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

Episode Date: May 10, 2025

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! Get your 2nd Date Update Merch For A Cause HERE!See omnystudio.com/listener for privacy information.

You're listening to an iHeart podcast. 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 Geminis 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. I found out I was related to the guy that I was dating. I don't feel emotions correctly. I collect my roommates' toenails and fingernails.

Those were some callers from my call-in podcast, Therapy Gecko. It's a show where I take phone calls from anonymous strangers as a fake gecko therapist and try to learn a little bit about their lives. I know that's a weird concept, but I promise it's very interesting. Check it out for yourself by searching for Therapy Gecko on the iHeartRadio app, Apple Podcasts or wherever you get your podcasts. The Made for This Mountain podcast exists to empower listeners

to rise above their inner struggles and face the mountain in front of them. So during Mental Health Awareness Month, tune into the podcast, focus on your emotional well-being, and then climb that mountain. You will never be able to change or grow through the thing that you refuse to identify,

the thing that you refuse to say, hey, this is my mountain. This is the struggle. Listen to Made for This Mountain on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Yo, K-pop fans, are you ready? It's your boy, BumHun, and I'm bringing you the K-PAC-ter, the podcast that takes you straight into the heart of K-pop. We're talking music, idols, exclusive interviews,

and even the real behind the scenes K-pop stories. Plus, you're the fans, you're part of the show. And you can get a chance to jump in, share your opinions, and be part of the conversation like never before. And trust me, you never know where we might pop up next. So listen to The K Factor starting on April 16 on iHeartRadio Apple Podcast, or wherever you get your podcasts.

This isn't just a podcast. It's a K-pop experience. Are you in? Let's go. I want you to ask yourself right now, how am I actually doing, because it's a question that we rarely ask ourselves. All of May is actually Mental Health Awareness Month. And on the psychology of your 20s, we are taking a vulnerable look at why mental health

is so hard to talk about. Prepare for our conversations to go deep. I spent the majority of my teenage years, of my 20s, just feeling absolutely terrified. I had a panic attack on a conference call. Knowing that she had six months to live, I was no longer pretending that this was my best friend. So this Mental Health Awareness Month, take that extra bit of care of your well-being. Listen to the psychology of your 20s on the iHeartRadio app Apple podcasts or wherever you get your podcasts Hey, welcome to your Saturday podcast is Brooke and Jeffrey and quick reminder tomorrow is Mother's Day. Yes I thought it was last week. So I sent my mom strawberries super early, which is better and sending them super late

Yeah, then I text her and I apologize and I didn't even call you I was so busy oh it's like honey it's not till next week I'm like okay I'll call you on Sunday so you did get out it yeah I got it myself dang it well listen if you're frantic for a gift I'm just gonna tell you you can go to our merch for a cause and buy a brand new second date update hoodie crewneck yes yes and listen I know it won't come tomorrow in time for Mother's Day, but all mothers are fine with a printed out piece of paper of what you got them. As long as it comes with a heartfelt note.

Yeah, that's cute. That says something like, dysfunctional dating makes me think of you, mom. Here's your second date update, merch for a cause. All right, go do that, because the link is in the show notes, and 100% of the proceeds go to a great organization called Convoy of Hope, which is a great nonprofit.

So get your merch for a cause, and let's get this show started. 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 the absolute worst thing you can do is be open to trying new things New experiences should scare you and you need to avoid them at all costs Instead reading the anti therapy blogs again No, you need to stick to the places that you've already been and people you already know nothing bad can ever happen

Okay, Jeff. This is how you end up in like my hometown, dating your cousin. So Brooke clearly supports it. You gotta be careful. 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. 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 to your new life. Low. Oh, I'm glad to be here. This is my first time ever doing that.

Are you feeling shame or excitement? No, definitely excitement. I don't, I'm not feeling shame. Okay, well. That comes later. Yeah, we're gonna 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 like a dating event. OK, that people put on and that this fancy house. OK, 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 I went by myself. Yeah, OK. That is so great. 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. Just a brief little thing like that.

