Brooke and Jeffrey: Second Date Update - Awkward Tuesday: Stop That Ugly Duckling

Episode Date: November 25, 2025

Is it ever okay for a person to meddle in their friends love life? It doesn’t matter because we’re doing it anyway before one listener's friend can go on a blind date!See omnystudio.com/listener for privacy information.

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I'm Evan Ratliff here with a story of entrepreneurship in the AI age. Listen as I attempt to build a real startup run by fake people. Check out the second season of my podcast, Shell Game, on the IHeart Radio app or wherever you get your podcasts. On this week's episode of next chapter, I, T.D. Jake, sit down with Denzel Washington, a two-time Academy Award-winning actor and cultural icon for a conversation about change, identity, and the moment everything shifted. I mean, I don't take any credit for it. It's nothing I did as special, you know, did knock down a few pegs and recognized. it, but I just didn't put me first.

I just put God first, and he's carried me. Whether you're rebuilding, reimagining, or just trying to hold it together, this one will speak to you. Listen to the next chapter podcast on the I Heart Radio app, Apple Podcast, or wherever you get your podcast, new episodes drop weekly. Don't miss you. one of them. On the podcast Health Stuff, we are tackling all the health questions that keep you up at night. I'm Dr. Priyankawali, a double board certified physician. And I'm

Hurricane Dabolu, 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 iHeart Radio app, Apple Podcasts, or wherever you get your podcasts. 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 IHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Oh, there's going to be so many awkward conversations this week because it's Thanksgiving week. Yay!

Welcome to the Sunday Day podcast. We have a classic awkward Tuesday phone call for your enjoyment, maybe your preparation on how you're going to handle your own awkward conversations coming up. Oh, yeah. Or what not to do. Yeah, sure. All of the things. All the things are important. And what's most important is you and being here and listening.

We'd love to read your comments. Yes, we love it. And Killa Kim said, Oh my gosh, Kim from Queens, New York City, sending love to y'all. You guys seriously help me keep my day moving. Also, Jose is my brother's name. And he wanted me to give a shout out

to all the Jose's in the world. Yay, all the Jose's, stand up. And Joseph's, because you count too. It's really hard not to like someone named Jose. I've never met anyone I didn't like name Jose. It wouldn't be controversial. I feel like there's a lot of people that don't like Jose.

No, I love you. You're the best. All right. Here we go. Awkward Tuesday starts now. It happens in movies and reality TV shows all the time. What's up? People meddling in the dating lives of their other friends.

Oh, yeah. It happens in real life all the time. Is it okay to do that? Because if it is, and Brooke, after this is over, Alexis says she has some thoughts on your current situation ship with the guy that you live with. Just if you're open to them. It's a marriage.

She's putting labels on it already. But Brooks life aside, we are about to do some love life meddling today. Because one of our listeners swears she has a really, really good reason she needs to stop her close friend from going out on a blind date. And she wants our help to block it. I don't know. I know you're skeptical, but you might be on her side when you hear why in a brand-end. new Awkward Tuesday phone call next. It's awkward. It's Tuesday.

It's awkward Tuesday phone call. As an adult, going out with high schoolers, bad idea. Terrible. Where did you go? Like, couldn't get worse. That's what I said. Bad idea. You said it's so nonchalantly, though. What about going out with people you knew from back when you were in high school? Is that okay?

Yeah, of course, Jeff. That is totally different. Well, one of our listeners, Carrie, says absolutely not. What? Terrible, horrible idea to date your old high school classmate. And apparently, that's why she needs our help today. Carrie, welcome to the show. Hi, thanks. Sounds like high school drama still following you right into adulthood, huh?

Yeah, it's weird. And let me just, let me just specify. I'm not opposed to other people dating people that they knew in high school, but not my friend Justin. Oh, just Justin. So it's not even other people from your high school. It's just Justin. This is a special case. What's going on with Justin?

Okay. So Justin and our friends. We've been friends, like you said, since high school. We're now in our late 20s. Okay. And the other day, he told me, hey, I'm going on a date. It's crazy. You can't even imagine who I'm going on date with.

