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Brooke and Jeffrey

Awkward Tuesday: Stop That Ugly Duckling

25 Nov 2025

Transcription

Chapter 1: Is it okay to meddle in a friend's love life?

0.233 - 27.591 Unknown

What are the cycles fathers pass down that sons are left to heal? What if being a man wasn't about holding it all together, but learning how to let go? This is a space where men speak truth and find the power to heal and transform. I'm Mike Della Rocha. Welcome to Sacred Lessons. Listen to Sacred Lessons on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

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30.17 - 51.113 Alexis

Dr. Laurie Santos from the Happiness Lab here. It's the season of giving, and this year my podcast, The Happiness Lab, is partnering with GiveDirectly, a nonprofit that provides people in extreme poverty with the cash they need as part of the Pods Fight Poverty campaign. Our goal this year is to raise $1 million, which will bring over 700 families out of extreme poverty.

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51.153 - 73.699 Alexis

Your donation will put cash directly in the hands of these families in need. And they'll get to decide how to use it, whether that's school transportation, purchasing livestock, or starting a business. Plus, if you're a first-time donor, your gift will be matched by giving multiplier, which means more money for those in need. Visit givedirectly.org slash happiness lab to learn more and to donate.

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73.72 - 76.663 Alexis

That's givedirectly.org slash happiness lab.

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The social media trend that's landing some Gen Zers in jail. The progressive media darling whose public meltdown got her fired. And the massive TikTok boycott against Target that actually makes no sense. You won't hear about these online stories in the mainstream media.

91.107 - 106.994 Unknown

But you can keep up with them and all the other entertaining and outrageous things happening online, in media, and in politics with the Brad vs. Everyone podcast. Listen to the Brad vs. Everyone podcast on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

107.014 - 111.843 Jeffrey

I didn't really have an interest in being on air. I kind of was up there to just try and infiltrate the building.

112.023 - 123.103 Unknown

From the underground clubs that shaped global music to the pastors and creatives who built the cultural empire, the Atlanta Ears podcast uncovers the stories behind one of the most influential cities in the world.

123.083 - 126.808 Brooke

The thing I love about Atlanta is that it's a city of hustlers, man.

Chapter 2: What reasons does Carrie have for stopping her friend from dating?

126.928 - 145.412 Unknown

Each episode explores a different chapter of Atlanta's rise, featuring conversations with Ludacris, Will Packer, Pastor Jamal Bryant, DJ Drama, and more. The full series is available to listen to now. Listen to Atlanta Ears on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

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the show was ahead of its time to represent a Black family in ways the television hadn't shown before. Exactly. It's Telma Hopkins, also known as Aunt Rachel. And I'm Kelly Williams, or Laura Winslow. On our podcast, Welcome to the Family with Telma and Kelly, we're re-watching every episode of Family Matters. We'll share behind-the-scenes stories about making the show.

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Yeah, we'll even bring in some special guests to spill some tea. Listen to Welcome to the Family with Telma and Kelly on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

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176.476 - 185.73 Jose

It happens in movies and reality TV shows all the time. What's that? People meddling in the dating lives of their other friends. Oh, yeah.

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185.75 - 187.153 Alexis

That happens in real life all the time.

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Is it okay to do that? Because if it is, then Brooke, after this is over, Alexa says she has some thoughts on your current situationship with the guy that you live with.

199.372 - 204.66 Alexis

Just if you're open to them. It's a marriage, Alexa. She's putting labels on it already.

204.64 - 233.096 Jose

But Brooke's 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 new Awkward Tuesday phone call.

Chapter 3: What is the backstory of the friend Justin and the girl Catalina?

233.117 - 261.398 Jose

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

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261.418 - 264.301 Jose

Well, one of our listeners, Carrie, says absolutely not.

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264.521 - 264.822 Brooke

What?

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264.842 - 274.152 Jose

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.

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274.604 - 275.385 Jeffrey

Hi, thanks.

275.726 - 291.352 Jose

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.

Chapter 4: How does Carrie feel about Justin's potential date with Catalina?

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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 Jess and I are 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 a date with.

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And it turns out to be this girl we knew in high school, Catalina Valdez.

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321.297 - 322.82 Alexis

Not Catalina.

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Trauma.

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323.802 - 324.303 Alexis

Why is that bad?

324.323 - 336.488 Jose

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.

338.527 - 364.939 Jose

awkward she was like the awkward smart sciencey 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 i mean that was our chemistry class i mean yeah in the trailer so is that that's bad news that your friend might be going out with your awkward kid from high school

365.459 - 370.808 Jose

Well, I'm going to give you a little more backstory before I tell you why that's bad. Okay.

Chapter 5: What strategies are discussed to prevent Justin from going on the date?

371.209 - 394.497 Jose

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. We're talking. He still has no clue what she looks like. No one could find her on social media. Well, I was curious. And I discovered that her parents got divorced and she took her mom's maiden name.

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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, Burton's net. 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.

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419.408 - 428.107 Jose

I don't want him to know, but I kind of have a thing for Justin. We've known each other for so long.

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Chapter 6: What rumors are suggested to deter Justin from dating Catalina?

428.167 - 455.115 Jose

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, 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.

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455.135 - 477.448 Jose

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? Is there any guy that's not into pretty women? 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?

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477.468 - 497.998 Jose

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. 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?

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499.97 - 504.859 Jose

The nicest thing to do, but I would do it probably myself, too. Yeah.

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Chapter 7: How do Carrie and Justin's feelings for each other evolve during the call?

504.879 - 521.708 Jose

But wouldn't 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. I mean, 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.

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521.688 - 538.111 Jose

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.

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538.131 - 563.387 Jose

So you didn't fully like him until he found somebody hotter and smarter. Yeah, listen, let me say, like, he's 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.

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Now the gloves are coming off now that this is happening. 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?

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572.701 - 598.358 Jose

yeah yeah this is convincing justin not to go out with her without you telling him that you like him exactly okay 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 uh Okay, listen, you don't have to keep rubbing in how gorgeous she is.

Chapter 8: What conclusions do Carrie and Justin reach by the end of the episode?

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I get that. I obviously know it. I've seen her.

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601.082 - 601.722 Brooke

Okay.

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601.742 - 606.449 Jose

I don't think you can be named Catalina without being absolutely drop dead gorgeous.

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606.469 - 607.01 Brooke

It's really pretty.

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607.17 - 612.157 Jose

She's not gorgeous. She's just stunning. And we're going to convince Justin to not go out with her.

612.297 - 614.42 Brooke

Could be bad stunning.

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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 Friday. If you're just joining us for this awkward Tuesday phone call, it's a story that really speaks to my soul. Does it? The awkward kid in high school who was maybe a little shy, did school plays and chess club.

637.38 - 668.79 Jose

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 undateable 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. Yeah, for real. And that ugly duckling has grown into an undeniable bubbling cauldron of raw desire. Oh, that's a hot dog.

668.77 - 690.693 Jose

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 did you want to do that?

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