Brooke and Jeffrey: Second Date Update - Second Date Update Classic: Cutecumber Couple

Episode Date: November 28, 2025

One of our listeners says he got his inspiration for his dating “MOVE” by watching on video online and gathering the courage to try it himself. Hear what it was in a Second Date podcast!See omnystudio.com/listener for privacy information.

The best dates happen when someone really gets your vibe, your niche references, your hot takes, even your reality TV obsessions. That's why it's so exciting to be partnering with Bumble. Dating feels easier on Bumble with prompts that show off your personality, shared interests that help you find common ground, and verification that gives you peace of mind that you're meeting someone real. So if you're ready to meet someone who really gets you in your energy, Bumble is the perfect place to start. What are you waiting for? Download Bumble and start your love story. Hi, I'm Dr. Priyanko Wally. And I'm Hurricane DeBolu. On our new podcast Health Stuff, we demystify your burning health questions.

You'll hear us being completely honest about her own health. My residency colon was like a cry for help, honestly. And you'll hear candid advice and personal stories from experts who want to make health care more human. I feel like they never felt like I truly belonged in medicine. We want to make health less confusing and maybe even a little fun. Find Health Stuff on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Hey there, Dr. Jesse Mills here. I'm the director of the men's clinic at UCLA, and I want to tell you about my new podcast called The Mail Room.

And I'm Jordan, the show's producer. And like most guys, I haven't been to the doctor in way too long. I'll be asking the questions we probably should be asking, but aren't. Every week, we're breaking down the world of men's health from testosterone and fitness to diets and fertility. We'll talk science without the jargon and get your real answers to the stuff. you actually wonder about. So check out the mailroom on the IHeart Radio app, Apple Podcasts, or wherever you get your favorite shows.

What do you get when you mix 1950s Hollywood, a Cuban musician with a dream, and one of the most iconic sitcoms of all time? You get Desi Arness. On the podcast star in Desi Arness and Wilmer Valderama, I'll take you on a journey to Desi's life, how he redefined American television and what that meant for all of us watching from the sidelines,

waiting for a face like hours on screen. Listen to starring Desi Arnaz and Wilmer Valdarama on the IHard Radio app, Apple Podcasts, or wherever you get your podcast. Podcasters, it's time to get the recognition you deserve. The IHeart Podcast Awards are coming back in 2026. Got a mic? Then you've got a shot. Every year, we celebrate the most creative, compelling, and game-changing voices in podcasting. Is that you?

Submit now at IHeart Podcast Awards.com for a chance to be honored on the biggest stage in the industry. Deadline December 7th. This is your chance. Let's celebrate the power of podcasting and your place in it. Enter now at iHeartPodcastawards.com. We know it's never going to end well when a listener gets their dating advice from the internet. Yeah. It's just, it's how it goes.

Yeah. Although that's our listeners right now listening to our show on podcasts. That's true. I feel like they're learning more what not to do instead of what to do. But, yeah. He got a pickup line or a pickup method, I guess. I would say from the World Wide Web, and he gave it a try.

You know, listen, see if you want to give this a world, too. It's about to start. Happy Black Friday. And do you have any comments, Alexis? Yeah, Vince said, my son and I listen to this show, and we absolutely love it. He's 10, and every morning he goes, we need to watch Brooke and Jeffrey in the morning.

That's right. And he'll echo the morning like it does on the show, like our sweeper that goes, Brooke and Jeffrey in the morning. In the morning. It's so rad. I love hearing that. I love that.

All right. Here we go. Episode starts right now. Second date update. What do you do? If you've been single for the last few years, you've been on over a dozen dates, on a dozen different dating apps,

and absolutely nothing has stuck. Oh, God. I accept that you're undidable. Oh, don't. No, that's not true, Jose. He was talking to me. Don't butt in. No.

Jose, you'd have to actually leave your house in order for that to count as like you're trying. Got it. You could become a monk. And take a vow of celibacy to make it seem like it was all your idea the whole time. Oh, that works perfectly. I mean, they do have, like, some of those places, beautiful views. Oh, yeah.

All virgins up there. Or you could do the most frightening thing in the world like our listener, Rob, did, and meet someone in real life. Oh. What the heck? People don't actually do that anymore, actually. It actually seems harder than being a monk. Rob. Yeah.

True. You scare me. Welcome to the show. Thank you so much. Thanks for having me. Hey. That's exciting. You know, I feel like we've heard a couple of these stories lately.

