Brooke and Jeffrey: Second Date Update - Second Date Update: Vacation No No

Episode Date: July 7, 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.

Hear insightful, entertaining discussions on today's important health and wellness topics on the Health Discovered podcast from WebMD. Through in-depth conversations with experts, Health Discovered covers everything from tips for healthier living to the latest on therapy and mental health. My goal is to really destigmatize mental health treatment and looking at it from a whole health perspective. Physical health and mental health can be intertwined. Listen to WebMD Health Discovered on the iHeartRadio app or wherever you get your podcasts. Welcome to your brand new second date update. We're so glad you're here. Yeah, you found the podcast as Brooke and Jeffrey in the morning. And what? Oh, today's about timing. How long a date

should be? Yeah, that's right. I love that your timing was kind of off as I didn't I didn't do it on purpose but this guy's first date lasted five days or that was his plan anyway yeah you're gonna hear the whole story in just a second how could that go wrong yeah and you may think that we have another man in the studio, but it's just Alexis. It's me. Yeah, who lost her voice. Yeah Stop me from reading your comment. That's right That in your sultry voice. Yes, well Lincoln Godfrey said I showed my personal trainer dad this podcast a couple months ago And ever since this whenever I stop in his gym,'s always playing this for his clients to work out too. Oh wait, do we make you work out harder or lazier?

It's good for your ab muscles if you laugh. Oh okay you're doing crunches. There it is. Alright I love that. Let's get this second date brand new started right now. Second date update. What do you do if you've been on the dating apps for so long you start seeing the same people on there over and over And over does that happen? Yeah, are you like delete it and two years later you get it and you're like you again

Start thinking like oh they haven't found somebody yet. Oh that catfish account is still active 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. Yeah. And that's where one of our listeners,

Patrick, found himself recently, and he chose to do something about it. What's that? 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? Yeah, 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. So I expanded my location. So you're willing to drive four hours for a date now? Basically. 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 every time, or 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 right there. Yeah. Okay. 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 can 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. Oh. Okay. That's not good. Why? Well, what happened? Well, I'm not quite sure actually. We were staying in the same room and of course we were going to restaurants. We were seeing the sights, doing all the stuff and having a really good time in my mind. Oh my gosh. Like you're staying in the same room. Did she like there's just so many

Yeah, you're meeting this person for the first time and you're gonna 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 That like makes it super awkward, right? Oh like you Ready and having Yeah, just like when you have to to 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, they're like a moment, bro

Like yeah, tell us about like, you guys got arguments? Tell us about the vibe of the vacation. Like how did it go up to that 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 sat at the door and said, hey, I need to talk to you 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 Was it one of those wine bike tours? Because after I drink sometimes I like to cry a lot too. There was no alcohol involved actually.

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. It was more dramatic I guess. It's not dramatic, it's just having feelings man. That's all right, I guess. No, it's not dramatic. It's just having feelings, man. That's all right. Either that or you got dust in your eye.

Could be either one. Sand in my eye. 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 Sounds like you planned a lot of activities for your vacation and some people when they travel they don't like to do that Mostly do beach time no bike tours Jose and I could never vacation together she realized you weren't compatible in that way yeah I mean if that could be she seemed to be into the little things I planned for us though it's just so much time together and she's adventurous enough to agree to a five-day vacation with a guy off a dating app you know 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 line. He'd be working and she was just getting How long has it been since that happened there's about a week ago, okay, okay? Obviously you're upset about it. Yeah, I'm very upset. I mean Cried in front of strangers upset. It hasn't cried in front of strangers. You're fine. Yeah Well, maybe she's still even there now. Maybe she's just parting it up wherever you guys went to 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 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. He jumps straight to a five day vacation for his first date with Lisa. At least it was supposed to be five days, but she cut things off after just a day and a half. But 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. Yeah. And the last thing he said to her was, Oh, Jeff, it's okay to cry. Cause 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. Well, not only that, but he's been on the dating apps for years, so it's like years

of pent up frustration just coming out. And I think it's worse when you think things are going well. Like oh, 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 your breath usually have gone, and I didn't have I'm not sure why that would prompt her to say I don't know why I can't make you happy

Yeah, I cannot recommend a dentist. Yeah, she didn't have gum either bro It's the romantic tragedy of the century. Now it makes sense. 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 gonna have to travel. Meeting up is a vacation in itself. Hey that made me 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 gonna dial her number right now. Let's see how this goes Hey, is this Lisa yeah Hey, thanks for Lisa? Yeah, hey Thanks for picking up. We're a radio show. We're called Brooke and Jeffrey in the morning. Hi, Lisa 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 named Patrick has asked us to reach out to you. Oh Wow, okay Oh, wow. OK. Oh, wow. Like, oh, wow. No, not oh, wow. Oh, OK. 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. Desperate.