And then once you did the questionnaire, I went inside the house, and it was, it 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. Dude, they have a chandelier? That rich. No, no broke people on channel. You get in 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're are supposed to meet once but we'd already hung out 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 See guess anyway that makes way more sense and the fact that it's on a silver tray makes me believe whatever is on it is like absolutely true and so who who was the 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. Had you already met Natalie or do you have to go find her? I had actually met her and she was like, obviously, on 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're like, yes, lucky red envelope. That's nice. Yeah, looking at all the ladies. She was like top of my list. Oh! So you're like, yes, lucky red envelope. That's nice. Yes, it was a total yes. Fist bump, yeah. OK. 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 just kept encouraging us to go back to the bar. And so, yeah, we did drink a bit. I admit it. I definitely was feeling abuzz. Nice. OK. 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. He's laughing now. 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 a head rush and I kind of fell into a bush.

Oh. 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, but you may have looked a little sloppy. Yeah. Yeah, I looked sloppy.

I didn't fall over, I was just so hammered that I was just passing out, that I was just like passing out But I definitely leaned into it hard. Let's put it that way Confident lean into a bush But she helped me out of it But like I'm pretty big guy so she couldn't really do it so this guy like kind of stepped over and kind of helped me Not your proudest moment, but it's probably not like a total deal breaker for you So how did it end that night but with you and Natalie?

Well at the end of the party I asked her she wanted to go up to have food, you know Oh cup 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. Then I haven't heard back for I mean I got her Haven't heard back for work. I mean I got her Yeah, exactly have you called her or or nothing I texted her once I don't want to be the dude who's spending multiple texts Definitely like damn I went to all that trouble and thought it was a good connection And then just seem 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 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. Yeah so we're gonna 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 gonna need to set the scene here for any listeners just joining us. I like the music. A picture of 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 is fancy. It does feel like something that happened

in Jeff's neighborhood garden. Yeah, yeah, a lot of ascots. Gimlets and mint juleps. Oh, mint juleps for sure. And what is a- Anybody want a lot of ask-ons. Uh-huh. 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 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 So they met up had a great time there until he fell into a bush outside Didn't ruin the night. It was just a member. the thing is he remembers it so he wasn't The problem is now Natalie is ghosting so Brooke take a break from putting your reservation in at the rent envelope house And what tell us how do you feel about it my hometown was more like bush light and you'd wrestle a pig The problem is is it's a singles party so she could have easily just met somebody else that night You'd wrestle a pig. You know, they started in the bushes.

The problem is, is it's a singles party, so she could have easily just met somebody else that night. Yeah. 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 talk. Oh, you're talking about before the envelopes were handed out. Yeah. Yeah. 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 before him. 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. That's like asking you to talk to them. 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 is in the red envelope for the first hour Jeff. It's a red envelope with a red flag attached I'm worried, but let's call Natalie. Here. I see what she has to say here we go Hello, hey, is this Natalie? 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. We're all here eager to talk to you. Hey Natalie! Um, 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 single 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

But this guy's name is Alvin. Oh Okay Remember him from the red on yeah I do I do remember him. I'm just surprised. I just 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 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 say her. Oh Well, I don't think he stayed very long either. Did you meet somebody else? Is that what it that's a week?

I know which is totally fine. That's the whole point of the party, right success for you 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've done these parties. I was really just trying to experience it and leave because my friends who've done these parties, they say that you should leave by midnight

if you don't wanna, you know, that it can get pretty crazy let's put it that way and I was just trying to get out of there is it really actually one of those I think I was right by accident? 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. Each one apparently has a theme. I don't know.

It's weird. Are you not calling Alvin back because you think he stayed? Or are you not calling him? 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

Not really my thing. I'm not into that after midnight 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 talked to Alvin himself Like such an innocent guy And you don't have to wait because Alvin is on the other because he seems like such an innocent guy when you 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, you there? Oh, my gosh. Yes, I'm here. Oh, my gosh. What is happening? Hey, Natalie. Hello.

