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Jeffrey
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Brooke
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Alexis
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Jeffrey
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Brooke
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Jeffrey
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Alexis
Hey, just want to start off the episode by saying happy Veterans Day.
Kendra
Yeah.
Jeffrey
Thank you guys so much.
Alexis
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 today we got an awkward Tuesday for you. Yes. Do you want to start with a comment? Alexis, you got something? Yes. R. 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 and 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. I have been plotting another merch for a cause. Yeah, well, I don't know if we're gonna have hats, but, you know, then.
Jeffrey
I won't be involved.
Alexis
Yeah, you have a hat on right now.
Jeffrey
All right, I wear it every day.
Alexis
Let's get our awkward Tuesday phone call going. And just keep your ears open, cuz something's coming.
Jeffrey
Ears. Ear.
Mark
Muff. Adding a hint.
Jeffrey
We're gonna tell earmuffs.
Alexis
It's freaking. Jeff.
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.
Announcer
Wow.
Alexis
Oh, please don't tell me it's the dead zone. Please don't tell me it's the dead zone. No, it's not.
Jeffrey
But one 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.
Alexis
Oh, wow.
Jeffrey
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.
Alexis
It's Tuesday.
Jeffrey
It's awkward. Tuesday. Phone call. When you run into an old friend or acquaintance from your past, is that except exciting for you? Is that kind of awkward? I just ran into an old friend the other day.
Alexis
That's who it is. I like it for, like, 25 minutes. And then after 25 minutes, I'm like, oh, that's why we don't talk anymore.
Jeffrey
Personally, if I see anybody I knew back in the day, I'm pulling the fire alarm and getting the heck out of there.
Alexis
Oh, wow.
Jeffrey
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.
Mark
Oh, my God. Thank you so much for inviting me. This is amazing.
Alexis
Oh, my God. Amazing because you like the show or amazing because the issue's that big?
Mark
Well, I mean, I listen to your show every day, but.
Alexis
Oh, that's nice.
Mark
I don't know. I got to talk to y'. All. I got to lay it down.
Announcer
Okay.
Alexis
Oh, it sounds like it's juicy.
Jeffrey
Who'd you run into from your past?
Mark
So I randomly bumped into my old childhood babysitter.
Announcer
What?
Jeffrey
Oh, wow.
Alexis
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?
Mark
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.
Jeffrey
What did she say?
Mark
She was just like, who are you?
Jeffrey
Oh, so that means. That means yes, I am, but I don't recognize you.
Alexis
Yeah, it's.
Mark
Okay.
Jeffrey
That makes sense. You were a kid. It's kind of awkward.
Alexis
Better than her saying, go to your room.
Mark
I said, oh, I'll give you a hint. I was like, kendall, can you put on my footy? Damn it. Oh, no.
Alexis
Oh, you talked in a baby voice.
Jeffrey
You went to baby voice, huh?
Alexis
Oh, that's so funny. What'd she say?
Mark
She's like, oh, my God, Marky.
Alexis
Oh, that's so cute. Can we call you Markie now? Yeah.
Jeffrey
No, we have to. So it worked.
Mark
I was just like, yeah, I'm all grown up. And we laugh and laugh. She's super cute now.
Alexis
Oh. Oh, so many. Marky's got a thing for the babysitter. It sounds like.
Jeffrey
Yeah, yeah, I'M curious, how old were you when you knew her?
Mark
So I was nine and he was 14 at the time.
Jeffrey
Oh, that's not too bad.
Alexis
A five year difference.
Jeffrey
Yeah. Now when you're adults, that's nothing. How old are you now? Are you, are you past your teens?
Alexis
Yeah, it's a valid question, I guess. This is three years.
Jeffrey
I am 87 years old. You're like, kendra, you're alive.
Mark
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.
Alexis
Okay, did you ask her out? What'd you do? Did you make a move?
Mark
So here's what happened. She was with another lady from her work. So she said, let's catch up over dinner sometime. And I was like, yes, absolutely. So, you know, 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. And so you.
