Brooke and Jeffrey: Second Date Update - Second Date Update: You Don't Know Jack

Episode Date: July 28, 2023

The woman in today’s Second Date SWORE she had the most romantic date of her life but it led to one of the weirdest calls we’ve ever made on this show.See omnystudio.com/listener for privacy information.

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It's funny, dating just 10 years ago, the goal was to find someone who checks all your boxes. They're attractive. They're witty. They're fun. They sweep you off your feet. You guys have a passionate whirlwind romance together and ride off into the sunset happily ever after. That sounds like a different age. I keep reading my diary, Jeff.

You're just looking for anybody who seems halfway normal and doesn't solicit pics from you in the first two DMs. And that's what happened to one of our listeners, Allison, recently when she met a guy. Allison, welcome to the show. Hi. Hey, Allison. How low is that bar for you? It's pretty low. Pretty low.

Okay. The last guy I dated was a homesteader. A homesteader? Wait, what? Like he goes out to the lake? Can you still do that? Yeah, they do. It's quite common from what he was telling me to go off the grid.

And I don't know, he was probably composting his own dinner. It's quite terrifying. I was like, where is the Starbucks? It was just, I couldn't imagine. You went back to the Little House on the Prairie, it sounds like. Hey, even they had a general store on Little House. Yeah. Okay.

And so who's the new guy that you met? Okay. So I met this amazing guy named Jack. And I was really happy to match with him, you know, after the homesteader, because this one seems completely normal. And he at least has a phone. It's funny in life how everything's by comparisons, you know? Yeah, so this was definitely an upgrade. And we just went to a bar, very low key.

And there wasn't anything special about this place. It was a little bit loud, a little crowded. And when we couldn't hear each other, Jack was like, hey, look over there. And there was like this emergency exit, but it had a bar across it that said do not enter. Okay. Okay. Oh, like a speakeasy? You know, like sometimes they do like a bar inside a bar? I was thinking it was like the office. The janitor's closet even. Yeah, something.

So he was like, yeah, let's be rebel. Let's go. So we kind of flipped off when the bartender wasn't looking with our drinks and headed up. Oh, that's definitely something a homesteader wouldn't do. That's exactly right. Sounds like you like a rebel type of guy. Yeah, rebel or normal, either one. I don't know.

A lot of people call me a rebel. Are you trying to come on to our listeners? No, I'm just stating a fact. Like, because I was on a date one time with a girl where I parked in a loading zone. And I ran into the convenience store, didn't even put my hazard lights on. Wow. Good story, Jeff. I'm just saying, us bad boys are out there.

You got to snatch us up while you still can. Did you get in trouble, Jeff? No, I didn't. Got away with it, too. So did you two get away with it? Yeah, we did, actually. It wasn't like a broom closet or some VIP room or anything. It was just a closed area.

Kind of like a balcony and it had like beach throw tables and chairs that just weren't being used. So it was a storage space. Yeah. And that was exciting to you? Because I would have been kind of disappointed. No, it was actually exciting because Jack, like he pulled out the chairs

and we just sat at this little bistro table with chairs on this balcony and kind of made a date of it. It was really quite romantic. He even got to lean in and sneak a kiss in. It was really fun.. He even got to lean in and sneak a kiss in. It was really fun. Oh. That was smooth. Yeah, that's a rebel move right there.

It was actually a really smart move on his part because we could hear each other talk and we enjoyed that part of the evening before the employee came up and, you know, clearly reminded us and said, do not enter. Oh, you got caught. But you had your own littleip moment for a little bit and it's fun to get caught together you know to like be on the wild side a little bit i don't know it's like oh we're doing something bad together fun yeah it was totally fun because after that just felt funny to go downstairs and sit in front of the same guy that reprimanded us so we

headed out and like got burritos in some taco truck honestly it was an impromptu wonderful night one of the greatest first dates ever not even a restaurant just a taco truck parked in a loading zone probably oh yeah no hazards on that truck i bet why do you think he's not calling you back i have no clue sometimes you have to wonder when something went so well and there was a connection. You have to think, well, maybe I just thought it was great, but this was just a normal Wednesday night for them or something. I don't know. He'd been through that door before.

