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Brooke
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Jeffrey
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Brooke
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Jeffrey
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Brooke
Uh, Limu is that guy with the binoculars watching us?
Jeffrey
Cut the camera. They see us. Only pay for what you need@libertymutual.com Liberty Liberty Liberty Liberty Savings Very underwritten by.
Announcer
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Brooke
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Vince
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. Yeah.
Brooke
Although that's our listeners right now listening to our show on podcast.
Vince
I feel like they're learning more whatnot instead of what to do. But yeah, he got a pickup line or a pickup method, I guess I would say from, from the world wide web and he gave it a try. He, you know, listen, see if you want to give this a whirl too. It's about to start. Happy Black Friday. And do you have any comments, Alexis?
Brooke
Yeah, Vince said, my son and I.
Vince
Listen to this show and we absolutely love it.
Brooke
He's 10 and every morning he goes, we need to watch Brooke and Jeffrey in the morning.
Vince
That's right.
Brooke
And he'll echo the morning like it.
Vince
Does on the show, like our sweeper.
Brooke
That goes, Brooke and Jeffrey in the morning.
Jeffrey
So rad.
Vince
I love hearing that. I love that. All right, here we go. Episode starts right now.
Jeffrey
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.
Vince
Oh, God.
Jeffrey
Except that you're undateable.
Vince
Oh, no, that's not true, Jose.
Jeffrey
He was talking to me.
Announcer
Don't butt in.
Jeffrey
Well, no, Jose, you'd have to actually leave your house in order for that to count as like, you trying. You could be become a monk and take a vow of celibacy to make it seem like it was all your idea the whole time.
Rob
Oh, that works perfect.
Vince
I mean, they do have like some of those places. Beautiful views.
Brooke
Oh, yeah.
Jeffrey
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. People don't actually do that anymore.
Vince
Actually harder than being a monk, Rob. Yeah, true.
Jeffrey
You scare me. Welcome to the show.
Rob
Thank you so much. Thanks for having me.
Vince
That's exciting that, you know, I feel like we've heard a couple of these stories lately. Maybe people are going back to this trend.
Jeffrey
It's either exciting or a real low moment in Your life. So which was it?
Rob
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.
Vince
Okay.
Brooke
Yeah.
Vince
So what'd you do to meet somebody in person? What was your trick?
Rob
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.
Vince
Oh, oh, you'd use a pickup line.
Rob
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.
Brooke
Huh.
Jeffrey
Yeah. You're allowed to not just like jokes. You have to like bad jokes.
Vince
It's pretty cheesy.
Jeffrey
Or maybe that one's a little bit too high brow that they don't understand it. Yeah, I mean, it's like vegetables and cute all in one.
Rob
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?
Jeffrey
Oh, I like that one.
Vince
To yourself?
Jeffrey
Yeah.
Vince
I mean, I'm starting to feel like it's not the app's fault that you're not meeting a lot of people.
Jeffrey
It's the wrong girl. You need a girl who's like, loves that silly stuff, brother.
Rob
That's what I'm hoping to find here.
Brooke
Okay.
Vince
Okay.
Jeffrey
So you said that's what you used to do. Those were your old strategies. Do you mean that you like a new thing that you were trying?
Rob
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.
Jeffrey
Oh, okay. Everybody listening? Write this down.
Rob
So you're at a, like a bar or something. You walk like right next to her, and then you lean over the bartender and you just say, I'll have an old Fashioned, she'll have a rainbow lemon drop. And then just say, put it on my tab. And then just walk away.
Brooke
Wait, what?
Jeffrey
She's like, oh, I'm allergic to a drink.
Vince
Yeah. And a gross free drink.
Brooke
Yeah.
Vince
Like, you get a good old Fashioned and she gets a rainbow lemon drop.
Jeffrey
I think it's just any drink, right? Like, you don't always have to. Yeah, you don't have to. Stick with the rainbow remnant. 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.
Brooke
And you think she wants to date.
Vince
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.
Rob
Yeah, no, the guy in the video said that. I'm 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.
Jeffrey
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?
Rob
So I actually just tried it the other night and it worked.
Vince
Okay.
Rob
Her name was Camilla.
Vince
Camilla. How long did it take for Camilla to get the drink and go find you?
Rob
Literally five minutes. Like, she had not finished the drink. She had it in her hand when she walked up to me.
Jeffrey
Okay, well, every time she looks down at the drink, she's thinking of you.
Brooke
Well, you must be pretty attractive because she wouldn't. You wouldn't do that if someone's not attractive.