Maybe people are going back to this trend. It's either exciting or a real low moment in your life. So which wasn't? No, I'm, like you said, I'm just completely done with the apps. Like, no one ever wants to meet up. It's just a waste of my time. Okay. So what did you do to meet somebody in person?

What was your trick? Well, normally, how I would try to meet someone. I'd be like if you know you were a vegetable you'd be a cute cumber Oh Oh you'd use a pickup line

And I'll say that on a dating app And stuff And I mean sometimes They'll work They'll respond to me And sometimes it just It just won't Huh

Yeah It's pretty Well you have to Not just like jokes You have to like bad jokes It's pretty cheesy Yeah Or maybe that one's a little bit

Too high brow That they don't understand It Cute cumber Yeah I mean it's like Vegetables And cute all in one

Another one that I've tried before that sometimes works excuse me you seem to have dropped something oh oh it's your standards can i buy you a drink oh that sounds like i like that one to yourself yeah i mean i'm starting to feel like it's not the app's fault that you're not meeting a lot of people it's the wrong girl you need a girl who's like loves that silly stuff brother that's what i'm hoping to find here okay okay so you said that's what you used to do those were your old strategies do you mean you have like a new thing that you were trying? Yeah, so I found this video online, and there was this guy who said that there's just one, like, super simple trick that you have to do.

Oh, okay. Everybody listening, right? Yeah. So you're at, like, a bar or something. You walk, like, right next to her, and then you lean over to the bartender, and you just say, I'll have an old fashion. She'll have a rainbow lemon drop, and then just say, put it on my tab. Ah, nice. And then just walk away.

Wait, what? And she's like, ew. I'm allergic to lemon. Yeah, and a gross free drink? Yeah. Like, you get a good old fashion and she gets a rainbow lemon drop? Well, I think it's just any drink, right? Like, you don't always have to be a rainbow one.

Yeah, you don't have to stick with the rainbow lemon job. Just like some sort of free drink for her. I'm getting something for me. Put it on my tab and then you walk away. Wait, and you think she wants to date you because you bought her a free drink? No, but it's a mystery, so you're going to follow him to find out who he is. No, that's the best part, not having to talk to the guy who buys you a drink. That's like a win.

Yeah, no, the guy in the video said that, just like you said, it kind of creates a mystery, you know? She's like, she's just going to start thinking about you and thinking about you. Different than most guys that buy people drinks because most guys will do it and then stick around and be like, all right, I bought you something. Now you owe me like 10 minutes of time. So did you do this out in the real world? So I actually just tried it the other night. And? It worked.

Damn. Okay. Her name was Camilla. Camilla. So how long did it take for Camilla to get the drink and go find you? Literally five minutes. Like she had not finished the drink. She had it in her hand when she walked up to me.

Okay. Well, and every time she looks down at the drink, she's thinking of you. Well, you must be pretty attractive because she wouldn't, you wouldn't do that if someone's not attractive. But like Jeff said, it's so nice not to owe anybody anything for something. You know, like it's such a relief probably to her. And I don't think it has anything to do with attractiveness. It's just like the mystery of it. Yeah.

If like an ugly guy gave you a drink and then walked away, you'd probably be like, huh. I wouldn't go talk to him, no. Yeah. I would. But it worked for Rob, so how long did you guys talk? We were talking for like maybe 10 minutes or so. She said she was waiting for a friend. So when her friend came, she did have to leave.

Oh, okay. So she was just lonely. I did give her, or she gave me my number. Yeah, she gave me her number. Yeah. It'd be scary if she gave you your number. Yeah. You better be a good number.

And I texted her, and she, like, replied right then, just, like, got it. So I know she didn't give me a fake number. Okay. So, wait. Did you guys go on in a date? I have not heard from her. I tried texting her and try to set something up, and I've got nothing. Okay.

And so the guy in the video on YouTube that you watch, he didn't have any follow-up divs. There was no part two, no. But a 10-minute conversation is basically like a long-term relationship in the modern dating world. Yeah, and face-to-face. You've been together for a very long time. But I guess we should ask, do we know 100% that this Camilla girl is single? Oh, that is a risk in this one because you buy him a drink before you hit on, you know, before you talk to them. That's true.

