Brooke and Jeffrey: Second Date Update - Awkward Tuesday: House Guest's Fiancee

Episode Date: September 29, 2026

Last week we promised a guy that we’d help him come clean about losing his job and lying about it to his fiancé… but he snuck in another bombshell we didn’t see coming! Hear what it was during your Awkward Tuesday Phone Call podcast!See omnystudio.com/listener for privacy information.

The miles change how you move, but more importantly, they change how you show up for your life. I'm Emily Abadi. On The Hurtle with Emily Abadi podcast, I sit down with elite athletes, record holders, coaches, and everyday runners to unpack the mindset behind pushing through when things get tough. Because the discipline, grace, and grit you build out there on the pavement, that's what helps you show up as your best self everywhere else. I'd just love to say, I never know who's watching. So you want to make sure you, you through and through, and you just stay true to who you are.

to Hurtle with Emily Abadi on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Welcome to Decoding Women's Health. I'm Dr. Elizabeth Pointer, chair of Women's Health and Gynecology at the Atria Health Institute in New York City. I'll be talking to top researchers and clinicians and bringing vital information about midlife women's health directly to you. A hundred percent of women go through menopause. Even if it's natural, why should we suffer through it. Listen to Decoding Women's Help with Dr. Elizabeth Pointer on the Iheart Radio app, Apple Podcasts, or wherever you get your podcasts. In February of 2024, celebrated illustrator and children's book author Patra Mathers and her husband Michael mailed letters to dozens of friends and family members to let them know they had died by suicide.

Dear honies, this is goodbye. By the time you get this letter, both Petra and I will be dead. Next stop, Wonderland. Why did they do it? And what did it do to the people they left behind? Listen to Death of an Artist on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. The new NFL season is here. And you should be listening to NFL Daily as we march along to Super Bowl 61.

It is in the name, NFL Daily. You'll have fresh content in your feed every day all season long. That game winning drive, maybe it's Herbert, maybe it's Gino. Maybe it's Mahomes. We'll have the highlights. If Fernando Mendoza or any of those rookies are balling out, will break down the tape. Join me, Greg Rosenthal,

and an all-star cast of co-hosts as we preview and recap every game. Listen to NFL Daily on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. I'm Brett Coleman. And I'm Trevor Sycamam. If you love football and want to understand what's really happening on the field, check out our show, NFL Pro. Every week, we break down the biggest plays, trends, and matchups

using exclusive next-gen stats insights, and NFL content you will not find anywhere else. Whether you're new to football, a fantasy football fanag, or a diehard fan. NFL Pro will help you analyze the game like a pro. Listen to NFL Pro on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. We're in for it today. We have our man back for your awkward Tuesday that we've been waiting a week to do. The longest week ever.

Thank you for finding the Brook and Jeffrey. Of course, second date podcast. This is the official one. What were people saying last week when he was on the show? Oh, yeah, we got a lot of he better come back. I can't wait. He needs to man up. Oh, a lot of we gave really terrible advice.

And by we, I mean, you and Jose. Sorry, there's just so many. Okay, let's hope today's better. Yes, of course. Brand new episode that you've been waiting for starts right now. Last week, we promised a guy that we'd help him finally come clean to his fiancé about losing. his job and lying about it. Why did we promise that?

I don't know, but we did. It would have been challenging enough if it was just that until he surprised us with another major bombshell that he also hasn't quite mentioned to her yet. Okay. And this new one makes the whole, I don't have a job thing, look like peanuts in comparison.

But like you said, we'd already promised him that we'd help. And this is why we shouldn't make promises. That's exactly right, Jeff. Brace yourself for the first ever double trouble awkward Tuesday phone call. It's coming up next. It's awkward. It's Tuesday. It's awkward Tuesday phone call.

A week ago, we had a listener email the show about a problematic house guest. Oh, yeah. A friend from college named Rick who asked one time, because he was in town, could he stop by and stay with her? Yeah, he's traveling for work. Just needed a spot to crash. Exactly. And she's married and went and asked her husband about it. They both agreed, sure, he could stay a bit.

