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Speaker 1: What's the toughest conversation that you could ever have with

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Speaker 1: your significant other?

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Speaker 2: Break up?

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Speaker 3: Good thing? I don't have one, Jeff.

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Speaker 1: Well, I mean the first one would probably be it's

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Speaker 1: not yours, the second one is it mine?

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Speaker 3: It's yours, and it has to be.

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Speaker 2: Well, if you're a guy, maybe you wouldn't know. But

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Speaker 2: it's a weird question to ask.

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Speaker 1: But maybe more important than any of those, is are

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Speaker 1: you going to finish that.

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Speaker 3: Question?

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Speaker 2: Wow, that was an extra gas.

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Speaker 3: Oxygen mask.

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Speaker 4: Well, you can believe it.

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Speaker 1: One of our listeners has a looming conversation even more

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Speaker 1: cringe than all of those combined. It's about to happen

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Speaker 1: with his longtime girlfriend. You're going to hear what it

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Speaker 1: is and see if we can help him out in

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Speaker 1: your awkward to day phone call.

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Speaker 4: Next, It's awkward.

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Speaker 2: It's Tuesday.

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Speaker 5: It's awkward Tuesday phone call.

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Speaker 1: On this segment, we've helped listeners tackle all sorts of

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Speaker 1: big pivotal moments in their love lives. We've helped people

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Speaker 1: ask somebody out, We've helped somebody propose before even help

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Speaker 1: someone on where to install the swing?

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Speaker 4: What room is it going to fit best in?

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Speaker 2: I don't remember that segment.

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Speaker 6: I do.

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Speaker 1: I'm just saying we've been there for all of our

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Speaker 1: listeners through all of their struggles, but today, I don't

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Speaker 1: think we've ever dealt with this particular issue in a

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Speaker 1: relationship before. It might be one of the biggest conversations

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Speaker 1: a couple could have. But good news is I've got

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Speaker 1: two of the best aes around.

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Speaker 2: Advice experts always be selling.

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Speaker 1: They're waiting to hear from Drew. So, Drew, welcome to

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Speaker 1: the show. How can we help you not screw up

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Speaker 1: your relationship?

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Speaker 7: What's up? Guys? So? Yeah, I definitely need some help here, Okay.

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Speaker 2: Can we start with who the relationship is with?

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Speaker 7: Sure? So her name is Kelsey?

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Speaker 2: Okay, okay?

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Speaker 4: And do you already have a swing installed? Is that

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Speaker 4: what this is?

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Speaker 7: We're not there yet, but we're talking about it.

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Speaker 4: Call back when you need help with that. But what

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Speaker 4: are you dealing with now?

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Speaker 7: So? I've been dating Kelsey now for the last couple

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Speaker 7: of years, so it's kind of serious.

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Speaker 2: Yeah you guys, do you guys live together?

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Speaker 7: No? No, not yet?

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Speaker 1: Okay, Okay, tell us a little bit more about Kelsey.

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Speaker 4: Who is she?

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Speaker 7: So? She's this great, amazing woman, so much in common

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Speaker 7: she loves camping, She drives a jeep. She's like just

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Speaker 7: super old fashioned. She doesn't have social media, which I

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Speaker 7: love it. I think it's refreshing, it's new, it's great.

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Speaker 4: Good. She's a different type of gal totally.

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Speaker 7: I met her because I'm in real estate. So I

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Speaker 7: was showing houses one day and she came in looking

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Speaker 7: for property with some friends.

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Speaker 8: And Okay, so she's got money too, right, I mean

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Speaker 8: she's successful.

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Speaker 7: She's looking at her Yeah. Yeah, So we have this

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Speaker 7: great relationship.

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Speaker 4: Okay, what's the problem.

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Speaker 1: Why why did you email us for help with this great, amazing,

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Speaker 1: perfect relationship with this jeep driving woman.

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Speaker 7: Well, so it's why I need you guys help because

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Speaker 7: it's really like kind of a sensitive thing. So I

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Speaker 7: was at the point after the one year mark where

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Speaker 7: I wanted her to move in with me.

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Speaker 4: Okay, that's big.

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Speaker 7: I asked her and straight up said, would you move

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Speaker 7: in with me? She goes, no, Okay, oh I was expecting.

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Speaker 2: Yeah, you were not expecting that.

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Speaker 7: No.

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Speaker 1: Why would he ask that if he thought that she

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Speaker 1: might say no by this point.