Dude, I'm dying. Did you stay after midnight Alvin? Do you know what she's talking about with the extra rooms that open up? Yes I do Oh you do And you're laughing Okay Well yeah I mean she laughed and like I said I was kind of feeling it you know and I was like oh I'm here I might as well stay

Am I jumping to the right assumptions on all I'm here. I'm gonna I'm afraid to go into any more details Actually happens. Did you partake or are you just enjoying the view brother? I was just enjoying the view Why in the world would you contact a radio show if this is the type of event that you Didn't mention any of this to us. 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. Okay.

Well, sure, but it's a pretty important detail, I think, to bring up. But like the story ends when Natalie left, like, I was just on this, you know. Okay, we don't need to. That's her story, and then I ended up not. You got a lot of good ideas there. 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.

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 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. People thinking of me. That's so well. Why do you have a party if

you're not into that type of people like Natalie? I mean, what are you doing? That's actually true. But sometimes you don't know until you try it. Yeah, I was trying to just do something outside of the box because I'm not super adventurous but I definitely have 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, the first time I ever went to one of these things. That's right, that's right. We're not judging you. If anything anything some of us are jealous of you. I was into a podcast about these. They're crazy. How long were you there? So like like three a little after three like 330. 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 You know ascots are like those ties like scarps. Oh, it's actually a smart idea

Pretty creative. Oh my god, so gross. I don't That's so gross. I don't know Well, he didn't use one of the ascots he just watched people with the ascots Oh, no, but I like no, I don't I don't I don't 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 before and 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 got to admit we were having a good time

At least I think we were that's a good point 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. I think 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

See you in the baby back room As long as there aren't extra rooms being opened up 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! Hey! Look out, janitor's closet! Congratulations! You got yourself another date!

Yes, I'm so glad. I really am. God, it's gonna be so sweet when you guys tell this story Everybody has red ascots in the wedding party. No, it's on honeymoon night is that Scott's The bellboy can watch Brooke and Jeffrey in the morning. I Found out I was related to the guy that I was dating. I don't feel emotions correctly. I collect my roommates' toenails and fingernails. Those were some callers from my call-in podcast,

Therapy Gecko. It's a show where I take phone calls from anonymous strangers as a fake gecko therapist and try to learn a little bit about their lives. I know that's a weird concept, but I promise it's very interesting check it out for yourself by searching for Therapy gecko on the iHeart radio app Apple podcasts or wherever you get your podcasts the made for this mountain podcast Exists to empower listeners to rise above their inner struggles and face the mountain in front of them So during mental health awareness month tune into the podcast, focus on your emotional

well-being and then climb that mountain. You will never be able to change or grow through the thing that you refuse to identify, the thing that you refuse to say, hey, this is my mountain. This is the struggle. Listen to Made for This Mountain on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Yo, K-pop fans, are you ready? It's your boy, Bom Han, and I'm, or wherever you get your podcasts. And you can get a chance to jump in, share your opinions, and be part of the conversation like never before. And trust me, you never know where we might pop up next. So listen to the K Factor starting on April 16 on iHeartRadio app, Apple Podcast, or

wherever you get your podcasts. This isn't just a podcast, it's a K-pop experience. Are you in? Let's go. I want you to ask yourself right now, how am I actually doing? Because it's a question that we rarely ask ourselves. All of May is actually Mental Health Awareness Month and on the psychology of your 20s, we are taking a vulnerable look at why mental health is so hard to talk about.

Prepare for our conversations to go deep. I spent the majority of my teenagers and my 20s just feeling absolutely terrified. I had a panic attack on a conference call. Knowing that she had six months to live, I was no longer pretending that this was my best friend. So this Mental Health Awareness Month, take that extra bit of care of your wellbeing. Listen to the psychology of your 20s

on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. My husband has a secret son from a past partner. Hold up, Sam, how do we know, have we done the DNA test? Well,, luckily it's Mother May I Have a DNA Test Week on the OK Storytime Podcast, so we'll find out soon. And this wife writes, My husband received a Facebook message from a woman saying that he is the father of a 5 year old. At first he didn't remember her, but then he realized they had a one night stand right before we started dating.

Wait, but do we have proof he's the dad? To hear the explosive finale, listen to the OK Storytime podcast on the iHeart Radio app, Apple Podcasts, or wherever you get your podcasts. You're listening to an iHeart Podcast.