Brooke and Jeffrey: Second Date Update - Awkward Tuesday: Dark Side of the Costume Contest

Episode Date: October 28, 2025

A new costume is causing MAJOR drama between a listener and his close friend, and he has no idea where else to turn! It’s a Halloween-themed Awkward Tuesday Phone Call!See omnystudio.com/listener for privacy information.

Johnny Knoxville here. Check out Crimeless, Hillbilly Heist, my new true crime podcast from smartless media, Campside Media, and Big Money Players. It's the true story of the almost perfect crime and the Nimrods who almost pulled it off. It was kind of like the perfect storm in a sewer. That was dumb. Do not follow my example. Listen to Crimless, Hillbilly Heist on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. Hey, I'm Cal Penn, and on my new podcast, here we go again, we'll take today's trends and headlines and ask, why does history keep repeating itself? Each week, I'm calling up my friends like Bill Nye, Lily Singh, and Pete Buttigieg to talk about everything from the space race to movie remakes to psychedelics. Put another way, are you high? Look, the world can seem pretty scary right now.

But my goal here is for you to listen and feel a little better about the future. Listen and subscribe to Here We Go Again with Cal Penn on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. I live below a cult leader, and I fear I've angered her. Wait a minute, Sophia. How do you know she's a cult leader? Well, Dakota, luckily it's I'm not afraid of a scary story week on the OK Storytime podcast. So we'll find out soon. This person writes, my neighbor has been blasting music every day and doing dirt rituals.

And now my ceiling is collapsing. I try to report them, but things keep getting weirder. I think they might be part of a cult? Hold up. A real-life cult? And what is a dirt ritual? No clue, Dakota. Find out how it ends. Listen to the OK Storytime podcast on the Iheart Radio app,

Apple Podcasts, or wherever you get your podcasts. What's up, everybody, it's snacks from the trap nerds. All October long, we're bringing you the horror. We're kicking off this month with some of my best horror games to keep you terrified. Then we'll be talking about our favorite horror and Halloween movies and figuring out why black people always die further. And it's the return of ton of tone. horror show

SideQuest written and narrated by yours truly. We'll also be doing a full episode reading with commentary. And we'll cap it off with a horror movie

Battle Royale. Open your free iHeart radio app and search trap nurse podcast and listen now. Two rich young Americans move to the Costa Rican jungle to start over,

but one of them will end up dead and the other tried for murder three times. It starts with a dream, a nature reserve, and a spectacular new home. But little by little, They lose it. They actually lose it.

They sort of went nuts. Until one night, everything spins out of control. Listen to Hell in Heaven on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Ooh, it's that special time of year where you get a Halloween awkward Tuesday phone call right here. I love it. We dive deep into this holiday. It's Brooke and Jeffrey, and this is your second date update. podcast so thanks for being here yes and that's coming up in just a second but first what's on the text board comments uh hannah victoria said i'm about to go on a first date and i'm listening to this beforehand dating advice from brook and geoffrey gonna get me through with some prayer hands

oh man don't have a bad wait i don't know would that help your date if you listen to bad dates it would lower your standards yeah but also it's in your head it's gonna suck yeah or it lowers your expectations anything good is good yeah what i mean like the small things. I don't know. Let us know. We need an update from that commenter after the date. Yeah, it was for a few days ago. So, Hannah, get back on here and you tell us how it went. Okay. I like that. I also now want to know, do you listen to second updates after a bad day? Yeah, yeah. Well, it makes you feel better. Yeah. It's true. It loves company.

Oh, this is a good thing. All right. But right now, it's awkward Tuesday. So, go right. Here we go. For years on this show, one Halloween costume has caused more drama than any other. Oh, I think I know what it is. It was about 12 years ago when I showed up in an extremely realistic gladiator outfit and Brooke was blushing for sure. I swear, like, you were wearing nothing at the office.