And it turns out to be this girl we knew in high school, Catalina Vibedin. Ooh. Not Catalina. Trauma. Why is that that? We don't know anything about her. What's with Catalina? Well, she was the awkward girl. She was, like, kind of, like, science geeky.

Are you still bullying the awkward girl in high school? Are we over that? No, no, no, no. Like, she knew she was awkward. She was, like, the awkward, smart, science-y girl. Listen, I was a little awkward. It's just I was able to play it off better than she was. I mean, Brooke, you must have had somebody at your school who was, like, bad at handling their meth.

And that was the awkward Yeah, why aren't you better at chemistry? That was our chemistry class, I mean, yeah, in the trailer. So that's bad news that your friend might be going out with your awkward kid from high school? Well, I'm going to give you a little more backstory before I tell you why that's bad. Okay, go ahead. He got hooked up through another friend of ours from high school who was connected. She had a crush on him from high school, blah, blah, blah.

So they, like, got each other's phone numbers. talking, he still has no clue what she looks like. No one could find her on social media. Okay. I was curious and I discovered that her parents got divorced and she took her mom's maiden name. So I found her on social media under her maiden name. Okay. Oh, good snooping. So why are you doing all this work? He's just going out on a date. Because she's gorgeous. I mean, she's like Scarlett Johansson Bert Nett. Oh, good for her. That's great.

That's amazing. Why is it bad? Yeah, generally that is great for her. I'm happy for her. Are you, though? But here's the thing, guys. I don't want him to know, but I'm I kind of have a thing for Justin. We've known

each other for so long. It just a few years ago started, and I'm not ready for him to know. I need more time. But if he gets put in front of this girl, I have no chance. And this is why it was good

being nerdy or awkward in high school, because she actually has probably a cool personality, too. Oh, God. You're not helping Jose. I mean, you sounded petty, and I get why. You're jealous. But you admit it. That all makes sense now. Yeah, I just, I don't think I could compete. Okay, you don't want Justin going out

with the now pretty girl. Is Justin the type of guy that's into pretty women? Or is he... Is there any guy that's not into pretty women? Well, sorry, no. Please, I'd prefer an ugly, stupid woman. So wait, what do you want to do, though? Do you just finally want to tell him how you feel before he goes out with her?

No, I'm not ready for that. I need more time. But I just need to figure out how to convince him not to go out with her. Oh. So that you could just stay in this, like, nothing. Friend zone, but I have a crush on you. I mean, this is tricky. Like, Alexis, what do you think about this situation trying to stop your friend from going

out with somebody hotter? Um, I don't know if it's the nicest thing to do, but I would do it probably myself, too. Yeah. But what did you just tell the guy that you like him? Yeah. Like, you're in your late 20s at this point. You've got to shoot your shot. Okay.

How many decades have you been waiting? Maybe she's waiting until he gets married and then divorced. So that his confidence is so low, he'll settle for anything. That could be a good strategy. Oh, yeah. What if he likes you too and you guys are both just living in this world of not telling each other? Well, I haven't, I mean, that's kind of why I feel like I need a little more time. Like, I haven't really tried to look for the signals and stuff like that.

This is like lighting the fire. Now you realize, uh-oh, he's not going to be single forever. So he didn't fully like him until he found somebody hotter and smarter. Yeah. He doesn't high school. Yeah. Listen, let me say. Like, he dated other girls and this is going to make me sound really superficial.

But they didn't feel like competition to me. And so I don't think that I really realized it until. like a woman came along that would totally blow me out of the water. Nice. Now I wouldn't have a chance. Okay. Now the gloves are coming off. Yeah. All right. She's out of your league. What do you want our help doing then? Like, are we calling Justin

and telling him not to go out with her? Yeah, yeah. This is convincing Justin not to go out with her. Without you telling him that you like him. Exactly. Okay. So ruin your friend's chances enough. That's our job. To come up with a way to convince Justin to cancel his date with the now gorgeous looking Catalina

without letting her know that she's gorgeous. Okay, listen, you don't have to keep rubbing in how gorgeous she is. I get that. I obviously know what I've seen her. Okay. I don't think you can be named Catalina without being absolutely dropped. It's a really pretty. She's not gorgeous.

