Brooke and Jeffrey: Second Date Update - Awkward Tuesday: Nanny Zoned

Episode Date: November 11, 2025

The guy in today’s Awkward Tuesday Phone call is desperate to spark a romantic connection with someone he’s known for years. They’re not exactly friends… but they've been close for years...See omnystudio.com/listener for privacy information.

On an all new episode of iHeartRadio's Las Culturistas, Jennifer Lawrence is dishing. Jennifer Lawrence. Let's go! Let's go! From her hilariously awkward run-ins with A-Lister's. I don't know what I was expecting, but he was just like,

nice to meet you. To her unfiltered take on beauty treatments. I'm so upset I think the Botox before that. And a jaw-dropping reveal you won't see coming. I don't know if I can announce this, but I'm just gonna. Open your free IHeard Radio app. Search Las Culturista. And listen to the full podcast now.

And she said, Johnny, the kids didn't come home last night. Along the Central Texas Plains, teens are dying, suicides that don't make sense, strange accidents, and brutal murders. In what seems to be, a plot ripped straight out of breaking bad. Drugs, alcohol, trafficking of people. There are people out there that absolutely know what happened. Listen to paper ghosts, the Texas teen murders, on the eye heart. Radio app, Apple Podcasts, or wherever you get your podcasts. On the podcast health stuff, we are tackling all the health questions that keep you up at

night. I'm Dr. Priyanko Wally, a double board certified physician. And I'm Hurricane de Bolo, a comedian and someone who once Googled, do I have scurvy at 3 a.m. And on our show, we're talking about health in a different way, like our episode where we look at diabetes. In the United States, I mean, 50% of Americans are pre-diabetic. How preventable is type 2?

Extremely. Listen to health stuff on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts. What do you get when you mix 1950s Hollywood, a Cuban musician with a dream, and one of the most iconics it comes of all time? You get Desi Arness. On the podcast star in Desi Arnaz and Wilmer Valderrama, I'll take you in a journey to Desi's life, how he redefined American television, and what that meant for all of us watching from me. the sidelines, waiting for a face like hours on screen. Listen to starring Desi Arnaz and Wilmer Valderrama on the IHard Radio app, Apple Podcasts, or wherever you get your podcast. I'm Robert Smith, and this is Jacob Goldstein, and we used to host a show called Planet Money. And now we're

back making this new podcast called Business History about the best ideas and people and businesses in history. And some of the worst people, horrible ideas, and destructive companies in the history of business. First episode, how Southwest Airlines use cheap seats and free whiskey to fight its way into the airline is. The most Texas story ever. Listen to business history on the Iheart radio app, Apple Podcasts, or wherever you get your podcasts. Hey, just want to start off the episode by saying, happy Veterans Day. Yeah. Thank you guys so much. Seriously, I'm the daughter and the granddaughter of a Marine, so, you know, thank you so much for all of your service out there. And and today, we got an awkward Tuesday for you. Yes. Do you want to start?

with a comment, Alexis, you got something? Yes, our Matlock said, please launch more merch. I wasn't listening to you guys the last time you did it. And since then, I've listened to hundreds of episodes across YouTube and TikTok. You guys are my daily podcast while I'm working and studying for grad school. You guys deal with some crazy people every day, and it makes me feel sane. And now I can say this, happy holiday. Hey, there it is.

I have been plotting another merch for a cause. Have you? I want to buy new hat. Yeah. Well, I don't know. we're going to have hats, but, you know. Then I won't be involved. Yeah, well, you have a hat on right now.

I know, I wear it every day. Let's get our awkward Tuesday phone call going and just keep your ears open because something's coming. Ears, earmuffs. We're going to sell earmuffs. It's freaking Jeffrey. If you thought being stuck in the friend zone was the worst feeling, we just heard about another hopeless zone of no romance that sounds even more frustrating. Oh, please don't tell me it's the dead zone.

Please don't tell me it's the dead zone. It's not. of our listeners is stuck in it right now. He's been desperately searching for a way to finally spark a love connection with a person that he's known for years. Wow. They're not exactly friends. Their relationship is a little stranger, more complicated than that.