Yeah, it was literally like a big she's smiling as she says that. It was so uncomfortable. Still, she brings it up in work emails to this day. Dude, he had six packs too. You had a whole six packs. Sure did. But after today's call, I think the. ogling may finally be over

because a new costume is causing major drama between a listener and his close friend. Not as much as yours yet. Well, actually more. It has not caused drama. He was just inappropriate in the workplace. Those are your words, but he has

nowhere else to turn. You're going to hear why this one outfit has become so controversial in a very special Halloween themed Awkward Tuesday phone call right after this. It's Awkward. It's Tuesday. It's awkward Tuesday phone call.

Halloween time means fun-sized candy with full-sized drama. I like that, Jeff. That's a good tagline for Halloween. Well, that's what brings our listener, Darius, to the show this morning. Apparently some Halloween drama has sprung up in his personal life. So he's ringing our doorbell, asking for help, and maybe a bite of Brooks' almond joy. We'll find out. No.

Darius, welcome to the show, man. Hey, thank you for having me. Don't come looking for my candy, Darius. I think Brooks the only one that loves an almond joy and we'll still fight for them. Dude, they're so good. I don't know if Darius, your drama involves candy at all, but tell us what made you reach out to the show for an awkward Tuesday phone call. Well, I have a problem, right? I'm a big Halloween guy.

Okay. All right, that's cool. Like, you love to dress up, you like to decorate your house. Like, what does that mean to you? all types of activities like dressing up going to parties just enjoying the spooky things

trying to come up with new ideas with different costumes Okay, you love a creative costume, me too Yeah, let's go Hanging outside of elementary schools and scaring kids on their way out Just to be part of the season I don't think Jeff was listening

He's in all sorts of Halloween activities Right? That's what you said, Darius No, no, I don't know I stay away from the school Okay, so maybe you're not as big into Halloween as you said you were but that's okay. He's an adult,

an adult festivities type of guy. That's fine. Yeah, partying. Okay, to each their own. But where does that drama come into your life right now? Well, during this past weekend, I was really sick.

And I missed a Halloween party downtown. Oh, man. This was the weekend to do it, like the biggest weekend of the year. It does suck that October. Like, Halloween falls and, like, flu season. It would get sick after the summer. It always happens.

Yeah. Especially if you put a lot of time into your costume. Yeah. Was your sexy costume just gone to waste then? Well, it didn't really go to waste. I don't want to get to that. But they had a big Halloween costume contest, and the prize was $500. Oh, okay.

Wow. And I thought I was really going to win because the outfit I had was a very unique outfit. It was the Darth Vader T-Rex outfit mixed together. Darts Vader T-Rex? What does that look like? I'm trying to imagine it. Is there a pun? scene in this?

No, no fun. But if you look at it like the inflatable T-Wex outfit with a lightsaber and a Darth Vader hat. Okay. You're going for the humor aspect of it. It's just really funny looking.

So wait, you didn't get to wear it, though, because you were sick, right? Right. I was a little sick. So my friend, Cherie's, I said, hey, take it, fly this on, go down to the party, and have fun. Oh, that's nice. You let your friend wear the costume. That's cool. You can't see yourself anyways, right?

Yeah. It's good for all genders. Yeah. Right. And she didn't have a costume anyway, so it was, like, I was helping her out. Oh, that's actually clutch then. She is going to get so much male attention. Oh, yeah.

Platable T-Rex, Darth Vader outfit. Dinosaurs, Star Wars. I mean, all the boys are going to be into that. Look at the tail on that one. Comes the hot bad boys, too. I love that. Damn right. So you sent her in your costume.

Did you hear about how it? Yeah, yes I did I heard how I went and it went well She actually won the costume No way That's really cool Yeah honestly yeah she really won And she and the grand prize is like $500

Yeah Wow Well you get to you should probably get some of that money Since it is your costume that she borrowed Right at least wouldn't have her Yeah Nice dinner And I agree with that statement

What she said I do totally agree with it And when she won we both was very happy that she won you understand. But she didn't offer me anything. What? What? Anything? Like at all?

