Brooke and Jeffrey: Second Date Update - Second Date Update: Red Envelope Regret

Episode Date: August 26, 2024

If only finding a date was as easy as ordering your favorite drink. One of our listeners had the perfect girl right in front of him all thanks to a new dating event that even YOU might want to try! Hear it in your Second Date podcast!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. If I've learned anything from reading countless dating blogs, they all say the absolute worst thing you can do is be open to trying new things. No, they don't.

That's the opposite of what they all say. New experiences should scare you and you need to avoid them at all costs. Too risky. Are you reading the anti-therapy blogs again? No, you need to stick to the places that you've already been and people you already know. And nothing bad can ever

happen. I'm not even new people? Okay, Jeff. This is how you end up in my hometown, dating your cousin. So Brooke clearly supports it. You got to be careful. The thing is, one of our listeners didn't take that advice. Thank God. And he's some sort of modern Renaissance man, decided to try something new and look where

it landed him. Oh, right here with us. Here on our show, which I'm guessing is another new experience for him that he's never done before. So yikes. We're the low point. We are. Alvin, welcome We're the low point. We are. Alvin, welcome to your new life low.

Awesome. Glad to be here. This is my first time ever doing that. Wow, Alvin. Now, are you feeling shame or excitement? No, definitely excitement. I'm not feeling shame. Okay.

That comes later. We're going to change that by the end of this segment. But you said that you tried something new for your dating life. What was that? Have you ever heard of a red envelope party? No, but it sounds kind of kinky. What's going on? I'm intrigued.

Yeah, what is that? What's a red envelope party? Well, it's like a dating event that people put on. And it was at this fancy house. Really nice neighborhood. And you went by yourself? You didn't bring a friend? Yeah, no.

This was a friend who hooked me up with this, but I went by myself. Okay, one of your friends suggested it to you. Yeah, and then you scan like a QR code and you fill out a questionnaire that's like about your interests and your values, you know, what kind of person you are. Like stuff you'd find on a dating profile, right? Yeah, yeah yeah just a brief little thing like that and then once you do the questionnaire

i'm inside the house and it was had the vibe of like a swanky private members club it was you know fancy furniture and well stocked bar chandeliers the whole you know if they have a chandelier that is rich no no broke people on chandeliers you get a house full of single people and you're only allowed to talk to one person that they give you an envelope of? Is that the rule? No, no. You're supposed to mingle and drink and have a good time. That's what I was doing. Okay.

About like an hour into it, maybe a little more, a waiter came around with a silver tray. And on the tray were red envelopes. And you find the one that has your name on it. And that has inside the person that you are supposed to meet. But we'd already hung out. Okay. I'm guessing the whole point is

so that you go around the room and actually try to find the other person, right? Yeah. It's more about talking to other people to find the person. I see. I mean, my guess anyway. No, that makes way more sense.

And the fact that it's on a silver tray makes me believe whatever is on it is absolutely true. And so who was the person whose name was in your envelope? My envelope had the name Natalie in it. Okay. Had you already met? Why are you laughing? I thought he said he had his own name in his envelope.

That would be your luck at one of these, Jeff. Jeff's like, and I still don't love myself. Wait, had you already met Natalie, or did you have to go find her? I had actually met her, and she was like, obviously, I'm there to date, so I'm looking around, you know, looking at all the ladies. She was like top of my list. Oh. So you were like, yes, lucky red envelope.

That's nice. Yes, it was a total yes fist bump, yeah. Okay. So you went and tracked her down. How did that go? It was great. We were having a really good time, and she was laughing a lot, and I was laughing. Oh, that's a good sign, because she could have been disappointed when she saw your name.

No, no, she seemed cool, and she kept encouraging us to go back to the bar. So yeah, we did drink a bit, I admit it. I definitely was feeling a buzz. Nice. Okay. yeah we did drink a bit i admit it i definitely was feeling a buzz nice okay but you're you know you're doing it together and it's a party scene like it seems appropriate yeah yeah it was appropriate amount and i was not alone you know it was everybody was having a good time and she was having a good time you know like i said we were laughing a lot these are all positive reviews is there anything in your mind that like was like a low moment of the night or

something that could have gone wrong yes yes there was oh he's laughing now i mean it's not it's not the worst but like we had been sitting for a while and we stood up and we walked outside and it was pretty warm night and i definitely had like a head rush and I kind of fell into a bush. Oh. Uh-oh. And this was in front of Natalie? Yeah, yeah. Oh, yeah. I was walking with her. Oh, okay.

So you may have looked a little sloppy. Yeah. Yeah, I looked sloppy. I didn't like fall over like I was just so hammered that I was just like passing out. But I definitely leaned into it hard. Let's put it that way. What did she say? A confident lean into a bush. But she helped me out of it. But like I'm leaned into it hard. Let's put it that way. What did she say? A confident lean into a bush. But she helped me out of it.

But, like, I'm a pretty big guy. So she couldn't really do it. So this guy, like, kind of stepped over and kind of helped me, too. Gave you a hand. Not your proudest moment, but it's probably not, like, a total deal-breaker for you. So how did it end that night with you and Natalie? Well, at the end of the party, I asked her if she wanted to go out to have some food, you know, soak up the alcohol.

