Brooke and Jeffrey: Second Date Update - Second Date Update: Barwreck

Episode Date: July 15, 2024

Today’s Second Date Update includes probably the MOST AWKWARD 20 minutes of a first date we’ve ever had on this show. And it’s all because of an embarrassing run-in that happened at a bar!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.

Joel, the holidays are a blast, but the financial hangover, that can be a huge bummer. If you are out there and you're dreading the new statement email that reveals the massive balance that you may have racked up, well, you could use our help. That's right. I'm Joel. And I am Matt. And we're from the How To Money podcast. Our show is all about helping you make sense of your personal finances so you can ditch your pesky credit card debt once and for all, make real progress on other crucial financial goals that you've got, and just feel more in control of your money in general. You know it. For money advice without the judgment and jargon, Listen to How to Money on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

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Ready to laugh and stay informed? Listen on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Second Date Update. You know, I googled the top ten most awkward things that can happen on a first date. They had severely late, your date talks too much, they don't talk at all,

or they talk out of a weird part of their body that isn't their mouth. How are they doing that, Jeff? I'd actually like to see that on a first date. Is that your knee talking? But none of those compare to what actually happened on one of our listeners' first dates. His name is Will, and today he needs our help. So, Will, welcome to the show. Hey, everybody. How's it going? Now, are you talking to us out of your mouth with that, Will, or where he needs our help. So, Will, welcome to the show. Hey, everybody. How's it going?

Now, are you talking to us out of your mouth with that, Will, or where is that voice coming from? Yeah. Not believable. I didn't believe it, Jeff. I'm not sure. I think he's got his phone somewhere else. Wherever you're talking out of, that's fine with us. Just tell us about why you emailed the show,

like you had a problem with your first date the other night. Yeah. So, I've been chatting with this girl her name's leanne okay you know she's really pretty and our chats online they've been really good uh but it's been heating up more and more oh okay yeah are you excited about that? Brooke is. Yeah. Brooke unzipped a little more on her sweater there. I wanted to meet up with her, you know, but I haven't officially set anything up for her or anything like that. And then the craziest thing happened.

I randomly ran into her. What? Yeah. I was out on another date with a different girl at a bar wait will what do you mean like you saw her down the bar she came up to you like um i was sitting at the bar top with my date and two people walk up to the bar and they sit directly to my right okay i look over and the person who's next to me, I don't recognize them,

but one chair over, it's Leanne. Wait. Oh, dude. Was she also on a date? No, it was some other girl. Maybe a friend. Oh, my God. I would be hiding the entire time.

I wouldn't turn around. Hide underneath the bar top. What do you do there, Will? Yeah, I mean, that would all be good and well, except for we locked eyes with one another. Oh, God. Who said something first? I introduced her to my date.

What? Oh, my gosh. As what? That's funny, though. I mean, you have to, right? Isn't that rude if you don't? What did you say? I dropped the F-bomb.

My friend Leanne. Oh. Friends owner. I think that's fine. That's fine from his perspective, but what's Leanne's take on that? The look on Leanne's face was basically like, are you effing kidding me? Oh, okay. I mean, but what other word were you supposed to use?

As long as you didn't introduce your date as like your wife or something, right? Your girlfriend. Yeah, I would imagine that you tried to cut off that conversation as quickly as possible i i tried i mean there's also another level to this because she'd asked me before if that same night worked for us to go out and i told her i couldn't because i was busy oh my god you lied you got caught busy you didn't say what he was busy with. You're not cheating. You're just talking to her. She probably wouldn't know if you were going on a date.

Like, he wouldn't want to know someone's going on a date that night. Yeah. There's no cheating or anything. It's just awkward. Just the whole thing is weird. Yeah. And, you know, in all fairness, I had booked a date with that girl before. So, technically, I was busy.

Okay. Can I ask you, who were you most excited to go out with? Leanne or the girl you were already out with? Oh, you know, I... Too long of a pause, Will. Too long of a pause. Well, here's an easier question.