She's like, wow, I won $500 on the costume you made. Awesome. And you're at home six. Sorry. No, right. She didn't split the winnings or anything. And I really don't know how to approach her about it. Because I'm like, I don't want to sound petty, like, in a sense, like, hey, I made that

costume that you won. Totally. And those costumes aren't cheap. You know, the inflatable T-Rex and then whatever you had to do to, like, construct. the helmet. I'm sure you made it yourself at the lightsaber. But you know, sometimes being good friends, like you don't know. Like, she honestly probably didn't think twice.

You guys jump. You celebrate, you hug. And then you're like, I'll see you later. It's just logic. Being a good friend. That's why maybe he says something. And she's like, oh my gosh. Oh, my gosh, you're right. I totally should give you some money. Like, what did you say when you talked to her? Like, how did that conversation go?

But when she said that she went, I was like, oh, great. I'm happy for you and everything. But I never brought up the subject of money. Oh. I kind of like left it there for her to bring it up. Okay. You were afraid because she looks like a giant T-Rex with a lightsaber and you don't want something bad to happen to you.

Yeah. I mean, that's even worse T-Rex. Totally. Yeah, I don't want to see that bad side. Is that what you're wanting our help with is to ask for part of the money, all the money, what do you want to do? I mean, I don't want all the money, but I can definitely use like at least $250. Okay.

Like half. That makes sense. It's fair and square. Friends and money is so tricky. It really is, dude. Oh my gosh, I absolutely hate it. That's going to be our job to figure out how to have that conversation while keeping the friendship still copacetic.

Yeah. And worst case, Brooke, will you give him $2.50? You're his friend. She's not going to say, no, that's a friend's do, bro. Right. So you need advice to call Cherise and convince her to give you at least part of the winnings for the costume contest that she won while wearing you. Your outfit that she made.

Seems pretty simple. Seems like a fair ass. Yeah. And I know you guys find creative ways to come up with stuff. I kind of meet you guys to do this. Okay. Okay. You want us to be on the creative side, not just blunt.

I like it. Because I don't want her to use a Jedi mind trick on us. Oh, that's good point. Well, we're all going to have to conquer our fears when we give you some advice and help you to confront T-Rex Darth Vader herself. When we come back with your Halloween-themed Awkward Tuesday phone call. right after this. Okay. Hold on, ma'am.

It's awkward. It's Tuesday. It's awkward Tuesday phone call. When dinoes turn to the dark side, things get awkward. It's a Halloween-themed Awkward Tuesday, where one of our listeners, Darius, needs help calling his friend Shurice, because she borrowed his homemade Darth Vader-T-Rex outfit for a costume contest just last weekend.

Yep. A contest she won, taking home first prize along with $500 cash money. So Darius thought, hey, that's awesome. But she hasn't offered to split the winnings with him like a good friend probably should. And that's why he needs our help on how to have that conversation delicately, because mixing friendship and finances, that can be a little bit tricky, especially when your friend is a prehistoric apex predator wielding a lightsaber. Tough position to be put in.

Maybe she's another concept of money. He's definitely not the father this time. Oh. I got it. Because it's a T-Rex. That was a hot Star Wars. Oh, Darth Vader, the father of Luke and deep cut. Okay.

Darius, I don't hear you laughing at the joke. There is always pretty funny. There we go. He'll give you a little credit. Maybe he's more interested in your advice, though. What advice do you have for me? I have good advice on this one, Darius. Okay.