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Speaker 4: They would have the conversation.

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Speaker 8: It sounds like you didn't have a Yeah, he didn't

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Speaker 8: have a conversation prior to asking, and that was the

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Speaker 8: issue that trying to.

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Speaker 4: Start or maybe the place that you live kind of sucks.

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Speaker 7: Well, she's explained. She gave me the reason she doesn't

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Speaker 7: want to live with a guy before she's married.

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Speaker 4: Oh you know, I you can see that.

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Speaker 8: Oh yeah, I didn't live with anybody until I met

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Speaker 8: my husband because it's so complicated.

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Speaker 2: You know, then you're like combining.

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Speaker 4: What are you talking about? You with your husband before

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Speaker 4: you were married to you know, when.

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Speaker 2: I married him, he's the only guy I ever list.

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Speaker 4: This is what she's saying. She doesn't want to live

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Speaker 4: with anyone until she is married.

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Speaker 7: I mean, she doesn't necessarily want it to be after.

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Speaker 7: She just wants like a solid commitment that makes sense.

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Speaker 8: Yea, Like by the time I moved in with my husband,

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Speaker 8: I knew this was the person I was going to

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Speaker 8: be with for the rest of my life.

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Speaker 2: Oh like I just knew that.

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Speaker 1: So she wants something that says that marriage is going

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Speaker 1: to be in the books. Like I'm assuming that's where

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Speaker 1: the conversation led to.

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Speaker 7: Basically, Yeah, I mean we talked about it. We didn't

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Speaker 7: dive too deep into it. Again, like out of the blue,

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Speaker 7: he goes, I'll even sign a prenup, which I was

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Speaker 7: not even expecting.

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Speaker 1: Whoa, whoa, that's like even more serious than marriage.

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Speaker 2: Can you do that before you're married? I have no idea.

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Speaker 2: I don't have a breed up. I have no idea.

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Speaker 2: I mean I could see where you.

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Speaker 8: Would want some sort of like is it because she's

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Speaker 8: worried about combining your stuff or saying I have.

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Speaker 3: Money like we were talking about and she doesn't want

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Speaker 3: you to take it.

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Speaker 7: Well, I kind of have the money. I mean, I

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Speaker 7: own a bunch of property and she knows that. So

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Speaker 7: that's why she said that.

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Speaker 3: So she's saying it's not about the money. She loves

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Speaker 3: you for you.

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Speaker 7: Yeah, And the problem is now it never feels like

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Speaker 7: the right time to tell her that I've already met

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Speaker 7: with the lawyer and I've already had these papers already

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Speaker 7: drawn up and all that, because I've done that and

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Speaker 7: I'm ready for.

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Speaker 5: This next set with lawyers, and he's he's drawn up

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Speaker 5: the prenup to secure his assets before he asks her

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Speaker 5: hand in marriage.

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Speaker 4: That's so romantic.

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Speaker 3: It is so you have to get down one knee

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Speaker 3: and say, will you take this pen and document?

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Speaker 2: Right, I'm your idea.

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Speaker 8: Well, she mentioned, but it sounds like you guys didn't

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Speaker 8: have a lot of conversations.

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Speaker 2: So where are you at right now with everything?

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Speaker 5: Yeah?

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Speaker 3: Good question.

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Speaker 7: So I want to mention it before I pose, not after.

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Speaker 7: You know what I mean, and I need help bringing

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Speaker 7: it up. You know it's not.

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Speaker 1: Weird, Okay, So you want our help to let her

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Speaker 1: know that there is a prenup ready for her to

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Speaker 1: sign whenever she wants, and then after that then we'll

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Speaker 1: start the engagements and serious commitments that she's always wanted.

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Speaker 7: Yeah, okay, why didn't you?

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Speaker 1: Okay, So I mean if if she was the one

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Speaker 1: who brought it up and it's her idea, then what

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Speaker 1: are you worried about?

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Speaker 2: Why didn't you just tell her? I don't understand that,

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Speaker 2: Like I.

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Speaker 7: Don't because it's not a it's a very sensitive topic

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Speaker 7: when it comes to money and assets. I feel a

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Speaker 7: little strange about having that discussion, to be honest, Well.

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Speaker 5: And even could have been not joking, but she could

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Speaker 5: have just been throwing it out there and not been

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Speaker 5: like actually serious and like wait, you actually drew up

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Speaker 5: the documents.

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Speaker 3: That's another level.