Who are we calling today? Oh. We're calling Leanne. Okay, so that's the answer you should probably give. That's probably because he already has another date lined up with the girl in the Zodiac. I need to know what happened to her. Well, you guys can edit that pause out, right? Sure. No.

No, we can't. Well, so that's already extremely uncomfortable for everybody involved. How did the rest of that night go? Well, add insult to injury, my Dave was like flirting and touching my arm the whole time. So like, I'm just over there. I'm trying to finish up my drink as quickly as I can so we can get the hell out of there.

You're like, I get it. I get it. I'm cute. Let's just get out of here. Come on. Yeah. But I mean, eventually Leanne and her friend got up and left. Ooh, they left first.

Okay. That's not a good look. Have you heard anything from Leanne? After the date, I texted her, and I was, like, just trying to do damage control. I'm like, hey, sorry, that was pretty awkward, but I really do want to see you. And, of course, I got no response, which sucked. Yeah, it could just be hard. Like, I mean, even though it's like you did nothing wrong, like, she'll never be able to see you without that other girl now you know right well you know

a lot of times when we do these types of calls that seem fairly obvious for the reason why you're not getting a call back it turns out not to be that so maybe i'm thinking leanne just had a bad snack at the bar had a little tummy ache had to go home or's like, he only had one date? What a loser. He should have had two girls next to him. Maybe. Alexis, is this fixable? Oh, yeah. I think so for sure. He didn't do anything wrong.

It's just awkward. So he's just got to make up for it. I mean, he never actually completely lied. He just said that he was busy. So that works in his favor. He must be very, very good looking if he has multiple women wanting to go out with him. And he didn't rub it in her face either that night. Like he could have been a jerk about it and been really open, but he was trying to be like coy and quiet and like get out of there.

These are all really good points. Yeah. As long as the other girl isn't like way more ugly or way more hotter than she is, I think it'll be fine. Yeah. Text us in some pictures of these girls. Yeah. There's a weird thing if you're're on either spectrum. That's true. It's like a turn off for some reason.

Well, we'll work on that. And in the meantime, we'll come back and we will call Leanne for you and try to convince her to give you another chance with your second date update right after this. Second date update. Out of all the bars and all the towns and all the world, our listener Will had to pick the worst one.

He was on a first date with a woman and another girl that he'd been chatting with on the dating apps just happened to walk in. Sit right next to him. Are you kidding me? So what do you do? He decided to introduce the two of them to each other. Oh, man. I can see it right next to him. Are you kidding me? So what do you do? He decided to introduce the two of them to each other. They had already made eye contact, Jeff.

There was no way back. Yeah, you can't hide at that point. And Leanne, the girl that we're about to call here today, is not texting Will back after that awkward bar encounter. I am, though, curious, Will, what about that other girl that you were with? Where are you at with her? Is that still on the table? Yeah,

totally still on the table. I'm just kind of... How do I put this? Shopping? Around? Yeah, I'm kind of waiting to see what Leanne says. So, I don't know. My mom always raised me, you know, a bird in the hand is worth two in the bush, right?

It means keep one on the line. Yeah. So, I don't know. My mom always raised me, you know, a bird in the hand is worth two in the bush, right? Got it. It means keep one on the line. Yeah. You know this. A roster. Yeah. Yeah, exactly. Sure.

You never know. Okay. But we're not going to say those things while Leanne is on the phone. No. I wouldn't recommend it. Birds in bushes. Don't say it. Are we going to bring up the fact that he was on another date, though? Yes, of course.

We should bring up the awkward encounter,'s on another date yes of course we should bring up the awkward encounter but we'll try and lightly gloss over he's putting more effort into this date with leanne obviously yeah yes yes we have a game plan let's call her we'll Hello? Hey, is this Leanne? This is she. Hey, Leanne, you're on the radio right now with a show called Brooke and Jeffrey in the Morning. Hey, Leanne. It's Leanne.

I know. What are you? Leanne. Did I say it? You did. Yeah, you did. Did my brain freeze? I'm sorry.

My co-host is frequently drinking during the show, so that's probably what's going on. I swear. Just to cut right to it, we're doing a segment here called the Second Date Update, and we're trying to help out one of our listeners who you've been chatting with online recently named Will.