Vince
But like Jeff said, it's so nice not to owe anybody anything. Yeah. Or something, you know, like it's such a relief probably to her.
Jeffrey
And I don't think it has anything to do with attractiveness. It's just like the mystery of it. Yeah, it's like a. 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.
Vince
No. Yeah, I would not.
Jeffrey
But it worked for Rob. So what. How long did you guys talk?
Rob
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. But.
Jeffrey
Okay, so she was just.
Rob
I did give her. Or she gave me my number. Sorry. She gave me her number.
Vince
Yeah.
Jeffrey
Scary. If she gave you your number.
Brooke
And.
Rob
I text her and she like replied right then just like, got it. So I know she didn't give me a fake number.
Vince
Okay, so wait, did you guys go out on a date?
Rob
I have not heard from her. I tried texting her to try to set something up and I've got nothing.
Vince
Okay. And so the guy in the video on YouTube that you watch, he didn't have any follow up tips.
Rob
There was no part two.
Jeffrey
Now, but a ten minute conversation is basically like a long term relationship in the modern dating world. And face to face, you've been together for a very long time. Yeah, but I guess we should ask, do we know 100% that this Camila girl is single?
Vince
Oh, that is a risk in this one because you. You buy him a drink before you hit on, you know, before you talk to him.
Rob
I mean, I didn't straight out ask her, but she was definitely, like, leaning into it. I feel like I'm pretty sure.
Jeffrey
But if she. If she was in a relationship, she probably wouldn't have, like, walked across and tracked you down. Like, struck up a conversation and her friend was there. How long has it been since that bar interaction?
Rob
About four days now.
Vince
Okay, not that long. How many texts have you sent?
Rob
Possibly like five or six.
Vince
Okay, enough.
Jeffrey
She's definitely ignoring you.
Vince
It's on the line of maybe too.
Jeffrey
Many, but, yeah, maybe she's gaming you back. Maybe this is like a girl strategy to pick the guy back up after you pick her up. But we'll find out, we'll come back, it's all going according to plan. When 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.
Vince
Oh.
Jeffrey
Today's pickup strategy comes from our listener, Rob, who tried something that he found in an online video where if you're at a bar.
Vince
God, with that voice. And when you say online video, it sounds like something we shouldn't be talking about.
Jeffrey
It's not like that. But you just. You 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.
Vince
Yes.
Jeffrey
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 cumber.
Vince
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.
Jeffrey
He decided to try something different. And it worked?
Vince
Yeah, kind of. Well, the girl approached him and they talked for 10 minutes. She even gave her number, but now.
Jeffrey
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?
Rob
Yeah, I mean, I think I do. The fact that she walked up to me, like, that's just crazy.
Jeffrey
You think she's a psychopath? Is that what you're saying?
Vince
I think Crazy in a good way.
Jeffrey
Okay.
Vince
Good, not crazy in a bad way.
Jeffrey
Crazy in love like Beyonce. Okay, we're going to call her right now. And remember, Rob, wait till we call you in in order to jump on.
Announcer
Okay?
Jeffrey
We've had a lot of people just springing on the line without permission, so. Yes. Have some self control over there.
Rob
Got it.
Vince
I don't know. He really feels like a wild card. Jeff.
Announcer
Yeah.
Jeffrey
All right, here we go.
Rob
Hello?
Jeffrey
Hey, is this Camilla?
Camilla
Yes, it is. Who calling?
Jeffrey
We're a radio station called Brooke and Jeffrey in the Morning.
Vince
Hey, Camilla.
Brooke
Hey.
Vince
Thanks for listening. Okay.
Camilla
How can I, how can I help you guys?
Jeffrey
Yeah, well, you went out with a guy who listens to our show.
Vince
I don't know if I'd say that. Yeah, I would say you met a guy at a bar who listens to our show.
Jeffrey
His name is Rob. And you guys met like four nights ago. Ish.
Camilla
Yeah.
Vince
Oh, you remember him?
Jeffrey
Oh, okay.
Camilla
Yeah, no, I, I, I know who you're talking about.
Vince
Okay.
Jeffrey
Okay, well, good. Rob, he, he bought you a drink and you guys ended up talking for a few minutes until your friend got there.
Vince
And he knows it wasn't like a lot of time together, but, you know, he was impressed by who you were.
Jeffrey
We're just wondering what were your thoughts about Rob.
Camilla
He was, he was nice.
Brooke
Okay.
Jeffrey
We always have a bad reaction when the only thing that they say is nice.
