Brooke and Jeffrey: Second Date Update - Second Date Update: Bidding On Brandy

Episode Date: July 17, 2026

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All right, we've heard of people going to extreme lengths on this podcast. to get another shot with somebody, but man, did this guy take it too far? Yeah, we were all in disbelief. It's, yeah, yeah, yeah. So take it as it is. Yeah.

Your brand new episode is about to start. Thank you for finding the official second date podcast. It's Brick and Jeffrey in the morning. Before we get to it, what do you see in comments, Alexis? Yeah, this comment made me laugh. Someone commented on another second date and said this one was wild, but not as wild is Jeff's claim of being with two women in his frat house. Yeah, right.

Maybe the two women were together. Yeah. Jeff was definitely not. I was at a party with Jeff once. He's going to hate me for saying this. I saw him with two women. They were consoling him because he got too drunk and he was crying. So I have seen two women all over him, but they were like hugging him.

That sounds more accurate. Yeah, I drove him home. It was a fun night. Oh, Jeff. Please never listen to this, Jeff. I'm sorry. Oh, that's so funny. All right.

Hey, thank you so much for being here. We're going to start your brand new episode right now. Brooke and Jeffrey in the morning. Second Date Update. In the 80s and 90s, persistence won the dating game. A young man standing outside your bedroom window, holding up a boombox in the rain while playing your favorite song. That got the girl. Yes.

In today's day and age, he gets a taser from both the front and the back for that type of move. So can you be persistent without being creepy? No. Well, can you respect boundaries? I don't know. It's the fine line. Our listener, Noah, though, had to walk. And now even he's not getting a call back.

So let's find out more about it. Noah, welcome to the show. Thanks, guys. Oh, Noah. If persistence is the issue here, we should not be on the phone with you. We are only going to make matters worse. Do you see what I'm saying? Maybe.

But let's find out how persistent and what he means by that. Tell us who you met and how that happened. Yeah, so I met this really beautiful girl off of Raya. Her name's Brandy. Oh, wait, isn't Raya, remind me, Alexis. Raya is the one where you have to be, you don't have to be a celebrity. You just have to be someone who's qualified enough. If you don't know about Raya, you don't deserve to know about Raya.

It's like used to, but now it's like... Now it's open to everyone. The floodgates have opened on Raya. Oh, they didn't make enough money on single sports. I saw like two people from my high school. Yeah, I mean, it's all gone to hell. So go ahead. Tell us more about that.

this wonderful woman. You said Brandy was her name? Yeah, her name's Brandy. And it took me like two months to get a day with her. Like, whoa. We would chat on the app like every day and she's busy. She says she's like in and out of town for business. And then finally she says, okay, you've asked me out like 30 times now or whatever. And she agreed to a date. Okay. So that's the persistence that paid off. Yes. You were just patient on the apps. You didn't give up. Exactly. Okay. Okay. See, Alexis, not creepy. You wear them down till they have no choice but to say yes. You're going to block me at any time or like unmat.

That's true. There you go. She didn't. She agreed to meet up with you. So what did you guys do? So I booked a really nice restaurant for dinner and we met there and she shows up and looks incredible. How are you feeling in that moment? Because this is like two months of buildup to this. Yeah. In that

moment I was like, oh wow, I've really scored. Oh. That's cute. So the date's already off to a good star. What about aside from her like physical beauty, what was your connection like? I thought it was pretty strong. I mean, there were definitely some good and some not so good parts of the date. Like, okay, so she's a dreamer like me.

She's a dreamer not so good. Yikes. No, no, no. Like for me, like, you know, I want a water view. I want big ceilings. I want big closets. Oh. Oh, you're dreaming about your dream house.

Yeah, yeah, yeah. Oh. Oh, like a physical thing. That came up on your date? Yeah, yeah. That was fun to talk about? Yeah, it was fun. But then the not so good was like, she seemed distracted.

Like she was checking her phone a lot. And like I think it's probably because her business has been going really well lately. That's why she's like in and out of town. So she like said she acquires fashion merchandising or something like that. I don't really know. It does sound like one of those jobs that you're like, cool, that sounds amazing. I have no question because I don't fully understand what it is. Yeah, so you're a drug dealer.

No, I'm kidding. Okay, fashion. I mean, it sounds like, I mean, in the two months leading up to this date, she was in and out of town for work. She may be one of those people that are just literally on the job 24-7. Yeah, like those people at Disneyland that are still making deals on their phone because they have to. Totally.

But yeah, like, I tried asking a lot of questions about her, you know, and the date ended with a hug and she grabbed an Uber. And, you know, but now she doesn't respond to text. So, like, I don't know. I mean, it took two months for me to, like, finally get a date with her and now I want to know what she actually thought. It's weird because nothing stands out. Like this could be a good or a bad date.

