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Brooke and Jeffrey: Second Date Update

Brooke Breaks You Up

22 Jan 2026

Transcription

Chapter 1: What special edition is being introduced in this episode?

0.031 - 19.447 Jeffrey

All right, you're in for a special one today. It's a brand new episode here on Brooke and Jeffrey's Second Date Update. Oh, yeah. We do not do these very often. Thank the Lord. But it's happening today. Brooke breaks you up. Yes, I love listening to them. Oh, God. You just wish you had my services earlier in your 20s, Alexis. Honestly, yeah.

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19.467 - 43.445 Unknown

I could use you. Okay, before we get to it, comments. Yes, Brian Alvarez said, your favorite state of Florida here. I'm on my third trip around the Brooke and Jeffrey universe. I start at the latest episode available and play you guys constantly in the background of my life until I get to the end. Then I start again. This is my third time starting. That is nice. Crazy.

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43.505 - 47.51 Alexis

I wonder how many new ones he hears by the time it gets to the end of the restart.

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47.63 - 48.991 Unknown

Right. How long it takes him.

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49.011 - 52.415 Alexis

Maybe he gets like 10 new second dates and then starts over, maybe 50.

52.755 - 60.884 Unknown

I hope that takes months to go through it all. I want to know the mental state from when you started to when you finished. Physical, like where you at?

60.904 - 63.047 Alexis

You keep doing it, so something's happening.

63.527 - 71.736 Jeffrey

Yeah. Well, wow. That is incredible. Thank you so much for being here and really, truly thank you for all that support. Your brand new episode starts right now.

73.353 - 77.46 Unknown

How do you deliver bad news to someone that you really care about?

Chapter 2: How does Brooke handle delivering bad news to listeners?

232.814 - 237.04 Jeffrey

She's an angel. I'm going to cry. I'm going to cry. Please tell me that part isn't true.

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237.06 - 257.627 Unknown

Now, I don't know if any of what I said is actually true. It's just a blind guess. But we will find out when we speak to Jack directly. Jack, was any of my guesses about your girlfriend right? No, not at all. Oh, no. I didn't even get the name right. What's her soon-to-be ex-girlfriend's name? Her name's Megan. Megan? Okay.

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257.868 - 261.733 Jeffrey

Why can't you do this yourself, Jack? Maybe she cheated on him. We don't know. Maybe it'll be easy.

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261.813 - 264.757 Alexis

Yeah, maybe you're going to not like her, Brooke.

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264.997 - 266.719 Jeffrey

I've liked every Megan I've ever met.

267.861 - 272.127 Unknown

Maybe that'll change here. Tell us the story of you and Megan and why it's not meant to be.

273.268 - 284.792 Jack

Yeah, well, I actually have tried several times to break it off myself, and I've been meaning to call this show... For a minute because Brooke, I mean, it's just, you're so good at it.

284.812 - 287.217 Jeffrey

Okay. Let's not butter me up.

287.237 - 287.437 Unknown

All right.

Chapter 3: What is the background story of the listener wanting to break up?

632.066 - 640.999 Jeffrey

Why do you care? You're not going to be with her anymore. That's the whole thing. If you want to break up with someone, you have to be okay with however they're going to feel about you afterwards.

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641.019 - 646.347 Unknown

Hearing those words just sends shivers down my spine. The coldness in Brooke's voice.

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646.367 - 650.994 Jeffrey

You want to dump a woman and then you want her to still like you? That's not going to happen.

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651.034 - 654.379 Unknown

You hear the ice in her veins, Jack? She is so ready for this.

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654.359 - 660.127 Jack

Well, as long as you do all of it, I don't really want to be talking with her.

660.768 - 674.106 Unknown

Yeah, perfect, Jack. Brooke is going to handle all of this. You don't have to say anything. You can just listen quietly and hear how it goes. We will have you in the sidelines if you do want to jump in and say something or if we need to call you in maybe to clarify a point.

674.086 - 675.488 Alexis

Is there a signal or something?

675.548 - 680.175 Unknown

Well, we may have to have him join at some point just because who knows how it's going to turn out.

680.636 - 681.598 Alexis

Brooke may not know something.

Chapter 4: What challenges does Jack face in his relationship with Megan?

766.178 - 788.958 Jeffrey

Okay. So the good is that it sounds like you're an incredibly strong, independent woman who knows exactly what she wants in life. And I love that. Yeah. Applause. Okay, so silence. That's fine. That's fine. The bad news, there is some bad news to that, is that Jack is none of those things. And you may already know that.

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788.978 - 790.36 Unknown

Wow. She's talking about her boyfriend there.

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790.38 - 794.888 Jeffrey

I mean, he's calling me to ask for help in a hard conversation.

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795.328 - 797.732 Megan

Yeah. I'm listening.

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797.915 - 798.396 Jeffrey

Okay.

798.897 - 800.44 Alexis

You're doing great, Brooke. Keep going.

800.46 - 802.964 Megan

Brooke's getting more nervous because she's doing all the talking. I know.

802.984 - 815.467 Jeffrey

It's going so well. He feels like this relationship, the relationship between you and him, isn't working anymore. So he feels like it would be better if you two went your separate ways.

815.667 - 820.865 Megan

I don't know what you're doing, but we're not breaking up. It's not happening. Thanks for the call.

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