Brooke and Jeffrey: Second Date Update - Awkward Tuesday: Prenup or Pre-NOPE

Episode Date: June 24, 2025

One of our listeners has a looming conversation coming up and it’s one of the most difficult things you could ever talk about with a loved one. Before it happens they want our help via an Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.

Why is a soap opera western like Yellowstone so wildly successful? The American West with Dan Flores is the latest show from the Meat Eater Podcast Network. So join me starting Tuesday, May 6th, where we'll delve into stories of the West and come to understand how it helps inform the ways in which we experience the region today. Listen to The American West with Dan Flores on the iHeartRadio app, Apple podcasts, or wherever you get your podcasts. I know a lot of cops and they get asked all the time,

have you ever had to shoot your gun? Sometimes the answer is yes, but there's a company dedicated to a future where the answer will always be no. This is absolute season one, Taser Incorporated. I get right back there and it's bad. Listen to Absolute Season One, Taser Incorporated on the iHeartRadio app, Apple podcasts,

or wherever you get your podcasts. The OGs of uncensored motherhood are back and better than ever. I'm Erica. And I'm Mila. And we're the hosts of the Good Moms Bad Choices podcast, brought to you by the Black Effect Podcast Network every Wednesday. Yeah, we're moms.

But not your mommy. Historically, men talk too much. And women have quietly listened. And all that stops here. If you like witty women, then this is your tribe. Listen to the Good Moms Bad Choices podcast every Wednesday on the Black Effect Podcast Network, the iHeartRadio app, Apple Podcast, or wherever you go to find your podcast. I'm Jeff Perlman.

And I'm Rick Jervis. We're journalists and hosts of the podcast Finding Sexy Sweat. At an internship in 1993, we roomed with Reggie Payne, aspiring reporter and rapper who went by Sexy Sweat. A couple years ago, we set out to find him. But in 2020, Reggie fell into a coma after police pinned him down and he never woke up. Well, then I see my son's not moving. So we started digging and uncovered city officials bent on protecting their own. Listen to Finding Sexy Sweat on the iHeartRadio app, Apple Podcasts, or wherever you get your

podcasts. Over the years of making my true crime podcast, Hell and Gone, I've learned no town is podcast. If there's a case we should hear about call 678-744-6145. Listen to Hell and Gone Murderline on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Hey, it's your second day podcast and today with Brooke and Jeffrey in the morning, we have an awkward Tuesday phone call because it's Tuesday. Yeah. But I was just looking through the stats on our podcast and I always think it's fascinating to see where people are listening from and I always look at like the top five countries it's like the US Canada the UK Australia the Philippines which is amazing but I scrolled all the way down to see where we get the least amount of listeners there's like one person yeah I love doing that we've got one listener in Sri Lanka if that's you please leave a comment yeah and one in Equatorial Guinea. All right

That's your update but we do love to look at the comments and we're about you all so what do you got Alexis? I saw one from you who said I'm not sure whether I should thank you guys or stop listening to this show The level of cringiness I can tolerate has increased tremendously Yes at the beginning. I would pause a segment just to breathe and get myself together But now I can listen to two to three segments in a row no matter how cringy the conversation is that's right Thanks, I guess love from Miami. Yep. We're breaking you down. We're moving your bar lower and lower Because right now it's your awkward Tuesday phone call. What's the toughest conversation

that you could ever have with your significant other? Oh. Breakup conversation? Good thing I don't have one, Jeff. Well, I mean, the first one would probably be, it's not yours. Oh, my god. That's way worse than I was thinking.

Yeah. Whoa. The second one, is it mine? Wait a minute, it's not yours and it has to be the others. Well, I mean, if you're a guy maybe you wouldn't know, but if you're a woman that's a weird question to ask. It's kind of 100% accurate on that. But maybe more important than any of those is, are you going to finish that? Food question! of those is are you gonna finish that? The food quest!

That was an extra gasp. Extremely shocking. Can we get some oxygen masks? Well, if you can believe it, one of our listeners has a looming conversation even more cringe than all of those combined. Yikes. Oh no. It's about to happen with his long time girlfriend. You're gonna hear what it is and see if we can help him out in your Awkward Tuesday phone call. Next.