She's just stunning. And we're going to convince Justin to not go out with her. Could be bad stunning. We'll give you a little bit of advice and let you make your awkward, Tuesday phone call right after this. It's awkward. It's Tuesday. It's awkward Tuesday phone call.

If you're just joining us for this awkward Tuesday phone call, it's a story that really speaks to my soul. Does it? Awkward kid in high school who was maybe a little shy, did school plays and chess club, and during field trips, he would crawl underneath the seats on the bus and then pop up from below and say, guess who? They were completely.

We were completely undatable back then. But a few years go by, and now they've matured mentally and physically. I feel like you still do that bus thing if you were on a bus together. And that ugly duckling has grown into an undeniable bubbling cauldron of raw desire. Oh, that's a hot duckling. It's undeniable. And our listener, Carrie, she's not that person. No. She's actually kind of threatened by that person.

That's why she wants our help to stop her friend Justin from going out with the awkward girl from high school who's now blossomed into the female me. Now, why? Why don't you want to do that? Because, I mean, secretly she does have some feelings for Justin, but isn't ready to tell him that. Carrie, your goal is to convince him to not go out with her, right? Yeah, exactly. All right. But how are we going to do that?

I think Jose has an idea for you. Yeah, so look, we kind of want him to just naturally not like her anymore and pass up on the date. We have to do the old-fashioned high school trick and start a rumor about her. Because you know what's that? I heard she made out with her brother. And it wasn't even

that long ago. Are you the one? That's what I heard. And the brother's review of the kiss was not good either. It was not even a good kisser, Jack. That's what I heard from her brother. You two are the words. Oh, well, I mean, I think it would be effective, but that's a little mean. Because that's gross.

A little mean. Exactly. You're going to have to play a little bit dirty to get what you want here. Come on. What do you think, bro? Okay, listen, I don't think it's about putting the hot girl down. I think it's about building him up. He doesn't even know this girl's hot.

All you need to say is, listen, you are so hot. You're so beyond blind dates. Like, you're so above that. Then you tell him, I have the most gorgeous friend ever that I have to set you. you up with. She's funny. She's everything you've ever been looking for. I like that. I can't tell you who it is. It's Brooke. No. She wants to go out with your guy.

Oh God, more competition. And then you drop it on him later when you're ready that the mysterious perfect woman is you. Oh, wow. Wow. You want to give him a puzzle to solve. Like, what if I like meet him at a restaurant? I'm the one

that walked in and then I have to deal with the potential rejection of him being like, what are you doing here? All guy friends want to sleep with their girlfriend. Wait a minute. There's Brooks' advice, just sleep around. All right. That's the real advice.

Let's just give him a call, and we're going to let you make your awkward Tuesday phone call and try and convince him not to go out on his date. Yeah, we're hot girl. We're here for you, all right? We're down on the number right now. Okay. Good luck.

Hello? Hey, how's it going? Hey, Carabera, what's going on? Not much, how are you doing? I'm just killing some time before I have to go to work. What's up? Oh, just, you know, just on the chat, say hey. Oh, did Billy get a hold of you?

Yeah, I assume you're talking about the blind date that I mentioned the other day. No, no, no, I just meant about. hanging out next weekend. Oh, yeah, we can definitely do that. But now that you mention it, are you still doing that? You're still going to hang out? I think so. I mean, I'm very curious.

I mean, he mentioned that Catalina's doing all kinds of neat things right now, and I don't know, I just figured what the hell. Yeah, that's cool. You know, this is kind of weird, but I kind of heard something really random recently about her, like a rumor. A rumor?

What are you talking about? Um, okay, so I heard that she was at a party, like a month ago and kind of made out with their brother. What? Where did you hear this? Yeah, I don't know, just randomly. Randomly, what? Yeah, I don't, I don't know. But, like, blindings are really weird, aren't they?

