Awkward Tuesday: Stop That Ugly Duckling

Oh, there's gonna be so many awkward conversations this week because it's Thanksgiving week. Podcast, we have a classic Awkward Tuesday phone call for your enjoyments. 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 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 kill a.

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 joss.

In the world.

Stand up Joseph, because you count too.

It's really hard not to like someone named jose. I've never met anyone I didn't like.

Name hose controversial.

I feel like there's a lot of people that don't like Jose.

No, I love you, you're the best. I'm not the best. All right, here we go. Awkward Tuesday starts now.

It happens in movies and reality TV shows all the time. People meddling in the dating lives of their other friends.

Oh yeah, in real life all the time, you know, is.

It okay to do that? Because if it is? And Brook, after this is over, Alexis says, she has some thoughts on your current situationship with.

The guy that you live with, just if you're open to them it's a marriage.

Yeah, okay, but Brook'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.

Oh.

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. Next, It's awkward, It's Tuesday. It's awkward Tuesday. As an adult going out with high schoolers. Bad idea, terrible idea. Get word, that's what I said, bad idea?

So DoD Chalantley though.

What about going out with people you knew from back when you were in high school? Is that okay?

Totally different?

Well, one of our listeners, Carrie says, absolutely not. What terrible horrible idea to date your old high school class mate. Apparently that's why she needs our help today, Carrie, Welcome to the show. Hi thinks sounds like high school drama is 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 just and our friends, we've been friends, like you said, since high school. We're now in our late twenties.

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 to date with. And it turned out to be this girl we knew in high school, Catalina Leana.

What's with Catalina?

Well, she was the awkward girl. She was like kind of like science peaky, a little.

Still bullying, the awkward girl in high school. Are we over that?

Oh no, no, no, no, Like she knew she was awkward. She was like the awkward smart science. Ye girl, listen, I was a little awkward. It's just I was able to play it off better than she was.

You must have had somebody at your school who was like that at handling their mess and that was the awkward.

Why are you better at chemistry? That was our chemistry class?

Right, Yeah, in about that. 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, 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 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

Okay, 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 Scarlet Johansson Britain's met.

That's amazing. Why is it bad? Yeah?

Generally that is great for her. I'm happy for her, But here's the same guys. I don't want him to know, but I'm I kind of have a thing for Justin.

It 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.

This is why it was.

Good being nerdier in high school, because she actually has probably a cool personality too.

Oh, they're not helping, Jose. I mean you sounded petty and I get why you're jealous. Can you admit it that all makes sense?

No?

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 there any guy that's not into pretty women?

Yeah?

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 at I need more time, but I just need this figure out to convince him not to go out with her.

Oh oh, you could just stay in this like nothing zone, but I have a crush.

Okah, 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?

I don't know if it's the nicest thing to do, but I would do it probably myself too.

Yeah, but why didn't you just tell the guy that you like him? Yeah, Like, you're in your late twenties at this point, you got to shoot your shot. How many decades have you been waiting?

Maybe she's waiting till he gets married and then divorced, so that his confidence is so low he'll settle for anything. That could be a good strategy.

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.

I'm like lighting the fire. Now you realize, Oh, he's not going to be single.

For fully like him until he found somebody hotter. And smarter.

Yeah yeah, listen, let me say, like he stated, 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. Now I wouldn't have a chance.

Okay, now the gloves are coming off this.

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, telling them that you like him exactly.

Okay, chances that's all 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. I obviously know what I've seen her.

Okay.

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

She's not gorgeous, She's just stunning. And we're going to Justin to not go out with her. We'll give us 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

I feel like you still do that bus thing.

And that ugly duckling has grown into an undeniable, bubbling cauldron of raw desire. That's acid, it's undeniable. And your listener, Carrie, she's not that person. 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 do that, Jeff? Because I mean, secretly, she does have some feelings for justin,

Her, right, yeah, exactly?

All right?

But how are we gonna 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, start.

A rumor about her.

What's that?

I heard she made out with her and it wasn't that long ago.

Are you that brother's review of the kids was not good?

You are the words I mean. I think it would be effective, but that's the little.