But one day turned into three days. And then he left and came back the next weekend. And then? And then another weekend. And then another. That's why she came to us asking, how do I tell this good friend politely, hey, I need my space. Overstage, you're welcome.

Stop coming over. And during the awkward Tuesday call from last week, when he didn't know that we were listening in, Rick admitted something. So let's listen. When I started staying with you, I was gainfully employed, but I am not anymore. I haven't had a job in about three weeks now. I got laid off. And I don't really want my fiance to find out about it. So I've been just kind of waiting until we're married, which is going to happen in 59 days.

Oh, my God. So if you could maybe help me out a little bit, you'd be really doing me a solid. I love that he was like, yeah, once I trap her with marriage, she can't go anywhere. Yeah. That's the truth. But, yeah, it was definitely a much bigger deal than we originally thought. For sure. And by the end, we told Rick, the house guest, hey, maybe you shouldn't lie to your fiancé all the way up to your wedding.

It might be better to tell her the truth in an awkward call with us. and we'll help you. You would hope that your partner is understanding and sympathetic and helps you through a time like that. Yeah, because it was her parents he's scared about too, you remember? Well, Rick agreed, and that's why he is back with us this morning. Rick, we're really glad we could have you back on the show. How's the last week been? It's been interesting, but the good news is that Molly and her husband have been really cool,

and they let me stay there until I can figure all this stuff out. Wait. Oh, wow. You haven't even been home. to your fiance yet? Well, he's busy traveling for work, Brooke. He doesn't have a job. Jeff is a lot.

Yeah, I've been staying at Mollies for the week. Oh, my gosh. She is an angel. Oh, my. I'm letting you stay. I feel like that's going to make this bomb bigger. Okay. Brooke, I'm sure that he feels nervous enough as it is.

We don't know we need to pile on for you, Rick. How are you feeling? I, you hit it on the head. I'm nervous. It can be. What's making you the most nervous? Yeah, I didn't really plan for it to get to this point. But the thing I'm really, really nervous about is for parents because, I mean, to be blunt, they're pretty well off.

And they have a certain attitude about me already. I think they might see me as a gold digger. Oh. So I don't really want to give them that impression. You're so newly unemployed. Exactly, Jose. It's not like you've been out of work for five years and not been able and just like borrowing their money for. Yeah.

Totally. Although it does sound like a pretty sweet life. Yeah. Yeah, no, I'm just out of a job right now. It's not going to be forever. I think that's probably a good thing to include when we get her on the phone and reassure her this is not a permanent situation. Totally. It's something that, I mean, honestly, I've gone through. I think most people have been laid off. It's a hard thing to get through for sure. Yeah. So that is definitely a big weight that's been on your shoulder. Are there any other details about this that we need to know before we give you some advice for it?

Did you just yell in the background? I just thought of it. It just hit me. There's probably something else I should tell her to. What? Is this a new thing? I don't know if it's a new thing, but it's a weird thing. It's from a long time ago. So I had a kid with somebody else a while back. Wait, and she doesn't know.

What? She doesn't know that you have a child? No, I'm not like, it's not part of my life, but it's not something that I'm involved with being a father. You know what I mean? Oh, no. Can we not do that on the phone and save that for your own time? Why has this not come up to your fiancé that you have a, you have a, you have a child? child. Trust me, it's not something I sleep easy about, but it's not entirely up to me. You know,

he has a mom that decided she wants her own life with her new husband and the kid. I'm just not a part of that life. But I do make my payments. I make my payments on time all the time, which is also not really helping my ongoing financial situation here. Oh, yeah. Well, you're helping your child. Okay. You want to combine this bomb with the unemployment thing? Well, I don't know. That's what I'm asking. Tell her all at once. Oh, my God. Wow. I mean, Brooke, I'm going to leave this one up to you.

I'm going to tell you it really reduces the impact of the unemployment. Like, that doesn't feel so bad. Yeah. Okay, Brooke, so maybe we should include it. Is that what you're saying? You absolutely have to tell her everything. Yeah. And something else if you think of.