Jeffrey
This was a, this was a date that you two went on?
Mark
It wasn't officially a date. It was more of a catch up.
Alexis
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 bath. Yeah, you watched them pick their nose. You know, where they kept their booger collection.
Jeffrey
It sounds like you guys have actually considered and thought about dating them, but you talked yourself out of it.
Alexis
I'm just thinking about 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?
Mark
So my take on it honestly was she was being pretty flirty. Back at me, I think.
Jeffrey
Okay, you felt the vibe a little bit.
Mark
That's good. Yeah, we definitely, yeah.
Alexis
Is there anything specific that you can bring up about that?
Mark
Yeah, I mean, she was twirling her hair, she was laughing. It was amazing.
Alexis
Like, okay, you twirl your hair when you're bored. Men don't believe that or whatever.
Jeffrey
Scientifically proven. You also do it when you're flirting. But you're right, it could be either. She could have been bored and not having a good time.
Alexis
I keep forgetting that this is isn't a second date. Right.
Jeffrey
Like, yeah, we're doing an awkward phone call here. What makes this awkward?
Mark
So things were going well till halfway through the meal, she leaned over and said, Markie, you need to finish your vegetables.
Kendra
What?
Alexis
Oh, wait, wait, wait.
Mark
Can I get a joke?
Alexis
Yes.
Mark
That's gotta be.
Jeffrey
Did you laugh?
Mark
I mean, I laughed and then she says, I'm serious. Wow. So I ate my vegetables while she washed me. And I was. It was embarrassing, though.
Alexis
Well, you are a stronger boy because you did eat those veggies.
Jeffrey
Let me ask you this. At the end of the night, how did you and Kendra leave things? Like, was it romantic at all?
Mark
We walked out, we had a huge hug. I told her I was going to text her.
Alexis
Yeah.
Mark
She was like, you better. It's important to keep promises.
Alexis
Oh.
Jeffrey
It'S kind of preachy. Yeah. In, like, teacher babysitter mode again. Yeah. How long ago was this?
Mark
It was just only a few nights ago, so.
Kendra
Okay.
Alexis
So what do you want our advice with? Because that's, like, the awkward thing is. Right, we give advice.
Mark
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.
Alexis
I'm not a kid anymore.
Jeffrey
Go on a serious date with him, I think.
Alexis
Stomp your feet and say, this is not fair, Brooke.
Jeffrey
No, really.
Alexis
Like, he wants our help. I get it. I get it.
Jeffrey
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.
Alexis
Ex babysitter. X not.
Jeffrey
That's a fair point. You're not still paying her, right?
Mark
No. No, I'm not paying.
Jeffrey
It's like, no wonder. All right, we're going to do it with your awkward Tuesday phone call next. It's awkward.
Alexis
It's Tuesday.
Jeffrey
It's awkward Tuesday phone call. 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 veggies so you can grow up to be a big boy.
Alexis
You know what's weird is I think that there's some people that are into that.
Kendra
Yeah.
Alexis
Thankfully, our listener isn't.
Jeffrey
It did actually happen, though, to one of our listeners named Marky. Well, I'm calling him Marky because the person 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. But does she see him that way? Well, she kept calling him Marky?
Alexis
Yeah, probably not.
Jeffrey
It's not a good sign.
Alexis
Not yet.
Jeffrey
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
Brooke?
Alexis
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. And 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.
Brooke
Okay.
Jeffrey
You ready to drop your body count on her?
Alexis
I didn't mean that.
Jeffrey
What do you think?
Mark
I don't want her to get, you know, jealous or anything.
Alexis
Yes, you do. You do want her to be jealous. Yeah.
Mark
Yeah, I do.
Alexis
Yes. You could just say like when I was traveling Europe with Candace. God, you know?
Jeffrey
Yeah, stuff like that. And traveling to Europe is a very.
Alexis
She was great, but she didn't really work out.