Vince
Yeah. 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?
Camilla
Honestly, I've never had something like that happen to me before. So I 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.
Vince
What do you mean?
Camilla
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, I was intrigued. I was confused, but I was intrigued.
Jeffrey
That's how we wanted you to feel, dude.
Rob
Yeah, it worked.
Vince
But what's crazy is it came across as timid to you. Not as like, uber confident.
Jeffrey
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 away with you. Confidence is the key though, right? Would that have helped?
Camilla
No, I probably would not have gotten the, the conversation out of me from that.
Vince
Okay, so it's not bad what he did.
Jeffrey
I mean, we're confused why you're not responding.
Camilla
Well. Okay, so I was there waiting for.
Vince
My friend, and he told us that.
Camilla
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 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.
Vince
Wait, what? What do you mean you got more? I think she means that other people did that for her the same night.
Camilla
The same exact night. These two other guys came up and did the exact same thing to us, both me and my friend.
Brooke
Oh, my.
Jeffrey
They stole Rob's move is anymore. They probably saw Rob do that across the bar, and they were like, oh, that worked. I think it was at a different place.
Vince
Yeah, I think it was a different ball.
Jeffrey
I don't know. Did you.
Vince
But did you go talk to the other two guys? I mean, you only went and talked to Rob, right?
Camilla
Well, the second guy that did it, I was like, hold up, hold up, hold up.
Jeffrey
Yeah. I gotta ask.
Camilla
Where is this coming from? Because obviously.
Jeffrey
Yeah, three times.
Camilla
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.
Jeffrey
Doesn't seem. Did the guy answer?
Vince
Yeah. What'd he say?
Camilla
Yeah, he. He literally pulled it up on his phone and showed me this, like, Instagram reel.
Jeffrey
Get the lines right.
Vince
So another guy ruined it for our guy. Because if. If you hadn't known that, if that hadn't happened, would you have contacted Rob?
Camilla
I. I mean, maybe, but I was just like, you know, you would?
Vince
I, like, maybe.
Jeffrey
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. Camila, quick, act nonchalant, bro.
Rob
Yeah, of course he is.
Jeffrey
Yeah. Robbie there?
Rob
Yeah, I'm here. And look, Camila, 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 if it'd work.
Camilla
Yeah, but, like, how many girls did you try that on?
Rob
It was just you. You were the first one, and I got your number, and I was so happy and. Oh, I'm sorry.
Vince
That's cute.
Jeffrey
I don't know.
Camilla
I feel like. I feel like some red flags are popping up on my radar here.
Vince
Like, what?
Jeffrey
You feel like Rob's a player?
Vince
Like, that wasn't sincere.
Jeffrey
Yeah.
Camilla
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 Insta whatever, being like, this is how you pick up chicks.
Vince
That was a really good impression, and I've never even seen the video.
Jeffrey
I want you to do these videos. I do follow that guy, though. He's pretty good.
Rob
I. 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.
Vince
Oh, wait.
Jeffrey
What?
Vince
Wait, did you like it?
Camilla
Oh, my God. No, no, no. That. That was funny like, that. That seemed way more you than. Than the lemon drop.
Jeffrey
Interesting.
Rob
That's how you should have been.
Camilla
That's how you should have come up to me.
Rob
It seems like you dropped something just now because. Oh, wait, it's your standard.
Vince
Don't say that.
Jeffrey
You like that.
Camilla
Where was this guy? Rob. Where was this guy?
Vince
Oh, this is definitely him.
Jeffrey
Wow.
Rob
I guess I'm just a thief because I'm here to steal your heart.
Camilla
Oh, my gosh. Okay, wait. Wait a minute. You might be taking it too far.
Jeffrey
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 gonna marry this man.
Vince
Just become, like, the cutest couple we've ever had on the show.
Jeffrey
A cucumber couple. Oh, God, make myself sick.
Rob
That's my. That's. I'm. I'm. I'm patenting that.
Jeffrey
By the way, that's all Rob's line 100 original. Okay. We would like to send you out on another date with Rob. Or I guess on your first official date with Ro. If you're up for it.
Camilla
You promise not to just try to buy me a lemon drop and be all mysterious?
Rob
I can't promise that I won't say some more cheesy lines, but I will. I won't get you a lemon drop.
Vince
Okay. He'll be himself. That's so sweet.
Camilla
Perfect. I am. I am not lactose intolerant. I want all the cheese.
Rob
Yeah, it was Gouda.
