Brooke and Jeffrey: Second Date Update - Second Date Update Classic: Adventure Envelope Excursion

Episode Date: August 26, 2023

One of our listeners brought 3 MYSTERY ENVELOPES with him on a first meetup and it lead to one of the most adventurous Second Dates of the whole year!See omnystudio.com/listener for privacy information.

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. Second date update. So I never do this, but in the interest of saving time here, because this is a more involved date than we normally get, I need to read a little bit from Josh's email before we bring him on the phone.

Oh, I love this. Okay. Josh, is that cool with you? Yeah. Yeah, of course. Okay. Because he basically transcripted out his entire online conversation with this girl, Haley. Oh, he did? And said she's very good looking, so he went above and beyond for her.

Because they matched on Hinge, and one of her dating prompts said, dating me is like an adventure. I'm spicy, spontaneous, and sweet. And Josh replied to that saying, Well, if we ever went out, we'd meet somewhere, and I'd give you the option of choosing one of three adventure envelopes. Whatever one you pick, we'll do.

And I promise none of them say, Go back to my place inside. That'd be quite the trick if all three of them said that. And two weeks later, she finally responds to that, saying, I'm intrigued. And so he wrote back, intrigued? Just wait till you see what's behind envelope number

three. What is it? I want to know. He's kind of teasing her here. Dude, that's really good. And she asked him, do I get an idea of the types of things in each envelope? And he told her, sure, get an idea of the types of things in each envelope? And he told her, sure, exactly from your bio. Envelope number one, spicy. Envelope number two, sweet.

And envelope number three, spontaneous. Am I chubby or do all three sound like food ideas to me? I mean, I did also draw the analogy to that. Food competitions for all of us. But look how interested you all are in finding out what it is. This is brilliant. They better have done the envelope date because I am going to be horribly disappointed if I don't find out what's in these things. After all this. That is how Josh locked down a date here with Haley.

So, Josh, this is really elaborate, man. Thanks, I guess. I don't know. I guess I just wanted to put some effort. Dude, it's awesome. But you are building yourself up pretty big here. Like, I would think the dates have to be really, really special. Really?

Because if she picked spicy date, and then you just ended up going to, like, McDonald's and trying the McChapotle milkshake, that would be kind of a letdown after all this buildup. That's the worst case scenario. But at the same time, you've got to realize the bar has kind of been set pretty low these days. Yeah. From what I hear. Right. So at the same time, too, like, I'd be a little bit classier than that.

It could be like a taco truck for spicy. Really? But that's such a big buildup to end up just going to a taco truck. Why not just go to a taco truck? He's not putting on The Bachelor right now, Jeffrey. He's just trying to make the intro to something a little bit more enticing. I don't know.

What envelope did she pick? She went with spontaneous. She went with spontaneous. Oh, interesting. So she opened the spontaneous envelope and what was inside? Well, so we meet up at the spot that I told her to meet up at. It's a public area. Don't worry

about it. Okay. And inside there was a piece of paper. Thank you. Oh! Wow. How wild of you. It's just glitter! Oh, spontaneous! Gotcha. What was on the paper? On the paper it said, follow the arrows.

Follow the arrows? What does that mean? There's an arrow on your chest pointing down. Oh, no. That would have been terrible. Sorry. I'm sorry. Go ahead, bro. Where are the arrows?

So there is an arrow. Like, she finally finds one on the ground. And it led to the corner. And there was another arrow there. Oh, it's like your date is following a GPS system. Like turn left here, turn right in 90 feet. You're tricking her into a walking date. No, no, no, no.

I wasn't trying to get my steps in or anything like that. Okay. Where did they end up? They're in a circle. Right, right. And meanwhile, by the way, she's loving this. I'm laughing. She's like looking at me like.

So where do they go, Josh? Where do the arrows go? So finally, there is, you know, one of those like merge arrow signs. Merge? Son of a bitch. I want less details on the arrows. I just want to know where you were. All right.

I taped an envelope on the back of the car. On the merge sign of the highway. Okay. Highway. She was just about to get on the freeway. It was just a street. I didn't put her in. It was her life.

Okay, so now we have another envelope. What's in the second envelope? So we were right by the train station. It was basically a made-up coupon that said, Hey, we can stop at any of the stops and stop at a restaurant at any of these places in town. Wait, so you're not talking Amtrak or something? We're talking just like the local.

Yeah, yeah. You tricked her onto mass transit for spontaneous. After walking through a bunch of confusing arrows. I kind of take back what I said earlier. You should have just done the taco truck. Yeah. Who would say there wasn't a taco truck where we were going? Was there a taco truck?

No. Oh. Darn it. You deased me with it. All right. We end up going to this small little restaurant in this terminal town. We have a wonderful dinner. We got to know each other along the way on the train, which is awesome.

And at the end of the meal, I reach in my jacket, and I pull out a flower and a note, and it says, I had a great time. And it says, follow the arrows home. So at the end of the night, looking back on it, were you thankful that she chose the spontaneous date as opposed to one of the other, spicy or sweet? Yeah, I mean, it was kind of a wild card either way. I mean, I thought all of them were pretty awesome. Okay. Did you get a vibe on what she thought of the spontaneous date? I thought she really enjoyed it.

I was using her smiling and laughing and what I thought was good rapport as the judgment for this. It actually sounds pretty cute and romantic. How did you guys end it? We took an Uber back and I dropped her off at her place and just, you know, made sure she got in okay. Small kiss and that was it. Yeah. And I texted basically, hey, I had a nice time and she responded like

so did I and that's basically been it. Okay. Well, I mean, she did take two weeks to even respond to your initial direct message. So maybe she's just slow mover. Yeah. she's just... Slow mover? Yeah. She's busy.

She dates at a turtle's pace. Yeah. Or maybe she even went back to the arrows looking for alternative routes, anything that she missed. Oh, she's too into it. She didn't merge correctly. We'll find out what the real answer is

when we call her and finish your second date update right after this, all right? Thank you. I appreciate it. Hold on. Second date update. Probably the most elaborate first date that we've ever heard on the show before. Yeah.

Because to recap, Josh met a really attractive girl online and got her to talk to him by setting up a big adventure date with three mystery envelopes, all based on how she described herself in her profile. Spicy, sweet, and spontaneous. She chose the spontaneous adventure, which led to basically a scavenger hunt for their dinner, with a bunch of arrows leading around the city to a busy highway, onto a commuter train, over to a nearby town, down to a hole-in-the-wall restaurant. Yeah, I mean, he got her on public transit and took her to a hole-in-the-wall.

I mean, yeah. It's an elaborate way to say they walked to the train station. If I'm reading the room right now, effort was obviously an A, but it sounds like you guys aren't all that impressed with how the date turned out. The execution could have been a little more crazy, like, oh, we're swimming with dolphins. You know what?

We're in a fancy car. You guys are all hating on him, but he put in some real effort to this. He did, and I A for effort. It's more than any of you Jokals have ever had in recent years. But Josh, I mean, what do you think may have gone wrong? Do you have any regrets about how the night panned out? No, not really. I mean, like, look, I'm going to be completely real with you.

I kind of outkicked my coverage with her. Outkicked my coverage. That means she's out of his league. Yeah. Oh. I was like, I got a 5G bar. Sports terms. Is it like a football analogy?

Is that what you're doing? I don't know. Now you want us to break down football for you, too. Let's go back to how many arrows were on the ground and what the fuck the arrows were. It was about... Dude, you had to visualize what he was doing, right? I think we just need to call her. Let's just call Haley and find out what Haley thought because that's the real issue here.

Are you ready to do this, Josh? Let's do it. Yeah. Yeah, I need you guys. This is also kind of spontaneous. This is actually very spontaneous. Let's kick off this by calling her. That's a sports reference, Brooke.

It wasn't a very good one. It's baseball, by the way. So here we go. They kicked the ball for the first pitch. Alright, let's score a home run and call this girl. Alright, manly boy. Let's go. Hello? Hey, is this Haley?

Yeah. Who is this? Hey, we're a radio show called Brooke and Jeffrey in the Morning. Hi, Haley. Hi. Whole show's on the phone right now, dying to talk to you. Honestly, that's true. We're really excited to hear from you.

Oh, okay. We want to ask you about a date that you went on recently with one of our listeners named Josh. Okay, what's this about now? It's part of a segment that we do called the Second Date Update. And so,osh told us

about the date that he set up for you which sounded pretty elaborate dude we were all hooked when he i mean he told us about the direct message and about how he said he has three different envelopes for you to choose from yeah i don't know what he's really told you sorry i know it probably sounds creepy that we already know everything about your date and we're really excited about it. We're living vicariously, so just let us. We really want to help out Josh because he told us the night went pretty well. Well, I mean, that was probably the most elaborate and thoughtful date I've been on. Oh, yeah.

That's so nice. I bet that made you feel really special. Yeah, I was totally impressed by his effort and all the thought he put into every detail. Yeah. Oh, so are you just like busy and that's why you're not calling him back? Or were there not enough arrows in the scavenger hunt because that was a theory oh no i mean i think everything happens for a reason oh okay yeah so you're saying it was too thoughtful what does that mean yeah i mean i

wouldn't take that date bath for anything oh that's so cute we'd never hear i was gonna say it's nice but i feel like there's a butt coming yeah but i i wouldn't i mean i wouldn't do it Oh, that's so cute. We'd never hear. I was going to say. Nobody says that ever. It's nice, but I feel like there's a but coming. Yeah, but I wouldn't do it again. What? That's okay. There's other date options, apparently, at least two more. Yeah.

Spicy and sweet. Why wouldn't you do it again? Well, when we got to the restaurant, the waiter was so cute. What? Yeah. And there was more attraction there. At the hole-in-the-wall restaurant you guys went to, you found a hot waiter. Brooke wants to know the name of the restaurant so that she could go there and check him out.

I mean, how does that even happen? How would a guy even hit on you while you're on a date with somebody else? Like, isn't that just a red flag right there? He didn't hit on me. I could just feel the energy between us. It was, I mean, it was just, you know, how, you know, something sort of meant to be. Whoa. No. It's just like sometimes it's the eye.

That's odd. Or the way he says something like, would you like any pepper on that salad? No, it wasn't like that. And so I followed my gut and went back to the restaurant. Wait, after the date was over? Yeah. The same night? Yeah.

Oh, my God. At least you knew he was still working. And did what? you asked the waiter out you're dating the waiter what what is happening yeah we've been on three dates and we're not slowing down wow oh god okay i mean it is kind of cute i love our friend though i know the fact that josh has been hearing all of this and has not said a word what yeah because hayley he's on the phone i yeah sorry yeah josh has been listening this whole time um yeah no i heard the whole thing she really uh she really lived up to this spontaneous label yeah wow tables really

turned on the whole spontaneous thing like you know just sucks that just really sucks i'm sorry uh yeah but i'm so happy that we went out and we got to know each other of course you're happy oh yeah my boyfriend now it's thrilling absolutely thrilling you could have just told me you know don't leave me like hanging on the line yeah that's a hard thing to tell somebody i mean I met somebody else on the date I was out with you. Don't even, but I mean, like, make something up. Don't just, like, ghost me. Like, even if it's just like, hey, I'm just not feeling it or whatever. Like, come on.

Yeah. I mean, maybe, Haley, were you, like, kind of keeping him in your back pocket as a backup plan in case this didn't work out? Or was there an arrow on the table pointing at the waiter and she was just following the arrows again? I just went where my heart was pointing. Oh, man. Oh, God, Jake. Seriously. It's just like, Josh, what are the chances? Like, you get on a train,

you pick a random restaurant, and there's an attractive waiter? Oh, my God. You put her on a train to her next boyfriend. Your date did work in helping find love, just not for yourself. For other people. Again, I'm absolutely thrilled about that. Poor Josh.

Think of the bright side. You have two other dates pre-planned and envelopes for some other lucky girl out there. Silver linings, I guess. And the silver lining here could be that she didn't know you were on the phone listening so you two are together right now and i'm going to give you a chance to win her back right over the phone live on the radio that must have happened for a reason this is the fourth good point read the signs hayley josh the floor is yours. Look, Haley, I put in a lot of effort, and I think that

says a lot about me and the kind of person that I am, and definitely way more effort than the waiter did. So, you know, what does he have that I don't, basically? An employee discount at that restaurant, for one. And also whatever tip money that Josh left. That's true. But besides that, what else,

Haley? I mean, I really appreciate the effort, Josh, and all your thoughts. You're a really special person. But I feel that things, again, will happen for a reason. I feel like she's like reading a sign on her wall right now. It's right on her family lip-lap-lap. With an arrow all over the side. All right, so it sounds like we're not going to be able to get you

another date here, Josh. That definitely seems apparent, yeah. I mean, we tried. We read the signs. Hey, you guys did try, and I do appreciate that. All right. Sorry, buddy.

Haley, I'm just curious, like, if you had chosen one of the other two envelopes, the spicy or the sweet possibility, do you think maybe things could have turned out differently and you'd be with Josh? That's a good question. I think that the way things have just turned out were the way they were supposed to turn out. Everything happens for a reason. Change the scene a little bit there.

Brooke and Jeffrey in the morning. All right, well, lesson learned. If you're a guy and you go out with an attractive lady, do not go within 100 yards of any other male on your date. It's too risky. She's probably going to fall in love and leave you. Oh, man. Never know.

I don't know where you're going to go without men. You have to go someplace where men are rare, like a nail salon. An OBGYN office. Yeah. A Bravo convention. One of Jose's comedy shows. It's all ladies at those. Actually, we have a very high ratio of ladies to dudes at my shows.

I don't know. That's thanks to us. That's thanks to our show. That's right. I'm just going to say, I think he lucked out. That woman and her motivational quotes, I just couldn't take them anymore. You mean the same one over and over? Yes.

Yes. We can officially add everything happens for a reason to the list of most hated single dating quotes along with you'll find love when you least expect it. It doesn't count if you're more than second cousins. What? I've never heard that one. Who says that? Oh, I say that.

People say it, trust me. But remember, if you ever want help getting another date, you can always email the show. We'll call that person who isn't calling you back. And you can find all our second date podcasts up on the Brooke and Jeffrey website or wherever you get your podcasts. Yeah. Brooke and Jeffrey in the morning. 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 John 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.