And she said she wanted to hang back and find this friend that she came with. And I don't know. That's it. Since then, I haven't heard back from her. I mean, I got her. Her number? Yeah, exactly. Have you called her or nothing?

I texted her once. I don't want to be the dude who's sending multiple texts. But I was definitely like, damn. I went to all that trouble and thought it was a good connection. And it just seemed weird that nothing has come since then. Maybe she confidently leaned on the same bush and is trapped inside of it right now, waiting for somebody to come pick her out. She's in a hedge as we speak.

So we're going to call. We'll see if she answers and try and get you your second date update. Fancy edition. Coming up right after this. Second date update. I'm going to need to set the scene here for any listeners

just joining us. Picture well-dressed men and women sitting on ornate couches, sipping on gimlets, mingling together at a red envelope party. What is this, like an old people?

It's fancy. It does feel like something that happened in Jeff's neighborhood growing up. Yeah, a lot of ascots. Gimlets and mint juleps. Mint juleps for sure. Anybody want a grasshopper? What's a red envelope party? I'm still not 100% sure I get the idea,

but one of our listeners, Alvin, attended one the other night where he went to a house in an upscale neighborhood. They have you fill out a dating survey, and then later, based on the answers to your questionnaire, they bring you a red envelope on a silver platter with the name of the person that you matched with and are supposed to meet that night. Yes.

And the name of Alvin's person was Natalie. Aww. So they met up, had a great time there until he fell into a bush outside. Well, that didn't ruin the night. It was just a memorable. It was a low light. He remembers it, so he wasn't too drunk. He wasn't like full team blackout.

The problem is now Natalie is ghosting. So, Brooke, take a break from putting your reservation in at the Red Envelope house. Tell us how you feel about it. My hometown was more like bush light and you'd wrestle a pig. They started in the bushes. The problem is

it's a singles party, so she could have easily just met somebody else that night. And everyone's forced to mingle like they said. Like, that's the whole point of the red envelope is so you go around and meet other people. Oh, you're talking about before the envelopes were handed out. Yeah, the hour when they just get to know.

And, like, the friend that she had to find at the end of the party, air quotes, was probably the person she was talking to beforehand. Alvin, did you notice Natalie speaking with any other guys? I mean, I did notice her speaking with other guys, but not like, you know. I'm sure. That's what the point is.

You talk to everybody, Jeff. It's not like they signed a contract that you could only go out with this person in the red envelope. They don't know who's in the red envelope for the first hour, Jeff. It's a red envelope with a red flag attached to it. I like it, Jeff. I i'm worried but let's call

natalie here and see what she has to say here we go hello hey is this natalie uh yes this is natalie who is this my name is jeff and i'm part of a radio show called Brooke and Jeffrey in the Morning. And we're all here eager to talk to you. Hey! What? Yeah, we actually were given your phone number by one of our listeners that went out. It was kind of on a sort of a date. Met you at a dating party yeah singles

singles okay and this segment is called second date update because we're trying to get you two back together and figure out if there's maybe chemistry or if you feel the same if you feel the same way thank you brooke um but this guy's name is alvin oh okay um oh my gosh remember him from the the red envelope yeah you have to remember him right i do i do remember him i'm just surprised i guess oh my god describe like what that party was like for you also if it's one of those parties you don't have to describe too much It's not. So I just, I had never been to one. So I don't know what to tell you about it because I didn't stay. You didn't stay? Later.

Well, I don't think he stayed very long either. Did you meet somebody else? Is that what it comes down to? Which is totally fine. That's the whole point of the party, right? Yeah, that's a success for you. Well, I've had friends who have done these parties. Like, I was really just trying to experience it and leave.

Because my friends who have done these parties, they say that you should leave by midnight if you don't want to, you know, that it can get pretty crazy. Let's put it that way. Oh, at midnight? I was just trying to get out of there. Is it really actually one of those i think i was right by accident can you what do you mean can you elaborate what do you know what happens at midnight i heard that they open up these like other rooms for activities after midnight and i just that's not really my jam like each one apparently has a theme i don't know are you not calling alvin back because

you think he stayed or are you not calling him like i don't understand why you still wouldn't be or the fact that he was at that party yeah i mean i think i made the assumption that he's been to more than one maybe a bunch of these and that's just not really my thing i'm not into that after midnight well even yourself say if you think that you're making an assumption there i don't know if it's fair to jump to a full conclusion until we actually talk to alvin himself because he seems like such an innocent guy when i talk to him and you don't even have to wait because alvin is on the other line right now listening to this conversation from a secret room in our studio. Don't say that, Jeffrey.

Alvin, are you there? Oh, my gosh. Yes, I'm here. Oh, my gosh. What is happening? Hey, Natalie. Hello. Dude, I'm dying.