On this segment, we've helped listeners tackle all sorts of big, pivotal moments in their love lives. Yes. We've helped people ask somebody out. Oh. We've helped somebody propose before Even help someone on where to install the swing. What room is it gonna fit best in? We've been there for all of our listeners through all of their struggles, but today I don't think we've ever dealt with this particular issue in

a relationship before it might be one of the biggest conversations a couple could have but good news is I've got two of the best a ease around eight account execs advice expert I wonder they're waiting to hear from Drew so Drew welcome to the show How can we help you not screw up your relationship? What's up guys, so yeah, I definitely need some help here, okay? Can we start with who the relationship is with sure so her name is Kelsey, okay? Okay, and do you already have a swing installed is that what this is?

We're not there yet, but we're talking about it. Okay? Call back when you need help with that, but what are you dealing with now? So I've been dating Kelsey now for the last couple years. So it's kind of serious. Yeah Do you guys live together? No, no, not yet. Okay. Okay. Tell us a little bit more about Kelsey. Who is she? So she's this great amazing woman So she's this great amazing woman Good start in common. She loves camping. She drives a Jeep. She's like this super old-fashioned She doesn't have social media, which I love it. I think it's refreshing. It's new. It's great. Good She's a different type of gal

Totally. I met her cuz I'm in real estate So I was showing houses one day and she came in looking for property with some friends and okay So she's got money too, right? She's that means she's successful she's looking for a house yeah yeah yeah so we have this great relationship okay what's the problem why why did you email us for help with this great amazing perfect relationship with this Jeep driving woman just calling the bra well so I need you guys help because it's really like kind of a sensitive thing so I was at the point after the one-year mark where I wanted her to move in with me. Okay

That's big. I asked her and straight up said would you move in with me? She goes no, okay Wait, oh, I wasn't expecting. Yeah, you were not expecting that no Why would he ask that if he thought that she might say no It sounds like Conversation prior to asking and that was the issue Or maybe the place that you live kind of sucks Well, she's flying she gave me the reason she doesn't want to live with a guy before she's married You know I can see that.

You know, I didn't- You can see that? Oh yeah, I didn't live with anybody until I met my husband. Because it's so complicated, you know, then you're like combining stuff and- What are you talking about? You lived with your husband before you were married to him. I know, but I married him. He's the only guy I ever lived with.

This is what she's saying. She doesn't want to live with anyone until she is married. No, I mean, she doesn't necessarily want it to be after she just wants like a solid commitment. Yeah, that makes sense. So like Brooke, then like by the time I moved in with my husband, I knew this was the person I was going to be with for the rest of my life. Oh, like I just knew that. So she wants something that says that marriage is going to be in the books.

Like, I'm assuming that's where the conversation led to. Basically, yeah, I mean, we talked about it. We didn't dive too deep into it, but then, like out of the blue, he goes, I'll even sign a prenup. What? I was not even expecting. Whoa. Whoa.

That's like even more serious than marriage. Can you do that before you're married? You don't have to be married. I have no idea. I don't have a prenup. I have no idea. I mean, I could see where you would want some sort of like, is it because she's worried about combining your stuff? Or she doesn't have money like we were talking about and she doesn't want you to take it.

Well, I kind of have the money. I mean, I own a bunch of property and she knows that. So my guess is why. That's why she said that. So she's saying it's not about the money. She loves you for you. Yeah. And the problem is now it never feels like the right time to tell her that I've already met with the lawyer and I've already had these papers already drawn up and all that, cause I've done that.

And I'm ready for this next step. He's met with lawyers and he's got the prenup ready to go. He's drawn up the prenup to secure his assets before he asks her hand in marriage. That's so romantic. It is Will you take this pen? She mentioned it yeah, but it sounds like you guys didn't have a lot of conversation So where are you at right now with everything? Yeah, good question So I want to mention it before I propose, not after. You know what I mean? And I need

help bringing it up so it's not weird. Okay, so you want our help to let her know that there is a prenup ready for her to sign whenever she wants to. That's right. And then after that, then we'll start the engagements and serious commitments that she's always wanted. Yeah. Okay. Why didn't you? Okay. So I mean, if she was the one who brought it up and it's her idea, then what are you

worried about? Yeah. Why didn't you just tell her? I don't understand that. Like, I don't, cause it's not, it's a, it's a very sensitive topic when it comes to money and assets. I feel a little strange about having that discussion to be honest. Well, and in my head head you could have been not joking

But she could have just been throwing it out there and not been like actually serious right like wait you actually drew up the documents That's another level just say it'd be a red flag to me, but I don't know I think it's a very romantic move I don't know why is trying to kill the romance in this segment I'm pretty anti-prenup, but not the whole other story. We're gonna go to work here for you, okay, Drew? We're gonna find out the most romantic, over-the-top way to tell somebody, I have a prenup ready for you to sign.