I mean, I didn't straight out ask her, but she was definitely, like, leaning into it. I feel like, so I'm pretty sure, but if she, if she was in a relationship, she probably wouldn't have, like, walked across and tracked you down and, like, struck up a conversation. And her friend was there. How long has it been since? that bar interaction? About four days now. Okay, not that long. How many texts have you sent?

Possibly like five or six. Okay. Enough that. She's definitely ignoring you. That's all the line of maybe too many, but... Yeah. Maybe she's gaming you back. Maybe this is like a girl's strategy to pick the guy back up after you pick her up.

But we'll find out. We'll come back. She's like, he'll call a radio station. That's what we're crossing our fingers for. It's all going according to plan. and we come back and call Camilla try and get you your second date update right after this. Second date update.

Welcome, my friends, to today's special edition of how to seduce a beautiful woman without speaking a word to her. Hey. It's Brooke and Jeffrey in the bedroom. Oh, wait. Now we're there?

Today's pick-up strategy comes from our listener, Rob, who tried something that he found in an online video where if you're at a bar, God, with that voice and when you say online video, it sounds like something we shouldn't be talking about. It's a TikTok. It's not like that, but you just go up next to the woman that you like. You don't talk to her. Just order yourself a drink, then without asking, order her a drink, and simply smile and walk away. And let the mystery do the work for you.

Yes, smooth. And that was different from Rob's previous strategy, which was to basically use cheesy pickup lines. Like, if you were a vegetable, I'd say you were a cute, come. I mean, we started talking to Rob, and he's like, yeah, it didn't work for 12 years. Yeah. He did 12 years of the same thing. He decided to try something different, and it worked. Yeah.

Kind of. Well, the girl approached him, and they talked for 10 minutes. She even given her number. But now she's not calling him back. But overall, I mean, after learning that move, Rob, do you feel like you're more confident in yourself? Yeah, I mean, I think I do. The fact that she walked up to me, like, that's just crazy.

That's crazy. You think she's a psychopath. Is that what you're saying? I think crazy in a good way, Jeff. Not crazy in a bad way. Crazy in love like Beyonce. Okay. We're going to call her right now.

And remember, Rob, wait until we call you in in order to jump on. Okay, we've got a lot of people just springing on the line without permission. Yes, have some self-control over there. Got it. I don't know. He really feels like a wild card, Jeff. All right. All right, here we go.

Hello. Hey, is this Camilla? Yes, it is. Who's calling? We're a radio station called Brooke and Jeffrey in the morning. Hey, Camilla. Hey. Thanks for listening.

Okay. How can I help you guys? Yeah, well, you went out with a guy who listens to our show. I don't know if I'd say that. I would say you met a guy at a bar who listens to our show. His name is Rob. And you guys met like four nights ago, ish? Yeah.

Oh, you remember him? Oh, okay. Yeah, no, I know who you're talking about. Okay. Okay. Well, Rob, he bought you a drink and you guys ended up talking for a few minutes until your friend got there. And he knows it wasn't like a lot of time together, but, you know, he was impressed by who you were. We're just wondering what were your thoughts about Rob? He was nice.

We always have a bad reaction when the only thing that they say is nice. First, I just want to hear, like, when he went up to the bar and he bought you a drink without saying anything, what was going through your head? Honestly, I've never had something like that happened to me before, so I was kind of just like, well, he was a little timid about it at first, so I didn't honestly know fully if he was talking to me or about me. at first. What do you mean? But then there really was no one else around us and he just walked away and there was a drink there for me.

So I was intrigued. I was confused. But I was intrigued. Just how we wanted you to feel. Dude. Yeah, it worked. But what's crazy is it came across as timid to you, not as like Uber confident.

He doesn't know how to pull it off. That was like the trick. Maybe he should have done like the Superman pose when he ordered it like, I shall have an old fashioned and She shall have a lemon drop. No, but confidence is the key, though, right? Would that have helped?

No, I probably would not have gotten the conversation out of me from that. Okay, so it's not bad what he did. All right. So we're confused why you're not responding. Well, okay, so I was there waiting for my friend. Oh, yeah. He told us that. Okay, so when she got there, we left.

We went and did our own thing. But you know how I said I had never had someone do something like that before? I can't say that anymore, obviously, because of Rob. But I would also have, like, three more nickels if I said I had a nickel every time that's happened to me since. Wait, what do you mean? You got more. I think she means that other people did that for her the same night. The same exact night.

