Brooke and Jeffrey: Second Date Update - Second Date Update Classic: Halloween Role Reversal

Episode Date: November 2, 2024

The guy on the phone today wants to try and recreate his perfect first date all over again… exactly one year to the day. It involves wearing children’s costumes and it’s happening in a Second Date Update!See omnystudio.com/listener for privacy information.

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It's awkward. It's Tuesday. It's awkward. It's Tuesday. It's Awkward Tuesday phone call. Everybody has their unique Halloween traditions that they personally like to do every single year. Like every Halloween, Brooke forces her husband to dress up in some elaborate homemade

costume that he has absolutely no interest in wearing. I don't know. He really liked being the vasectomy doctor that one year. Gross. Were you the vasectomy? No, no. That was the year that I went as before and after parenthood.

Interesting that those were back-to-back years. No, it was the same year. We did it together. Oh, I got you. It was a couple's costume. Alexis has a Halloween tradition where she must throw up bright red punch into the cup holder for a

ride home, or she can't go back into her apartment. It's how you know it's a successful Halloween? Yes. And those are sacred, and one of our listeners needs help with an annual Halloween tradition he does that's going to require an awkward phone call this time around, so let's talk to Andrew about it.

Andrew, welcome to the show. Hey, guys. Thanks for having me. God, I hope we're your new Halloween tradition, Andrew. It's year one. I'm sure you'll be back next year for another Halloween. Bad problems happen to him every year? Sure.

Okay. Well, one of us wishes ill on your Halloween. The rest of us actually want to help you. So tell us what's going on. Well, I kind of have a weird tradition that has only happened once, having the first time last year, but I want to keep it going. Okay. So it's not a tradition yet. You're hoping to make it a tradition. Hey, all traditions have to start somewhere, Jeff. Yeah, true. That is true. What is it? So I met a girl last year. Her name was kate we met on a dating app and i was

completely honest with my height with her i'm about five foot five maybe five foot four and three quarters okay you're a shorter guy hey brooke don't say that no i think it's good he wears it with confidence i think it's fine she's making a statement she's oh i tell women all the time to date short men You work so much harder I stop listening every time Brooke starts saying this Those tall guys they just like Phone it in you know You want a guy that loves you you get a short hottie

Someone with low self esteem Isn't that right Right Andrew Well you know self deprecation Is my favorite There you go Okay she's how tall You know, self-deprecation can go in my favor. Yeah. There you go. Cool.

Okay. She's how tall? She's six foot one. She's not short. Dang. Okay. So you guys are kind of role reversal there. That's cool.

So I called her through the dating app. I was like, I know you're probably not going to message me back, but I'm into taller women, and I think you're beautiful, but I'm only 5'5". Dude, I get it. I like to be picked up, too. What? Someone who's strong enough to pick you up. Okay. Picks her up and spins her in a circle. He's a grown man, Brooke. He's not

a baby. I'm a grown woman. Okay. Alright. Brooke just wee! Sorry about that, Andrew. So, that's a bold thing to be honest in your message did she respond she did and to her credit she was like sure what the heck let's meet up so that's awesome great yeah and what it came down to was that we both weren't doing anything on the day of halloween like on the actual like october 31st. Okay. And it was on a weekday. So we just met up at a bar and we instantly hit it off.

So we may look mismatched, but our personalities were perfect. We're both like very sarcastic senses of humor. That's awesome. Nice. That's refreshing. Yeah. So we drank and we laughed for like about an hour. And then I had the funniest idea.

I was like, okay, what if we went back to my place and I put on one of my old Halloween costumes. Oh, I like where this is going, my man. Keep going. Hold on. After he says go back to my place, I was like, all right. Sorry, should have interrupted you. This might be the opposite of what you're thinking.

Oh, no. We put on the Halloween costumes and we go around the neighborhood trick-or-treating together and we pretend that she's my mom. Oh, my God. What? Okay, that is so not hot. I like my idea in my head better. It's so funny. But it's funny.

It's funny, but, like, aren't you romantically interested in this woman? Yeah, definitely. Definitely. funny but it's funny it's funny but like aren't you romantically interested in this woman yeah definitely definitely but like at the time it was halloween night and we had a couple drinks and what's brooke what's not romantic about going trick-or-treating with your mom on halloween nobody wants to be a man's mom it's just not hot like here's the thing though he's using humor to bond with her and connect. He already said he was 5'5". We don't need him to pretend to be a kid, too. Yeah.