Jeffrey
It was gouda Okay, I can't get off the phone with you fast enough.
Vince
Enough.
Jeffrey
We're so happy for you. Congratulations. Please keep us updated but only through email. Please.
Brooke
Brooke and Jeffrey in the morning you.
Jeffrey
Need to check out legends.com today. Legends is a free to play social casino and sportsbook with all of the games that you know and love. They even have Plinko and live blackjack and that's L E G e n d z.com whether you're a seasoned player or just starting out, their games are designed to entertain and thrill. The best part is you get free coins every day so you can play for free. And redemption. Redemption to your bank account is instant. It's legit and new players get an exclusive welcome bonus. Join thousands of players on legends with a Z.com today. No purchase necessary. Legends International Void we're prohibited by law 18 terms and conditions apply.
Brooke
Time for a sofa upgrade. Introducing Annabe sofas where designer style meets budget friendly prices. Every Ana Bay sofa is modular allowing you to rearrange your space effortlessly. Perfect for for both small and large spaces. Anabe is the only machine washable sofa inside and out. Say goodbye to stains and messes with liquid and stain resistant fabrics that make cleaning easy. Liquids simply slide right off. Designed for custom comfort, our high resilience foam lets you choose between a sink in feel or a supportive memory foam blend. Plus our pet friendly stain resistant fabrics ensure your sofa stays beautiful for years. Don't compromise quality for price price. Visit washablesofas.com to upgrade your living space. Today. Sofas start at just $699 with no risk returns and a 30 day money back guarantee. Get early access to Black Friday now. The biggest sale of the year can save you up to 60% off plus free shipping and free returns. Shop now@washablesofas.com Offers are subject to change and certain restrictions may apply.
Jeffrey
Oh my God. How weird was that?
Camilla
I thought it was so cute.
Vince
You thought it was weird?
Jeffrey
Well, just that it worked.
Rob
Yeah.
Vince
Oh my God. I just thought like it just proof that he should have just been himself in the beginning and it all would have been so much better.
Jeffrey
But the hardest part about the call is like we couldn't say anything to blow his cover.
Vince
Oh about the one like that. He just came up with that one line on the side because in part.
Jeffrey
One he said that those are the cheesy lines about the cucumber. Those used to be his go to before he tried.
Vince
Really well I mean why would we call him out on that well, yeah.
Jeffrey
There was just no way to bring it up.
Vince
Harmless. Exactly.
Jeffrey
Like we weren't gonna blow up his spot. But it's just crazy that the old stuff worked on this new girl before the next date.
Vince
I can tell you right now he is ferociously googling new pickup lines to come up with.
Jeffrey
Yeah, as cheesy as they can go. Maybe. The key is he was doing them over text and dms and those types of things only work in person.
Vince
Oh, okay.
Jeffrey
Maybe.
Brooke
Yeah.
Vince
I think I'm gonna go back to just be yourself.
Brooke
But sure.
Jeffrey
Yeah.
Vince
Yeah.
Jeffrey
And I'm like, don't steal other people's jokes. Try and be as original as you can. I think that's the less we learn. 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. Hey, Ryan Reynolds here wishing you a very happy half off holiday because right now Mint Mobile is offering you the gift of 50% off unlimited. To be clear, that's half price, not half the service. Mint is still premium unlimited wireless for a great price. So that means a half day.
Brooke
Yeah.
Jeffrey
Give it a try@mintmobile.com Switch upfront payment.
Brooke
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Podcast: Brooke and Jeffrey: Second Date Update
Date: November 28, 2025
Host: iHeartPodcasts
This episode of "Second Date Update" features Rob, who asks for the show’s help after a promising encounter at a bar didn’t result in a second date. Rob had tried a new dating approach, inspired by a viral internet video, and seemed to make a good impression on Camilla. The episode delves into modern dating tactics, authenticity, and the pitfalls of copying viral pickup moves.
Rob’s Viral Move Attempt:
Viral Move Backfires:
Cheesy Lines Win the Day:
The episode is playful, self-deprecating, and filled with banter and light teasing. Much of the humor comes from the hosts’ reactions to modern dating gimmicks and Rob’s earnest but awkward attempts at connection. The show encourages authenticity, highlighting that sincerity and being oneself—cheesy puns and all—often leads to real connections.
The “Cutecumber Couple” episode playfully illustrates the risks of following viral dating trends and the enduring appeal of just being yourself. While viral tactics may create a “mystery,” they rarely outshine authentic personality—even if it comes wrapped in layers of puns and dad jokes.