Means that's gross. We're gonna You're gonna have to play a little bit dirty to get what you want. 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 is hot.

All you need to say is, listen, you are so hot, you're so beyond blind.

Dates like 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 like that.

I can't tell you who it is.

It's Brooke. She wants to go with your guy.

Competition and then you drop it on him later when you're ready that the mysterious perfect woman is you?

Oh wow?

Like what if I 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?

All guy friends want to sleep with their girlfriends.

There is Brooks advice just sleep around. All right, let's just give him a call and we're gonna let you make your awkward Tuesday phone call and try and convince him not to go out on his date. We're here, We're here for you, all right, We're down the number right now?

Okay, good luck?

Hello? Hey, how's it going? Hey care? Bara? 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?

You know?

She wanted to 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're gonna Now that you mention it, are you Are you still doing that.

He's still going to hang out with I mean, I'm very 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?

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 know. But like, blind needs are really weird, aren't they? Like, are you sure you really wanted 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.

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 then 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. What have I set you.

Up with her? Instead?

You 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 Helen, and no one has seen her.

None of us is like talk 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 was great, you know, like you would. I think you really like her. She's you would totally get along. I know you guys have a lot in common, and I know one hundred percent that she does not make out with her brother at party.

I certainly hope not.

Laughing too hard?

Justin, Hey, justin, Well, are you at a party or something? What's all that laughter?

I think we're kind of a party. We're we're a morning radio show. Justin called Brook and Jeffrey in the Morning.

Why did you go.

With Thodays Advice?

I thought that was solid, though.

I am so lost right now.

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 because of the brother thing or I.

Mean, that's just one of many many.

Reasons, because car Carrie does have someone really cool that she wants to set you up with.

Harry, What exactly is going on here? This is is a little weird.

Okay, listen, justin, I I haven't been super honest with you. I have not been the best friend in the sense that I discovered Katalina's social.

Media, and well you found her social media. What does she look like?

That sound is probably all you need to know.

Just new rumor coming in. I hear she looks like oscar the Grouse, 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? Just come on?

Like I said, at the very least, we would just get a cup of coffee and catch up a little bit. That doesn't mean we go on the second date or anything.

Yeah, it starts with coffee drinking. Next thing you know, brothers are kissing.

Okay, I don't feel like any of this is helping you. Guys, did 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.

Say the thing.

Carrie, what thing?

What?

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.

It is, m what do you think?

So you dragged me through a whole radio show to finally spill the beams here.

Be maybe she was nervous.

Obviously, I realize now this is not the.

Right way to do it. I just I just thought it like maybe we needed some more organic time to let it evolve. But then I saw Katalina and I would have no chance if you met her.

That is not true, justin don't you think that Carrie is amazing? Could you see something more between you two?

Have you ever picked 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. Is so finally getting this out in the open. But hey, might make a great story for our first date.

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.

Yeah.

Really it sounds justin like you have liked her for a long time.

To be probably honest, I have.

Yeah, Oh my god, I.

Was afraid that I was in the 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 yeah, both kind of been idiots.

In all of our years here. I never thought brooks advice of just sleep with all of your friends what's the worst happen would actually work. Good job, bro, you gonna find out.

Brooking Jeffrey in the morning. Actually, I think that one was really cute. Yeah, we were. I had an update from them.

I mean a lot of drama to just ask someone out that you've known for a long.

Yeah, it's true.

Just telling your closest friend.

Hey, I have a crush on you.

Crossing that borders hard.

They can't kiss you. That's what I'm straight.

For, straight for it after ten years of friendship.

Yeah, Bill, the first time I kissed one of my best friends, Oh this is I was like sixteen, 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, I was like.

And he was like, she goes Brooke, don't ever do that again. You're close enough he could tell you that.

Yeah, he's still one of my best buddies.

Yeah, so any this couple, Pa, I think what I think.

What this is is if you have a crush, just tell him all right, there's nothing, yeah, friendship and then when that backfires, call us okay and we'll do it another awkward Tuesday for you, or you can always submit on our website is Brook and Jeffrey dot com and always follow us on socials at Brick and Jeffrey