Like it sounds like a normal, typical, there were good things, there were bad things, and then she left. Have you waited a week for her response? Because that seems like that was the... That was the... Five to seven business days between text messages. I didn't wait a week, but I waited like two days. Oh, it's only been two days since your date. No, no, no, no.

Now it's been a week. Oh. I see. Two days to text her. Yeah, yeah, yeah. Two days is perfect. That's not a bad timeline. Did you ever talk about future on your date?

I mean, you were talking about dreams. Did any of them include both of you? Like marriage? Is that what you mean, Brooke? I mean, like, what you're doing on your next date? Or what are you looking for on Ryan? On a honeymoon sort of situation. I think we're both interested in like a relationship.

That's the sense that I got, but like we didn't get like really specific about it. Okay. All right, but if that's a sense you got, it's, you don't have to split. you don't have to spell everything out on date one. Right. But if you are planning a dream home together, that does feel like you're planning for the future. I mean, you are thinking about your down payment.

Maybe she was upset at the number of bathrooms you had planned. Maybe you aren't dreaming big enough. Oh, I mean, yeah, we did talk about closets. Okay, well, I hope you didn't say you wanted to share one. No, I'm not. Alexis, I'm curious to hear your take. What do you think about the date that he just described? I don't know.

I mean, she's out of town a lot, right? like mostly DJs that live all over the world. Maybe she's out traveling. Did that ever cross your mind? Wait, is this Paris Hilton? Yeah, maybe she's a DJ. I don't know. She's on Ryan. I meant there's whatever.

She meant Alexis meant she's dating DJs. Yeah. Oh, maybe. Well, we'll figure it out. If she answers the phone, we're going to call this wonderful woman Brandy. Oh my gosh, we can't take very much time. She sounds very busy. Yeah. We'll just see which DJs she's been dating when we come back. do your second date update right after this.

Thank you. Hold on. Brooke and Jeffrey in the morning. Second date update. Getting a new passport usually takes four to six weeks. Yeah. Yeah, it's a process. Closing on a house, around 30 to 40 days.

But getting one date with a girl named Brandy off Raya took our listener two full months. That's right. Before she finally caved and agreed to go out to dinner. Dang, harder than closing a house. And after all that effort, Noah is never. not getting a call back. Waited an entire week and has finally come to us seeking help. Which, I mean, in that timeline, it feels impatient.

Yeah, compared to the two months situation. Yeah, do wait a year. Yeah. But before we do call, Brooke, what is your take? What do you think about this whole situation? I mean, I know you say that she's interested in a relationship. It just sounds like she doesn't have time. You know, honestly.

Like, she's trying to make it happen, but her career is really important. She may even say that and think she's ready for a relationship. Yeah, it's just, you know, it's hard to have it all. What do you think about getting her to quit her career, Noah? How do you say it? Oh, um. That's not the real question. That was a joke, Noah.

She's trying to think about it. Well, if her problem's the job, then, you know. I mean, I'm open to asking that. No, no, no. No. She sounds highly successful. I think the solution is you quit your job and just follow her around. You've got to fit in with her life.

Yeah. Well, I mean, I don't even know if she likes me because I'm not getting a call. I don't know about that yet. Is that really important that she likes you if she's super rich and successful? Yes. Okay. Well, I have some self-respect. Look at most celebrity rich people.

They don't like each other. That's what I figure. Hey, if you're into it for like the actual connection, good for you, man. Let's try and make this happen. We'll see if Brandi even answers, but I'm going to dial her number right now. Here we go. Hey, is this Brandi? This is Brandi.

Hey, Brandi, thank you so much for answering. We hear you're a very busy woman and we don't want to waste your time. but we are a radio show called Brooke and Jeffrey in the morning. Okay. Welcome to the show. Why are you calling? We're doing something called the second date update. Yeah, we're not here for the Brandy Ted Talk, Jeff.

Wait, this is the brandy? Like the owner of Brandy, the liquor? Wow. Sorry, we're not even 100% sure what you do, Brandy. It's something in fashion, but... Yeah, I'm not really sure how that plays into the radio. It plays in because we heard about your job through a guy you went on a date with named No.

Noah. Okay. You remember Noah who took you to a really nice restaurant? That was cool, right? Yeah, I remember Noah. Okay. All right. He would really like to see you more, but he came to us seeking help because he's been

having trouble figuring out if there's going to be another date or if there's a reason why you're not talking to him. Yeah, I mean, I don't really think he wants to hear why. Oh. Well, actually, he does. Yeah. That's why he reached out to our show because he's not getting the answers directly from you. Okay, okay, sure.

All right. What do you think about Noah? I don't know how to put it. Well, okay, so you ever hear that candy commercial that's like sometimes you feel like a nut and other times not really or something like that. Sometimes you feel like a nut. Are you talking about for almond joy? And mounds. And yeah.

