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D
Oh, there's going to be so many awkward conversations this week because it's Thanksgiving week. Welcome to the Second 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, you know. Or what not to do. Yeah, you know, all the things. All the things are important. And what's most important is you and being here and listening. We 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 Joses in the world.
B
Yeah, all the Joses stand up. And Joseph's, because you count too.
D
It's really hard not to like someone named Jose. I've never met anyone I didn't like named Jose.
B
It would be controversial. I feel like there's a lot of people that don't like Jose.
D
No, I love you. You're the best. You're the best. All right, here we go. Awkward Tuesday starts now.
A
It happens in movies and reality TV shows all the time.
D
What's up?
A
People meddling in the dating lives of their other friends.
B
Oh, yeah.
D
Happens in real life all the time.
A
You know, 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 situationship with the guy that you live with.
D
Just if you're open to them. It's a marriage, Alexis.
A
Yeah, okay.
B
Yeah, she's putting labels on it already.
A
Wow. 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.
D
I don't know.
A
I know you're skeptical, but you might be on her side when you hear why in a brand new Awkward Tuesday phone call. Next. It's awkward.
D
It's Tuesday.
A
It's Awkward Tuesday phone call. As an adult, going out with high schoolers. Bad idea.
D
Terrible idea.
A
That's what I said. Bad idea.
D
You said it so nonchalantly, though.
A
What about going out with people you knew from back when you were in high school? Is that okay?
D
Of course, Jeff. That is totally different.
A
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.
E
Hi. Thanks.
A
Sounds like high school drama. Still following you right into adulthood, huh?
E
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.
D
Oh, just Justin. So it's not even other people from your high school. It's just Justin. You.
A
This is a special case. What's going on with Justin?
E
Okay, so Justin and I are friends. We've been friends, like you said, since high school. We're now in our late 20s.
D
Okay?
E
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. And it turns out to be this girl we knew in high school, Catalina.
D
Ooh, not Catalina.
B
Drama.
A
We don't know anything about her. What's with Catalina?
E
Well, she was the awkward girl. She was like, kind of like science geeky a little.
D
Are you still bullying the awkward girl in high school? Are we over that?
E
No, no, no, no, no. Like, she knew she was awkward. She was like, the awkward sm. Listen, I was a little awkward. It's just I was able to play it off better than she was.
A
I mean, Brooke, you must have had somebody at your school who was, like, bad at handling their meth, and that was the awkward.
D
Yeah. Why aren't you better at chemistry? That was our chemistry class, I think. Yeah, in the trailer.
A
So is that. That's bad news that your friend might be going out with your awkward kid from high school?
E
Well, I'm gonna give you a little more backstory before I tell you why that's bad.
A
Okay.
E
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.
D
Wow.
E
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.
B
Okay, good snooping.
D
So why are you doing all this work? He's just going out on a date.
E
Because she's gorgeous. I mean, she's like Scarlett Johansson brunette. That's cool.
D
That's amazing.
A
Why is it bad?
E
Yeah, generally that is great for her. I'm happy for her.
D
Are you, though?
E
But here's the thing, guys. I don't want him to know, but I'm. I kind of have a thing for Justin.
F
It.
E
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.
B
And this is why it was good being nerdy or awkward in high school, because she actually has a. Probably a cool personality too.
D
Oh, you're not helping, Jose. I mean, you sounded petty, and I. I get why you're jealous.
B
And you admit it.
D
That all makes sense.
E
Yeah, I just. I don't think I could compete.
A
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.
E
Is there any guy that's not into pretty women? Sorry. No, please. I'd prefer an ugly, stupid woman.
D
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?
E
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.
D
Oh, so that you could just stay in this, like, nothing friend zone. But I have a crush on you.
A
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?
D
I don't know if it's the nicest thing to do, but I would do it. Probably myself too. Yeah, but wouldn't you just tell the guy that you like him? Yeah, like you're in your late twenties at this point. You gotta shoot your shot.
E
Okay?
D
I mean, how many decades have you been waiting?
A
Maybe she's waiting till he gets married and then divorced that his confidence is so low he'll settle for anything? That could be a good strategy.
B
Oh, yeah?
D
What if he likes you too, and you guys are both just living in this world of not telling each other?
E
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.
B
It's like lighting the fire. Now you realize, oh, he's not gonna be single forever.
D
She didn't fully like him until he found somebody hotter and smarter.
B
Classic high school.
D
Yeah, classic high school.
E
Yeah. Listen, let me say, like, he's dated other girl. And this is gonna 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.
G
I see.
E
Now I wouldn't have a chance.
A
Okay, now the gloves are coming off. Now that this is happening, she's out of your league.
D
What do you want our help doing then? Like, are we calling Justin and telling him not to go out with her?
E
Yeah, yeah, yeah. This is convincing Justin not to go.
D
Out with her without you telling him that you like him.
E
Exactly.
D
Okay, so ruin your friends chances at all.
A
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.
E
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.
D
Okay, I don't think you can be named Catalina without being absolutely dropped.