Jeffrey
You know, she sound like a snobby boyfriend.
Alexis
Just trying to make him sound rich, adult and well traveled.
Jeffrey
Jeffrey, those are good things to remember. Act rich, act grown up and act well traveled.
Mark
I think I can do that.
Announcer
Okay.
Jeffrey
All right. And we're here for you, brother. We all believe in you, buddy. We're gonna call Kendra for you, your ex babysitter, and let you try and make this thing official with her. Get a real date.
Alexis
Okay.
Jeffrey
Sorry, not official was the wrong word.
Mark
Yeah.
Jeffrey
Should you call her Ken? Is that more of like an adult? No, I think just. Just go. Respectful. Okay. Manly. We're here for you. Okay. I'm down the number right now. Here we go.
Kendra
Hello?
Mark
Kendra, it's me. Who is this? It's. It's Mark.
Kendra
Oh, my God. Marky.
Mark
Hi.
Kendra
I must not have saved your number right in my phone.
Alexis
I don't.
Kendra
Didn't pop up with this number. How are you?
Mark
I'm great. How are you?
Kendra
I'm good. I'm good. I'm just kind of hanging out. I just ordered some food, waiting for it to show up. Cool.
Mark
I love food. Food's great.
Kendra
I know. I remember that. You do.
Mark
I know you? Yeah. I kind of need to admit something to you.
Kendra
Okay.
Mark
So when I was 9, I kind of had a crush on you.
Kendra
Oh, my God. Tell me something I don't know.
Mark
Wait, you knew that?
Kendra
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, so.
Mark
Oh, my God, I totally forgot about that. But it was kind of cute anyway. Oh, you said that was cute?
Kendra
Yeah, it was so cute.
Mark
Anyway, did you have a good time the other night when we hung out?
Kendra
Yeah, I did. It was really nice. But it was, like, a little late.
Mark
What do you mean?
Kendra
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.
Mark
Well, I'm older now, so I don't really have a bedtime.
Kendra
Well, I know that, but, like, everybody needs their sleep. Even, like, big boys like you.
Mark
Yeah, I mean, I guess that's true, but I should probably listen to you more.
Kendra
I mean, you should. How was the meeting?
Mark
It was good. I mean, I think I made a good impression.
Kendra
Did you brush your teeth before?
Mark
Yeah. Look, look, here's the conflict that I have, and I'm just gonna be honest. I don't know if you see it, but I feel like there's, like, an attraction between us.
Kendra
I mean, yeah, I feel that.
Mark
Right? But, like, you've heard of people being, like, friend zoned before. I feel like I'm being nanny zones.
Kendra
Wait, what are you talking about?
Mark
You know, like, the brush your teeth comment. And on the date, you made me eat vegetables. This is stuff you would have said to me as a kid. And I don't want the potential of this to have some the same mammy kid power structure.
Kendra
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.
Mark
Okay. Yeah, that sounds good.
Kendra
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 ones. And the best part is, if you stay out past 11, I won't make you go home.
Alexis
Oh.
Mark
Oh, wow.
Kendra
Yeah. Yeah, you can stay over and I'll read you a bedtime story and tuck you in.
Alexis
Come on.
Jeffrey
This is brutal.
Alexis
Is she joking?
Jeffrey
Oh, my God.
Mark
Hello?
Jeffrey
Hey, Kendra. Hey.
Kendra
Who. Who is this?
Jeffrey
Surprise.
Alexis
Kendra.
Jeffrey
Kendra, you're on the radio right now with a show called Brooke and Jeffrey in the Morning.
Kendra
Huh?
Jeffrey
Brooke and Jeffrey. 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.
Alexis
Conversation with you about, like, dating, not about bedtime stories.
Kendra
Mark, what's happening right now? I don't like this.
Alexis
Oh, sorry.
Jeffrey
We don't really like it either, to be honest. Mark, do you want to explain?
Mark
So listen, I have feelings for you and I want you to see me as an equal because I really. I really see us being a thing.
