Brooke and Jeffrey: Second Date Update - Awkward Tuesday: Sharing Aaron

Episode Date: May 20, 2025

One of our listeners came across an overbearing mother and what went down between them is either gonna be the biggest misunderstanding ever, or the most awkward roommate convo of her life!See omnystudio.com/listener for privacy information.

You're listening to an iHeart podcast. Amy Robach and T.J. Holmes here. Diddy's former protege, television personality, Danity King alum Aubrey O'Day joins us to provide a unique perspective on the trial that has captivated the attention of the nation. It wasn't all bad, but I don't know that any of the good was real. I went through things there. Listen to Amy and TJ Presents, Aubrey O'Day,

covering the Diddy Trial on the iHeart Radio app, Apple Podcasts, or wherever you get your podcasts. We asked parents who adopted teens to share their journey. We just kind of knew from the beginning that we were family. They showcased a sense of love that I never had before. I mean, he's not only my parent, like he's like my best friend. At the end of the day, it's all been worth it. I wouldn't change a thing about our lives.

Learn about adopting a teen from foster care. Visit adoptUSkids.org to learn more. Brought to you by AdoptUSKids, the US Department of Health and Human Services, and the Ad Council. That's the fun part about being an artist that you need to have the patience for finding your pen. I'm La Gata, the culture's favorite reggaeton historian and musicologist.

On an episode of my show, the Reggaeton con La Gata podcast, I sit down with Goldie, a Boricua reggaetonera who's demanding her place in the male-dominated music industry. That's the game, like who stays and who leaves, you know? Listen to Reggaeton con La Gata Hey, I'm Dr. Maya Shankar. I host a podcast called A Slight Change of Plans that combines behavioral science and storytelling to help us navigate the big changes in our lives. I get so choked up because I feel like your show

and the conversations are what the world needs, encouraging, empowering, counter-programming that acts like a lighthouse when the world feels dark. Listen to a slight change of plans on the iHeart Radio app, Apple Podcasts, or wherever you get your podcasts. I've seen a lot of stuff over 30 years, you know, some very despicable crime and things that are kind of tough to wrap your head around. And this ranks right up there in the pantheon of Rhode Island fraudsters. I've always been told I'm a really good listener, right?

And I maximized that while I was lying. Listen to Deep Cover, The Truth About Sarah on the iHeartRadio app, Apple podcasts, or wherever you get your podcasts. Hey, you found it, the Second Date podcast. Thank you so much for being here. Hey, and for everybody that subscribes, we truly appreciate it.

I know that it may not feel like that makes a difference, but it really does make a difference. I go through our subscription list every day and I kiss you all on the forehead. Good night every single night. That is so precious. Every single one of you. That is so precious.

Hey, by the way, the guy, user 01444114, your forehead's a little salty Yeah, so please like and then subscribe we got a brand new awkward Tuesday phone call for you today And I know this one struck a chord with Jeffrey because it has to do with it overbearing mother Oh my god, there's no mother more overbearing than hell Yeah, but before we get to that let's see some comments here. What do you got, Alexia? Yeah, Halle Cruz said, hey, guys, I'm a dog groomer, and I listen to you guys every day.

It helps me stay calm when I have a crazy dog on the table. Love you. That's so cute. Oh, my goodness. Aw, that's so sweet. Wait, does our show calm the dogs down or make them, like, nippy? I don't know.

I'm scared if she has a reaction to us talking and accidentally, whoop, shaves the dog in the wrong way, you know? Then she's just gotta do the whole thing. Yeah, that's true. You gotta act like it's on purpose. Now you got a bald dog. There we go. Alright, let's get this second- oh, nope, Awkward Tuesday. That's what we're doing.

Brand new. It starts right now. Some mothers can be a little overbearing. Oh yeah. Like, maybe when you turn 21, they set up a secret j-date profile to find you a nice Jewish wife without telling you about it Next thing you know suddenly you're getting DMS from some Yenta It's a synagogue trying to send you unsolicited Mondal bread in a ziplock of her homemade rugelach When you never asked your mom for help in the first place made Rougala when you never asked your mom for help in the first place. Yeah, that's traumatic.

That's the Mandelbread is good. Oh, okay. You took it. Anyway, one of our listeners came across a mother that was just like that. And what was said to her is either going to be the biggest misunderstanding ever or the most awkward roommate conversation of all times. You're gonna hear it in your brand new awkward Tuesday phone call right after this. There's certain events that always seem to create drama where

guaranteed by the end somebody is going to be crying in a bathroom or fist fighting out in the parking lot. Okay. We're talking bachelor-bachelorette parties, Thanksgiving dinners, and of course, Brooks out of wedlock baby showers. Wait, what? Always somebody's crying at the end of those. Did I throw for other people? Yeah, sure. But you don't normally expect to find drama while attending your parents' work event.