Okay. But you're not chatting with online recently named will okay wait but you're i mean you're not laugh i love it you're not chatting with him anymore according to him definitely not i cannot wait to hear your side of this story because yes we have heard about kind of an awkward run-in that happened between you and him at a bar oh he was on a date with another woman super super awkward oh my god tell us what i mean from the beginning you walk into the bar and then what i mean i was totally shocked because he told me he couldn't meet up that night because he was busy which i guess i mean he wasn't lying he was busy yeah right not the excuse you wanted to see. But I mean, we understand that you probably didn't feel great about what you saw. Yeah. No. And I mean, it was uncomfortable to be sitting there, but it was literally the only seat.

And my friend was like, oh, there's two seats at the bar. And she led us over there. And I sat down and I looked over and there was Will. And I was like at first, like initially kind of thinking oh what a coincidence maybe he's just here and then I see there's a girl next to him and I was like mortified I thought I was gonna die um I don't know clearly there was someone more important than me because he chose another girl that kind of sucks too yeah he already had that day like buy them a drink I don't think that you should take it personally. I think he was really excited about you.

He had just already made plans with somebody else. I decided I'm not playing that game. I'm bound out. Wait, you think it's a game? Yes. I mean, if you're dating a ton of people, it's not something that you're looking for a real connection. You're just looking for connections. And that's not what I'm looking for.

So you're not talking to anyone else? No. I was looking to talk to one person. And when I found somebody that I connected with, I don't really talk to anybody else because that's just not my vibe. Yeah. I 100% hear what you're saying. And I think I would feel the exact same way as you do if I was in your shoes.

Like, I feel like I'm getting passed over for somebody who's being chosen ahead of me. But here's the thing. We've actually talked to Will. And he told us how much he was connecting with you and how excited he was to eventually meet up with you. And how terrible he felt about the situation that happened like is there any possible way that you could see yourself being open to just having a conversation with him about it what what is there even to talk about like we both know what happened i'm surprised he even wants to go this route why why he's not doing anything wrong like what he's doing is more normal like he didn't know probably even that you only wanted to talk to him.

I definitely said, I am not someone who sleeps around. I'm not someone who dates around. Okay, but everybody says that. You know, they don't really mean it. It just sounds like you have different dating patterns. Morality isn't really the strength of this show, so... I mean, who hasn't said,

I never do this? That's why I think we need to hear what Will has to say in this situation because he is on the phone right now listening and wanting to talk to you. He's on the phone? Yeah. That's how this segment works. I think he's there. Hello.

I have said right now. Yeah, he heard all that. Don't you want to hear it? Not really. That's why I did not respond to him. I didn't really want to talk to him really that's why i did not respond to him i didn't really want to talk to him at all he's trying to talk to you so now i don't have a choice i have to talk to him whether i'm or not okay leanne hi um there it is look i i just want to say i am so sorry you felt disrespected i mean to be to be honest with you, I felt terrible the entire time. I mean, like, what are the odds

that we would end up at the same exact bar on the same night? Actually, I think a pretty good odds because now that I've talked with a few of my girlfriends about it, apparently this probably would have happened regardless. What? Huh?

Why is that? I mean, I went home that night after the bar immediately told my friend about what happened showed her your photo and she goes oh my god are you kidding he's been chatting with me about going out too no what shut up he's just dating around a lot your friend dating the whole city ah it's a small town come. It's a little weird that you're coming at me for just talking to a lot of girls. That's normal. Did you know you were talking to her friends?

No. I'm not stalking people on their social media. Men don't usually go that far. We're just like, are they good looking? I'm going to look at all her friends now. Have you gone on a date with her best friend already they had planned it they just haven't done it yet oh she was on the sketch huh okay it was like a loose oh no so you

weren't so will's roster of potential dates is too big for your liking potential dates we haven't actually gone out with any of these women yet but just the fact that they're even in the lineup it's're like pre-dates. It's a no. I mean, if it's your best friend, that is kind of weird. Yeah. The one best friend. You guys need to talk more.