Really? He's going to tell us all about it. We're going to try and help him get out of that zone in a brand new Awkward Tuesday phone call. Next. It's awkward. It's Tuesday. It's awkward. When you run into an old friend or acquaintance from your past, is that exciting for you?

Is that kind of awkward? I just ran into an old friend the other day. I like it for like 25 minutes. And then after 25 minutes, I'm like, oh, that's why we don't talk anymore. Personally, if I see anybody I knew back in the day, I'm pulling the fire alarm and getting the heck out of there. Oh, wow. Not rehashing old memories with you today. Sorry.

But, you know, I know some people are a little bit more amicable to that idea. Like our listener, Mark, who recently ran into someone from his past, and now he's looking to get a little bit of advice. So, Mark, welcome to the show, man. Oh, my God. Thank you so much for inviting me. This is amazing. Oh, my God. Amazing because you like the show or amazing because the issue's that big?

Well, I mean, I listen to your show every day, but I don't know. I got to talk to y'all. I got to lay it down. Okay. Oh, it sounds like it's juicy. Who'd you run into from your past? Oh, I randomly bumped into my old childhood babysitter. Wow.

That's crazy. Did she recognize, or he, I guess I shouldn't say that, but all my babysitters were girls. Did they recognize you? Not at first. So I was at a coffee shop, and I saw her come in while I was waiting for my drink, and I went up there and I just yelled, Kendra? Question mark? What did she say?

She was just like, uh, who aren't you? Oh, so that means, that means yes, I am, but I don't recognize you. Yeah, it's okay. It makes sense. You were a kid. It's kind of awkward, though. It's better than her saying, go to your room. I said, oh, I'll give you a hint.

I was like, Kendall, can you put on my footie gamut? Oh, no. Oh, you touched you to baby voice, huh? Oh, that's funny. What'd she say? She's like, oh, my God, Marky? Oh, that's nice. Can we call you Marky now?

Yeah, no, we have to. So it worked. I was just like, yeah, I'm all grown up, and we've laughed and love. She's super cute now. Oh. Uh-oh. So many. You're a man now.

Marky's got a thing for the babysitter. It sounds like. Yeah. Yeah. I'm curious, how old were you when you knew her? So I was nine and he was 14 at the time. Oh, that's not too big. A five-year difference.

Yeah, now when you're adults, that's nothing. How old are you now? Are you past your teens? It's like, valid question, I guess. He's like, this was three years ago. I'm 87 years old. You're like, Kendra, you're alive? No, no, no.

I'm around 25 right now, but we just couldn't stop telling stories and we were joking around. You could tell there was a vibe, you know, between us. Okay. Did you ask her out? What'd you do? Did you make a move? So here's what happened. She was with another lady from her work.

Okay. So she said, let's catch up over dinner sometime. And I was like, yes, absolutely. So, you know, a few days later, we went to dinner. It was amazing. I mean, it felt better than going on a normal date because we already had a connection. So this was a date that you two went on?

It wasn't officially a date. It was more of a catch-up. So, here's the thing. Like, from his side of the story, It's like cool and sexy and hot. As someone who, I'm sure Alexis feels the same, has been a babysitter. It would be really weird, even as adults, because you just still see that person as a kid. I gave them back.

Yeah, you watch them pick their nose. You know where they kept their booger collection. It sounds like you guys have actually considered and thought about dating them, but you talked to yourself out of it. I'm trying to think from her side, what was her reaction to this? Did she give any indication that she had any interest? So my take on it, honestly, was she was being pretty flirting back at me. Okay. You felt the vibe a little bit?

That's good. Yeah, definitely, yeah. Is there anything specific that you can bring up about that? Yeah, I mean, she was twirling her hair. She was laughing. It was amazing. Okay. You can twirl her hair when you're bored.

Men don't believe that or whatever. It's like scientifically proven you also do it when you're flirting. But you're right. It could be either. She could have been bored in that. not having a good time. I keep forgetting that this isn't a second date, right? Like, yeah, we're doing an awkward phone call here.