Yeah, and then like he's the don't. I don't understand the analogy What I mean is like I thought he was going to be like a fun and playful guy But he just turned out to be like blah Oh his personality Like blah in what way He's just an overall boring person to be with like Have you ever heard somebody say that they'd rather be like watching paint dry

It's like that That analogy works better than your candy bar thing Just so you know Makes more sense I think we get the sentiment You were bored I mean and then we're there At dinner and it's like

A few questions We would just eat and silence And then questions Have a sip of a drink And then more questions Like I'd rather have dinner With my parents Than they're awful

That's all You parents are awful I felt like my parents Yeah So there was no like Fun back and forth It wasn't fair No I mean like

I don't know What else to say But just like I didn't really want to hurt His feelings but it's just like that was the most like boring-ass date I've been on in like the entire year. I wish we could sugarcoat that for him.

Yeah. We kind of have to tell him and you because you don't know this brandy but here he is Mr. Boring America. What is that? That's me telling you that he's been on the line listening to this phone call. Wait, what?

What do you mean boring? We talked about closets, Randy. Oh, fuck. Yeah. Wait a minute. Exactly. Boring. I'm sorry, girls love closets.

They, like, dream about big shoe closets and lock in closets. That shouldn't be boring to you. You work in fashion. I don't think I've ever had one closet discussion with my girlfriend. Yeah. And I mean, it's like we dream about the stuff that goes inside the closet, not the actual closet space. And you're literally giving me, like, dimensions and type of doors. I thought it was fun.

I mean, it's fun to dream and plan. Yeah, well, my plan is like not to be with you. Sorry. Oh, wow. Was it just the closet? It feels like there's something else we're missing. I mean, there was clearly two months of buildup before the two of them met. In Brandy's mind, it was going to be something really spectacular out of this world and not just closet talk.

Yeah. It had to have been more than that. I mean, Noah, stand up for yourself. Like, there had to have been more on the date. I mean, it was a 45-minute date. So, I mean, we did talk about closets for a good part of it. But we also talked about other things. And I don't know.

I just feel like, you know, you're going to ditch me after one short date because I'm too boring. My personality sucks. I mean, those are your words. Oh. Oh, they were also yours. They came from your mouth first. But think about this. He's a guy who's so exciting that he called a radio station.

I mean, that's pretty cool. Noah, you're exciting, right? Shower. I'm excited. I'm just like, look, look, I really like spending time with you, and I appreciate you and your busy schedule, and I really want to hang out again and not talk about closets. And if you would, then I'd be willing to pay you right now, $200. What? Wait, what the heck?

Why would you pay her? That feels weird. And illegal. Look, look, she's obviously jumping to conclusions that I'm boring after 45 minutes, and I'm not. I know I'm not, and I'm confident that I'm not. And if I have $200 and, look, she can. get compensated for her time, and I'll show her that I'm not born. Whoa.

What? Has this ever happened on our show before where the listener has offered to pay money to go on another date? We always offered to pay for the date. I know. That's kind of our thing. I don't know what the legality on this one is. We're not offering it. It's between the two of them. Yeah, but it's like being at a drug deal and saying that you're not taking the cash.

I don't know. Brandy, where is your head at? That's so insulting. $200. Wait. Is it insulting that he's trying to pay you to go out or is it insulting the price? I mean, $200, that's all he thinks I'm worth. That's what I mean.

Okay, $300. Well, we're in a biddy for? Brooke, you started this. I didn't. You were the one that said show your value. I meant show how exciting you were. Like, tell her that you went, I don't know, cliff jumping last week or something. This is exciting.

It's like being in an auction. Okay, $300. Where are you at, Brandy? Three-Bendie. Who was $3.50? I see in the back, $350. Brandy? I mean, I literally have Lips liner that costs more than that.

No. Oh, wow. Does that exist? That's a bad deal. I'm not about that. Well, okay, I just want to go to another day with you. I'm not trying to, like, upgrade your whole makeup kit. He makes a point.

Yeah, I just also sounds like you couldn't afford to upgrade my makeup even if you wanted to. Oh, my gosh. Final offer. $500 to go on one day with me. I mean, that's a pretty good thing. You are going to have girls texting into our show asking for your money, brother. Oh, my God.

Don't buy love like this. This is so desperate. Brandy, you've heard them $500 on the table. And you pay for my Uber? What? You're thinking about it? We're negotiating this? Okay, fine.

I'll pick you up at an Uber and I'll pay for it. Wow. Wow. Okay. I don't know what's going on. If she says no to this, this would be the worst rejection I've ever heard. Noah is offering. $500 and to pay for the Uber ride if you'll meet up with him again, Brandy. If you sit in the front and I get to sit in the back, then, yeah, okay, $500.