Like, are you sure you really want to know blind date? I mean, you're so cool and, like, you're good-looking, and you're, you're good-looking, and you're really want to like go through the awkwardness of a blind date and all that well I mean it's just a blind date I'm not going to marry the girl just figured meet up for a cup of coffee and just

talk you know you know what how about this like I have a friend she's awesome she's great she's super hot um what if I set you up with her and set you um you want to set me up on a blind date no it's not a blind date because

I've seen her and I know her well but like Helena, no one has seen her. None of us have, like, talked to her in a long time. I mean, I guess you guys have been texting that's something, but, like, you know, I don't know. This might be better. Well, tell me about this friend of yours. I mean, she's great. You know, like, I think you'd really like her.

You would totally get along. I know you guys have a lot in common. And I know 100% that she does not make out with her brother at party. I certainly hope not I certainly hope not um what I think we're laughing too hard

Hey Justin Hey Justin What are you at a party or something What's all that lounge of life? Yeah This chick's making out with her brother Yeah what the heck I think we're kind of a party

We're a morning We're a morning radio show Justin called Brooke and Jeffrey in the morning Why did you go with Jose's advice? I thought that was solid, though. I was kind of kidding. I am so lost right now. What the hell?

You're on the radio right now, man. Okay. We're doing a segment called an awkward Tuesday phone call. Carrie reached out wanting a little bit of help to talk to you about your upcoming blind date with this girl. We're not so unsure it's a good idea for you to go out with her. Just looking out for you. Because of the brother thing?

No. I mean, that's just one of many, many reasons. Rumors. Because Carrie does have someone really cool that she wants to set you up with. Carrie, what exactly is going on here? This is a little weird. Okay, listen, Justin, I haven't been super honest with you. I have not been the best friend in the sense that I discovered Catalina's social media.

You found her social media? What does she look like? that sound is probably all you need to know new rumor coming in I hear she looks like Oscar the Grouch like a Muppet whatever who cares what she looks like you're not the type of guy that bases a relationship on looks are you Justin like I said at the very least we would just

get a cup of coffee and catch up a little bit it doesn't mean we go on the second date or anything yeah starts with coffee drinking next thing you know brothers are kissing what I don't feel like any of this is helping, you guys. Yes, because you need to do the thing. I mean, okay, okay, I think this has become too much of an awkward quagmire for me

not to say the thing that I have been trying to not say. Yay! Say the thing, Carrie. What thing? I still don't know what the hell is going on here. We have such a good connection, and I just kind of wondering if, like, maybe there's a mutual attraction beyond friendship between us. There it is.

Hmm. What do you think? So you drag me through a whole radio show to finally spill the beams here, Carabair? Maybe. She was nervous. Obviously, I realize now this is not the right way to do it. I just thought that, like, maybe we needed some more organic time to let it evolve.

But then I saw Catalina and I would have no chance if you met her. Don't say that. That is not true. Justin, don't you think that Carrie is amazing? Could you see something more between you two? Have you ever pictured me? I wouldn't have been friends with her for the last decade if I didn't think she was amazing. We've talked about this.

You always, you know, undersell yourself. See? And to be perfectly honest, yeah, I think you kind of went about this the wrong way. So finally getting this out in the open. but, hey, might make a great story for our first date. Oh, wait a second. So, Justin, you're into the idea of maybe going out with Carrie here? Not a friend date, like a romantic date.

I wouldn't mind one bit. Yay! Really? It sounds, Justin, like you have liked her for a long time. To be perfectly honest, I have, yeah. Oh, my God. I was afraid that I was in the friend zone, but, you know, I just kind of, I just, you know, like you said, We've been friends for a long time.

I didn't know how you felt, so I didn't want to, like, ruin a good thing. But, um, yeah. Both kind of been idiots. I mean, in all of our years here, I never thought Brooke's advice of just sleep with all of your friends. What's the worst that could happen? Would actually work.