Oh, come on. That's a pretty harsh judgment for someone that you hung out with for, like, a day. Yeah. A day and a half. Give that half. Trust me, you'd be saying the same thing if you knew all the things that he said and did. Really? Really?

Okay. What? Desperate's like a different level of thirsty. That's so wild. Look like we talked to him. He seemed so mellow. Yeah. Maybe it's you, because he's not loving you like he would. That's not fair either I was sensing love vibe 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.

you two finally connected. He was behaving as if he loved me. Oh. Oh, geez. What happened to make you say that? Because I don't think we have the full story. We know that he did a lot, like a vacation. 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 me to be like, oh, yeah I'm like, well, I'll be so lovely one day

You know, I don't know. I was like, well, it'll 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? Like, was he like, this is my future wife?

How did he say it? Is it funny even if he was kidding? There was a note of kidding but it was not enough to like I mean he sounds kind of like an earnest guy who can be a little awkward yeah he's right when we talked to him no this is beyond like he then wanted to stop in the jewelry store and he was like hey let's go check out some rings. 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 that I don't need it on my first date. Let's get to know each other first. Yeah, that's true. Ring shopping is wild. I mean, not still.

I was almost engaged and we still never went ring shopping. Maybe it was a local artisan shop But he was just being a tourist He's looking for a necklace. Yeah 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 you No. Yeah. He's on one knee, I think.

No. No, he is. He's sweet. Give him a chance. Patrick, are you there? Oh, god. Yeah, I'm kind of bummed out that I haven't heard from you. You haven't returned any of my calls or messages.

Well, like I said, it really, I didn't think it was a good fit. I didn't think we were handling the pace of 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 that 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. Okay, but I bet they were on the same page. I think that's a good timeline to lay out after what she just said. Yeah. Yeah, and that reminds me of the time also you said, I bet they were on the same page. 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 uss. Wow.

You got a lot done in a day and a half. Yeah, bro. 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 it's not why people we should have known a guy who invites a girl on a five-day vacation is yeah 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 you're never playing hard to get bro yeah I'm skeptical if he's capable of that but 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? At least 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'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 then. I mean, it 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.

I think she's gonna wake up in bed with a ring on her finger. Yeah. Oh, geez. 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 wanna 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 Would you give him one more chance I am open to it I just I need some confirmation that I'll be dialed back like 90s. I've already down there back Oh already down Sure he likes you anymore honestly Yeah, why don't we just talk on the phone for a while and see where things go from there We could start there that's yeah See Lisa you were wrong.

You can make him happy. Hey. Definitely. She just made me happy with the phone call, for sure. Oh, okay. She's like, not getting into that call. This is not happening. Brooke and Jeffrey in the morning.

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history, and war intertwine as I share the tall tales and hard truths that have helped me understand Uncle Chris. This collection of stories will make you laugh, it'll make you cry, and if I do my job right, they'll let you see the world and your place in it in a whole new way. I can't wait to tell you all about Uncle Chris. Listen now to Uncle Chris on Will Ferrell's Big Money Players Network on the iHeartRadio app, Apple Podcasts, or wherever you listen to podcasts. Man, that was a missed opportunity on my part. I apologize to everyone. What'd you mean?

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. I have a feeling that she might not answer the phone call. Yeah.

We should try to get them for an Awkward Tuesday. Something. I guess, you know, we're gonna 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 gonna be a true love connection or not. That's gonna be up to them. I would like an update from them.

Yeah. If they end up talking for a minute. Totally. I'd like to hear where they're at. By the time two months hit, they should have three kids by then. Yeah. 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. Hear insightful, entertaining discussions on today's important health and wellness topics on the Health Discovered podcast from WebMD.

Through in-depth conversations with experts, Health Discovered covers everything from tips for healthier living to the latest on therapy and mental health. My goal is to really destigmatize mental health treatment and looking at it from a whole health perspective. Physical health and mental health can be intertwined. Listen to WebMD Health Discovered

on the iHeartRadio app or wherever you get your podcasts.