Honestly, the more minutes and seconds that go by that she doesn't have this information, the worst of a person you are. Yeah. Okay. So just to be clear, You guys are saying he does a double dose of bad news on this call. Yeah. You tell her after the wedding, this is what annulment was made for.

Oh. Yeah. It was the double awkward sound effect. Oh, yes. You know what, Jose, thankfully you're focusing on the positive parts of this experience. Yeah, the sound effects. That's why I'm glad that you're here. So I get one to hear it.

I don't know how your engagement makes it out of this. Honestly. Well, that's why you're going to give the best advice ever, Brooke. when we come back and we tell Rick what he should say to his fiancé about where he's been staying for the past few months, his job situation, and his child that is not kind of in his life, but he does make payments on. You make it sound like a used car. Anyway, we're going to do it with your super easy, awkward Tuesday phone call. Rick, how does that sound? Like, I'm about to change my mind.

Don't do it. You have to do this, Rick. Yeah. Literally. It's the right thing to do. And we're going to send you payment requests for it, too. So make sure you pay, and we'll do your call right after this. Hold on.

I'm just kidding about the pay, by the way. Okay, let's do that. Don't hang up. It's awkward. It's Tuesday. It's awkward Tuesday phone call. We're in the middle of a totally fun and exciting awkward Tuesday phone call. I like that attitude, Jeff.

Maybe one of the easier calls that we've ever had to make. Oh, my God. Because we've got a guy named Rick on the phone with us here. And all Rick needs our help doing is telling his fiancé that he lost his job recently. And he's been secretly staying with some friends so that her parents won't find out that he's unemployed. Yeah. Because they're judgy people. And that's not cool.

And what's the other thing, Jeff? Oh, one more thing. He needs to let his fiance know he has a secret child that he's not really involved in that child's life for the last. some odd years, but he does... I think it's all the years. He's ever met him. He wouldn't know. He doesn't get to hang out with the kid because the mom doesn't want him in their life,

but he has been making payments. Yeah. Like a good biological dad does. You know what? He's what, like 50 days from the wedding now? Yeah. Three weeks, I think. Rick, did I miss anything? Any details I left out? No, Rick. It sounds pretty awful when you say it like that.

Hey, I think you should know that you're actually finally doing the right thing by telling her all this stuff. So this is the first right in hopefully correcting a lot of wrongs. Yes. And you came to us seeking advice. So that's what we're here to give you. Jose. What do you think Rick needs to do here?

Well, Brooke kind of mentioned this in part one. But the firing of the job and lying about it doesn't look as bad with this new secret. Yeah. It's like nothing. That's why exactly. That's why the order is very crucial here. The order of what he tells her, you have to do kid secret first. You have to tell her about the kid right away

Because then the rest of the stuff is going to be Pebbles compared She won't even hear it I completely agree That's what I was thinking Wow okay Big bomb first, little bomb second Yeah

When everything's destroyed Yeah nothing's left Perfect Brooke what's your advice You know honestly I I think you need to tell her Why this marriage is so important You need to lead with that And then before you even

Tell her the truth You need to tell her why you lied because I just have a feeling if it's because you're so scared of her parents she probably feels exactly the way that you do. I mean she might have some of those same pressures from her mom and dad.

So she may at least go into the truth with some understanding of why you haven't told her everything. And maybe it kind of bonds you together even tighter because now you're both keeping a secret from her parents. That feels good. I don't know that that's the answer. I think we need to be done.

done with the lies, period. Just between the fiancés. That's where the lies are going to end. But we're going to call your fiancé, Megan. Do we have to? We have to. Yes. You have no choice, Rick.

I mean, that's not true. There's always the choice to go on the lamb. No. He wants to get married, Jeff. Well, we'll call that option C, but we're going with telling the truth first, and we'll see how that goes. I'm going to dial Megan's number right now. Good luck, Rick, okay? Oh my God, this is going to be a tough one.

It's an understatement. All right, you got this. Here we go. Hey, babe. Hey, I can they recognize the number. How are you? I'm good. How are you?

