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Brooke and Jeffrey

Second Date Update Classic: Senior Moment Slip Up

25 May 2026

Transcription

Chapter 1: What are the unwritten rules of dating that listeners should know?

0.031 - 11.959 Brooke

Hey, it's Brooke and Jeffrey in the morning. And you know, we get all the credit for all these second dates. Yeah. But really, it's our listeners and their terrible dating decisions that we have to thank. Yes. And the people who ghost people. Yes. They're helping us out.

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13.061 - 15.106 Jeffrey

Thank you. Your toxicity has made us so funny.

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15.186 - 15.627 Brooke

Yes.

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15.607 - 17.129 Jeffrey

So thank you.

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17.83 - 30.505 Brooke

And don't forget, we do have 45 more minutes of this. We've got a full show over on the Brooke and Jeffrey main feed. If you'd like it, follow that one as well. And let's get into your second date. Brooke and Jeffrey in the morning. Second date update.

31.947 - 42.214 Unknown

I feel like this gets brought up a lot. After you match with someone online, how long should you wait before meeting up with them? Two to three hours.

43.375 - 47.46 Brooke

Two to three minutes. I feel like people typically talk like a week or two.

47.48 - 54.508 Unknown

Hey, I'm at your window right now. Can you open it? I'll climb right in. I brought over some special juice for us to split.

54.688 - 58.252 Brooke

No, that sounds sketchy. I don't see any red flags. Jeff's got a weird app.

Chapter 2: How long should you wait before meeting someone from online dating?

59.053 - 61.075 Brooke

Yeah, what app is that, Jeff?

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61.236 - 62.898 Unknown

I'm not going to remember.

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62.918 - 65.02 Jeffrey

Don't make me the weird one here.

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65 - 82.553 Unknown

i'm just saying the woman on the phone apparently isn't quite as eager as some of us because she waited much much longer than two hours to meet up with her guy her name is gail gail welcome to the show gail three hours hi how long did you wait before you met up with the guy from online

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83.191 - 88.697 Gail

Yeah, I mean, we chatted on and off for like a month before we actually went out.

89.938 - 92.921 Brooke

Why a month? I mean, is that like something you typically do?

92.941 - 102.311 Gail

I guess. I mean, we didn't like chat every day and I had like some work stuff going on and I feel like it took them a while to ask me out.

102.511 - 111.561 Brooke

Oh, and after you talk for a month, is there a lot of anxiety going into that first meeting? Because you've invested quite a bit of time at that point.

111.727 - 114.851 Gail

Yeah, I mean, a little, but I was more excited.

Chapter 3: What was Gail's experience leading up to her date with Jonathan?

173.308 - 178.962 Gail

I mean, I don't know. Maybe it's the way I talk. or like I used correct grammar. I don't know.

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178.982 - 184.834 Unknown

Or maybe the fact your name is Gail. Well, there's that too.

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184.914 - 187.92 Brooke

Okay, so it sounds to me like he meant it as a compliment.

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187.985 - 193.833 Gail

I mean, I guess. And then at one point, he asked me how old I really was with, like, a smiley face.

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194.314 - 194.454 Unknown

Oh.

194.574 - 199.281 Gail

Like, as if I was lying on my profile or something. I don't know. I thought it was kind of rude.

199.721 - 205.149 Jeffrey

Oh, weird. That could be a joke, though, where, you know, tell me the real age, make you laugh.

205.169 - 213.461 Brooke

I don't know, man. Yeah, because he's looking at your pictures. Like, I mean, it's all based on photos. Like, I'd be like, thank you. No.

213.721 - 220.318 Unknown

Well, no, they'd been talking a few weeks, though, so they have that familiarity. What did you say to him? I said you'll have to meet me to find out.

Chapter 4: How did Gail prank Jonathan during their dinner date?

551.402 - 568.603 Unknown

I'm calling his number right now. Hello? Hey, is this Jonathan? Yeah, who is this? I don't believe you that you're Jonathan now.

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569.579 - 574.566 Brooke

I can't believe you didn't go in with the old man voice. I thought for sure that we were going to hear Alan Winterbottom.

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575.367 - 578.292 Jonathan

Old man? What's up, actually?

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578.592 - 579.513 Brooke

Sorry, Jonathan.

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579.934 - 580.455 Unknown

Huh?

580.475 - 581.376 Brooke

What did he say?

582.558 - 585.061 Jonathan

There it is. It's not overplayed. I still love it. You happy now, Brooke?

585.201 - 585.582 Brooke

I am.

585.682 - 586.263 Jonathan

Anyway.

Chapter 5: What awkward moments occurred during Gail's date with Jonathan?

848.699 - 857.992 Unknown

Oh. Gail? Yeah. Uh, hey.

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858.012 - 860.296 Gail

Hi, Jonathan.

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860.916 - 863.08 Unknown

Yeah, it sounds like you guys have a lot to talk about here.

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864.021 - 870.21 Jonathan

Look, I mean, you're cool and all, but I'm, there's something, that date, it just made me realize I want someone older.

871.085 - 882.721 Unknown

I'm just confused and kind of shocked, I don't really know what to say. You want someone like 50 years older than you? Like, is that why you kept asking?

882.741 - 886.327 Jonathan

I didn't say 50. Oh, exactly 50 would be great.

888.21 - 890.874 Brooke

Wait, 50 years older or exactly 50 years old?

890.974 - 895.562 Jonathan

Exactly 50 years old. Okay. That's the sweet spot for him.

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