What, what makes this awkward? So, things were going well till halfway through the meal. She leaned over and said, Markey, you need to finish your vegetables. What? Oh. Wait, wait, wait, wait. Yeah, that's got to be. Did you laugh?

I mean, I laughed, and then she says, I'm serious. Oh. So I ate my vegetables while she washed me. Oh, my gosh. It was embarrassing, though. Well, you are a stronger boy because you did eat those veggies. Exactly. Let me ask you this.

At the end of the night, how did you and Kendra leave things? Like, was it romantic at all? We walked out. We had a huge hug. I told her I was going to text her. Yeah. It was like, you better. It's important to keep promises.

Oh. Okay. That's kind of preachy. She's like in, like, teacher babysitter mode again. Yeah. How long ago was this? It was just the only a few nights ago, so Okay, so what do you want our advice with?

Because that's like the awkward thing is, right? We give advice. Yeah, I just need advice on how to, just to say that I'm grown and that I feel like you need to see me as someone that can be with you. I'm not a kid anymore. And go on a serious day with him. I think stomp your feet and say, this is not fair. Brooke, no, really.

I know, I get it. I get it. I get it. Let's try and figure this out. We're going to come back. We're going to give you some solid advice on how to help you ask out your babysitter so that she sees you as a man. Ex-babysitter. Yeah, yeah, yeah.

That's a fair point. You're not still paying her, right? No, no, I'm not paying her. No, okay. All right, we're going to do it with your awkward Tuesday phone call. Next. It's awkward. It's Tuesday.

It's awkward Tuesday. Imagine going out with a girl you haven't seen in years. You're at the dinner table together. She looks over at you seductively. Leans in and says, Eat your veggie so you can grow up to be a big boy. You know what's weird as I think that there's some people that are into them. Maybe talking more.

Thankfully, our listener isn't. It did actually happen, though, to one of our listeners named Marky. Well, I'm calling him Marky because the person of across the table was his ex-babysitter from when he was younger. He was nine years old. She was 14 at the time, but now they're both grown adults, and

Mark wants to play Doctor the real way. What? Yeah. But does she see him that way? Well, she kept calling him Marky. Yeah, probably not. That's not a good sign. Not yet. Not yet. He needs to get our advice on how to change that for himself.

So let's go to Brooke for a little advice. What do you think he should do, Brooke? Well, I've been thinking about this a lot. And, I mean, you have to switch her mindset, right? You have to have her start thinking of you like a man. I never suggest this, but I think you should bring up exes. Because if she can see you in an adult relationship, if she can imagine that, maybe then she can imagine herself in an adult relationship with you. You ready to drop your body count on her? Yeah. I didn't mean that. What do you think, Mark?

I don't want her to get, you know, jealous or anything. Yes, you do. You do want her to get jealous. Yeah, yeah. I do? Yes. You could just say, like, when I was traveling Europe with Candace, God, you know. Yeah, stuff like that.

And traveling to Europe is a very important. She was great, but she didn't really work out, you know. Yeah. It makes you sound like a snobby boyfriend. Yeah. Just trying to make him sound rich, adult, and well-traveled, Jeffrey. Those are good things to remember. Act rich, act grown-up, and act well-traveled.

I think I can do that. Okay. And we're here for you, brother. We all believe in you, buddy. We're going to call Kendra for you, your ex-babysitter, and let you try and make this thing official with her. Get a real date. Okay.

Sorry, not official was the wrong word. Should you call her Ken? Is that more of like an adult? No, I think just go respectful. Manly, we're here for you. Okay, I'm down the number right now. Here we go. Hello?

Kendra, it's me. Who is this? It's Mark. Oh my God, Marky! Hi! I must not have saved your number right in my phone. I didn't pop up with this number. How are you?

I'm great. How are you? I'm good. I'm just kind of hanging out. I just ordered some food waiting for it to show up. Cool. I love. I love food. Food's great.

I know. I remember that you do. I know you, yeah. I kind of need to admit something to you. Okay. So when I was nine, I kind of had a crush on you. Oh, my God. Tell me something I don't know. Oh. Wait, you knew that?