Good. I miss you. I miss you. I miss you way more, I promise. The grind has really got me. I mean, you are the hardest worker, honey. It's been gone for so long. I know it's been too long

so I needed to hear your voice and kind of pick me up a little bit Yeah it's nice to hear you are Is there anything you need or like You're just calling to check in I was calling to talk There's something that's been on my mind a little bit And I just thought maybe I should share it with you

Okay So you remember how I've told you a bunch of stories about how I used to host those crazy keg parties in college. Yeah. Yeah, well, this is kind of tough, but there was something about those parties I didn't mention before. And that's that there was this girl that came to the parties every once in a while. And we randomly hooked up one time.

Okay. And this was like 13, 14 years ago. Like, this is ancient history. Yeah. I don't really know why we need to talk about this now, but... Well, um... Did you like see her or something? I never told you...

I never told you that we had a dog together. What? You had a dog? Sorry, no, that's actually... That's not it at all. I don't know. I was trying to soften the blow or something. No, we had a kid. See?

Oh, God. That's worse. You're a dad? I mean, in name, yeah. I've only met the kid one time for a few minutes, and it was right after he was born. He went off and married somebody else, so he's been getting raised by another guy his entire life.

I just make my payments, and that's kind of the end of it. You know, they're so not involved in my daily life that I almost completely forgot to even tell you. You forgot you have a son. Okay. I mean, just the timing of this is a little, odd because, you know, we are about to get married. Yeah, well, that's why I'm calling you right now, because I'm really sorry about not

telling you, and I, actually, there was something else I wanted to tell you. Something else. Yeah, and you're going to think this is really funny, but I got fired for my job, and I've been staying with someone else for a while. Why would you say funny? Yeah, but wait, you said it wasn't even smooth. Oh, man. Wait, I'm...

Oh, man. I just, I need a minute. She can't even hear us. I mean, I don't blame you. Megan, can you hear other voices? Yeah, I can hear you. Who are you? Yeah, we're a radio show called Brooke and Jeffrey in the morning.

Oh, my God. Stop. So sorry. Oh. We are trying to help Rick with this awkward situation that he is currently found himself in. That he made for himself the bed he made. The bed he made. He's finally trying to be honest.

Let's not talk about beds after all the college party talk. I doubt that was a bed. Fou tons. Whatever it was. Listen, Rick wanted help coming clean about some things that he hasn't told you yet. And he wanted to do that because he loves you very much. And he wants to be totally honest before you guys get married. So, Rick, you didn't talk to me about this, but you called the radio?

This is what they do. babe, they talk people through weird situations like this. This is weird. Wait, you got fired? I'm sorry, I just, that just kind of hit me. Wait, you, you got, you work for a moving company.

How do you get fired from a moving company? I mean, he is traveling. Oh, yeah, I guess that explains why he's all over the country. How'd you get fired, Rick? This is the kind of funny part. The company found out that I was maybe putting some personal belongings

from customers into my storage unit. You were stealing. I thought you got laid off because the company downside. gave it all back. The police helped. Oh, the police helped him give it back. Well, that's good. Okay.

All right. He's a thief with an illegitimate. Okay. This is funny. We're running out of time and we can't finish this call. I'm so sorry to say that. Megan's going to have to re-listen to this eight times on the podcast just to process all of them. I think the two of you need to talk off the air.

Yeah, I would agree. You know, maybe at home, when you're coming home, right? Wait, you're still inviting them back to the house? I feel like this is a conversation that should happen in person and not on the phone with people. I don't know. I'm sorry. I'm sure you're lovely. No, it's okay.

We're really not, though. Yeah, you're much nicer than me. I definitely would have changed the locks. Trust me, babe, no one is as sorry as I am, and I am so thankful, which was finally able to get that off my chest. So glad you're feeling so much better. He could have told her he was cheating and it would have been a easy thing to process than this.

You better bring all the flowers you can find before this conversation. But that you buy yourself, Jose. Yeah, maybe you don't bring something from someone else's house. That would be great. I mean, it sounds like he's a changed man, Megan. He's really turned a corner today. So I'm really sorry. Okay.