What? Whoa. No, that sounds boring. Yeah. Apparently not, because that's what happened to one of our listeners, Kayla, and now she needs our help with a little awkward Tuesday phone call.

Kayla, welcome to the show. Hi, thanks for having me. Oh my gosh, I can't wait to hear if you're the starter of the drama or if it's somebody else's fault. And why'd you go in the first place? That's a good question. That's true. The fact that you even still talk to your parents is just impressive. But tell us, what is this work event that you wound up at somehow? Okay, so recently I went to a work event that my dad's company was throwing.

Wait, does your dad own the company? Sorry, maybe I'm reading that wrong. Yeah, yeah, my dad owns the company. OK. Yeah. And you can't be part of it and have nepotism if you're not there. I'm expected to go. So they have this big like family day picnic for the whole company. Oh, okay. I mean, cute.

Cute. Yeah. So I'm there with my parents and they're talking with some of my dad's coworkers. And of course they do what all old people do. They show each other photos of their kids. I mean, young parents do that too. Well yeah once you reach a certain age. Once you have kids you want to show them off. Well yeah if you're proud of them. Not everybody is. Okay so they're showing

pictures of kids? Yeah and there was this one woman there and she's showing me a picture of her son and she's saying oh he he's so cute, right? And he's your age and single if you're interested Love to do that and always it took everything in my power not to react because I recognized him Well her son has been dating my roommate for over a year now. Wait, what? A year? He hasn't told his mom about her?

Yeah, why is she trying to set him up if he's in a committed relationship? I don't know, so I kinda hinted to her, oh wow, he's really handsome, it's hard to imagine no girl has snatched him up. And the woman says to me me well he was in a relationship but he broke up with her six months ago so what like clearly he's been telling his parents something but he's been lying to them he's been telling them

something that's not true okay you're sure he's dating your roommate like he's been over in the passage yeah no that's actually a good question absolutely okay she's my roommate like I know what he looks like Hold on not to like defend this guy But I have overbearing parents and I definitely don't tell them everything about my personal I don't tell my mom if I'm dating someone so it's like years in Do some on the second date What? Yeah, same with me.

Oh my god. I usually introduce him on the second date. Oh no. Oh god. Especially not with my dating life. So he may have a reason for keeping that information from his parents. Yeah. I don't know.

I mean I think Jeff might be onto something because it could also be, what if the mom hated your roommate? And so he just lied and said, oh we broke up so we didn't have to hear her complain anymore. Did she seem like a hateful woman when you were talking to her? No, no, she seemed totally nice, and she's obviously trying to set up her son Yeah, that is the keystone mark of a hateful person So wait so did you tell your roommate about this? Not yet. I got his number from her phone and I feel like I need to talk to him first and be like,

why do your parents think that you're single right now? Like what's going on? And you didn't bring it up to his mother? No, because like, again, I don't know what's going on, but I feel like everybody should be on the same page. And I'm put in this really awkward position of knowing, but not knowing what to do. Yeah, that is a weird position. And what's your relationship like

with your roommate's boyfriend? I mean, like, we don't hang out a lot, but he's at our place, obviously. So I see him and we've had some good times together, but okay, obviously This is just a really like sticky situation Yeah And so the advice that you're looking to get before you make your call to the boyfriend It sounds like what what are you wanting to hear from us? I guess like how do I?

Confront him me like your mom told me that you said you were single But I know you're dating my roommate. Yeah, I mean that does come across as a little accusatory right up that right Yeah, you kind of just want to put him on the spot and see what he has to say how he defends himself Well exactly sounded a little harsh We'll put him somewhere Sounded a little harsh. Yeah You know what I mean put them on a pedestal We'll put them somewhere We're gonna do something with it before first We're gonna give you our advice though right if we come back and let you make your awkward Tuesday phone call to figure out what's really going on with your roommates boyfriend. right after this. Hold on. It's awkward.

It's Tuesday. It's awkward Tuesday phone call. As a woman, I imagine it would be the ultimate compliment when an older lady comes up to you in public and says, hey, you seem nice and desperate enough to date my single son. How about it? No?

I feel like that happened to you all the time, Brooke. It didn't. You didn't seem nice enough. No, I don't think I've ever been nice enough for somebody's son. But that- Will you do this for your son, though? I'll just tell you, the only reason I don't think it's a compliment is because everyone that my mom has ever thought was cute was not. Yeah, their worst case.