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Speaker 2: Just feel like it'd be a red flag to me,

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Speaker 2: but I don't know.

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Speaker 1: I think it's a very romantic move. I don't know why,

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Speaker 1: just trying to kill the NaNs in this segment, was you.

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Speaker 3: Lawyered up before you?

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Speaker 2: I'm pretty anti preno?

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Speaker 4: Yeah, well know what, We're going to go to work

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Speaker 4: here for you, Okay, Drew.

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Speaker 1: We're going to find out the most romantic, over the

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Speaker 1: top way to tell somebody. I have a prenup ready

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Speaker 1: for you to sign.

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Speaker 7: I appreciate that I need help with your so much.

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Speaker 2: You could like dot your eyes with a heart.

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Speaker 4: The ideas are already flowing.

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Speaker 1: We're gonna start your happily ever after when we do

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Speaker 1: your awkward Tuesday phone call right after this.

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Speaker 4: It's awkward.

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Speaker 2: It's Tuesday.

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Speaker 4: It's awkward Tuesday phone call.

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Speaker 1: I think we need to clarify something here before we

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Speaker 1: move on. Because the listener on the phone, Drew asked

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Speaker 1: his girlfriend to.

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Speaker 4: Move in with him.

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Speaker 2: Yeah, that was a while ago.

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Speaker 1: She said no because she wanted to have proof of

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Speaker 1: a long term commitment before anything else could happen, whether

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Speaker 1: that was a proposal or a ring or something. And

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Speaker 1: in that conversation she said the words I'll even sign

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Speaker 1: a prenup yeah.

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Speaker 3: Yeah.

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Speaker 1: Now, there was some people in the room who thought, oh, well,

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Speaker 1: maybe she was just joking when she said that.

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Speaker 4: But if I'm.

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Speaker 1: Drew and I'm asking my girlfriend to move in with me,

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Speaker 1: that's not really like a joking environment. Like to me,

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Speaker 1: that's a serious thing. What do you think, Drew from

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Speaker 1: her tone in the moment, did you feel like she

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Speaker 1: was serious?

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Speaker 7: I got the vibe that she was serious for sure.

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Speaker 8: I hope so, because he went to a lawyer and

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Speaker 8: actually had one drawn up.

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Speaker 1: Lawyers, So Drew needs our helped to bring it up

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Speaker 1: to her because, like Brook said, it's been a while

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Speaker 1: since that conversation happened and she hasn't brought it up since.

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Speaker 1: And I know this is a pretty sensitive topic. I've

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Speaker 1: personally never been in this situation. I know Brooke has

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Speaker 1: not dealt with it in her marriage. Alexis wishes somebody

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Speaker 1: would have this conversation with her, but nowhere near the

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Speaker 1: assets there. It's a tricky topic and that's why I

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Speaker 1: feel like the safe thing to do is to give

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Speaker 1: it to someone who really knows about this.

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Speaker 8: Jose what advice do you have for Drew all those

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Speaker 8: long Relationshipjesus oay one time it lasted eight months, broke,

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Speaker 8: don't all right?

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Speaker 5: Okay, this entire conversation can't just be about the prenum

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Speaker 5: or it's gonna sound like a downer, right, you need

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Speaker 5: to hide it in between the wedding and ring shopping

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Speaker 5: and then the prenum.

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Speaker 2: Seriously, what a man thinks when they have important news?

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Speaker 1: What do you distract her with shiny promises that will

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Speaker 1: only work on Jose?

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Speaker 7: Okay, in theory, sure it sounds kind of sneaky, I

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Speaker 7: don't know, man like, but legally you.

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Speaker 3: Still mention it.

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Speaker 1: It's a terrible idea like that a little bit about

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Speaker 1: the engagement in the future.

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Speaker 4: But Brook, what do you think?

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Speaker 8: I think you you make sure that you frame it

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Speaker 8: as you are doing something for her. You say, listen,

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Speaker 8: you said that you wanted this done.

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Speaker 7: I did it.

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Speaker 8: Some people, you know, all talk, But I'm a doer

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Speaker 8: and that's how I'm going to be in this relationship.

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Speaker 8: If you want something done, I'm the guy to get

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Speaker 8: it done.

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Speaker 4: Look at I'm doing stuff for you. What have you

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Speaker 4: ever done for me? Maybe you should sign this?

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Speaker 1: Yeah, I'm.

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Speaker 2: That's a good idea to frame it that it's her idea.