I could see it. I hate to ask, but it's not like he's taking advantage of you or something. Did you guys hook up or anything? I don't know how to ask that politely. No, just a kiss. Just a kiss. just a credible kiss, you know? Well, that's a good thing because if he was just, oh, I got what I wanted, I'm not calling you back,

that'd be a different story. So since that night, how long has it been since you last talked to him? A week ago. It was a week ago. Yeah, you said it's a something by now. We're in the danger zone here. At least you got another rebel on the phone, woman, Jeffrey. Maybe they can bond. You live in the danger zone. That's right.

I got to speak to him rebel a rebel, and we'll get some answers when we do your second date update right after this. All right, Allison? Okay, thanks. All right, you sit tight. We're going to take care of you. That's weird.

How rebels do. Hold on. I'm not going to go willy-nilly. Second date update. I think I finally found my bro. Oh, my gosh. Not this music. I haven't talked to him yet, but my wild wingman is out there somewhere.

I call him Rebel Jack. He's got whips because he's a rebel. That's right. Rebel Jack don't play by the regular rules of dating. He takes women to crowded bars, walks through restricted areas, and then orders burritos

at taco trucks with low health grades. That's right, because he's Rebel Jack. And he's one over the heart of our listener, Allison, who wants a second crack with Rebel Jack, who ain't calling back.

Whoa. Wow. You're such a bad boy, you rhyme. That's how rebels do. Allison. I hope he really has a win. Yeah. How are you feeling before we call Rebel Jack?

I'm feeling pretty good. Oh, you weren't turned on by that intro? I thought for sure you'd be more excited. I mean, Jeffrey was speaking your language there, wasn't he? I mean, no. I'm feeling good about this. The date was pretty good, so I'm feeling good. She just knows our show.

She's like, Jeff is being Jeff. I think I'm more on her wavelength. Enough with the sound effects. I love it. Let's do this. I'm done with the pleasantries, let's just get to dialing We're on Jeff's time Here we go, I'm calling Jack

Hello Hey, is this Jack? Yeah, who's calling? Your future partner in crime, young Jeffrey. Stop with the whip sound effect. You're going to scare him off. It just happens naturally. Hello.

Hi, Jack. Sorry, Jack. We're just two rebels sharing one phone line right now, Jack. And a whip. Okay, what's going on here? Sorry to bug you, Jack. And a whip. Okay, what's going on here? Sorry to bug you, man. We're doing a segment on our radio show called A Second Date Update, and we're looking to hook you back up with one of our listeners, Allison, who you went out with recently.

Allison? What's going on here? Well, let me explain. Allison emailed us because she said she had a great time with you and wants to see you again. That's not the vibe I got. I mean, that's what she said to you guys. That's not the vibe you got? I thought you guys like shared a kiss even.

I don't know what she told you. I definitely tried to kiss her, but she denied me. She told us you guys went to a bar together and you made the bold move to ignore the signs on the door and go into a restricted area up on a balcony where you shared a hot romantic kiss.

No. There's that whip again. That never happened. We didn't go up sneaking upstairs at all. I mean, classic rebel move. Deny, deny, deny. No, are you just like, what do you mean it never happened? I mean, our date ended with just a handshake.

That was it. There was no kiss. There was no balcony. I mean, it literally was just kind of a restaurant bar. We were watching some sports games and I tried to give her a kiss. I'm so sorry. I'm so sorry.

I'm so sorry. You're supposed to wait till we call you in. Sorry. It's important. Can I just talk to you guys in private for a second? It's hard to do on the radio. Yeah, if you could put him on hold? Yeah, if you could put him on hold.

What's going on here? Hello? put him on hold. Brooke, what do we do here? I don't know. Do what she wants. Hey,

Jack, No, I'm not doing what anybody wants, not Rebel Jeff. I want to keep him on the line. Allison, wait, why do you have something

that you can't tell Jack? Yeah, just let us know. Um, this is really embarrassing. So I guess there's two Jacks in my phone, and I was quickly trying to get you the number. Oh, my God.