These two other guys came up and did the exact same thing to us, both me and my friends. friend. Oh my, they stole Rob's move. If everybody uses the same Riz, it's not Riz anymore. They probably saw Rob do that across the bar and they were like, oh, good thinking, Jeff. That worked. I think it was at a different place. Yeah, I think it was a different bar. Did you? You're doing a good job, though, Jam. But did you go talk to the other two guys? I mean, you only went and talk to Rob, right? Well, the second guy that did it, I was like, oh, hold up, hold up, hold up. Yeah, I got to ask. Where is this coming from? Because obviously, I'm not, I'm not. saying that Rob is not possibly a trendsetter in his own circles of life, but I don't think

I would be giving him credit for it if I had to guess. Doesn't seem to the guy answer? Yeah. What do he say? Yeah, he literally pulled it up on his phone and showed me this like Instagram real. He doesn't say. Dude. He's practicing it.

Get the lines right. So another guy ruined it for our guy. Oh, no. Because if you hadn't known that. If that hadn't happened, would you have contacted Rob? I mean, maybe, but I was just like... You know, you would have. I like maybe.

Okay. We can work with maybe. And I think Rob can probably work with maybe, too, because he just might be on the other line right now, listening and wanting to talk to you, Camilla. Quick, act nonchalant, bro. Of course he is. Yeah.

Rob, you there? Yeah, I'm here. And look, Camilla, I am... I'm honestly embarrassed. I'm sorry I did I saw it on a TikTok video

I was just nervous and like you were really pretty I just kind of wanted to see it could work yeah but like

how many girls did you try that on it was just you you were the first one and I got your number and I was so happy and I'm sorry that's cute

I don't know I feel like I feel like some red flags are popping up on my radar here like What? You feel like Rob's a player? Like, that wasn't sincere?

Yeah. I don't know. At first you think, okay, this guy's buying me a drink and seems nice and seems cool. And then you find out that it's just some dumb guy on YouTube or TikTok or instant whatever, being like, this is how you pick up chicks. That was a really good impression. And I've never even seen the video. I want you to do these videos. I do follow that guy, though. He was pretty good.

I did see you across the bar, though. And, like, I chose you. I thought you were so cute from a distance. And when I got up to you, like, if you were a vegetable, you'd be a cucumber or something. She laughed. Oh, wait, what? Wait, did you like that? Oh, my God.

No, no, no. That was funny. Like, that seemed way more you than the lemon drop. Interesting. Hey, no, that's how you should have been. That's how you should have come up to me. It seems like you dropped something just now. because, oh, wait, it's your standard.

No, no, no. Shut, don't say that. You like that. Where was this guy, Rob? Where was this guy? Oh, this is definitely him. Wow. I guess I'm just a thief because I'm here to steal your heart.

Oh, my gosh. Okay, wait, wait a minute. You might be taking it too far. Okay, sorry. I don't think any of us can take any more of this conversation. I think we just need to offer to send you guys out on another date that we would pay for. If you don't do it, I'm going to marry this man. Did you two just become, like, the cutest couple we've ever had on the show?

A cucumber couple. Cucumber couple. Oh, God. Make myself sick. That's mine. I'm patenting that, by the way. That's all Rob's line, 100% original. We would like to send you out on another date with Rob, or I guess on your first official date with Rob.

If you're up for it. You promise not to just try to buy me a lemon drop and be all mysterious? I can't promise that I won't say some more cheesy lines, but I won't get you a lemon drop. Okay. He'll be himself. That's so sweet. Perfect. I am not lactose intolerant.

I want all the cheese. Yeah. I love it. They're meant to be. They are meant to be. Yeah. It was Gouda. It was Gouda. Okay.

I can't take any more. I can't get off the phone with you fast enough. We're so happy for you. Congratulations. Yeah. Please keep us updated, but only through email, please. Brooke and Jeffrey in the morning. No one can resist a rule of culture.

So here's one for the dating files. Rule of culture number 72. Chemistry isn't just vibes, it's values. Because what's the point of matching with someone if you can't talk about the shows you binge, the books you dog ear, or all the hot takes, you'll defend it brunch? I mean, you definitely have friends

who have met their partners on Bumble, and it makes sense. It's not just about matching with someone. It's about finding someone who gets your references, your obsessions, your whole vibe. With shared interests and prompts, you don't just see a profile. You get a glimpse of someone's personality, which makes it even easier to start conversations that actually lead somewhere. Plus, with photo and ID verification, you can trust that the person you're talking to is real. With that added peace of mind, it's so much easier to show up as your full self.