It's like, we don't need to lead with personality, mom. Well, that's the situation that one of our listeners, Kayla, found herself in recently, and it would have been flattering, except she knew the guy from the photo that the lady was showing her. Yeah. Yeah. It's a guy who's currently dating her roommate,

and has been for over a year. Yeah, they're like in a real relationship. But now it just gets smaller. The moms told her, no, he's single and he has been for months. Yeah. So that's a giant red flag because obviously he's not. And she never told the mom that day about it, never brought it up to her roommate either. Instead, she's turned to the most trusted source on the entire planet. A radio show named Brooke and Jeffrey in the morning.

That's right. To help her. Can we just applaud her, too, for not blowing things out of proportion before she gets an answer from the boyfriend? Like, that's what she's doing right now. Dude, what is that? Thank you. Yeah.

Now, hopefully we have some decent advice for you, Brooke. Do you have anything to? Okay, listen, this is what you need to do. When you call him, be like, oh my God, I have the funniest story to tell you. I ran into your mom and she tried to set me up on a date with you. Okay.

You know what I'm saying? I don't know, I just feel so awkward. Like, and I've never really talked to him on the phone before, so. I know, you're like and I've never really talked to him on the phone before so I know you're Like Alexis phone calls are hard But I think there's some merit to that if you're really nice to him it'll make him put his guard down I'm definitely gonna be nice Just scared of silence like Alexis would be

Embrace the silence and if all else fails threaten to release his nude photos What I'm saying, but I'm gonna dial this guy's number have we even learned his name yet, um, his name's Aaron, okay scumbag Aaron. Let's give him a call. Potentially scumbag Aaron. Thank you. Alleged potential scumbag. I think he's actually a good guy. I think he's fine. Yeah you think all of them are. Okay here we go I'm gonna dial it and we're gonna step away let you make your awkward Tuesday phone call we'll jump in if you feel like you need a little help okay Kayla? Okay okay. Okay you got this here we go hello hey Aaron um this is Kayla how are you oh hey yeah hey, what's, what's up? What's going on? Um, I just, something kind of funny happened the other day and I just, um, I just wanted to ask you about it. Um, if that's okay. Do you have a minute? Uh, yeah. Is everything okay? I mean, it's kind of odd for you to call me out of the blue. Yeah, I know. I know. I normally just like see you. Um, but I just, I had to ask you something, uh, privately. So, um, but yeah, if you, if you have a minute, can I just ask you something real fast?

I mean, sure. What's, what's up? Sure. What's, what's, what's up? Okay. So the other day my dad's company had a, had a party and I ended up seeing your mom there and she, she showed me a photo of you and she's like, Oh, my son is single. Um, which was just really weird because I know you've been obviously with my roommate. So I just wanted to like ask you what was going on. Like does your mom think that you're single or is that just like a mistake or something?

So this is really funny you even asked that. I mean, my mom found out she was going to your parents party, right? And I was like, another daughter, she's really cute. And my mom, she was like, well, you should date her. I mean, she's better than who you're dating. And... Okay, well, obviously that's not true, but okay.

Well, I mean, it is true, but anyways, I was like, that would be weird, mom. And she's like, well, you've met my mom. She's like, let me try, let me try. I'll talk to her, let me try. And I'm like, it's not the worst idea, right? So I was like, okay, yeah, sure. Wait, so hold on.

I'm trying to wrap my brain around this. You are with my roommate, but you told your mom it was fine to tell me you were single? Yeah, and my mom was she's all about it. She's like, oh yeah, I like to listen, you know, you've met my mom. She's very yeah. So she yeah. Sorry, I'm, I'm just, I'm, I'm having trouble understanding why. Come on. I mean, is it really that crazy? What is that crazy? What is what crazy? I mean, you and me, I mean, that's not so crazy, right?

Are you, listen, now that I'm out there. Are you being serious right now? Yeah, I mean, what do you think? Oh. What do you mean, what do I think? You're with my roommates. Temporarily. Oh, I mean, listen, it could be you and me. I mean, we, we get along and then you're not as messy as her. And you know, and listen, your, your lease is up in three months and I figured, well, you could just move move out get your own place and then we can

start dating on the you know on the down low. Wow you have it all planned out. Sorry I hit the awkward before I heard her answer. What is going on? Alexis you're right he is a good guy. I didn't know he was a cheater. I didn't see that coming. I got a good feeling about this. Yeah he is a good guy. I didn't know he was a cheater. I didn't see that coming. Alexis, I got a good feeling about this. Yeah, that was trying to cheat. Yeah, that's true. He's not a cheater.