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Speaker 4: Yeah, guilt into signing it.

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Speaker 7: All right, what do you think, Dre, No, that actually

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Speaker 7: makes a lot more sense because ultimately it was her

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Speaker 7: idea and I went forward with it thinking she was

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Speaker 7: serious about it, because why wouldn't she be.

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Speaker 2: Now, she may be angry that you didn't include her

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Speaker 2: in the actual writing it up and stuff, but what

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Speaker 2: that's boring.

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Speaker 1: Okay, if she gets mad about you bringing up tell

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Speaker 1: her to be mad at herself for bringing it up

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Speaker 1: in the first place.

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Speaker 2: That's not going to end well for him.

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Speaker 4: But sure that was Brooks advice. So here we go.

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Speaker 1: We're gonna call Kelsey your girlfriend for you and see

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Speaker 1: if she's ready to sign a prenup and then hopefully

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Speaker 1: move in together.

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Speaker 3: Oh I hope I don't cry during this one.

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Speaker 2: I'm so romantic.

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Speaker 7: I'm so nervous.

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Speaker 1: We wish you a lot of luck, Drew. Don't be nervous.

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Speaker 1: We're all here to support you. Okay, yes, thanks, all right,

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Speaker 1: here we go, Dolly your number right now?

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Speaker 6: Hello?

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Speaker 7: Hey, cal, Hey, what's that babe? How's your day? You work? Yeah?

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Speaker 6: Yeah, it was fine. It was just some normal you know,

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Speaker 6: the usual.

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Speaker 7: Yeah, usual stuff. Do you have a minute at your

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Speaker 7: get time? Are you busy or yeah, I can keep

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Speaker 7: a second.

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Speaker 6: What's up?

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Speaker 7: I wanted to ask you something. Remember that day we

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Speaker 7: had that conversation we talked about moving in. Do you

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Speaker 7: remember that vaguely? Yeah?

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Speaker 6: I think I said no, right, yeah, and which.

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Speaker 7: Is fine, you know he said no. But it got

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Speaker 7: us talking, right, I got us talking about the future,

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Speaker 7: and it was kind of super romantic and we started

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Speaker 7: going ring shopping together. So it was it was like

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Speaker 7: a fun little day. It was cute.

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Speaker 6: Yeah, I mean it was like more than cute. I

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Speaker 6: think it was kind of important, like put us on

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Speaker 6: a new path together.

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Speaker 7: Mm hmm, yeah, I agree.

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Speaker 6: Why are you being so weird? What do you mean

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Speaker 6: you agree?

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Speaker 7: No? I mean I just I just wanted to bring

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Speaker 7: up what you had mentioned when I asked you to move.

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Speaker 8: In with me.

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Speaker 7: If you remember, do you remember anything about the agreement?

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Speaker 6: You might have said or just said, I don't want

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Speaker 6: to move in with you until we get married, like.

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Speaker 7: I told you that. Yeah, you said another word?

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Speaker 6: Also, what's going on?

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Speaker 7: Can you just say you know what? You know the

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Speaker 7: word I'm talking about? Can you just say it just

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Speaker 7: helps me? And you know my anxiety and.

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Speaker 6: I don't right now?

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Speaker 7: So I'm gonna need you to say it. It's it

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Speaker 7: starts with the P. You know what I mean?

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Speaker 6: What's it ends with.

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Speaker 5: Up?

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Speaker 6: Karna? Okay?

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Speaker 7: Yes, okay, so you did say that? Great? Okay?

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Speaker 6: Is there other No?

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Speaker 7: No, no, no, no, it's you. I'm just like outside,

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Speaker 7: there's like a lot of people outside running around whatever.

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Speaker 7: So I went ahead, I moved forward with that word

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Speaker 7: that that pre word. I had some lawyers involved.

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Speaker 6: And just say lawyers. You hired a lawyer?

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Speaker 7: Yeah, you know it's it's not legal, bigle stuff, you

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Speaker 7: know what I mean? Like you kind of have to

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Speaker 7: when you do this.

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Speaker 6: I don't know what you're talking about right now? Can

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Speaker 6: you get to the freaking point?

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Speaker 7: So I don't want you to get upset? This is ridiculous.

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Speaker 7: So I wanted to prove my commitment to you, like

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Speaker 7: we talked about, and I went ahead and got the

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Speaker 7: paperwork for you to sign it.

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Speaker 6: What do you mean you want me to sign it?

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Speaker 6: This is your idea?