Well, apparently it's more than just a best friend. It's an entire apartment building of friends that he's been lining up with. Oh, my God. What's your gender radius on 0.01 miles? I think more than anything, what's your profile tips? Because it sounds like you're killing the game. What was your name again? I'll just change it to that.

No, I'm sorry. Well, you wanted to say something. Go ahead. Listen, I understand I may be talking to too many people, but look, you know, we hung out and I promise to drop that number under 10. To under 10. To under 10. Wow. How do you even remember

who it is? Leanne, we've talked to a lot of guys on this show and I can say that is a extreme gentleman move right there.

Thank you. And the other thing, I can even show you the profiles. They are really, like really good looking women too. And I would give that up.

Wait, you're going to show the ones that you're willing to drop to prove to her? That's not a flex. Not for girls. Show it to your bros, if anything. Actually, maybe she should see them and make sure there's no other connections. Wait, that's my sister! You know, we're running out of

time here, so I got an offer. Leanne, we would like to send you out on an official date with Will. By the way, Will must make a bunch of money if he's got all these dates. He doesn't go on them. Oh, you're right. Will doesn't need money because we're going to pay for this date if you agree to it, Leanne. Oh, even better. And he knows a bargain, so there you go.

What do you think, Leanne? Will's down. Come on. He wants to buy dinner at this point. So there you go. What do you think, Leanne? Will's down. Come on. He wants to party dinner at this point. He got excited. All right, Leanne, what is it? I just got to say I'm not interested, and I can say my roommate isn't interested either.

Oh, you're speaking to her. Wait, is the roommate the best friend, or are these two different? Oh, no. It's an important clarification. Either way, it's a double no, which we rarely ever get on this show. Two no's from two different people, Will. I'm sorry.

Now Will only has seven other options. He has 700 other options. There's more than that. Good luck whittling it down, buddy. I'm sorry, Will. All right. In all fairness, look, I'm bummed, Leigh-Anne. Are you?

Oh, you bummed him. Yeah, you're going to be bummed for about five minutes until you text the next girl. You text the next girl, I'm bummed. Brooke and Jeffrey in the morning. Dating really has changed a lot. Dude, I thought she was being, like, such a stickler, you know? Like, I was like, oh, come on. And then the more he talked.

Yeah. They were just a complete opposite ends. Like, there's got to be a middle ground somewhere Where you can date a few people It feels like he's talking to probably like 50, 60 women all at once Maybe more I mean that's like Leonardo DiCaprio Dating Rose and everybody else on the Titanic

All at the same time He's got girlfriends in first class In second class All the way down in the boiler room Absolutely He should have picked a girlfriend That was on a boat for God's sake. Pick the one on the door.

Yeah. Didn't work out well. Get them away from each other. Anyway, make sure you listen to our podcast. I know it didn't work out for us here, but we are actually pretty decent at getting these second dates. Yeah. So you can hear all of them and make sure to slide into Jose's DMs if you have a second

if you want a good time. Please do. I'll show you a great time before I annoy you. I mean, Will's got extras, right? Brooke and Jeffrey in the morning. 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. Joel, the holidays are a blast, but the financial hangover, that can be a huge bummer. If you are out there and you're dreading the new statement email that reveals the massive

balance that you may have racked up, well, you could use our help. That's right. I'm Joel. And I am Matt. And we're from the How To Money Podcast. Our show is all about helping you make sense of your personal finances so you can ditch your pesky credit card debt once and for all. Make real progress on other crucial financial goals that you've got and just feel more in control of your money in general. You know it.

For money advice without the judgment and jargon, listen to How to Money on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. John Stewart is back at The Daily Show, and he's bringing his signature wit and insight straight to your ears with The Daily Show Ears Edition podcast. Dive into John's unique take on the biggest topics in politics, entertainment, sports, and more. Joined by the sharp voices of the show's correspondents and contributors. And with extended interviews and exclusive weekly headline roundups, this podcast gives you content you won't find anywhere else. Ready to laugh and stay informed? Listen on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.