All right, that's your awkward Tuesday phone call. Is that it? I feel worse at the end of it. Okay, well, we still have to call the kid next week. So stay tuned. I might need you to help me call my parents. The saga continues. Brooke and Jeffrey in the morning.

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Guess who's probably going to be available soon? Surprise. It's Rick. And he is just an endless well of questionable choices and weird secrets that he's kind of half buried over the years. I have to get an update from these two. There's no way the wedding is going to happen. I know.

Every minute something new came out that he hadn't confessed before. And that's only the ones he was willing to talk about on the radio. That's all of them though, right? Why did I feel like the first two, like the kid and the job could maybe be worked through? But then when you added the stealing, it was like it was like the, what breaks the Campbell's back? Some straw, the straw. That was the straw. The camel is broken.

It's in a million pieces. That camel is buried under a giant pile of hay. There's so much straw. But, you know, maybe some women find it kind of fun. Nope. To date a guy with lots of surprises. Don't put that. You'll keep you on your shoes.

Toes. Nope. I feel bad for that girl and I hope she has a really good best friend. Yeah. Yeah. Yeah. But I don't know. I wonder if the wedding's going to happen.

No. We'll try to get an update from those two and see what goes down when they finally do reunite. But listen. Yeah. What are you going to sell, Jeff? What are you going to promise? We're great advice. Are we?

We'll give it. We'll give it to you. And then you can listen to nothing that I say. Yeah. No one ever listens to it. But we'll sit here while your life unravels. We'll help you do it with your awkward Tuesday. Email us if you need a little bit of help

and go check out all of our awkward calls. They're available online wherever you get your podcast at Brooke and Jeffrey in the morning. The miles change how you move, but more importantly, they change how you show up for your life. I'm Emily Abadi. On the hurdle with Emily Abadi podcast, I sit down with elite athletes,

record holders, coaches, and everyday runners to unpack the mindset behind pushing through when things get tough. Because the discipline, grace, and grit you build out there on the pavement, that's what helps you show up as your best self everywhere else. I'd just love to say I never know who's watching. So you want to make sure you, you through and through, and you just stay true to who you are.

Listen to Hurtle with Emily Abadi on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Welcome to Decoding Women's Health. I'm Dr. Elizabeth Pointer, chair of Women's Health and Gynecology at the Atria Health Institute in New York City. I'll be talking to top researchers and clinicians and bringing vital information about midlife women's health directly to you.

A hundred percent of women go through menopause. Even if it's natural, why should we suffer through it? Listen to decoding women's help with Dr. Elizabeth Pointer on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts. In February of 2024, celebrated illustrator and children's book author, Patra Mathers, and her husband Michael mailed letters to dozens of friends and family members to let them know they had died by suicide. Dear honies, this is goodbye.

By the time you get this letter, both Petra and I will be dead. Next stop, Wonderland. Why did they do it? And what did it do to the people they left behind? Listen to Death of an Artist on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. The new NFL season is here,

and you should be listening to NFL Daily as we march along to Super Bowl 61. It is in the name, NFL Daily. You'll have fresh content in your feet. every day all season long. That game-winning drive, maybe it's Herbert, maybe it's Gino, maybe it's Mahomes. We'll have the highlights. If Fernando Mendoza or any of those rookies are balling out,

will break down the tape. Join me, Greg Rosenthal, and an all-star cast of co-hosts as we preview and recap every game. Listen to NFL daily on the IHeart Radio app, Apple Podcast, or wherever you get your podcast. I'm Brett Coleman. And I'm Trevor Sycamma.

If you love football and want to understand what's really happening on the field, check out our show NFL Pro. Every week we break down the biggest plays, trends, and matchups using exclusive next-gen stats insights and NFL content you will not find anywhere else. Whether you're new to football, a fantasy football fanag, or a diehard fan.

NFL Pro will help you analyze the game like a pro. Listen to NFL Pro on the IHeartRadio app, Apple Podcasts, or wherever you get your podcast.