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Speaker 7: Remember, this is fun.

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Speaker 6: This is just like a weird phone call. I feel

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Speaker 6: like you could have talked to me in person about this.

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Speaker 7: I didn't know how to bring it up. You have

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Speaker 7: no idea. I've been losing sleep about this whole damn thing,

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Speaker 7: and I asked this radio station to help me.

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Speaker 6: The radio station, what.

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Speaker 2: A team of radio people.

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Speaker 3: I always want to hang up at that point.

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Speaker 2: I don't want to be here.

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Speaker 1: I feel like it probably went just about as well

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Speaker 1: as their first conversation about.

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Speaker 6: I don't understand what's happening right now.

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Speaker 3: We're a team of lawyers.

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Speaker 2: That makes it sound like a joke.

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Speaker 6: We don't want to do that.

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Speaker 1: We're a radio show. This segment is called an Awkward

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Speaker 1: Tuesday phone call, oh.

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Speaker 2: Man, and we really emphasized that title today.

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Speaker 1: We were trying to help our listener here, Drew have

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Speaker 1: what he knew was going to be a little bit

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Speaker 1: of an awkward conversation with you.

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Speaker 4: Uh huh.

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Speaker 8: Apparently he he thought that you wanted a prenup, you know,

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Speaker 8: because like he wants to move in with you and

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Speaker 8: move forward and go down the marriage road.

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Speaker 6: Well, yeah, I said that, but he never like talked

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Speaker 6: to me about pursuing it and hiring lawyers and filling

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Speaker 6: out paperwork.

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Speaker 4: Yeah, he should have written it all up himself. I

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Speaker 4: do agree with that.

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Speaker 8: But no, Jeffrey, oh my god, I mean I can't

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Speaker 8: tell what your emotion is right now, maybe it's just shocked.

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Speaker 3: Didn't you want this?

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Speaker 2: Maybe you don't care, maybe you're mad. Where are you at?

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Speaker 6: I'm just like in the middle, really because I just

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Speaker 6: wish he was more honest and I feel like we

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Speaker 6: could have worked on it together.

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Speaker 2: Okay, yeah, all right, so that's not bad.

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Speaker 7: I mean, that's if I'm being honest. This wasn't one

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Speaker 7: hundred percent my idea to do it this way. The

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Speaker 7: radio is your idea, you people, you people talking microphone whatever,

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Speaker 7: you radio people, It was your idea to do this way.

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Speaker 2: What it wasn't our idea for you to hire a

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Speaker 2: team of lawyers.

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Speaker 4: You called us way after that, you emailed us.

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Speaker 7: I just wanted to do a love shout out to

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Speaker 7: show I care about my my girl.

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Speaker 6: Right, you know what?

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Speaker 4: Oops? Did I screw that one up again?

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Speaker 2: The world's longest shutout.

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Speaker 1: Yes, it's three hundred and eighty seven mistakes since yesterday.

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Speaker 4: I'm never going to get this job right.

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Speaker 1: I'm sorry, Drew, my bad for misunderstanding your awkward Tuesday

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Speaker 1: phone request shout out.

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Speaker 4: Yes, excuse me again? Three hundred.

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Speaker 2: Wait, does that mean you're still wanting her to sign

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Speaker 2: the prenup, Drew.

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Speaker 7: I don't want you guys to pressure her to go

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Speaker 7: ahead and want to sign it, that's for sure.

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Speaker 3: Yeah, sorry about that.

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Speaker 2: Yes, that's I was actually on the other band sign it.

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Speaker 2: But yeah, I know so much about prenup. Sorry. Would

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Speaker 2: we hire a twenty four? I love she brought it up.

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Speaker 1: Yeah, we thought we would roll with it, all right,

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Speaker 1: that's our bad as long as you two are.

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Speaker 4: Good, right, Yeah.

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Speaker 6: I think we'll figure it out.

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Speaker 3: Maybe have a couple more talks about this.

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Speaker 7: Yeah, we'll go on a camping trip and ride in

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Speaker 7: the jeep top down or something. They'll thin out.

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Speaker 3: Everything's better top down in a jeep.

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Speaker 2: Seems way more chill than you, Drew.

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Speaker 3: I think she's confused.

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Speaker 7: Love Kelsey too.

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Speaker 3: It's something we can shout.

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Speaker 4: Out mission successful, Awkward

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Speaker 8: Tuesday, Freaking Jeffrey in the morning,