So whether your rule of culture is, the best first dates start with the shared hot take on Renaissance, or compatibility as having the same hometown bodega order, download Bumble, and turn those connections into something bigger. Download Bumble and start your love story. A decade ago, I was on the trail of one of the country's most elusive serial killers, but it wasn't until 2023 when he was finally caught. The answers were there, hidden in plain sight. So why did it take so long to catch him? I'm Josh Zeman, and this is Monster, hunting the Long Island serial killer,

the investigation into the most notorious killer in New York, since the son of Sam, available now. Listen for free on the IHeart Radio app, Apple Podcast, wherever you get your podcasts. Oh, my God. How weird was that? I thought it was so cute. You thought it was weird?

Well, just that it worked. Yeah. Oh, my God. I just thought, like, it was just proof that he should have just been himself in the beginning and it all would have been so much better.

But the hardest part about the call is like we couldn't say anything to blow his cover. Oh, about the one, like, that he just came up with that one line on the spot. Because in part one, he said that those are the cheesy lines

about the cucumber. Those used to be his go-to before he tried. Well, I mean, why would we call him out on that? Well, yeah, there was just no way to bring it up. And it was like harmless. Exactly. Like, we weren't going to blow up his spot, but it's just crazy that the old stuff worked on this new girl. Before the next date, I can tell you right now, he is ferociously Googling new pickup lines to come up with.

Yeah, as cheesy as they can go. Yes, exactly. Maybe the key is he was doing them over text and DMs, and those types of things only work in person. Oh, okay. Again, I think I'm going to go back to just be yourself. But sure. I'm a comedian. I'm like, don't steal other people's jokes.

Oh, okay. Try and be as original as you can. I think that's the lesson that we learned. And another lesson that you learned is you can always email us for help with your dating life. It's Brooke and Jeffrey in the morning. Hi, I'm Dr. Priyanko Wally. And I'm Hurricane DeBolu. On our new podcast Health Stuff, we demystify your burning health questions.

You'll hear us being completely honest about her own health. My residency colon was like a cry for help, honestly. And you'll hear candid advice and personal stories from experts who want to make health care more human. I feel like they never felt like I truly belonged in medicine. We want to make health less confusing and maybe even a little fun. Find health stuff on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. What do you get when you makes 1950s Hollywood, a Cuban musician with a dream and one of the most iconic sitcoms of all time.

You get Desi Arness. On the podcast starring Desi Arnaz and Wilmer Valderrama, I'll take you in a journey to Desi's life, how he redefined American television and what that meant for all of us watching from the sidelines, waiting for a face like ours on screen. Listen to starring Desi Arnaz and Wilmer Valderrama on the IHard Radio app, Apple Podcast,

or wherever you get your podcast. Hey there, Dr. Jesse Mills here. I'm the director of the men's clinic at UCLA, and I want to tell you about my new podcast called The Mailroom. And I'm Jordan, the show's producer. And like most guys, I haven't been to the doctor in way too long. I'll be asking the questions we probably should be asking, but aren't. Every week, we're breaking down the world of men's health from testosterone and fitness to diets and fertility.

We'll talk science without the jargon and get your real answers to the stuff you actually wonder about. So check out the Mailroom on the IHeart Radio app, Apple Podcasts, or wherever you get your favorite shows. Podcasters, it's time to get the recognition you deserve. The IHeart Podcast Awards are coming back in 2026. Got a mic? Then you've got a shot. Every year we celebrate the most creative, compelling, and game-changing voices in podcasting. Is that you?

Submit now at iHeartPodcastawards.com for a chance to be honored on the biggest stage in the industry. Deadline December 7th. This is your chance. Let's celebrate the power of podcasting and your place in it. Enter now at IHeart Podcast. Podcastawards.com. Hi, Kyle. Could you draw up a quick document with the basic business plan?

Just one page as a Google Doc. And send me the link. Thanks. Hey, just finished drawing up that quick one-page business plan for you. Here's the link. But there was no link. There was no business plan. I hadn't programmed Kyle to be able to do that yet.

I'm Evan Ratliff here with a story of entrepreneurship in the AI age. Listen as I attempt to build a real startup run by fake people. Check out the second season of my podcast, Shell Game, on the iHeart radio app or wherever you get your podcasts.