Brooke and Jeffrey: Second Date Update - Second Date Update: I'm Cabo Single

Episode Date: May 1, 2024

It’s been YEARS since the two people on the phone went on a date in an exotic location, but after a little bit of romance, a few drinks and a long layoff we’re gonna try to see if they’re the perfect fit for a Second Date Update!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.

Jon Stewart is back in the host chair at The Daily Show, which means he's also back in our ears on The Daily Show Ears Edition podcast. Join late-night legend Jon Stewart and the best news team for today's biggest headlines, exclusive extended interviews, and more. Now this is a second term we can all get behind. Listen to The Daily Show, ears edition 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. So that's why we created The Big Take from Bloomberg Podcasts, to give you the context you need to make sense of it all.

Every day in just 15 minutes, we dive into one global business story that matters. 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. 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. Right. 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. Whoa. So this is probably going to be interesting. I'm curious to know what the story is. Yeah.

Bo, welcome to the show. Hey, thanks, guys. Now, I understand playing hard to get, but two years, it's a little extreme there. Some guys wait understand playing hard to get, but two years? It's a little extreme there. Some guys wait two days to call. I wait two years, Jeffrey. 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. 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 yeah for sure party party town yeah party city lots of booze all that sort of stuff 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 and the thing about them that i noticed was they seemed like kind of out of place because they weren't partying like crazy like everybody else and okay i i like that because i wasn't going too hard either that That's not so much my scene. 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.

Jeff's so bored right now. Well, no, someone has to babysit. I understand. You need a few responsible people. Yeah. 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 i start talking to the girl that i think's really cute 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 what we do and all this stuff And it turns out we're staying at the same hotel. Okay. Whoa. Hey.

Are you guys from the same city? 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. Oh, okay. Interesting. Okay.

I don't know what I was thinking. I was into this girl, and so I told her my room number. And I was like, hey, why don't you hit me up tomorrow and let's go get lunch. Okay. That's cool. It's a very sober way to ask let's go get lunch. Okay, that's cool. It's a very sober way to ask somebody out in Cabo. Well, it's not very forward. I mean, like, honestly, like, you're in Cabo, you're partying, even if you're not going as hard.

Like, I would just think hookup, right? Like, that's what I would think. That's where I thought the story was going, not like a lunch date the following day. When you say, here's my room number, that's just about itself, right? There's some implication there but maybe not with beau and shayla would you like to go get some fresh squeezed juice in the morning so we part ways say good night middle of the night she calls my room yeah exactly what you were hoping for be honest well yeah but it didn't turn out that way so she calls the room she is freaking out why oh? 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. You're just going to go back to bed? I'm going to call.

I'm not going to intervene. I'm going to get like 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. I don't know. Sorry, I just didn't think of it like that. One of the most romantic things you could do is get beat up for a girl.

I've done before. At least you try to fight. 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. Oh, whoa.

And they were just being a**holes. I guess that they'd like seen them earlier in the day in the room and they were... Dude, that's 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 through the door. She liked that and she asked if she could come back to my room

and she did and then we ended up making out. Yeah, you did. Bro, that's awesome. You earned that kiss. You're a hero. It was a good makeout sesh but that's it. That's all we did. Okay, that's awesome. You earned that kiss. You're a hero. It was a good makeout sesh, but that's it.

That's all we did. Okay, that's cute. So I 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, she didn't pick up and I left her voicemail. And that was that. And that was two years ago. Are you sure she was single? Oh, yeah. 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 her if she was single? Well, no. No. I just sort of assumed if she wasn't, she wasn't going to do anything.

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 like he was in cabo oh well that's a different that's a whole different business this is crazy though because you haven't seen or spoken to her in two years and now we're gonna reach out randomly out of the blue to see if she remembers you yeah how are we even gonna

say like nick from cabo do you think that's it well yeah his name's beau so that would help maybe she also had a nick and cabo maybe that's why she's not calling me back oh no she's like oh my god that's the one that brooke made out with on her family vacation sorry okay no i 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, yeah.

But it wasn't like that. She wasn't crazy like that. No. She was having cocktails. Yeah, 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. She's still in Cabo right now. Hold on. Second date update. 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. All right. What did I have on the beach. All right.

Got to have it to someone. What if I have my passport in that? Shoot. It's 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. Aww. Aww, Beau.

