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Brooke and Jeffrey

Second Date Update: Pursue Me Please

24 Jun 2026

Transcription

Transcript generated automatically by AI and may contain errors.

Chapter 1: What is the main premise of this episode?

0.031 - 18.047

Just when we're about to start this, our producer calls Jose out of the room. Yeah. Come on, Boyd. Come on. It's like right when we go to start recording, he's always like, and I'm going to interrupt right now. All right. Hey, you know what? We're doing it anyway. It's Brooke and Jeffrey, and we've got a brand new episode for you on your Second Date podcast. Thanks so much for being here.

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18.107 - 39.856

And before we get to it, let's do comments. Yeah. Debo77 said, I've purposely been slacking on listening, so I have a nice chunk of five to six episodes to listen to all at once. Oh, my gosh. Love ya. Yeah, you're one of those that loves our back-to-back classics on Saturdays. Yeah, you are, Debo. For sure. All right, let's get to just your one new episode. It's going to start right now.

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Brooke and Jeffrey in the morning. Second date update.

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44.064 - 48.212 Jonas Brothers

When was the last time someone in this room picked up the book The Great Gatsby?

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I'd say my junior year, maybe.

52.863 - 66.845 Jonas Brothers

Oh, perfect. Then you obviously remember the entire novel is basically following Gatsby's pursuit of Daisy, while Daisy the entire time plays hard to get, much like Elizabeth Bennett from Pride and Prejudice and Mr. Darcy.

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I thought it was more of a societal look on what wealth does to people. I don't know.

71.993 - 85.336 Jonas Brothers

Yeah, I mean, sort of. I'm more focused on the courtship aspect of it. I hope you don't mind me using early literary references of it, where the man must prove himself through persistence in order to gain her affection.

85.356 - 92.087

I'm glad you did, but probably half of our listeners just tuned out, but that's cool. Including me. Yeah. Perfect.

Chapter 2: How does the dating scenario unfold for Sheena?

259.13 - 264.357 Jonas Brothers

Okay. That's self-awareness. That's nice. So what happened after the ew, no text?

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265.218 - 271.386 Sheena (Caller)

He wrote back, okay. And then I left him on read for like three days.

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271.887 - 272.528 Jonas Brothers

Oh, man.

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This is exhausting.

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273.89 - 274.37 Jonas Brothers

Yeah, it is.

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You guys haven't even seen each other in person and I'm already tired. He doesn't care. Look at him. He keeps trying.

279.577 - 281.84 Jonas Brothers

She's enjoying the pursuit, clearly.

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But after three days, what do you write finally?

284.408 - 290.574 Sheena (Caller)

I just uncharacteristically wrote to him and I said, well, and then nothing.

Chapter 3: What challenges does Sheena face in her dating life?

414.835 - 421.724 Jonas Brothers

I mean, one day you're telling them, no, don't show up at my place of business. And then the next thing, they're not doing that?

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Talk about being clear and respecting boundaries. Yuck. Am I right, Sheena? Yes, you are right. That's right.

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No, you don't want the reverse of that.

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434.685 - 446.007 Jonas Brothers

No, he's given up. Matt asked her out multiple times. Sheena has reluctantly been forced to turn him down over and over again because her schedule is just too busy and too crazy.

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I should have known that the text well meant yeah.

449.514 - 450.295 Jonas Brothers

Keep going.

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Yeah.

450.796 - 468.433 Jonas Brothers

Don't give up. But for some reason, Matt's thrown in the towel. He's waving the white flag. And Sheena does not appreciate that. That's why she's come to us for help today. And just to clarify, Sheena, at the end of this, are you saying that you want us to ask to send Matt on a date with you?

Chapter 4: How does Sheena feel about Matt's persistence?

525.883 - 541.303 Jonas Brothers

Okay. So what that is, is if we have a listener who's gone out on a date with somebody or in your case has just been talking to someone for a really long time and they've never met up in person, we can reach out on their behalf to figure out if there's a reason why.

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Yeah. Why the date hasn't happened, materialized.

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543.927 - 544.067 Jonas Brothers

Mm-hmm.

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545.347 - 549.672 Matt (Caller)

I feel like I know where you guys are going with this, but maybe.

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That would be shocking to me if you knew what we were talking about. Let's give him a hint.

554.657 - 555.177 Matt (Caller)

Well.

555.618 - 564.427 Jonas Brothers

You got it now, right, bro? That's pretty good. Because we're talking about a girl you've been talking to named Sheena. What?

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Okay. He did not expect Sheena.

566.549 - 573.717 Jonas Brothers

Okay. Well, we've heard that there's been developments in this relationship. We're trying to figure out where your head's at.

Chapter 5: What unusual request does Sheena make regarding her date?

871.044 - 875.591 Sheena (Caller)

Actually, the thing Friday, I have to go away for a few days. I'm kind of gone the whole weekend for the work thing.

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Don't choose weekends.

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876.652 - 877.213 Jonas Brothers

Yeah.

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Is that it, Matt? You don't want to try another day? We don't want to go through all seven days of the week. Monday could be good.

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Or future months. Monday might be possible.

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Who knows?

887.148 - 889.431 Jonas Brothers

I feel like the person that would know would be you, Sheena.

890.035 - 900.265 Sheena (Caller)

I know, but my schedule just changes so rapidly and there's so much going on. Oh, shoot. Darn. But don't give up, Matt. Don't give up. I like to keep asking.

900.802 - 918.749 Jonas Brothers

You know what? I think maybe I'll just take it from here. So we would love to have you guys go out on a date. Oh, how do we coordinate it? I don't know how to do that, but maybe we can agree to send you on a date at a future time to be determined. And when that time is determined, we would pay for it.

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