Aw, I'm gonna tear up. All right? I appreciate that, I need help with this so much. Maybe you could like dot your eyes with a heart when you sign it. That would help. The ideas are already flowing. We're going to start your happily ever after when we do your Awkward Tuesday phone call right after this.

It's Awkward. It's Tuesday. It's Awkward Tuesday phone call. I think we need to clarify something here before we move on because the listener on the phone Drew asked his girlfriend to move in with him. Yeah, that was a while ago. She said no, because she wanted to have proof of a long-term commitment before anything else could happen,

whether that was a proposal or a ring or something. And in that conversation, she said the words, I'll even sign a prenup. Yeah. Yeah. And now there was some people in the room who thought oh well Maybe she was just joking when she said that but if I'm drew and I'm asking my girlfriend to move in with me That's not really like a joking environment Like to me, that's a serious thing. What do you think drew was from her tone in the moment?

Did you feel like she was serious? I got the vibe that she was serious for sure I hope so because he went to a lawyer and actually had one drawn up So drew needs our help to bring it up to her cuz like Brooke said it's been a while since that Conversation happened and she hasn't brought it up since and I know this is a pretty sensitive topic I've personally never been in the situation. I know Brooke has not dealt with it in her marriage Yeah, Alexis wishes somebody would have this conversation with her Near the assets there. It's a tricky topic That's why I feel like the safe thing to do is to give it to someone who really knows about this Jose

What advice do you have for Drew all those long relationships? What advice do you have for Drew? All those long relationships he's had. That's what this came down to. Hey, one time it lasted eight months, bro. Don't make fun of me. Oh, wow. All right. Okay, this entire conversation

can't just be about the prenup or it's gonna sound like a downer, right? You need to hide it in between the wedding and ring shopping and then do the prenup. And everything's gonna be so good. Is this seriously what a man thinks when they have important news to share? What do you think, Drew?

Distract her with shiny promises. Yes! That will only work on Jose. And then squeeze it in. Okay, Drew? No, I'm excited for ring shopping. In theory, sure, it sounds kind of sneaky. I don't know, man.

Like- It's always sneaky. But legally, you still mention it. No. I don't think it's a terrible idea to- I don't like that. There we have it on tape. To tease her a little bit

about the engagement in the future. But Brooke, what do you think? I think you make sure that you frame it as you are doing something for her. You say, listen, you said that you wanted this done. I did it. Some people, you know, are all talk, but I'm a doer and that's how I'm going to be in this relationship. If you want something done, I'm the guy to get it done.

I'm doing stuff for you. What have you ever done for me? Maybe you should sign this premium. Yeah, there you go. That's a good idea. You need to frame it that it's her idea. Yeah, guilt her into signing it. All right. What do you think?

No, that actually makes a lot more sense because ultimately it was her idea. And I went forward with it thinking she was serious about it because why wouldn't she be? Yeah, now she may be angry that you didn't include her in the actual writing it up and stuff But whatever that's boring. Okay She gets mad about you bringing up tell her to be mad at herself for bringing it up in the first place That was Brooks advice So here we go. We're gonna call Kelsey, your girlfriend for you and see if she's ready to sign a prenup

and then hopefully move in together. Oh, I hope I don't cry during this one. It's so romantic. I'm so nervous. We wish you a lot of luck, Drew. Don't be nervous. We're all here to support you, okay? Yes.

Thanks, guys. All right, here we go. I'm dialing your number right now. Beep, beep, beep, beep. Beep, beep, beep, beep. Beep, beep, beep, beep. Hello? Hey, Cal. Hey, what's up, babe?

How's your day? You at work? Yeah, yeah, it was fine. I was just some normal, you know, the usual. Yeah, usual stuff. Do you have a minute? Do you have time? Are you busy or? Yeah, I know, the usual. Yeah. Usual stuff. Do you have a minute? Are you, do you have time? Are you busy or? Um, yeah, I can take a second.

What's that? Um, I wanted to ask you something. Remember that day we had that conversation. We talked about moving in. You remember that vaguely? Yeah. I think I, I said no, right? Yeah, which is fine, you know, he said no, but it got us talking right got us talking about the future and

It was kind of super romantic and we started going ring shopping together It was like a fun little day. It was cute. Um Yeah, I mean it was like more than cute. I think it was kind of important and like put us on a new path together. Mm hmm. Yep. I agree. Um, why are you being so weird? What do you mean you agree?

No, I mean, I just, I just wanted to bring up what you had mentioned. Um, when I asked you to move in with me, if you remember, do you remember anything about, um, the agreement you might've said, or just say, I don't want to move in with you until we get married. Like I told you not, you said another word also. What's going on? Can you just say, you know what?