Well, I kind of had a feeling. I mean, when my boyfriend stopped by that one time, you called 911 and told them there was an intruder at the door. Oh, my God, I totally forgot about that. But it was kind of cute. Anyway, you said that was cute? Yeah, it was so cute. Anyway, did you have a good time? The other night when we hung out?

Yeah, I did. It was really nice, but it was like a little late. What do you mean? I mean, well, you know, you told me you had a big meeting the next day, and I felt like I was keeping you up past your bedtime. Well, I'm older now, so I don't really have a bedtime. Well, I know that, but, like, everybody needs their sleep, even, like, big boys like you.

Yeah, I mean, I guess that's true, but I should probably listen to you more. I mean, you should. How was the meeting? It was good. I mean, I think I made a good impression. Did you brush your teeth before? Yeah. Look, here's the conflict that I have, and I'm just going to be honest.

I don't know if you see it, but I feel like, there's like an attraction between us. I mean, yeah, I feel that. Right. But like, you've heard of people being like friend zone before. I feel like I'm being nanny zoned. Wait, what are you talking about?

You know, like the brush your teeth comment and on the date, you made me eat vegetables. It's just stuff you would have said to me as a kid And I don't want the potential of this to have some The same nanny kid power structure Okay, okay How about this? How about you come over to my place this Friday night

I'll make you dinner And I won't make you eat vegetables, okay? Yeah, that sounds good. Yeah, and then we can watch a movie That's, you know, not too scary because I remember that you don't like the scary one. And the best bar is if you stay out past 11, I won't make you go home. Oh.

Oh, wow. Yeah, yeah. You can stay over and I'll read you a bedtime story and talk you in winter. Come on. This is brutal. Is she joking? Oh, my God. Hello?

Hey, Kendra. Hey. Who is it? Oh, Kendra. Kendra, you're on the radio right now with a show called Brooke and Jeffrey. in the morning. Huh? We're a

morning radio show. Right. And we're doing a segment with Mark called Awkward Tuesday phone call. We're trying to help him have this conversation

with you. About like dating, not about bedtime stories. Mark, what's happening right now? I don't like this. Oh, sorry. We don't really like it either

to be honest. Mark? Mark, do you want to explain? So, listen, I have feelings for you And I want you to see me as an equal because I really, I really see it being a thing. Do you feel like there's a connection there, maybe, Kendra?

Like a grown-up, mature, romantic connection? I mean, I kind of see something. But at the same time, it's just, like, really hard to shake the image I have of you as a little boy. Like, in my mind, you're still a little boy. That's what the girl said. But listen to his voice. That's a man voice. You know, and you're sitting across from him at the dinner table.

He's got facial hair. Give him a chance. You say something manly right now, Mark. Go ahead. I mean, I do have facial hair. I mean, come on. Wow. I'm certainly convinced.

Yeah. I just think he's adorable, but I just can't like, he's just Markey. I don't know. He's Marky, and I can't. Okay. But you admitted, you admitted there was an attraction when you two were talking. I heard you.

You said, yeah, I get it. But then she told him to make sure he brushes his teeth every night. I know, like equals each other out. Do you realize that you're doing that, Kendra? Do you even know that? It's habit. What do you want for me? It's habit.

With just him, right? This could just be a case of two people trying to force a romantic connection when really it is what it is. And maybe you're just meant more to be just friends. Yeah, or Mark just wants his girlfriend to do everything for him, you know, like, changes. How do you know? Putting Mark down. It's just like, I mean, he obviously kind of likes it because, like, how could anyone listen to that and still be attracted?

I mean, I like when she does that, too. I like when she reads me back time stories. Maybe he does like it, bro. Maybe the tickle monster can come out again and be like the grown-up tickle monster. Oh, no, that's creepy. Yeah. Okay. Maybe we're all just trying too hard to make this happen.

and it's not going there naturally. Maybe you're right. I mean, do you see that, Mark? I mean, maybe in another lifetime. If she wasn't my babysitter, there could have been something. Okay. You're giving up. You're letting it go.