Yay! Yeah, we got to listen to Brooke. Good job, Brooke. Oh, so you're going to find out. Brooke and Jeffrey in the morning. Okay, friends, real talk. You are working. the weight. We've all been there, giving our energy to connections that didn't honor ours and watching

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respect your boundaries, your energy, and your time. Thinking about dating again, take this as your sign. Start your love story on Bumble. Hi, Kyle. Could you draw up a quick document with the basic business plan? Just one page as a Google Doc and send me the link. Thanks. Hey, just finished drawing up that quick one page business plan for you. Here's the link. But there was no link. There was no business plan. It's not his fault. I hadn't programmed Kyle to be able to do that yet. My name is Evan Ratliff. I decided to create Kyle, my AI co-founder, after hearing a lot of stuff like this from OpenAI CEO Sam Aldman. There's this betting pool for the first year that there's a one-person billion dollar company, which would have been like unimaginable without AI and now

will happen. I got to thinking, could I be that one person? I'd made AI agents before for my award-winning podcast, Shell Game. This season on Shell Game, I'm trying to build a real company with a real product run by fake people. Oh, hey, Evan. Good to have you join us. I found some really interesting data on adoption rates for AI agents and small to medium businesses. Listen to Shell Game on the IHeart Radio app or wherever you get your podcasts. Actually, I think that one was really cute. Yeah. I want to update from them.

I mean, a lot of drama to just ask someone out that you've known for a long time. Yeah. It's true. Just telling your closest friend, hey, I have a crush on you. Crossing that border is hard. Just saying, can I kiss you? That's what I'm into. Yeah, you're straight for it.

After 10 years of friendship, hey, Bill. Yeah, Bill. Did I kiss you? The first time I kissed one of my best friends. I was like 16, right? And it was like my second kiss I'd ever had. And the first one went horribly wrong. So this one was really good and I got so excited.

I high-fived him afterwards. Oh, that's so Chris. And I was like, this was amazing. Oh my gosh. He goes, Brooke, don't ever do that again. Oh, okay. At least you're close enough he could tell you that. He's still one of my best buddies.

Let's go back to this couple, please. I think what this is, is if you have a crush, just tell them, all right? There's nothing to lose. There's a lot to lose, a friendship, Brooke. And then when that backfires, call us, okay? And we'll do another awkward Tuesday for you. Or you can always submit on our website, it's brink and jeffrey.com. And always follow us on socials at Brick and Jeffrey.

Hi, Kyle. Could you draw up a quick document with the basic business plan? Just one page as a Google Doc and send me the link. Thanks. Hey, just finished drawing up that quick one page business plan for you. Here's the link. But there was no link. There was no business plan. I hadn't programmed Kyle to be able to do that yet. I'm Evan Ratliff here with a story of entrepreneurship in the AI age. Listen as I attempt to build a real startup run by fake people. Check out the second season of my podcast, Shell Game, on the IHeart Radio app or wherever to get your podcasts. On this week's episode of next chapter, I, T.D. Jake, sit down with Denzel Washington, a two-time Academy Award-winning actor and cultural icon for a conversation about change,

identity, and the moment everything shifted. I mean, I don't take any credit for it. It's nothing I did as special, you know, I didn't knock down a few pegs and recognize it, but I just didn't put me first. I just put God first, and he's carried me. Whether you're rebuilding, reimagining, or just trying to hold it together, this one will speak to you.

Listen to the next chapter podcast on the I Heart Radio app, Apple Podcast, or wherever you get your podcast. new episodes drop weekly. Don't miss one of them. On the podcast Health Stuff, we are tackling all the health questions that keep you up at night. I'm Dr. Priyankawali, a double board certified physician.

And I'm Hurricane Dibolu, 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. 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 there, Dr. Jesse Mills here. I'm the director of the men's clinic at UCLA, and I want to tell you about my new podcast called The Mail Room. And I'm Jordan, the show's producer. And like most guys, I haven't been to the doctor in way too long. I'll be asking the questions we probably should be asking, but aren't. Every week, we're breaking down the world of men's health from testosterone and fitness to diets and fertility. We'll talk science without the jargon and get your real answers to the stuff you actually wonder about. So check out the mailroom on the iHeart radio app, Apple Podcasts, or wherever you get your favorite shows.