You know the word I'm talking about. Can you just say it? It just helps me. And you know, my anxiety. I don't right now. So I'm going to need you to say it. It's, it starts with a P. You know what I mean?

What's it end with? Um, it starts with a P, you know what I mean? What's it end with? Um, up a pre not. Oh, okay. Yes. Okay. So you did say that. Great. Okay.

Is there other, no, no, no, no, no, no. It's here. I'm just like outside. There's like a lot of people outside running around, whatever. Um, so I went ahead and moved forward, um, with that word, that, that pre word. Um, I had some lawyers involved and you say lawyers, you hired a lawyer. Yeah. Um, you know, it's not legal, big old stuff.

You know what I mean? Like you kind of have to, when you do this, I don't know what you're talking about right now. Can you get to the fricking point? So I didn't want you to get upset. This is ridiculous. So I wanted to prove my commitment to you. Like we talked about, and I went ahead and got the paperwork for you to sign it.

What do you mean you want me to sign it? This is your idea babe, remember? This is your idea. This is fun. This is just like a weird phone call. I feel like you could have talked to me in person about this. I didn't know how to bring it up. You have no idea I've been losing sleep about this whole damn thing and I asked this radio station to help me You've asked the radio station. What? Radio people Just about as well as their first conversation I don't understand what's happening right now. We're his team of lawyers. Oh, no.

Don't do that. That makes it sound like a joke. We don't want to do that. We're a radio show. This segment is called an awkward Tuesday phone call. Oh, man. And we really emphasize that title today. Nailed it.

We were trying to help our listener here, Drew, have what he knew was going to be a little bit of an awkward conversation with you. Apparently, he thought that gonna be a little bit of an awkward conversation with you Uh-huh. Apparently he thought that you wanted a prenup You know cuz like he wants to move in with you and move forward and go down the marriage road Well, yeah, I said that but he never like talked to me about pursuing it and hiring lawyers and filling out paperwork. Yeah It's a good he should have written it all up himself. I do agree with that I mean, I can't tell what your emotion is right now. Maybe it's just didn't you want this? Maybe you don't care Maybe you're mad. Where you at? Um, I'm just like in the middle really cuz I just wish he was more honest and I feel like

We could have worked on it together. Okay. Yeah. All right. So that's not bad. I mean, that's... If I'm being honest, this wasn't 100% my idea to do it this way. The radio is your idea, you people, you people talking microphone, whatever you radio people, it was your idea to do this way. What? It wasn't our idea for you to hire a team of lawyers, you called us way after that. Yeah, you emailed us, Drew. I just wanted to do a love shout out to show I care about my- my girl.

Oh! Right. You know what? Oops. Did I screw that one up again? Oh man. Oh yes, again. The world's longest shout out. That's 387 mistakes since yesterday. I'm never gonna get this job right. Darn it, Jeff!

I'm sorry, Drew. My bad for misunderstanding your awkward Tuesday phone request. Shout out! Yes, excuse me. Again, 388 mistakes. There it goes. Wait, does that mean you're still wanting her to sign the prenup, Drew? I don't want you guys to pressure her to go ahead and want to sign it. That's for sure. Yeah, sorry about that Actually on the other band Yeah, I know so much about prenup sorry Yeah, we thought we would roll with it. All right.

That's our bad. As long as you two are good, right? I don't know. Yeah, I think we'll figure it out. Maybe have a couple more talks about this. Yeah, we'll go on a camping trip and ride in the Jeep top down or something. We'll figure it out.

Everything's better top down in a Jeep. Kelsey's... Kelsey seems way more chill than you, Drew. I think she's confused. Yeah. Yeah. And... Love you, Kelsey. I love chill than you Drew. I think she's confused. Yeah. Love you Kelsey.

I love you too. That's something we can- The shout out. Mission accomplished. Shout out. Successful Awkward Tuesday. Brooke and Jeffrey in the morning. Over the past six years of making my true crime podcast Hell and Gone, I've learned

one thing. No town is too small for murder. I'm Catherine Townsend. I've received hundreds of messages from people across the country begging for help with unsolved murders. I was calling about the murder of my husband at the cold case. I have never found her and it haunts me to this day.