Jeffrey
Do you feel like there's a connection there? Maybe, Kendra? Like a grown up, mature, romantic connection?
Kendra
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.
Jeffrey
That's what girl said.
Alexis
But listen to his voice. That's a man voice. And you're sitting across from him at the dinner table. He's got facial hair.
Jeffrey
Give him a chance to say something manly right now, Mark. Go ahead.
Mark
I mean, I do have facial hair. I mean, come on.
Alexis
Wow.
Jeffrey
I'm certainly convinced.
Kendra
Yeah, I just think he's adorable, but I just can't. Like, he's just Marky. I don't know. He's Marky and I can't.
Alexis
Okay, but you admitted. You admitted there was an attraction. When you two were talking, I heard you. You said. Yeah, I get it.
Jeffrey
Yeah, but then she told him to make sure he brushes his teeth every night. So like equals each other out. Do you. Do you realize that you're doing that, Kendra? Or. Yeah. Do you even know that I.
Kendra
It's habit. What do you want from me? It's habit with just him, right?
Jeffrey
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.
Alexis
Yeah, or Mark just wants his girlfriend to do everything for him. You know, like changes.
Jeffrey
How are you putting Mark down?
Alexis
I mean, he obviously kind of likes it because like, how could anyone listen to that and still be attracted?
Mark
I mean, I like when she does that too. I like when she reads me bedtime stories.
Jeffrey
Maybe he does like it, bro. Maybe the tickle monster can come out again and be like. The grown up tickle monster. No. 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?
Mark
I mean, maybe in another lifetime, if she. If she wasn't my babysitter, there could have been something.
Alexis
Okay, so you're giving up? You're letting it go. Maybe you guys can be friends or you can stay nanny zoned or is.
Jeffrey
Trying to find a time machine to go back and cancel her as the babysitter.
Mark
I'm working on it. And I'm starting tonight Kendra, are you.
Jeffrey
Okay just staying friends with Mark?
Kendra
Yeah, I think that's fine for me.
Jeffrey
Okay. You should still probably try to not do the babysitting terms around him a lot to just be like normal adult friends.
Alexis
Did you not hear him? He likes it. Yeah.
Jeffrey
Stay in friends, stay in touch and see what happens and maybe something will naturally develop from there.
Kendra
Okay.
Alexis
What's your favorite bedtime story, Mark?
Mark
Oh, I got Thumbelina.
Jeffrey
You are a man.
Alexis
Brooke and Jeffrey in the Morning there's.
Brooke
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Alexis
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 revisit of it from what 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, pick up their stuff off.
Jeffrey
The floor, fix their mistakes.
Alexis
Yeah, exactly. Be all cute and babysitter y.
Jeffrey
Good life.
Alexis
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 gonna 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 brookeandjeffery.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 78592 or always follow our socials at brookeandjeffrey. And thanks for being here one more time. Happy Veterans Day and stay safe. We'll see you tomorrow.
Brooke
There's no championship league for small business owners, but if there was, you'd be at the top of the standings. Because going pro with Lenovo Pro means you've got the winning formation. One on one advice. IT solutions and customized hardware powered by Intel Core Ultra processors help you stay ahead of the competition. Business goes pro with Lenovo Pro. Sign up for free@lenovo.com Pro Lenovo.
Mark
Lenovo.
Jeffrey
What a matchup we got, y'.
Mark
All.
Jeffrey
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Alexis
Mmm.
Jeffrey
Yeah, that taste always hits the right note. Just like the band at halftime. And just like that, we're back at it. Passionate fans, school colors everywhere. And in ice cold Coca Cola. That's a winning combo. No matter the sport, no matter the yard. Everybody knows fan work is thirsty work. So grab a Coca Cola and keep that HBCU pride going.
Alexis
You know what a girl's best friend is?
Kendra
Not diamonds.
Brooke
Her lawyers.
