Brooke and Jeffrey: Second Date Update - Second Date Update UPDATE: Cabo Single

Episode Date: November 14, 2024

We reunited the couple on the phone today after years apart and now they’re BACK on our show for a Second Date Update UPDATE to tell us all about their happily ever after! Hear the call in the podcast!See omnystudio.com/listener for privacy information.

Ugh, we're so done with New Year, New You. This year, it's more you on Bumble. More of you shamelessly sending playlists, especially that one filled with show tunes. More of you finding Gemini's because you know you always like them. More of you dating with intention because you know what you want. And you know what? We love that for you. Someone else will too. Be more you this year and find them on Bumble.

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Thank you so much for being here. We don't normally do this, but you are really special to us. So Jose is going to give out his personal phone number right now. Yeah! Okay. If you need to call him. So text 78592. Okay. That's our show's text board. If you're lonely, you can text us. I'm on it all night long. Okay. So like 1 a.m.

You probably want to cuddle. So you're on it more than your own phone texting, basically. I mean, it's a better way to reach him. That's all we're saying. Yes. And don't forget, we've got 45 more minutes. It's a full show, an hour long. Oh my God. Can you take that much? If you want it, go for it. It's over at the Brooke and Jeffrey main podcast feed, but right now we're all about the second date. So let's get it started. Second date update. Normally when we do these second date calls, people are asking for help with the person they went out with a few days ago, maybe a couple weeks back, sometimes even up to a month. And they're disappointed the other person

isn't responding. But one of our listeners, Bo, says he wants to reconnect with a girl through us that he hasn't seen or spoken to in almost two years. So this is probably going to be interesting. I'm curious to know what the story is. Bo, welcome to the show. Hey, thanks guys. Now I understand playing hard to get, but two years, it's a little extreme. Some guys wait two days to call. I wait two years. Why wait that long to reach out? Well, let me give you a little bit of background okay so this happened when i was on vacation in mexico two years ago um and she was also on vacation she was there with a friend i was there with a group of buddies it was like cabo and the whole place kind of had these like spring break vibes okay so this is already a lot different than a lot of the second dates

where we do where people are meeting on apps and stuff you're meeting on a spring break basically yeah so we go into this one bar and i see these two girls that are sitting down at the other end of the bar one of them i thought was really cute but they seemed like kind of out of place because they weren't partying like crazy like everybody else boo wait who said that yeah that was rude So they weren't entering the wet t-shirt contest. They were just enjoying themselves. They were having a cocktail. They were being chill, you know. I like that because I wasn't going too hard either.

Jeff's so bored right now. Well, no. Someone has to babysit. I understand. You need a few responsible people. Yeah. That's a good point, too. So did you go talk to him, I assume? Yeah, yeah. So I go over there. I sit down and I start talking to Shayla. Yeah. and we sort of bonded over that we were both the two lame ones in this crazy group it's kind of funny so we talk you know we learn like where we're from and like it turns out we're staying at the same hotel okay are you guys from the same city or no no i mean are we going

to try to get a hold of her across the country? She's from a different state. She's from a different state. Interesting. I don't know what I was thinking. I was into this girl. So I told her my room number. We part ways, stay the night.

Middle of the night, she calls my room. Exactly what you were hoping for. Be honest. It didn't turn out that way. She calls my room. She is freaking out. were hoping for be honest well yeah but it didn't turn out that way so she called the room she is freaking out why oh why she tells me there's like these drunk dudes that are banging on her door and it's scaring her and her friend oh my god that's scary yeah so i get dressed i go to her room oh you went good yeah i did you're just gonna go back to bed i'm gonna call like a you

problem i'm not going to intervene. I'm going to get hotel security or something. I don't want to get involved. That is a smart thing to do is hotel security. One dude against a group of men. You're not going to do Jack. Sorry, I just didn't think of it like that. How many bones did you break, Bo, when you went and tried to stop the drunk guys?