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? Uh, you know, I just had a birthday and I went, I'm not getting any younger and 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. And I still have your hair or whatever

it is. No, no, no, Jeff. Well, somewhere in the middle of those is what we're going to go with. Okay. You ready to do this, man? You haven't talked to her in two years. And don't be insulted if she doesn't remember who you are. Yeah. She won't. Brooke doesn't even remember who you are and we talked to you five minutes ago. Bo. His name's Bo. Bo is right. Good job. Yeah. She won't. Brooke doesn't even remember who you are, and we talked to you

five minutes ago, so. Bo, his name's Bo. Bo is right. Good job. He got the name right. He's strong and strapping is what he told us. Yeah, she remembered that part.

He's a hero that took on four to five men. Yes. Now you're talking to Brooke. It's a little bit much, but I like it. 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 just a friendly morning radio show called Brooke and Jeffrey in the morning.

Hey, Shayla. Hey. Or Shayla. Hola. Morning. Hey, Shayla. Hey. Or shall we say hola? Hey. Okay, this again. I can do that. She doesn't remember yet. We have to get there first.

So I'm really sorry to interrupt you, whatever you're doing, Shayla, but 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? Okay. Yeah. That was a long time ago. 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 yeah yeah oh my god he's the guy who rescued you from all those men pounding on your door which i can't believe would be so scary oh my god yes that was such a long time ago i hadn't really thought about this guy forever oh that's okay well now you're thinking about him now and you sound you sound happy at the memory uh 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 a relationship weren't you god i i was engaged at the time oh my god oh my god girl well you were engaged 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 are you saying that so casually? Okay. So, like, back then I was a hot mess. 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 oh wow wait you said yes because you felt bad 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 okay wait did you get a ring i did get a ring that was a nice gratuity from my trip. They know the American culture. That's one proposal. How did the, where is the second proposal? So I leave Italy and I go home to my other boyfriend. Oh, you had a boyfriend?

Oh, wow. And 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 were engaged to two men and made out with Bo. Yes, which made things even more complicated, and 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. 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. Yeah, all right. But to him, he's like, mom, dad. Wait, wait. 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, I mean, 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 end it. 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 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.

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 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 liked you enough to make out with you. Ouch. I mean, this is a lot right now. It's hard because you weren't just the other guy, Beau.

You were the other other guy. Yeah, so obviously. You were Mr. Right Now. You know what I mean? That hurts. That hurts so bad, but it's true. Yeah, 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. I mean, honestly, we probably should have done this as a closure call. 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 mean but sorry i guess i was just gonna sort of ask shayla you know i mean i i did take in the fact that you were single yes that did register with

me and i'm kind of single yeah it wasn't like fully single. Yeah, I guess in this whole scenario, kind of single is essentially single. Yeah, Cabo is single. We'll call it Cabo single. In this scenario, everything is single. Cabo is single. I like that. Casually in a relationship, sure. No, no, no.

Cabo is single, Brickers. 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. Not the flight. I've also been told long distance relationships

don't need too much trust. Oh, no. She's very reliable. It might be just their type, actually. We really need to ask Shayla this. You've had two failed proposals, but the third time's the charm is what they say. Let's not rush to that, okay?

She'll say yes. Yeah, unless 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

Congratulations, Bo, you're Mr. Right Now again Yay I'll take it Brooke and Jeffrey in the morning. If there was a children's fairy tale about their story, and there really should be, it would be called

The Girl Who Couldn't Say No. She went into the fraternity house late at night. This frat bro is too swole. This frat bro is too thin. What's going on here? This frat bro is too swole. What? This frat bro is too thin. What's going on here? This frat bro is just right. I'm going to marry them all.

Oh, that's funny. And they all lived happily ever after. Oh, she left without saying goodbye. I don't know why you put her in a frat house. Nobody proposes in a frat house, Jeff. Where is that children's fairy tale book? I'd buy it. Please don't write it.

You guys were so glossing over the fact that she's not even single. Yeah, so? Casual. She was casually seeing someone. When you have a person who is engaged to two people at once and making out with another one, I don't know how much you would trust her perception

of casual. You just don't trust her. She's married. I feel like they need to go back to Cabo together and finish what they started officially. Maybe we should do the show live. Yes! Live from Cabo all because of their date.

Someone has to translate Spanish for me, though. Yeah. You guys speak more than I do, ironically. I mean, you never know. It could actually work out. But make sure you go check out

all of our second dates wherever you get your podcasts at Brooke and Jeffrey. 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. Jon Stewart is back in the host chair at The Daily Show, which means he's also back in our ears on The Daily Show,

ears edition podcast. Join late night legend Jon Stewart and the best news team for today's biggest headlines, exclusive extended interviews and more. Now this is a second term we can all get behind. Listen to The Daily Show, ears edition 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. So that's why we created The Big Take from Bloomberg Podcasts, to give you the context you need to make sense of it all.

Every day in just 15 minutes, we dive into one global business story that matters. 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.