I don't want you to ask for the money. I don't want you. to tell her she owes you. I want you to just make the call with the wild assumption that you already have it, right? What? Already have the money? Yeah, you're like, oh my God, I've been thinking about it. I am so excited about this. How are you going to spend your half? This is what I plan to do with my half of the winnings. That's a good thing to say. Like the agreement was implied. It doesn't even need to be said. What do you think about that, Darius? I do like that a little bit. It's a little bit of Jedi-mind trick point. Yeah. Oh, there you go. It's very passionate.

of aggressive. Okay, so you hold on to that. Jose, what do you think? Well, to really get her to care about the situation, don't even bring up the costume, bro. I would mention your short on rent this month. Play on her, on her emotions, on her sympathy for you. I see what you're saying. And as a friend, she'll probably just offer like, oh my gosh, I can help you. Maybe he could cough, like, like if he's still sick to make it sound more pathetic. Oh, there you go. And can you cry on command too, Darius? Bob, that was too much. It's a little heavy, but yeah.

Maybe dial it back a little bit, but you can always use it if you're really, really desperate. You can always cry. Maybe you'll get more than $2.50 if you say the rent. Oh, yeah. Bump that up to it. Full G. Okay. So that's our advice for you, Darius.

You can use however much you want to, but we're in your corner no matter what. I'm going to dial your friend, Cherise, and let you make this call. You feel ready? I'm ready. All right, man. Good luck. Here we go. Thank you.

Hello. Hey, Shriis, what's going on, my girl? How's everything? Hey, Darius? Did you get a new phone or this isn't your regular number? No, this is my work phone number. Oh. Oh, okay.

So, what's up? Yeah, well, first of all, congratulations on winning the prize. I'm so excited I'm so excited that I want to take my ass and pay my rent with it. Oh. Okay.

I don't know. I was it. I've kind of combined it all together. Oh, that's hilarious. That's funny. That's, yeah. No, for a little. How's your week?

What's going on? Well, I've just been working, so I think I'll probably just do a spa day, honestly. It's a good day for it. I can get my nails done. So, yeah. Have a lot.

What about you? Oh, that's good. So with the earning from the costume? I mean, it definitely doesn't hurt. When did you start pocket watching? Oh. Well, I'm not pocket watching. I'm just, you know, listen, let's be honest.

I made the costume. You wore the costume. And I think it should be nice of you to go ask with me on it. Or break me off a little something. You know, I didn't say my rent was due. There is everybody's rent is due. That is true I think you know my situation

A little bit better than most people So that's why I'm talking to you I'm asking you nicely You know, thank you about your boy I thought I was your boy You are my boy And that is true But we both know Darius

When I put that costume on It looked better on me We do know that What are you talking about? T. Rex costume Nobody can really even see your body Like what's going on That doesn't make sense to me

everybody can see my tail in that okay let's not be let's not even joke okay there's a lot of tail I know that much I do know that but yeah no seriously I'm a little shocked that you're saying that because we won that contest together that's how I look that's opposite because we're friends right I hear you Darius I definitely understand where you're coming from but if it wasn't for me the costume wouldn't have made it to the contest okay so what are you saying you not going to break me off a little bit of the earnings. I really

kind of deserved that because I did work hard to make that costume. Yeah, I made the costume and you wore the costume. So that's in my mind's eye that sounds like a 50-50 kind of deal. Oh. Well, Darius, I'm so sorry to tell you, I

can't give you that money. What? Why can't you give me that money? Because it was money that we wasn't expecting to win. I actually got sick because of you. What? So I had to let my cousin go in the costume and

she's actually the person I won. So we split the money. Wait, wait a whole time out. Wait a second. No, hold on. Wait a thing. You sublet it my costume to some random person? She's not a random person. She is my cousin. You met her. The one you were trying to get her phone number. So now she's random. Let's not play. Okay. You're trying to get her phone number too?

There are two of all these people in the background? I thought she said you were at work. Yeah. He's at all. Our work, a radio show called Brooke and Jeffrey in the morning. Oh, my gosh. Yeah, you're on a segment called The Awkward Tuesday phone call right now. Wow. Darius reached out to our show for a little bit of help talking to you. This is unbelievable.

You rented my costume out to someone else, and you split their earnest with them. It's unbelievable to me that you call me on the phone through the radio. Like, this is Judge Judy. I don't know. I mean, what are we doing? Wow. Oh, man. So wait, you already split the money.