Did you say after midnight, Alvin? Do you know what she's talking about with the extra rooms that open up? Yes, I do. Oh. You do? oh you do and you're laughing okay bro well yeah i mean she left and like i said i was kind of feeling it you know and i was like oh i'm here i might as well am i jumping to the right assumptions on all of this or am i i'm afraid to go into any more details of what actually happened. Did you partake or are you just enjoying the view, brother?

I was just enjoying the view. Oh, okay. Calvin, why in the world would you contact a radio show if this is the type of event that you went to? You didn't mention any of this to us. That's true. You guys asked me to talk about the date part. That's the part that I was

interested in talking with you guys about. The rest of the party and the event and stuff is like another story. Well, sure, but it's a pretty important detail, I think, to bring up. But like the story ends when Natalie left. Like afterwards, that was just on this, you know. Okay, we don't

need to. That's her story. You got a lot of good ideas there. Is this making you feel better or worse, Natalie? I mean, I don't need to. That's her story. You've got a lot of good ideas. I mean, is this making you feel better or worse, Natalie? I mean, I don't like the idea of him watching other people. Yeah. I don't, like, why does he want to contact me? Because you're the person I'm interested in. Like, I was thinking about you the whole rest of the night.

Like, that's all I was thinking about. But you're watching other people thinking of me? That's so... Well... Yeah. That's coming out wrong. But also, why do you go to the party if you're not into that type of people like natalie when i mean what are you doing that's actually true but sometimes you don't know until you try it right yeah i was trying to just do something outside of the box because i'm not super adventurous but i definitely had boundaries as far as not wanting to participate in the late-night activities.

Okay. You guys are making it sound like I'm some kind of total freak who's into, like, these wild things. This is the first time, just like Natalie, this is the first time I ever went to one of these things. That's right. We're not judging. If anything, some of us are jealous of you.

I listen to, like, a podcast about these. They're always crazy. I bet. How long were you there? So, like, three, a little after three, like, 3.30. Damn, bro. In the morning? You watched for three hours?

I mean, I only really actually watched, like, this one room called the Ascot Room. That's, like, the only one that I even looked at. The Ascot Room? What does that even mean? You know what ascots are? Like, those ties? Like those ties, like scarves. Oh, it's actually a smart idea. They're really silky.

They were pretty creative. Oh my gosh, that's so gross. I don't know. What am I supposed to say to that? Well, look, he didn't use one of the ascots. He just watched people with the ascots. I know, but I, like, no. I don't, I don't, I don't know know why i shouldn't have pulled you out of that bush i'm i don't know

before i ask officially alvin is there anything else that you want to say to natalie like a like a final plea maybe i just want to say like i thought we had a good time beforehand it's not like like i said i'm not like into that scene that's not like my place and my people or something and you gotta admit we were having a good time at least i think we were that's a good point yeah and he obviously his intentions was to meet one person okay well i just need to know are you going to go to the next one i mean if you wanted to go with me to one of those, that would be cool. But I'm not going to be going by myself. That was a little soon to say that, my friend.

I don't know. But it's not too soon to ask if we can facilitate another meetup between the two of you. We have a red envelope party over at Chili's. I'm going to see you in the baby back room. That's what I was going to say. As long as there aren't extra rooms being opened up after hours. So you're saying yes? Okay.

You're open to it? You know what? I am because, like I said, I'm trying to be adventurous, and it sounds like he went and he committed to the experience, but it doesn't sound like it's something that he does all the time. Oh, my God. Look out, janitor's closet. Congratulations.

You got yourself another date. Yes, I'm so glad. I really am. God, it's going to be so sweet when you guys tell this story at your wedding. Where you were when you met. Everybody has red ascots in the wedding party. No, just on honeymoon night, it's ascots.

No. Oh, come on. Uh-oh, role play. The bellboy can watch. Brooke and Jeffrey in the morning. That's weird. I just opened my email and got an invite to a black envelope party. Wait a minute.

They say they provide you with a free wheelchair if you attend. Does anybody know what this is? Yeah, I do, Jeff. You know what? I'm just going to accept it. Yeah, I'm feeling you're free that night. Yeah, I'm going to stay after hours and just see what happens. I think you'll be fine more than anybody, honestly.

Yeah. But is anybody else shocked that Natalie said yes to the second date offer? I am a little bit. I'm still shocked he called into a radio station after attending something like that. I know. That is like, it's beyond me. Here's my theory, and it's a total theory. She is still slightly in the back of her head in a weirdest way interested.

She showed up to the party, looked around. She left. She knows what happened, and she knows what happened and she knows what happened after and she still said yes well she's looking for somebody to be her sherpa to help like guide her to the post midnight activity i don't know if he's the guy he could just be the help why he's honest he said he just watched yeah okay for four hours i don't know if that's good when do you become an expert how many hours do you have to get in i don't know is that how that works are you an expert or they

kick you out i don't know you would think if you're a first timer at one of these you'd leave after 10 minutes but yeah right it really stayed and soaked it up nothing shakes this guy yeah a lot of research anyway we need to go but make sure to listen to any of our second dates wherever you get your podcasts they're available at brooke Brooke and Jeffrey. You can always email the show too. We'll try and call that person who's not calling you back. John 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.