They think it's funny. Okay. So you did it? You pitched her this idea? Yeah. And because I felt like we have the same kind of sense of humor and really connected, I thought that she would say yes. Yeah.

And she did. Oh. What? Oh, my God. In your face, Brooke. She's doing it for the plot. We got into the Halloween costumes and we would walk around. She would say things at the door like, sorry, he doesn't talk a lot, but he's a really nice boy.

Because you couldn't say anything or else people would know with your voice. I mean, maybe you found your person. If she was into this, maybe this is the person for you. Right. How did it go? It was definitely fun. And we got a good amount of candy. No.

Dude, that's not even the point. Did you go home and spread it out on the floor and like do tradesies? Oh, you didn't take a photo of that? I can't believe you even said that. Well, we actually went to a park at the end of the night and we split the candy and drank some beers from my fridge. And honestly, I got to tell you, this was the best Halloween I have had since I was like eight. But you didn't have another date with her. Is that what you're saying?

No. So we've sort of for the last year just sort of been like texting or like commenting on each other's social media posts. I've been texting her to try to organize it because I'd really love to do it again. And she's not responding to me. Yeah. And you don't want a six foot one dad to come along with you. You want a six foot one mom. But in all seriousness, I really thought Kate was a really cool person.

And even if she doesn't want to do this just like hanging out in person again is something i'm really shooting for here okay it's like a monster mashup of second date and awkward tuesday yeah a year later okay yeah we'll try and get it done we'll come back give you a little bit of advice right after this okay thank you second date update i know i said at the start that this was an awkward Tuesday phone call. Yeah, just change your mind. The more we hear this story, the more I started to think it's not really awkward. It's more of a second date update.

Just a year after the first meetup. I was kind of thinking that. Honestly, the first time he asked her to pretend to be his mother should have been the awkward phone call. After she said yes. That's because before we had him on, we didn't know the full story, but Andrew basically wants to take Kate

out on another date. He says either an adult trick-or-treat adventure like last time, which he's already pitched to her over text, or if not that, he's willing to settle for a lifelong romantic Hallmark-style relationship. He's not picky. He'll take whatever he'll get.

He really does love Reese's, though. He does. A date that includes them. We're officially going to switch it up here. No awkward Tuesday anymore. It's a second date update from here on out. Are you cool with that, Andrew? Is that okay? Sure, yeah. I'm cool with that. Isn't that like break our system?

Yeah, you guys wouldn't have had advice anyways. That's true. That means that we're doing the talking then when we call her. Yes, that's how our second date updates work, Brooke. Remember, welcome to the show that you've been working on for over a decade. I don't need the sarcasm, Jeffrey. Does it make you feel better that we're

taking over the work and you don't have to do all the talking, brother? Yes. Okay. There you go. The one word answer says yes. I don't think he's confident in us. Yeah. Just before we do this, for context, when is the last time that you texted Kate, Andrew?

Last time I texted her was a few days ago because I was like, hey, are we doing this Halloween trick-or-treating thing again or what? Oh, where you act like her son. Very straightforward. Yeah, did she respond to that? No. Oh, okay. He's like, yeah, she said we're doing it. All right. That's why we're here.

Let's just call her and I'll ask that question and see if we have better luck this time, okay? We're going to ask something and then if we have better luck this time. Okay. Different question. Yeah. We're going to ask something and then something will happen. Here we go. I'm going to dial the number.

I'm nervous. Hello. Hey, is this Kate? Yeah. Who's this? Hey, Kate, you're on the radio right now with Brooke and Jeffrey in the morning. Oh, no. Did I?

Why? Oh, no. Oh, no. Oh, no, he's the co-host now. Oh, yes. Welcome to the show, Kate. Yay. Yeah.

No, this is a good thing, Kate. We're doing something with you called a second date update. Oh, Kate. Oh, man. You will never guess who called us about you. Yeah. It's been a minute. It has been a while since you were on a date with this person, at least officially. His name is Andrew.

Oh, yeah, yeah. He's been in contact with me. Oh, okay. That's a cute giggle. We've kind of heard about you guys being in contact. He's trying to organize another meetup, and you're taking him up trying to organize another meetup and you're taking him up on the offer or at least you're not responding like we we're trying to help him figure out what's going on because he's confused i mean it seems you know we don't know that's why

we're asking right so like um i'm just yeah i'm kind of confused too because i'm just kind of like not wanting to go out with him and all of his friends like he's kind of doesn't understand he didn't mention his friends when he talked to us he was just talking about you and with this halloween thing do you mean like going around trick-or-treating where he pretends to be a kid and you pretend to be his mom because you're like so much taller than him apparently i can't believe he told you guys that yeah but earlier you mentioned his friends. Like, what are you talking about his friends? He wants me to take him and all of his friends trick-or-treating.