A
She's not gorgeous. She's just stunning. And we're going to convince Justin to not go out with her.
B
Could be bad stunning.
A
We'll give you a little bit of advice and let you make your awkward Tuesday phone call right after this. It's awkward.
D
It's Tuesday.
A
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.
D
Does it?
A
The awkward kid in high school who was maybe a little shy.
E
Didn't.
A
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 undateable back then.
D
Yeah, high school.
A
But a few years go by and now they've matured mentally and physically.
D
I feel like you still do that bus thing if you're on a bus together.
A
And that ugly duckling has grown into an undeniable bubbling cauldron of raw desire.
B
That's a hot duckling.
A
God, 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. Why? Why did you want to be Jeff? 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?
E
Yeah, exactly.
A
All right, but how are we gonna do that. I think Jose has an idea for you.
B
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? What's that? I heard she made out with her brother and it wasn't even that long ago. That's what I.
A
The brother's review of the kiss was not good.
B
Not even a good kisser, Jeff.
A
That's what I heard from her.
D
You two are the word.
E
I mean, I think it would be effective, but that's a little mean.
B
That's gross.
A
I think you're going to have to play a little bit dirty to get what you want here. What do you think, bro?
D
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 up with. She's funny. She's everything you've ever been looking for.
B
Like that.
D
I can't tell you who it is.
A
It's Brooke.
B
She wants to go out with your guy.
E
Oh, God. More competition.
D
And then you drop it on him later when you're ready. That the mysterious perfect woman is you. Oh, wow.
A
Wow.
B
Brooke, you want to give him a puzzle?
D
Ye.
E
Like, what if I, like, meet him at a restaurant? I'm the one that walks in. Then I have to deal with the potential rejection of him being like, what are you doing here?
D
All guy friends want to sleep with their girlfriend.
B
Wait a minute.
A
There's Brooke's advice. Just sleep around.
B
All right, here we go.
A
Let's just give him a call. And we're let you make your awkward Tuesday phone call and try and convince him not to go out on his date.
E
Yeah.
A
Hot girl, we're here for you. All right, we're dialing the number right now.
E
Okay.
A
Good luck.
F
Hello?
E
Hey, how's it going?
F
Hey, Care Bear. What's going on?
E
Not much. How you doing?
F
I'm just killing some time before I have to go to work. What's up?
E
Oh, you know, spawn the chat. Say hey. Oh, did Billy get a hold of you?
F
Yeah, I assume you're talking about the blind date that I mentioned the other day.
E
No, no, I just meant about hanging out next weekend. Oh, yeah, we can definitely now that you mention it, are you still doing that? You still gonna hang out?
F
I mean, I'm very. I'm very curious. I mean, he. He mentioned that Catalina's doing all kinds of neat things right now, and I don't know, I just figured, what the hell?
E
Yeah, that's cool. You know, it's kind of weird, but I kind of heard something really ra. Silly about her. Like a rumor.
F
A rumor? What are you talking about?
E
Okay, so I heard that she was at a party like a month ago and kind of made out with her brother.
A
What?
F
Where did you hear this?
E
Yeah, I don't know. Just randomly.
F
Randomly what?
E
Yeah, I don't. I don't know. But, like, blind dates are really weird, aren't they? Like, are you sure you really want a blind date? I mean, you're so cool and, like, you're good looking and you really want to, like, go through the awkwardness of a blind date and all that.
F
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?
E
You know what? How about this? Like, I have a friend. She's awesome. She's great. She's super hot. What if I set you up with her instead?
F
You. You want to set me up on a blind date?
E
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.
F
Well, tell me about this friend of yours.
E
I mean, she's just 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 parties.
F
Okay? I certainly hope not.
C
Awkward.
A
Because we're laughing too hard. Awkward. Hey, Justin.
D
Hey, Justin.
F
What, are you at a party or something? What's all that laughter?
A
I think we're kind of a party. We're a. We're a morning radio show. Justin called Brooke and Jeffrey in the morning.
D
Why did you go with Jose's advice?
A
I thought that was solid, though.
B
I was kind of kidding, but I kind of.
F
I am so lost right now. What the hell?
A
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 sure it's a good idea for you to go out with her.
B
Just looking out for you.
F
Because of the brother thing? Or.
A
I mean, that's just one of many, many reasons.
D
Because Carrie does have someone really cool that she wants to set you up with.
F
Terry, what exactly is going on here? This is a little weird.
E
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 and you found her social media?
F
What does she look like?
A
That sound is probably all you need to know.
B
New rumor coming in. I hear she looks like Oscar the Grouch. Muppet. Whatever.
A
Who cares what she looks like? You're not the type of guy that bases a relationship on looks, are you?
B
Justin, come on.
F
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 a second date or anything.
A
Yeah, starts with coffee drinking. Next thing you know, brothers are kissing.
E
Okay, I don't feel like any of this is helping you guys.
D
Yes, because you need to do the thing.
A
I mean.
E
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.
D
Say the thing, Kerry.