And I gave you, there's one from Bumble and one from Tintin and I. I'm so sorry. I gave you the wrong Jack. This is the wrong Jack. Yeah, I'm so sorry. No, I went out with this Jack three months ago. This is not the Jack I was calling for the update. Jack, are you still there?

Yeah, I'm still here. Listen, this is... Sorry? Jack, the good news is she kept your number in her phone. Hey! Well, usually I do that so I know not to text them back ever again. I say text, but... Jack, the good news is she kept your number in her phone. Hey. Well, usually I do that so I know not to text them back ever again. Oh. I say text, but.

She didn't block you, it sounds like. Maybe, you know, I probably wouldn't text you back now that I know what type of person you are. So, I don't know. Okay. Jack, I'm really sorry. I didn't mean to disturb you today. I wasn't trying to call you. I apologize.

It was a mistake. You want us to call the other Jack from your phone? Let's hang up with him. No, let's not hang up. Now I want to hear what this Jack guy is all about. Let's put Allison on hold. Allison, you can give the other Jack's number to our producer. I'll put you on hold here for a second.

But I'm going to have the other Jack stay on the line, too, because it'll be more entertaining. Why would we do that? For entertainment purposes. Jack, do you want to do that? You want to be on the other line while she tries to get a date with Jack number two? Honestly, I do now because I want to hear what the story is all about. How are we going to even talk to Jack when we have two Jacks? We got to call him something different.

Okay, we'll call this one. Which dating app did you meet on, this Jack? I met on Bumble. Okay, we'll call this one. Which dating app did you meet on? I met on Bumble. Okay, we'll call you Bumblejack. And we'll call the other guy Hingejack. Bumblejack Hingejack. That is going to be so confusing. I love this. It's like a reality dating show.

Oh, my God. All right, let's punch Allison back up. Allison, you there? Yes. Okay. You gave the number to our producer. So I'm going to call Hingejack. And I need both of you guys to stay quiet while we call him.

It's going to be weird if he doesn't answer after all this. Wait, what? Allison, I need to talk to her about why she's letting the other Jack stay on the phone. Brooke, stop trying to stop the rebel train. It's already left the station. I mean, it may make her look more wanted, right, to have another dude. I like it. We're just trying to do entertainment.

She's got two options right now. Hello? Hello? look more wanted right to have another dude i like it we're just trying to do entertainment two options right now hello hello is this jack from hinge uh what yeah it probably depends jeffrey what is going on here i you're on the radio right now with broken jeffrey in the morning and we want to know if you met someone off Hinge like a week ago that you're not calling back named Allison. Oh my god. Are you serious? Can we please make sure this is the right Jack?

Did you go through a restricted door and go on a balcony? Yeah, but what exactly is going on here? I don't know. We have the right guy finally. She likes you a lot. Congratulations. She's like super into you. I don't know what to do. We have the right guy, finally. She likes you a lot. Congratulations. She's like super into you. I mean, so what if she's

into me? Well, just by hearing the tone of your voice, I can tell you're feeling her too. Normally, I don't do this, but real quick, would you like to go on a second date with Allison? We will pay for it. Do we just not have time? Is that a yes that I heard?

I heard him say yes. Man, that is so cool of you, Jack from Hinge. Congratulations. You know what, guys? No. I absolutely don't want to go on another date with her. Sorry to bug you, man. Why? Why don't you want to go on a date with her? Uh, I mean, do you want to know the truth?

I mean, that's preferable. But before we hear that, look, Jack, I know you're hearing all of our voices, and that's probably a little bit confusing to you, but I'm going to toss in two more. I want you to meet Allison, the girl you went out with a week ago, and Jack from Bumble, the guy that Allison went out with three months ago. Who's also on the other line. Three months ago. We accidentally called him instead of you because there was two Jacks in her phone.

So now we have two Jacks on the phone. Allison and Bumblejack, go ahead and say hi. Hi. What's going on, Jack? Sounds like this girl's obsessed with anyone named Jack. That's what I was saying. We have Bumblejack coming with the jokes. I like it.

Hey, Bumblejack, could you be quiet for a moment? I'm dealing with this jack. Oh. Fine. Go ahead. Yeah, don't be rude. So you were going to tell us why you weren't calling Allison back after one week, after your rebellious first date?