So you only got $2.50 from the winning, Cherise. I only got $2.50, and it's basically already spent. Oh, and then the cousin makes the most out of all of this? Yeah. Right, that doesn't make sense. That just feels wrong. Darius is the one who put all the effort into putting the costume together, coming up with the idea, buying all the supplies.

Like, doesn't that, like, factor into your thought process at all? He was sick. I mean, what was I supposed to do? He told me to take the costumes, I did. The costume, yes, but not all the profits from it. It's like he's the producer, right? And you're the performer. and he wrote the music

and now he gets a cut. Yeah, but you get all the credit or the cousin gets all the credit. I would totally agree with you if there was some type of agreement, Judge Judy, but it was not. Oh, my God. Honestly, he should have talked about it before.

She just calling me Judge Judy now? Well, he wouldn't expect her to win, though. Do we have a signed contract? No, we're friends. So why would I have you signed a contract saying that you would have won that you only part of this earning? I don't think she meant it, actually.

in writing, I think she just met a discussion. Yeah. But true friends do make each other signed documents in order to prove their friendship. And I don't believe your cousin has my money. Our money, actually, because you sub-ledded my outfit. And then, and then, on top of it, you lied to me by saying, you know, I look better in the outfit, and you didn't

even wear the outfit. Oh, she did lie a little bit. I did not lie. I tried it on. You saw me, and I do look better in it. That's how she got sick. I can see. has that T-Rex, Darth Vader energy going on. Fills it out.

Yeah, but all those germs trapped up inside of it ruined her plan. Yeah, it feels like things are kind of canceling out with people getting each other sick, people winning each other contests. I don't even know who to side with

in this scenario. The person you need to side with the one who's short on rent, and that's me. Okay. You're not really short on rent, though, bro. Honestly, though, I think you owe Darius

125, and I think your cousin also owes Darius 125. That would be half of the 250. I don't want to mess with a cousin. She has an attitude. She's very mean. You're scared of her. She's more T-Rex than Cherise's.

Okay. I mean, Cherise, there has to be some sort of compromise we can reach here because Darius is getting the complete short end of the stick. And he paid for all that stuff to make the costume. I have a $50 home depot gift card. That's what I can do. Okay. That's something, Darius.

Do you have any home improvement items? Well, how much is left on it? Maybe like 40 bucks Maybe your landlord will accept $40 in Home Depot credits Go towards your rent Not what I wanted, but at least it's something You actually sounded like Darth Vader right before that It's because he's sick, he's having breathing issues

Brooke and Jeffrey in the morning Here we go Hey, I'm Cal Penn And on my new podcast, here we go again We'll take today's trends and headlines and ask, why does history keep repeating itself? You may know me as the second hottest actor from the Harold and Kumar movies,

but I'm also an author, a White House staffer, and as of like 15 seconds ago, a podcast host. Along the way, I've made some friends who are experts in science, politics, and pop culture. And each week, one of them will be joining me to answer my burning questions. Like, are we heading towards another financial crash, like in 08? Is non-monogamy back in style?

And how come there's never a gate ready for your flight when it lands like two minutes early? We've got guests like Pete Buttigieg, Stacey Abrams, Lili Singh, and Bill Nye. When you start weaponizing outer space, things can potentially go really wrong. Look, the world can seem pretty scary right now, because it is. But my goal here is for you to listen and feel a little better about the future. Listen and subscribe to here we go again with Cal Penn on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. The Crying Wolf Podcast is the story of two men,

bound by injustice, of a city haunted by its secrets, and the quest for redemption, no matter the price. White victim, female, pretty, wealthy, black defendant. Chicago, a white woman's murder, a black man behind bars, for a crime he didn't commit. I got 90 years for killing somebody, I have never seen.