F
What thing? What? I still don't know what the hell is going on here.
E
We have such a good connection, and I just kind of wondering if, like, maybe there's a mutual attraction beyond friendship between us.
B
There it is.
D
What do you think?
F
So you dragged me through a whole radio show to finally spill the beans here, Care Bear?
B
Maybe she was nervous.
E
Obviously. I realize now this is not the right way to do it. I just. 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.
C
Say that.
D
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 her?
F
I wouldn't have been friends with her for the last decade if I didn't think she was amazing. You. 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 as to finally getting this out in the open. But, hey, might make a great story for our first date.
A
Wait a second. So, Justin, you're into the idea of maybe going out with Carrie here.
B
Not a friend date. Like a romantic date.
F
I wouldn't mind one bit.
D
Yay.
B
Really?
D
It sounds, Justin, like you have liked her for a long time.
F
To be perfectly honest, I have. Yeah.
A
Oh, my God.
F
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.
E
But wow. So we've both kind of been idiots.
A
I never. 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.
D
Yeah.
B
We gotta listen to Brooke.
A
Good job, Brooke.
D
How else are you gonna find out? Brooke and Jeffrey in the morning.
B
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D
Actually, I think that one was really cute. Yeah, Isn't that weird? I want an 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. It was just telling your closest friend, hey, I have a crush on you.
B
Crossing that border is hard.
D
Just saying. Can I kiss you? That's what. I'm straight for it. Yeah, Straight for it after 10 years of friendship.
B
Hey, Bill.
G
Yeah, Bill.
D
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.
B
Oh, that's so cool.
D
And I was like, this was amazing. And he was like. He goes, brooke, don't ever do that again. At least you were close enough he could tell you that. Yeah, yeah. He's still one of my best buddies. Yeah. So, anyway, let's go back to this couple, please. I think what it. I think what this is, is if you have a crush, just tell him. All right? There's a lot to lose. Yeah, okay. There's a lot to lose.
B
A friendship.
D
And then when that backfires, call us. Okay. And we'll do another awkward Tuesday for you.
E
Ye. There you go.
D
Or you can always submit on our website. It's brookeandjeffery.com and always follow us on socials. RickandJeffrey.
B
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What a matchup we got, y'.
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All.
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Podcast: Brooke and Jeffrey: Second Date Update
Date: November 25, 2025
Episode Theme:
A real-life romantic dilemma unfolds as long-time friends struggle with hidden feelings when one is threatened by an "ugly duckling" from high school who's now blossomed into a catch. The show grapples with jealousy, honesty, and the dangers (and comedic fallout) of meddling in friends’ love lives.
This episode centers around Carrie, who enlists the help of Brooke, Jeffrey, and the team to convince her friend Justin not to go on a blind date with Catalina—a former high school classmate now turned stunning. Carrie's motivation? She secretly has feelings for Justin but isn’t ready to confess them, fearing Catalina is now “out of her league.” The team explores awkward truths, jealousy, and what happens when you finally risk honesty in your oldest friendships. Enter: the Awkward Tuesday Phone Call.
"People meddling in the dating lives of their other friends. Happens in real life all the time." – Jeffrey (04:12)
"She was the awkward girl... She was like, kind of science geeky." – Carrie (06:38)
"Because she's gorgeous. I mean, she's like Scarlett Johansson brunette." – Carrie (07:56)
"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." – Carrie (08:09)
"Wouldn't you just tell the guy that you like him? You're in your late twenties at this point. You gotta shoot your shot." – Alexis (09:30)
"I heard she made out with her brother and it wasn't even that long ago." – Jose (13:14, joking)
"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." – Brooke (13:35)
[15:00-21:21]
The radio team cuts in to explain the prank.
Carrie finally admits her feelings:
"I just kind of wondering if, like, maybe there's a mutual attraction beyond friendship between us." – Carrie (19:45)
Justin responds with warmth and openness: "I wouldn't have been friends with her for the last decade if I didn't think she was amazing...I have liked her for a long time." – Justin (20:32, 21:07)
| Timestamp | Segment / Content | |-----------|------------------| | 04:08-05:46 | Hosts introduce the meddling dilemma and Carrie’s case | | 05:46-08:17 | Carrie's backstory and her feelings about Catalina | | 08:09 | Carrie admits her feelings for Justin | | 12:51-14:44 | Hosts strategize sabotage vs. honesty, joke about fake rumors | | 15:00-18:19 | Awkward Tuesday call: Carrie tries to dissuade Justin | | 19:45 | Carrie openly confesses her feelings | | 20:32, 21:07 | Justin reciprocates and admits he’s liked Carrie for years | | 21:21 | Hosts celebrate the outcome, wrap up the segment |
This episode is a classic case of meddling gone right (eventually): childhood friends Carrie and Justin awkwardly stumble into romance after years of silence thanks to some questionable advice, a fake rumor, and the push of a morning radio crew. It's a relatable, sweet, and funny reminder that shooting your shot is nerve-wracking, but sometimes the other person is just as nervous—and just as hopeful.