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Brooke and Jeffrey

Second Date Update Classic: Cutecumber Couple

28 Nov 2025

Transcription

Chapter 1: What dating advice does the listener share from the Internet?

0.031 - 7.363 Unknown

We know it's never going to end well when a listener gets their dating advice from the Internet. It's just it's how it goes.

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7.483 - 8.164 Alexis

Yeah.

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8.284 - 8.705 Unknown

Yeah.

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8.725 - 12.572 Alexis

Although that's our listeners right now listening to our show on podcast.

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12.672 - 30.755 Unknown

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 whirl too. It's about to start. Happy Black Friday. And do you have any comments, Alexis?

30.775 - 46.758 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. In the morning. So rad.

46.798 - 54.102 Unknown

I love hearing that. I love that. All right. Here we go. Episode starts right now.

55.381 - 65.79 Brooke

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?

66.511 - 69.493 Jose

Oh, God. I accept that you're undateable.

Chapter 2: What is the listener's experience with online dating apps?

118.264 - 119.967 Unknown

Maybe people are going back to this trend.

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120.007 - 122.552 Brooke

It's either exciting or a real low moment in your life.

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122.692 - 123.694 Unknown

So which was it?

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123.995 - 131.363 Rob

No, 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.

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131.403 - 135.427 Unknown

Okay. So what'd you do to meet somebody in person? What was your trick?

136.168 - 144.056 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.

144.116 - 147.019 Unknown

Oh. Oh, you'd use a pickup line.

147.719 - 152.765 Rob

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

153.125 - 154.367 Jeff

Yeah. Yeah.

Chapter 3: What pickup line does the listener use to break the ice?

280.647 - 283.536 Unknown

What? Damn. Okay.

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284.018 - 284.961 Rob

Her name was Camilla.

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285.302 - 290.217 Unknown

Camilla. So how long did it take for Camilla to get the drink and go find you?

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290.703 - 295.429 Rob

Literally five minutes. Like, she had not finished a drink. She had it in her hand when she walked up to me.

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295.71 - 296.591 Jose

Okay.

296.611 - 296.691 Rob

Wow.

296.711 - 299.355 Jose

Well, and every time she looks down at the drink, she's thinking of you.

299.375 - 310.31 Unknown

Well, you must be pretty attractive because 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.

310.33 - 319.021 Brooke

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.

Chapter 4: How does the listener's new approach differ from previous strategies?

425.462 - 426.082 Rob

I hope so.

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426.102 - 435.253 Brooke

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. When we come back and call Camilla, try and get you your second date update right after this.

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436.855 - 438.497 Jose

Second date update.

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439.557 - 461.295 Brooke

Welcome, my friends, to today's special edition of How to Seduce a Beautiful Woman Without Speaking a Word to Her. It's Brooke and Jeffrey in the bedroom. 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...

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461.275 - 467.247 Unknown

God, with that voice and when you say online video, it sounds like something we shouldn't be talking about.

467.567 - 488.405 Brooke

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. 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.

488.465 - 491.53 Brooke

Like, if you were a vegetable, I'd say you were a cute cumber.

492.091 - 497.279 Unknown

We started talking to Rob, and he's like, yeah, it didn't work for 12 years. He did 12 years of the same thing.

497.299 - 499.602 Brooke

He decided to try something different, and it worked.

Chapter 5: What happens during the listener's encounter at the bar?

606.528 - 608.711 Camilla

He was nice.

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610.072 - 616.2 Brooke

We always have a bad reaction when the only thing that they say is nice.

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617.461 - 625.05 Unknown

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?

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625.334 - 650.234 Camilla

Honestly, I've never had something like that happen 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... I was intrigued.

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650.315 - 652.597 Camilla

I was confused, but I was intrigued.

653.358 - 656.062 Brooke

Just how we wanted you to feel. Yeah, it worked.

656.082 - 660.367 Unknown

But what's crazy is it came across as timid to you, not as like uber confident.

660.728 - 662.61 Jose

He doesn't know how to pull it off. That was like the trick.

662.811 - 670.801 Brooke

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.

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