Yeah, I mean, first of all, you guys kind of threw me off here. I mean, you said that she went on a date three months ago. She told me her last date was a year ago. Oh, wow. Oh. Yeah, she went on a date with me three months ago. So that me she, her last date was a year ago. Oh. Oh. Yeah, she went on a date with me three months ago. So that can't be true. So this girl's a liar.

Uh-oh. Allison. Okay, I'm not a liar. That's not how this works. You tell everybody that you haven't been dating a lot or this is my first one in a while. It's just what you say to make someone feel special. Is it?

Oh, it feels like a lie? Yeah. You can start using that. You know what, Allison? Since you're on the line, I'm going to just be honest with you. I kind of just got the feeling, almost like a desperate vibe from you.

Desperate, like she'd call a radio station for another date with someone, like that type of desperate? Yeah, I mean, I just, I don't know, like, you know, it was kind of clingy. I could be wrong, but that's just the vibe that I got. I mean, wow wow i did not know that i would was coming across as clingy i thought we were having a great date and we really

had a connection and we're vibing well i yeah but you know what you were kind you were always saying like you know i'm the first normal guy that you've been with you know that you've dated in a long time and you know oh my god is that what because you were sorry you were. Sorry, it's a dating app. It's harder for girls. Bumblejack, that has to be hard for you to hear. He's still listening, Allison. Why was he not normal? I totally forgot.

Jack, I'm sorry. Oh, wow. Very forgettable. That's pretty lame. I just meant that there's a lot of crazies out there, and I guess I've gone out with a really crazy... Well, guess what? Guess what?

I think I avoided a crazy. I think you're crazy. He's saying you're the common denominator. Here's something crazy. Why don't all three of you go out on a date together, and we'll pay for it? Jack and Allison? Yeah. Wait, do we have the budget for three people eating dinner?

It's a double Jack sandwich. Yeah. Actually sounds kind of good. Bumble jack first from three months ago. Yes or no for the triple date? Absolutely not. No way. I'm not seeing this girl again.

Okay, we're down to a one jack sandwich. That was the only yes I thought you were going to get. Hinge jack, do you want to go out with Allison? I don't. I really don't. Allison, do you want to go out with Allison? I don't. I really don't. Allison, do you want to go out with Allison? Apparently not. I guess I'm not the winner today.

Three no's for Allison. Three no's. Allison rejected herself. This is a new low for the second date update. That's okay. I'm sure there's plenty of Jacks out there. No, avoid Jacks. Don't do another one Have we ever had a girl get rejected twice by two different guys on a single second date update? I don't think we need to rub it in

I'm not trying to rub it in Those are just facts, I think it's a first for our show And you guys were all against having Bumblejack on the phone, but we needed him. I don't think so. That was a terrible choice. You needed to hang up and we needed to call Hinge Jack. No, we needed the Jacks to team up. Yeah.

And stand together. Jacks united. Jacks didn't like each other, Jeff. They didn't like each other. They didn't like her. Nobody liked each other during the last three minutes. Yeah, she didn't like one of them. I liked both of the Jacks. I bet you did. Well, you like a lot of dudes. Yeah. I thought, in fact, I think Hinge Jack may

have been better than Rebel Bumble Jack. No, no. Hinge Jack was Rebel Jack. Bumble Jack was the non-rebel. Yeah. See, you can't even keep them straight. I don't know. It was a terrible idea. Whoever wanted to put them on at the same time. I don't know whose idea that was.

I'm just glad we got at least to there. I feel like there was a missed opportunity that the Jacks couldn't hang out on a bros date. Oh, you wanted them to pivot and do their own thing. Yeah, want a little Jack on Jack action. Oh, okay. And maybe we can help somebody else out there get their Jack. Get their Jack on? Yeah.

Just don't get it the other way yeah okay if you want us to help uh help you out with a love interest you can always email the show they don't have to be named jack by the way yes they do jack's only jack's only for our second date updates email the show we'll call the jack that isn't calling you back brooke and jeffrey in the morning. Jon 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.

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