He's still clean for now. Hey, what's going on here? What is going on, please? Somebody explain to me. No, Aaron, you heard us. Oops, so guest cat's out of the bag. You're on the radio right now with a show called Broken Jeffrey in the morning.

Dude. What? No, no, no, no, no. Yeah, yeah, yeah. No, no. You guys need to delete this, really. We'll delete it after we post it. And send it to your girlfriend.

And send, yeah. Okay. Why would you guys do this, Kailin? Why would you do this? This is ridiculous. What are you talking about? It's not her fault. It's not her fault.

These are your words, your actions. I was just asking the question. I mean, what are you talking about? This is ridiculous. You left me out on the radio like this? You are the most upset, innocent person I've ever heard. That's a great statement, bro. Clearly, Erin, you're aware that this breaks some social rules here.

Otherwise, you wouldn't be as upset as you are right now. I mean, the cat's out of the bag. Sure, sure I get it but you can't blame a guy for trying. It is so weird how cavalier you were about it. How like you just thought she was gonna go along with this. Why would you ever think that? It wasn't my idea, it was my mom's idea come on! And I thought about it and I thought yeah, that's great. I think they do say mother's no best By honey, you should cheat on your girlfriend. Yes, mom is telling me But I don't know Kayla. What are you thinking now that you're hearing all this? I'm thinking that this is absolutely

Disgusting and absolutely come on wait, so you never thought about you and him together I was a joke Aaron even if she was attracted you in any way I'm sure her friendship means way more than some random dude I know if you're not happy with your current girlfriend, that's okay, but don't bounce over to the roommate It's like 20 feet away, especially before you broke It wasn't my idea my mom came up with this and I just went with it You understand that right Kayla Yeah, because what every girl wants is a guy who can't think for himself and only has his mom to listen to

Okay, well it was definitely an awkward call but the good news is at least the truth did come out I mean the mom is obviously a wackadoo, but like I thought. I don't know. Take out our 1950s encyclopedia. I think it used to be a swear word. You know what I'm saying? No. I'm just so thankful for you guys helping me out, because otherwise I would have thought he was innocent, too.

It seemed like a misunderstanding. You need to go get a bottle of wine to bring home to your roommate tonight, some ice cream and have a good long chat. So that Aaron and his roommate can split it and have a nice romantic evening, just the two of them. He is not invited. Hey, I'm coming, I'll be there.

No, no. It's a party. Brooke and Jeffrey in the morning. Amy Robach and TJ Holmes here. Diddy's former protege, television personality, Denity King alum Aubrey O'Day joins us to provide a unique perspective on the trial that has captivated the attention of the nation.

It wasn't all bad, but I don't know that any of the good was real. I went through things there. Listen to Amy and TJ Presents, Aubrey O'Day, covering the Diddy trial on the iHeart radio app, Apple Podcasts, or wherever you get your podcasts. Dime a ver, I'm La Gata, the culture's favorite reggaeton historian, musicologist, public scholar, and recording artist. Yes, that means I've done the work.

On my show, the Reggaeton con La Gata podcast, I'm not only talking to Flor Menon, who has the number one reggaeton track in the world right now, I'm also going beyond Perreo to speak with music inhibitors like Rainao who is known for her media roquera tracks and collaborating with artists like Bob Baldy who are also giving you the culture breakdown straight from the source. Listen to Reggaeton Cueva Gata on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. We asked parents who adopted teens to share their journey. We just kind of knew from the beginning that we were family. They showcased a sense of love that I never had before. I mean, he's not only my parent, like he's like my best friend.

At the end of the day, it's all been worth it. I wouldn't change a thing about our lives. Learn about adopting a teen from foster care. Visit adoptUSkids.org to learn more. Brought to you by adopt us kids, the US Department of Health and Human Services and the Ad Council. Hey, I'm Dr. Maya Shankar. I host a podcast called a slight change of plans that combines behavioral science and storytelling to help us navigate the big changes in our lives.

I get so choked up because I feel like your show and the conversations are what the world needs encouraging, empowering, counter programming that acts like a lighthouse when the world feels dark. Listen to a slight change of plans on the iHeartRadio app, Apple podcasts, or wherever you get your podcasts. I've seen a lot of stuff over 30 years, you know, some very despicable crime and things that are kind of tough to wrap your head around. And this ranks right up there in the pantheon of Rhode Island fraudsters. I've always been told I'm a really good listener, right?

And I maximized that while I was lying. Listen to Deep Cover, The Truth About Sarah on the iHeartRadio app, Apple podcasts, or wherever you get your podcasts. You're listening to an iHeart podcast.