Like a chouffer? Okay. No, you really want this. You don't want to say yes to her. It's not even a date at this point. Look, like I said before, I need a second chance and if this is what it takes, I'm doing it. All right. Wow.

She just wanted a little more personality out of it. Well, it's at this point I'd like to toss in a $20 gift card to Chili's on top of the 500 in the Uber. That's going to steal the deal. You guys can go over like a cookie after. And we're going to take credit for paying for the whole day. Brandy, are you still in? Yeah, I'm in. So for 500 bucks, she's willing to be bored out of her mind.

She is a good business woman. I promise you, Brandy, nothing is going to be boring about our next date. Oh, no. Why do I feel like he's going to be so annoying? Hey, I just bought tickets to the circus. Let's talk about crawl space. Brooke and Jeffrey in the morning. Hey, I'm Ruby Carr, the host of the podcast, Encore.

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I mean, there's no way that she's going to milk this for another $500 date for numbers three and four afterwards. She wouldn't do that. I always wondered how these relationships started and we got to hear it. Like she set the tone immediately and now he knows her worth. It's like $500 minimum to get her out. I just think that she just didn't want to waste her time

and she's a business lady. I don't even think it's about like the money per se. So that was her way of him just to say no. And he just said yes. I don't know. I mean. No, it's a win-win for her. What if?

What if? Because I was kind of a nays hair. What if he's actually fun? Yeah. And what if they actually hit it off? And it all started over $500. Yeah. And what if it goes so well?

She's actually like, you know what? I'm going to give you back the $500. And I'm going to pay for the Uber myself. That's not going to happen. She already negotiated a pretty good deal. I mean, why don't you go back on it? That's bad business, Jeff. I'm saying that's what a good woman would do, right, Brooke?

Yeah. I mean, I don't know. I've never. Okay, whose side are you on? I don't understand. I was hoping that they'd get married. Me too. I'm sure that's what's going to happen.

I choose to believe in love. How much do you think you'll pay for her to marry him? Yeah. That's going to be a different bill. That's a time for another segment, another way down the road. But if you believe in love like we do, go to our podcast and help spread the gospel of second date update on Spotify, I heart, YouTube, and wherever you listen, Just search Brooke and Jeffrey in the morning.

A home world cup only happens once in a lifetime, and we are not missing a second. I'm Castle 1021. On the 1021 podcast, me and the crew, break down every match like it's personal, the drama, the upsets, the debates you'll be having all day, soccer, culture, and chaos in one place. Pick aside, we already did.

Listen to the 1021 podcast on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. My first guest is Terence Hilton, Shakira, Luke and Yerrin. Have surprises? Many surprises. Welcome to the Sweet 305 podcast where the group check comes to life. What on? You're the only person I know that loves a yellow starburst.

It's lemonade. This is Sweet 305. Here, oversharing is encouraged. Listen to Sweet 305 with Lele Pons on the IHard Radio app, Apple Podcast, or wherever you get your podcasts. On Raiders of the Lost podcast, we explore cinema like no one else, including huge interviews with stars like Ryan Gosling on Project Hail Mary. It was like the Jaws shark. Didn't always work, came with its own problems. That's what made it great.

The cast of obsession. On set, there was so much magic happening with each scene we were putting together. Deep dives into classics like 2001 of Space Odyssey or Fight Club, plus weekly episodes on all industry news. Listen to Raiders of the Lost podcast on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. And for more, follow at Raiders of the Lost podcast and at TikTok Podcast Network on TikTok. Hey, Portlandia fans. Carrie Brownstein and Fred Armisen here. The Dream of the 90s is alive in podcast form.

We're launching Podlandia, AEO rewatch, our brand new podcast where we revisit every episode of Portlandia together, breaking down sketches, going deep on our iconic characters. and pulling back the curtain on how it all got made. And we'll also be joined by the people who helped bring it all to life. Guestrars, collaborators, and friends, including director Jonathan Chrysall, the mayor himself, Kyle McLaughlin, legendary musician Amy Mann, and many more. Kyle is going for it here. You fully improvised, not just words, but a song.

Well, I thought you were all going to write a song. I remember you thinking that. Listen to Podlandia. A.O. Rewatch on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. What's up, fam, it's sports journalist Ari Chambers. Hey, what's up y'all? It's your girl, Sam Jay. And we're the hosts of Everyone Watches Women's Sports, a new podcast from together. We're breaking down the biggest headlines, the viral moments, and the stories everyone's talking about across women's sports. From game-changing performances to culture-shifting

conversations, we'll give you our takes, our debates, and a few laughs along the way. Because everyone watches women's sports. Listen to Everyone Watches Women's Sports. from the iHeartRadio app, Apple Podcasts, or wherever you get your podcast.