Jeffrey
From executive producer Ryan Murphy comes a fiery new legal drama.
Alexis
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Jeffrey
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Announcer
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Alexis
Showtime, ladies.
Announcer
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Alexis
Room like a storm no one saw coming.
Jeffrey
Hulu Original Series All's Fair now streaming on Hulu and Hulu on Disney for bundle subscribers. Terms apply.
Alexis
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Date: November 11, 2025
Host: iHeartPodcasts
Episode Theme: When your childhood nanny can’t stop seeing you as a kid, even as an adult.
This episode of Brooke and Jeffrey’s “Awkward Tuesday Phone Call” features Mark, a young man who has reconnected with his childhood babysitter, Kendra. After a surprisingly flirtatious catch-up dinner, Mark feels “nanny zoned”—Kendra sees him more as the little boy she used to babysit than a potential romantic partner. The hosts try to help Mark navigate this bizarre, comical situation to confess his adult feelings and see if a romantic spark is possible.
“I just yelled, ‘Kendra?’ … She was just like, ‘Who are you?’” — Mark ([06:08])
“She was twirling her hair, she was laughing. It was amazing.” — Mark ([09:05])
“I ate my vegetables while she watched. It was embarrassing.” — Mark ([09:45])
“I just need advice... Just to say that I’m grown and... can be with you.” — Mark ([10:28])
“You have to switch her mindset... I think you should bring up exes.” — Brooke ([12:15])
“When I was 9, I kind of had a crush on you.” — Mark ([14:33])
“Tell me something I don’t know... I kind of had a feeling. ...when my boyfriend stopped by that one time you called 911…” — Kendra ([14:41])
“I felt like I was keeping you up past your bedtime.” — Kendra ([15:23]) “Everybody needs their sleep, even big boys like you.” — Kendra ([15:39])
"I feel like I’m being nanny zoned... This is stuff you would have said to me as a kid. I don’t want the potential of this to have the same nanny-kid power structure.” — Mark ([16:19])
"How about you come over to my place this Friday, I'll make you dinner and I won't make you eat vegetables. ...you can stay over ...and I'll read you a bedtime story and tuck you in." — Kendra ([17:03])
“Do you feel like there’s a connection there? Maybe, Kendra? Like a grown up, mature, romantic connection?” — Jeffrey ([18:19])
“It’s really hard to shake the image I have of you as a little boy. ...he’s just Marky and I can’t.” — Kendra ([18:26], [19:00])
“But listen to his voice... that’s a man voice. ...He’s got facial hair.” — Alexis ([18:41]) “I mean, I do have facial hair. I mean, come on.” — Mark ([18:52])
“Maybe you guys can be friends or you can stay nanny zoned…” — Alexis ([20:19]) “Yeah, I think that’s fine for me.” — Kendra, confirming friendship is best ([20:36])
"Can you put on my footy pajamas?" — Mark ([06:36])
"When I was 9, I kind of had a crush on you." — Mark ([14:33])
"Everybody needs their sleep, even like big boys like you." — Kendra ([15:39])
“I feel like I’m being nanny zoned. ...This is stuff you would have said to me as a kid.” — Mark ([16:19])
“You can stay over and I'll read you a bedtime story and tuck you in.” — Kendra ([17:19])
“Maybe the tickle monster can come out again and be like… the grown up tickle monster.” — Jeffrey ([19:57])
“I like when she reads me bedtime stories.” — Mark ([19:52])
“Nanny Zoned” delivers outsized laughs and a healthy dose of empathy, proving just how hard it can be to escape outgrown roles from childhood. Despite flirtation and chemistry, the power dynamic is too entrenched for romance (for now), and Mark and Kendra settle for friendship—with a wink toward bedtime stories and “big boy” jokes. The hosts deftly balance humor with genuine support, making this an episode both entertaining and surprisingly sweet for listeners.
Memorable Sign-off:
“What’s your favorite bedtime story, Mark?”
“Oh, I got Thumbelina.” ([20:54])