Well, no bones were broken. There were. There were like four or five dudes and they were just being told i guess that they'd like seen them earlier in the day in the room and they were scary yeah it was super weird so i go down and i tell them to get the hell out of there they did they left nice okay i bet she was so grateful did you talk to her she was yeah you know she of course heard the whole thing to the door she liked that and she asked if she could come back to my room and she did and and then we ended up making out yeah you did you're a hero it was a good makeout sesh but but that's it that's

all we did okay that's cute so got her number, and that was it. But the thing is, I didn't see her the rest of the trip. At all? Like, I tried, but either she wasn't in her room when I tried calling her room, or she never texted me back. Oh, no. And I called her one time after I got back home, and she didn't pick up, and I left her voicemail. And that was that, and that was that. That was two years ago.

Are you sure she was single? Oh. Yeah, that's a good point. You know, like she got wrapped up in the moment. She only kissed you and then she was just like, oh my God, I did something terrible.

That happened on Brooke's last Mexican vacation. And my husband was with me. I know. Super awkward. Did you ask Mexican vacation. And my husband was with me. I know. Super awkward. Did you ask her if she was single? Well, no.

No. I just sort of assumed if she wasn't, she wasn't going to do anything. Well, it's also been two years now. So even if she got single, she still hasn't called him. Yeah. Like, I mean. And I think the rule in Cancun is everybody is single. When he was in Cabo.

Oh, well, that's a different, that's a whole different business. It's more political. We need to tread lightly on this one. They have a different rule set. This is crazy, though, because you haven't seen or spoken to her in two years, and now we're going to reach out randomly out of the blue to see if she remembers you. Yeah, how are we even going to say, like, Nick from Cabo, do you think that's it?

Well, yeah, his name's Bo, so that would help. Maybe she also had a Nick in Cabo. Maybe that's why she's not calling me back. Oh, no, she's like, oh, my God, I love Nick. That's the one that Brooke made out with on her family vacation. Sorry, Bo. Sorry. You know, look, I know

it's a long shot. It was so long ago, but I figure if anybody can do it, you guys can. And she wasn't drinking, so she should remember. I think she was drinking. She wasn't drinking as hard. Yeah, yeah, yeah, yeah. But it wasn't like that.

She wasn't crazy like that. No. She was having cocktails. She was just injecting stuff. It was fine. So we're going to come back. We'll call Shayla and try and get you your second date update two years after you last saw her. Wow.

Right after this. But she's still in combo right now. Hold on. Right after this. But she's still in Cabo right now. Hold on. Second date update. You're in the middle of a second date update update, and we're going to find out how the couple is doing right after you hear part two. For most young single people, a trip to Cabo is all about tequila shots, wet t-shirt contests, getting your wallet stolen on the beach.

Alright. What if I have my passport in that? Shoot. Not an authentic Mexican trip if you're not robbed somehow. But that wasn't the case for our listener, Beau. The only thing stolen from him was his heart. When he met a woman named Shayla

at a bar there two years ago. And the craziest part? They were both sober when this all happened. Sober-ish, Jeff. They both were drinking cocktails. They just weren't as wasted as their friends. Even still, that's shocking. And Bo has thought about her ever since that trip, has never been able to reach her.

That's why he wants us to try and do it for him today. I don't know that we asked. What motivated you to finally take this step? I'm not getting any younger. Might as well shoot my shot. Let's not tell her that. Desperation hits us all at some point. Your biological clock is ticking is what I hear there, Bo.

We're just going to go with the more romantic version of that story. I haven't stopped thinking about you. Thank you. Okay, here we go. I'm dialing Shayla right now. Hello? Hi, we're looking for Shayla. Yeah, this is she.

Who's calling? It's okay. You don't have to be afraid oh i don't know this would be such a weird call to get we're we're just yeah a friendly morning radio show called brooke and jeffrey in the morning hey shayla hey uh hi we're trying to help out one of our listeners with a segment called second date update okay okay and this is a guy that you met two years ago on a trip to Mexico. We know that's a while ago. She says wow. Yeah.

Yeah, you were in Cabo? Yeah, that was a long time ago. Oh, oh my God. A light bulb just went off. We heard it. Oh my God. So there's this guy named Bo that you hung out with a little bit? Oh, my God, yes.

That was such a long time ago. I hadn't really thought about this guy forever. That's okay. Well, now you're thinking about him now, and you sound happy at the memory. Kind of, but, like, so much has happened since then. Okay. Okay. What is this about well this whole

segment is about seeing if you remembered beau because i don't know if you know this but after your trip ended beau said he tried to reach you right right yeah but like back then everything was so complicated i mean i knew it you were in, weren't you? I was engaged at the time. Oh my God. Engaged? Oh my God, girl. Wait, does that mean you're married? Are you married? No. I was engaged to two guys, actually. At the same time? Two guys? Why is that so casually? Okay. So like back then I was a hot mess and And I did a study abroad in Italy, and I met this guy, and we hit it off, and he ended up proposing. And I said yes because I felt bad. Oh, wow.

Wait, you said yes because you felt bad? No, this is how Alexis is married. Yes, it is. That's what literally I was going to say. I mean, I was leaving, and I was like, yeah, I'll marry you. And then, you know, I left, and then I never talked to him again. Oh, that's one proposal. Where is the second proposal?

So I leave Italy, and I go home to my other boyfriend. Oh, you had a boyfriend? Oh, wow. Oh, jeez. I guess he missed me, and he proposed, and I, you know, I said yes. Yeah. Wow. So then you went to Cabo while you're engaged to two men and made out with Bo.

Yes, which made things even more complicated. I felt so horrible about it. Well, you're lucky Bo didn't propose to you because you probably would have said yes to that too. Maybe. Maybe. That's where I was at in my life. life so wait did you end up getting married to anyone i know they both fell through like karma eventually caught up to me i guess wait okay so what's your relationship status now i'm casually dating someone it's nothing serious just casual

relationship with my husband it's like not that serious it's hard i mean honestly though it's hard to trust you yeah it is i guess but i told you the truth i'm an open book now yeah okay why would you make up all that embarrassing stuff about yourself i believe her yeah well you know what on the radio that is definitely kind of an embarrassing story it's nice that you were able to tell us the truth here so now it's our turn to tell you the truth. Uh-oh. We're engaged. So embarrassing, Jeff. The truth is we want to help you bring back some of your past right now.

Why? Not your fiancés. That is a terrible way to go. Your Mexico fling beau is on the phone right now listening to this conversation, wanting to talk to you. All right. Should I hang up right now? No. Bob is on the phone right now listening to this conversation, wanting to talk to you. All right. Should I hang up right now? No.

Bob is on the line. No, hear Bo out. Bo, are you there? I am here. Jeffrey, you're acting like Bo is going to be excited after hearing all of that. Like, yeah, Bo. That was a lot.

Yeah. So let me get this straight. So when we hung out two years ago, you were engaged to two different guys, one of whom you weren't even really talking to anymore. Well, right. I'm no longer talking to any of them. But hi, by the way. Hi.

It's very good to hear your voice. And I really like hanging out with you. And I know it's crazy because, like you said, literally all we did was make out one night. But I just, I can't, I can't stop thinking about you. And I guess you're still thinking about me? Did you just laugh? It was an awesome night. I mean, but like, can I ask, did you even like me?

Like, were you actually into me or was this just a nothing thing? I mean, i like you enough to make out with you i mean this is a lot right now it's hard because you were you weren't just the other guy bo you were the other other guy yeah so you were you were mr right now you know what i mean it hurts it hurts so bad but it's true, I get it. But it's really sweet of you. I thought about you. And he's gone through all of this effort reaching out to our show. This is a pretty complicated process in order to get this done.

Well, think about it. He kept your number for years just in case, hoping he could use it again. Does anybody delete people's numbers? Who deletes a contact? I mean, that doesn't happen. I'm trying to tell my friend here? I mean, sorry, I guess I was just going to sort of ask, Shayla, you know, I mean, I did take in the fact that you were single. Yes, that did register with me.

Kind of single. Yeah, it wasn't like fully single. Yeah, I guess in this whole scenario, kind of single is essentially single. Yeah, combo single. We'll call it combo single. Everything is single. We'll call it Cabo single. Everything is single. Cabo single. I like that. Casually in a relationship, sure.

No, no, no. Cabo single, break your head. I guess I was just going to say, like, this whole thing has been the biggest long shot ever. And I know we don't live in the same city and all that. And I don't know about logistics or any of that stuff but like would you be open to like some kind of a long distance dating thing and if you're open to that idea of possibly making it work then we would love to help facilitate that by paying for your official first date yeah not the flight because i've also been told long distance First date Long-distance relationships don't need too much trust

Shayla this you've had two failed proposals, but the third time's the charm is what they say She'll say yes, yeah her casual relationship proposes first. That's true. Then it'll be the fourth. You know what? I say let's give it a shot. I bet. All right.

It's hard to be enthusiastic. Okay, good. I'd like to follow up with that. So we're getting rid of the side guy, right? No, I don't think so. By the time we go on a date, he'll be history. Don't worry about it. By the time.

Great. Thank you. Thank you, guys. You're welcome. Congratulations, Bo. You're Mr. Right Now again. Yay! I'll take it.

I'll take it. All right. Brooke and Jeffrey in the morning. Last we left Shayla and Bo, they were talking about trying a long-distance relationship once she was free from all of the other men that she was actively dating and engaged to. Honestly, out of all the updates we've done,

I am most shocked that they're on the phone with us right now. It's crazy. I would have never... Wow. So, Shayla and Bo are back. Where are you guys at now? We're divorced. Oh my God.

Wait, what? You got married and divorced in the time since we've talked to you? Yes, actually. What? We went back to Cabo where we met and we had a couple of wild nights and we got hitched. In Cabo? Wait, is he on the phone, too? Yeah, I'm here.

Honestly, to be totally frank with you, I don't know what the hell is going on, but I'm into it. Wait, into what? Are you guys completely separated? No, no. No, no, no, no. We came back from Cabo. We went too much too soon.

Yeah. Yeah, yeah, we jumped into it too soon, but, you know, we're still that we might have. Too much too soon. Yeah. Yeah, yeah. We jumped into it too soon. But, you know, we're still smitten with each other. We're still dating. Okay. So you met him while engaged to someone else, broke up with them, married, and then divorced Bo, and now you're happily dating each other?

I think you messed that up. She was engaged to two people. Oh, okay. Yeah, yeah. Engaged to multiple other people. I mean, no need to bring that up, but okay. Girl, you move fast. I mean, technically, she was now engaged to three people, you know.

Your relationship is all over the place. Yeah. I mean, it's our story. It's not for everyone, you know. It's funny. I got to say, it's going to be great at any sort of dinner party. Absolutely. Yeah.

Yeah. I mean, other than that, it's your normal boy meets girl story. But, you know, thank you for taking the time to come on and give us an update, you two. Yeah, and I guess congrats on the divorce. And the marriage. Thanks. Can we have an open invite to, like, the next wedding or divorce or whatever? Like, just something's going to happen with you guys.

Sounds like they're not very planned. Yeah. It's Brooke and Jeffrey in the morning. Brooke and Jeffrey in the morning. Catch Jon Stewart back in action on The Daily Show and in your ears with The Daily Show Ears Edition podcast. From his hilarious satirical takes on today's politics and entertainment to the unique voices of correspondents and contributors,

it's your perfect companion to stay on top of what's happening now. Plus, you'll get special content just for podcast listeners, like in-depth interviews and a roundup of the week's top headlines. Listen on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. I'm Emi Olea, host of the podcast Crumbs. For years, I had to rely on other people to tell me my story. And what I heard wasn't good. You really f***ed last night.

It felt like I lived most of my life in a blackout. I was trapped in addiction. You had to grab the lamp and smash it against the walls. And then I decided I wanted to tell my own story. Listen to Crumbs on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Welcome to My Legacy. I'm Martin Luther King III. And together with my wife, Andrea Waters King, and our dear friends, Mark and Craig Kilberger, we explore the personal journeys that shape extraordinary lives.

Join us for heartfelt conversations with remarkable guests like David Oyelowo, Mel Robbins, Martin Sheen, Dr. Sanjay Gupta, and Billy Porter. Listen to My Legacy starting January 20th on MLK Day on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. The forces shaping markets and the economy are often hiding behind a blur of numbers. Apple Podcasts, or wherever you get your podcasts. You'll hear from Bloomberg journalists like Matt Levine. A lot of this meme stock stuff is, I think, embarrassing to the SEC. Follow the Big Take podcast on the iHeartRadio app, Apple Podcasts, or wherever you listen. $1.4 billion in NFL quarterback contracts. The untold stories behind the biggest deals in football history. I'm AJ Stevens, Vice President of Client Strategy at Athletes First,

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