He says the police are his friends, and then that's it. They turn on it. A corrupt detective. How he was interrogated the techniques. That's crazy. A snitch and a life stolen. They got the wrong guy. But on the inside, Lee Harris finds an ally in his sally, Robert, who swears to tell the truth about what happened to Lee and free his friend.

And if you're with me, you're golden. I'll take care of you. I'm going to be with you. You stuck with me for life. Listen to the Crying Wolf podcast, starting on October 22nd, on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Look, I didn't want to say this. Who only spends $10 at Home Depot? How is that even possible?

Jeff, obviously she combined it with other gift cards that she had. Do you know what I'm saying? And it was like the end of it. Okay, fine. I'll give her a little bit of grace on that. Dude, we did not do him justice. But that's the thing. It's like with a lot of these calls that we do with friends and money when that's the problem, it's difficult for us to tackle.

Well, and who knew we were supposed to be calling the cousin? Who sounds scary? I'm actually kind of glad that we don't have to do it because I'm scared, just hearing about it. Maybe she actually won the costume contest because the person that was judging it was just frightened to not let her out. It's probably in his best interest to let them keep the costume at this point. At that point, I think she deserves the money. Absolutely. So things worked out the way they did.

But we will try for you. If you're going through something with a friend or a family member, reach out to our show. We'll do our best to make it worse. Oh, yes, that's right. Or at least get you a partially used gift card to Home Depot. That's a promise. Somehow expires.

Yeah. That's working Jeffrey in the morning. Hello, America's sweetheart Johnny Knoxville here. I want to tell you about my new true crime podcast, Crimless, Hillbilly Heist, from Smartless Media, Campside Media, and Big Money Players. It's a wild tell about a gang of high-functioning nitwits who somehow pulled off America's third largest cash heist. Kind of like Robin Hood had except for the part where he steals from the rich and gives to the poor.

I'm not that generous. It's a damn near inspiring true story for anyone out there who's ever shot for the moon, then just totally muffed up the landing. They stole $17 million and had not bought a ticket to help him escape. the worst saying, like, oh, God, what do we do? What do we do? That was dumb. People do do not follow my example. Listen to Crimeless, Hillbilly Heist on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. Hey, I'm Cal Penn, and on my new podcast, here we go again, we'll take today's trends and headlines and ask, why does history keep repeating itself? Each week, I'm calling up my friends, like Bill Nye, Lily Singh, and

Pete Buttigieg to talk about everything from the space race to movie remakes to psychedelics. Put another way, are you high? Look, the world can seem pretty scary right now. But my goal here is for you to listen and feel a little better about the future.

Listen and subscribe to here we go again with Cal Penn on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. I live below a cult leader and I fear I've angered her. Wait a minute, Sophia. How do you know she's a cult leader? Well, Dakota, luckily it's I'm not afraid of a scary story week on the Okay Storytime podcast, so we'll find out soon.

This person writes, My neighbor has been blasting music every day and doing dirt rituals, and now my ceiling is collapsing. I tried to report them, but things keep getting weirder. I think they might be part of a cult. Hold up, a real-life cult? And what is a dirt ritual? No clue, Dakota.

Find out how it ends. Listen to the Okay Storytime podcast on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. What's up everybody It's next from the trap nerds and all October long We're bringing you the horror Boogity Boogity

We're kicking off this month With some of my best horror games To keep you terrified Then we'll be talking about Our favorite horror and Halloween movies And figuring out why black people Always died perfect And it's the return of Tony's horror show

SideQuest written and narrated by yours truly We'll also be doing a full episode reading With commentary And we'll cap it off with a horror movie Battle Royale Open your free IHard radio app And search trap nurse podcast And listen now.

Two rich young Americans moved to the Costa Rican jungle to start over, but one of them will end up dead and the other tried for murder three times. It starts with a dream, a nature reserve and a spectacular new home. But little by little, they lose it. They actually lose it. They sort of went nuts. Until one night, everything spins out of control. Listen to hell in heaven on the.

iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.