Maybe you guys can be friends or you can stay nanny zoned. Or he's trying to find a time machine to go back and cancel her as the babysitter. I'm working on it and I'm starting tonight. Kendra, are you okay just staying friends with Mark? Yeah, I think that's fine for me. Okay. I'm still probably trying to not do the babysitting terms around him a lot. They'd just be, like, normal adult friends.

Did you not hear him? He likes it. Yeah, and it sounds like he needs it, too. I'm trying to help. Stay in friends, stay in touch, and see what happens, and maybe something will naturally develop from there. What's your favorite bedtime story, Mark? Oh, my God, um, bumbulina.

That's interesting. They are a man. Brooke and Jeffrey in the morning. This is a couple I wish we could get an update from. Yes, I need to know if things got more romantic. Yeah, I don't know. I think they got less. I think that it's gone to where he's probably just paying her hourly at this point to come over and cut up his steak for him.

Like he got a little, like, he got a little bit from when he's living. He's like, wait, this is, I see why we hired her now. Yes. She was good. I mean, to his credit, kids haven't made. They just wait for people to make them food, make up their stuff off the floor. Fix their mistakes. Yes.

Exactly. Be all cute and babysittery. Good life. It is a good life. I don't blame them at all. Hey, if you ever have an awkward, you know, conversation that you need to have and you want poor advice, you should definitely contact our show. Yes. It's pretty easy to do. I was going to say, or more nanny situations. You know, I want to see if it works out for anybody. Yeah, you can just go to our website. It's brook and jeffrey.com, and there's a big submit button there where you can submit to be on the show. You can also text us to the number 7-8-5-92 or always follow our socials at Brooke and Jeffrey. And thanks for being here one more time.

Happy Veterans Day and stay safe. We'll see you tomorrow. On an all new episode of IHeard Radio's Las Culturistas, Jennifer Lawrence is dishing. Jennifer Lawrence. Let's go. From her hilariously awkward run-ins with A-Lister's. I don't know what I was expecting,

but he was just like, nice to meet you. To her unfiltered take on beauty treatments. I'm so upset I think the Botox before that. And a jaw-dropping reveal you won't see coming. I don't know if I can announce this, but I'm just kind of. Open your free IHeard Radio app. Search Lust Cultureista. And listen to the full podcast now.

She said, Johnny, the kids didn't come home last night. Along the Central Texas Plains, teens are dying. Suicides that don't make sense. Strange accidents. And brutal murders. In what seems to be, a plot ripped straight out of Breaking Bad. Drugs, alcohol, trafficking of people. There are people out there.

absolutely know what happened. Listen to Paper Ghosts, the Texas Teen Murders, on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. On the podcast health stuff, we are tackling all the health questions that keep you up at night. I'm Dr. Priyanka Wally, a double board certified physician. And I'm Hurricane Dibolu, a comedian and someone who once Googled, Do I Have Scurvy at 3am? And on our show, we're talking about health in a different way,

like our episode where we look at diabetes. In the United States, I mean, 50% of Americans are pre-diabetic. How preventable is type 2? Extremely. Listen to health stuff on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. What do you get when you mix 1950s Hollywood, a Cuban musician with a dream, and one of the most iconic sitcoms of all time? You get Desi Arnest.

On the podcast star in Desi Arnaz and Wilmer Valderrama, I'll take you in a journey to Desi's life. how he redefined American television and what that meant for all of us watching from the sidelines, waiting for a face like hours on screen. Listen to starring Desi Arnaz and Wilmer Valderrama on the IHard Radio app, Apple Podcasts, or wherever you get your podcast. I'm Robert Smith, and this is Jacob Goldstein, and we used to host a show called Planet Money. And now we're back making this new podcast called Business History about the best ideas and people and businesses in history. and some of the worst people, horrible ideas and destructive companies in the history of business. First episode, how Southwest Airlines use cheap seats and free whiskey to fight its way into the airline is.

The most Texas story ever. Listen to business history on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts.