Second Date Update Classic: Adventure Envelope Excursion

Published Aug 26, 2023, 1:00 PM

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!

Second date of date.

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, Hayley, 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 will do. And I promise none of them say go back to my place inside.

Hah.

That'd be quite the trick if the all three of them said that.

Ye.

And two weeks later, she finally responds to.

That, saying, oh two weeks wow.

I'm intrigued. Wow, And so he wrote back intrigued, just wait til you see what's behind envelope number three?

What is it? I want to know?

It'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, exactly from your bio envelope number one, spicy, envelope number two sweet, and envelope number three spontaneous, all three like food.

I mean, I did also draw the analogy to that competitions for all.

But look how interested you all are in finding out what.

Is brilliant and 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 an 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 because if she picked spicy date and then you just ended up going to like McDonald's and trying the Mick Chipotle milkshake, that would be kind of a letdown after all this build up.

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 from what I hear. So at the same time, too liked be a little bit classer than.

That, like a taco, like a taco truck special.

But that's such a big build up 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 like the intro to something a little bit more enticing.

I don't know.

What envelope did she pick.

She went with spontaneousous.

So she opened the spontaneous envelope and what was inside, well.

So we made up at the spot that I told her to public area, don't worry about it, Oh god. And inside there was a piece of paper.

Thank you?

Oh how wild scotcha?

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?

That would have been terrible. I'm sorry, Go ahead, bro, Yeah, where are the arrows.

So there is an arrow like she finally finds one on the craft and it led to the corner and there was another arrow there.

Oh, it's it's like your date is following a GPS system like turn left here, turn right in ninety feet 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.

Where they go?

Josh, So finally there is, you know, one of those like merge arrow signs.

I want less details on the arrows. I just want to know where you were, all right.

I had taped an envelope on the back of the on.

The merge sign of the highway, just about to get the street.

I didn't put her in their life.

Okay, so that 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 and said, hey, we can stop at any of the stops and stop at a restaurant at any of these places in town.

You're not talking amtrak or something. We're talking just like the local. Yeah, yeah, you tricked her onto Mass Transit after walking through a bunchetus.

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?

All right? All right? We go 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, reach it in my jacket and I pull out of flour and a note and it says I had a great time.

So and it says follow the arrows home.

Yea.

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 others Spici 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, you know, I was using her smiling and laughing and what I thought was good rapport, as is the judgment for.

This, It actually sounds pretty cute and romantic. How did you guys end it?

So we took an uber back and I dropped her out 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 slowmover.

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.

Yeah, yeah, she merged correctly.

Yes, 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.

Date 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 her self in her profile spicy, sweet, and spontaneous. Yeah, 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 station, all right, 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.

Been a little more crazy, like oh, we're swimming with dolphins.

A fancy car.

You guys are all hating on him. But he put in some real effort to he did, and it's more than any any of you jocals 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?

Uh?

No, not really. I mean, like, look, I'm going to be completely real with you. I kind of out kicked my coverage with her.

Right that means she's out of this league. Yeah.

Yeah, it's like a football analogy.

Is that what you're now?

You want us to break down football for you to Let's go back to how many arrows were on the ground and what the.

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. You are you ready to do this, Josh, Let's do it?

Yeah? Okay, yeah, I need you guys.

Okay, this is also kind of spontaneous.

This is actually very spantigo.

Let's kick off this by calling her. That's a sports reference.

Brook, It wasn't a very good one.

It's baseball. But yeah, so here we go the first. All right, let's score a home run and call this school. All right, boy, let's go.

Hello.

Hey, is this Haley?

Yeah, piss is Hey.

We're a radio show called Brooke and Jeffrey in the Morning.

Haley.

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 call the second Date Update. And so Josh told us about the date that he set up for you, which sounded pretty elaborate.

Did 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, but.

We're loving 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 the probably the most elaborate and thoughtful date I've been on.

Oh so nice. I bet that made you feel really special.

Yeah. I was totally impressed by his effort and like all the thought he put into every detail.

So are you just like busy and that's why you're not calling it back?

Or were there not enough arrows in the scavenger because that was a fear?

No? I mean, I think everything happens for a reason.

Okay, what does that mean? Yeah, I mean I wouldn't take that date back for anything.

That's nice.

We'd never hear.

It's nice. But I feel like there's a butt coming.

Yeah, but I wouldn't mean 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?

Uh?

Oh?

When we uh got to the restaurant, the waiter was was so cute.

What yeah?

And uh there was more attraction there.

At the hole in the wall restaurant you guys went to, you found a hot waiter.

Brook 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.

Yeah.

No, it's just like sometimes the way he says something like would you like any pepper on that salad?

Well, 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, I 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.

Oh god, it's kind of cute, friend, though.

I know the fact that Josh has been hearing all of this and it's not said a word. Yeah, because Haley, he's on the phone. Yeah, sorry, Josh has been listening this whole time.

Yeah, now I heard the whole thing.

She really she really lived up to this spontaneous stable.

Yeah. Wow, tables really turned on. The whole spontaneous thing. You know. Just sucks.

I just really, I'm sorry, but I'm so happy that we out and we got to know each other.

Oh yeah, yeah, 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 met somebody else on the date I was out with you, But I.

Mean, like, make something up, don't you, like ghost like, 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 cases 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. Seriously, just like.

Josh, what are the chances like you get on the train, you pick a random restaurant and there's.

An attractive waiter, So yeah.

You put her on a train to her next boyfriend. Your date did work in helping find love, just not for your self, yeah, for other people.

Again, I'm absolutely thrilled about that, John Brideside.

You have two other dates pre planned and envelopes for some other lucky girl out there.

Silver linings, I guess. Yeah. Yeah.

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 read the signs, Haley, 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. Uh. So you know what does he have that I don't.

Basically an employee discount at that restaurant, for.

One, but yeah, and also whatever tip money that Josh.

Left, that's true, But besides that, what else? Harry?

I mean, I really appreciate the effort, Dush and all your thoughts. You're a really special person. But I feel that things, again, it will happen for a reason.

I feel like she's like reading a sign on her wall right now.

It's right off.

Her family lived 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 try, all right, you guys did try, and I do appreciate that.

Alright, Yeah, sorry, buddy.

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.

Hmm, that's a good question. I think that's the way things have just turned out, were the way they were supposed to turn out.

You know, everything happens a little.

Bit there, freaking 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 one hundred yards of any other male. Too risky. She's probably going to fall in love and lead.

Oh man, I don't know where you're going to go without men.

To go someplace where men are rare, like a nail salon O often. Yeah, a Bravo convention of Jose's comedy shows. It's all ladies at those. Actually, we have a very high ratio of ladies dues at my show. I think that's our show.

I'm just going to say, I think he lucked out that woman in her motivational quotes.

I just couldn't take him any.

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. I heard that people say, 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 Brook and Jeffrey website or wherever you get your podcasts.

Yeah, Brook and Jeffrey in the Morning

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