podcast, What Happened in Nashville, tells the story of an IVF clinic's catastrophic collapse and the patients who banded together in the chaos that followed.

We have some breaking news to tell you about. Tennessee's attorney general is suing a Nashville doctor. In April 2024, a fertility clinic in Nashville shut down overnight and trapped behind locked doors were more than a thousand frozen embryos. I was terrified. Out of all of our journey, that was the worst moment ever. At that point, it didn't occur to me what fight was going to come to follow. But this story isn't just about a few families' futures. It's about whether the promise of modern fertility care can be trusted at all. It doesn't matter how much I fight. Doesn't matter how much I cry over all of this.

It doesn't matter how much justice we get. None of it's going to get me pregnant. Listen to what happened in Nashville on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. For 25 years, I've explored what it means to heal, not just for myself, but alongside others. I'm Mike Delo Rocha. this is sacred lessons,

a space for reflection, growth, and collective healing. What do you tell men that are hurting right now? Everything's going to be okay on the other side, you know, just push through it. And, you know, ironically, the root of the word spirit is breath. Wow.

Which is why one of the most revolutionary acts that we can do as people just breathe. Next to the wound is there are gifts. You can't even find your gifts unless you go through the wound. That's the heart. heart thing. You think, well, I'm going to get my guess. I don't want to go through all that. You've got to go through the wounds you're laughing.

Listening to other people's near-death experiences, and it's all they say. In conclusion, love is the answer. Listen to sacred lessons as part of the Mike Gutura podcast network, available on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. Man, that was a missed opportunity on my part. I apologize to everyone. What did you mean? Yeah. Because she said that she agreed to a phone call. Yeah. Why didn't we hang up? and call her back right there.

Could have just knocked it out while we were on the radio. That's awesome. Maybe got some dirty talking. I didn't need to hear any more of that. No. I have a feeling that she might not answer the phone call. We should try to get them for an awkward Tuesday. Something.

I guess, you know, we're going to let them work it out on their own because they agreed to talk off the air. So that's good. Who knows if it's going to be a true love connection or not? That's going to be up to them. I would like an update from them. If they end up talking for a minute. I'd like to hear where they're at. By the time two months hit, they should have three kids.

In his eyes. At least. But even if it didn't work out for them, lately we've had plenty that did, and you can hear them all on our second day podcast. They're up online wherever you get yours at Brooke and Jeffrey. You know the shade is always shady is right here. Season 6 of the podcast Reasonably Shady with Jazele Bryan

and Robin Dixon is here dropping every Monday. As two of the founding members of the Real Housewives Potomac were giving you all the laughs, drama, and reality news. you can handle. And you know we don't hold back. So come be reasonable or shady with us each and every Monday. Listen to reasonably shady from the Black Effect Podcast Network on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. Welcome to Decoding Women's Health. I'm Dr. Elizabeth Pointer, chair of Women's Health and Gynecology at the Adria Health Institute in

New York City. I'll be talking to top researchers and clinicians and bringing vital information about midlife women's health directly to you. A hundred percent of women go through menopause. Even if it's natural, why should we suffer through it? Listen to Decoding Women's Health with Dr. Elizabeth Pointer on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Michael Lewis here. My best-selling book, The Big Short, tells the story of the build-up and burst of the U.S.

housing market back in 2008. A decade ago, the Big Short was made into an Academy Award-winning. movie. Now I'm bringing it to you for the first time as an audiobook narrated by yours truly. The Big Short Story, what it means to bet against the market, and who really pays for an unchecked financial system, is as relevant today as it's ever been. Get the Big Short now at Pushkin.fm. Or wherever audiobooks are sold. Hi, I'm Danny Shapiro. We were in the car, like a Rolling Stone came on, and he said there's a line in there about your mother.

And I said, what? What I would do if I didn't feel like I was being accepted is choose an identity that other people can't have. I knew something had happened to me in the middle of the night, but I couldn't hold on to what had happened. These are just a few of the moving and important stories on my 13th season of Family Secrets. Listen to Family Secrets on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Greatness doesn't just show up. It's built. One shot.

One choice, one moment at a time. From NBA champion, Stefan Curry, comes Shot Ready, a powerful never-before seen look at the mindset that changed the game. I fell in love with the grind. You have to find joy in the work you do when no one else is around. Success is not an accident. I'm passing the ball to you. Let's go.

Steph Curry redefined basketball. Now he's rewriting what it means to succeed. Shot Ready isn't just a memoir. It's a playbook for anyone chasing their potential. Discover stories, strategies, and over 100 never-before-seen photos. Order shot ready now at stephen currybook.com. Don't miss Stephen Curry's New York Times bestseller, Shot Ready, available now.