The murderer is still out there. Every week on Hell and Gone Murder Line, I dig into a new case, bringing the skills I've learned as a journalist and private investigator to ask the questions no one else is asking. If you have a case you'd like me to look into, call the Hell and Gone Murder Line at 678-744-6145. Listen to Hell and Gone Murder Line on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

I know a lot of cops and they get asked all the time, have you ever had to shoot your gun? Sometimes the answer is yes. But there's a company dedicated to a future where the answer will always be no. Across the country, cops call this Taser the revolution. But not everyone was convinced it was that simple. Cops believed everything that Taser told them. From Lava for Good and the team that brought you Bone Valley,

comes a story about what happened when a multi-billion dollar company dedicated itself to one visionary mission. This is Absolute Season 1, Taser Inc. I get right back there and it's bad. It's really, really, really bad. Listen to new episodes of Absolute Season One, Taser Incorporated on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

Binge episodes one, two, and three on May 21st, and episodes four, five, and six on June 4th. Ad free at Lava for Good Plus on Apple Podcasts. I mean, and who said romance wasn't dead? Oh, yeah. Preenups before moving in. That's a lot. Or anything. Yeah.

I think in today's society, this is good for legalities. I'm going to put this in my Tinder bio. If you swipe right, you agree to a prenup. Yeah. So if we match, she's already legally in, bro. I just have a lot of problems. Yeah, and then you can put in little tiny words all the stuff that she owes you.

Yeah, yeah, yeah, yeah. A thousand dollar deposit. You're like, you didn't read the terms and conditions. That's on you, my man, or my friend, or my gal, whoever you end up dating. Everybody. Yeah. And we did get a lot of comments already

from this Awkward Tuesday. Yeah, prenups always have mixed responses, you know? But most... I just threw my wedding ring on. Oh, Brooke! You said the word prenup. What just happened? The ring flew off on its own will.

My bad. Oh, that was just the universe. Get it together. I shouldn't be married. I'm not a prenup lady. If you didn't listen to Awkward Tuesday. Yeah, anyways, a lot of people saying prenup before proposing, that's crazy in place of it.

There should be a long conversation. Before moving in, a lot of red saying pre-nup before proposing, that's crazy in place of it. There should be a long conversation. Before moving in, a lot of red flags, you know. Yeah, some mean words. I'm not gonna read these. Oh, there's mean words even. Wow, you guys went hard already. All right, leave your comments. Thank you for being here.

We'll be back tomorrow with another second date update right here on, you know, we're gonna call it your favorite podcast just because we wanna lie to ourselves. Yeah, let's call it that. Yeah, subscribe and call it that. Yeah, subscribe and share. It's Brooke and Jeffrey in the morning. Why is a soap opera western like Yellowstone so wildly successful?

The American West with Dan Flores is the latest show from the Meat Eater Podcast Network. So join me starting Tuesday, May 6th, where we'll delve into stories of the West and come to understand how it helps inform the ways in which we experience the region today. Listen to the American West with Dan Flores on the iHeartRadio app, Apple podcasts, or wherever you get your podcasts. I know a lot of cops. They get asked all the time, have you ever had to shoot your gun? Sometimes the answer is yes. But there's a company dedicated to a future where the answer will always be no. This is Absolute Season 1, Taser Incorporated. I get right back there and it's bad. Listen to Absolute Season 1, Taser Incorporated, on the iHeart Radio app, Apple podcasts, or wherever you get your podcasts.

The OGs of uncensored motherhood are back and badder than ever. I'm Erica. And I'm Mila. And we're the hosts of the Good Moms Bad Choices podcast, brought to you by the Black Effect Podcast Network every Wednesday. Yeah, we're moms, but not your mommy.

Historically, men talk too much. And women have quietly listened. And all that stops here. If you like witty women, then this is your tribe. Listen to the Good Moms, Bad Choices podcast every Wednesday on the Black Effect Podcast Network, the iHeartRadio app, Apple Podcast, or wherever you go to find your podcast.

I'm Jeff Perlman. And I'm Rick Jervis. We're journalists and hosts of the podcast Finding Sexy Sweat. At an internship in 1993, we roomed with Reggie Payne, aspiring reporter and rapper who went by Sexy Sweat. A couple of years ago, we set out to find him. But in 2020, Reggie fell into a coma after police pinned him down and he never woke up.

But then I see, my son's not moving. So we started digging and uncovered city officials bent on protecting their own. Listen to Finding Sexy Sweat on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Over the years of making my true crime podcast, Helen Gone, I've learned no town is too small for murder. I'm Catherine Townsend. I've heard from hundreds of people across the country

with an unsolved murder in their community. I was calling about the murder in their community. Each week, I investigate a new case. If there's a case we should hear about, call 678-744-6145. Listen to Hell and Gone Murderline on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.