Wait, what? Oh, no, no, no, no. His adult friends or his kid friends? Are all of his guy friends really short? I haven't met them, but he said that they're all short like him. I can't believe that they're as short as him because he's really short. Oh my god. Kings unite. So is the turn-off

like you acting as his mother, or is the turn-off you acting as his mother to not just him, but all of his friends? Both. Both. Now, I'll tell you this. He didn't mention to us anything about wanting to bring other friends along on the

trick-or-treat date experience he just said it was just you and him and he also mentioned that he's like romantically interested in you like he would be fine hanging out with you outside of just it would be smart if he brought friends they could stack on each other's shoulders and do the trench coat thing and then they'd be the same height then they can yeah do the adult parties perfect it's supposed to be so much hotter. Yeah, I mean, just as men don't like to be made fun of for being short, women don't like to be made fun of for being tall. Well, just humor.

But going back to what Brooke said, do you feel like you're romantically interested in him still? I mean, I don't know. You know what? In fact, don't even answer that. Let's just go over to our other phone line where we actually have Andrew eagerly awaiting your response. Andrew, mask off. Say hello. Hi. Hi, Kate. Good to hear your voice. Hi. Yes, you too.

Kate, you did say last year, like, how much fun you had doing this with me. And, like, we promised at the end that we'd do it again next year so just think about how much more fun it would be if there was like a group of us going together brooke always says more children more fun oh god i have never said that in my life it's like if you want me to meet your friends first of all we've only gone on one date so it's like i'm not really ready to go and meet all of your friends. You have this group of these little guys and you want me to be the tall

chaperone to you and all your friends. It just doesn't make sense to me. It's not sexy. Can you guarantee her that it'll be sexy? Gross. It's what she wants.

Last year you guys were also drinking too. This must be different planning it sober and ahead of time. Just being someone's mom is not hot. Drunk or not drunk. Maybe Andrew, you could be her dad on this one. You can balance it out.

Is that worse? Let's just be like two adults yeah i think what we want to do is take the trick-or-treating date off the table completely someone throw a halloween party out of your friends i don't think we're gonna make any progress romantically with that as the date andrew i don't want to do that just to be honest all right okay, Kate, if I'm picking up what you're putting down here, you don't want to do this trick-or-treating thing. And I imagine that in the last year, you know, you've started dating someone. You're not single anymore.

That would be my guess. I don't know if she said anything like that. I am single, but that has absolutely nothing to do with this. Are you listening to what she said? She just said she doesn't want that. No, how could she not want it? Right? This sounds like the best night ever.

I'm not alone in this, right? Maybe to you it sounds fun. He's very sold on his own idea. I think you just go trick-or-treating without a parental guide. I legit think he promised all of his friends she would chaperone, and now he's freaking out. Now they're like, what do we do? You're not lying about that.

I did talk to my friends about this and they really like the idea. Okay. Kate, you don't want to let Andrew's friends down on this. What do you say? One more date and we would pay for it and you can chaperone him around the neighborhood with his little buddies. Do you want to help, Brooke? I'm not tall enough i'm so sorry no you don't need to apologize i just kind of feel

a little creeped out about the whole thing okay no hey we're not trying to do that she's never dating a short guy again ever brooke tries to stand up for that i know this is what happens andrew man i'm sorry it sounds like we're not going to be able to get you a date here. Kate doesn't want to be your chaperone. Okay, fine, but you're really missing out. Do you have any other

tall female friends that might want to be involved in this? Maybe a sister? Anybody who really wants to be a mom for just one night? Yeah, I don't think so

at this point. Aw. Shocking. Yeah. All right, Brooke, put on the stilts. You're up. Yay, Brooke! and entertainment to the unique voices of correspondents and contributors, it's your perfect companion to stay on top of what's happening now. Plus, you'll get special content

just for podcast listeners, like in-depth interviews and a roundup of the week's top headlines. Listen on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Hi, this is Alex Kantrowitz. I'm the host of Big Technology Podcast, a longtime reporter and an you get your podcasts. actors from companies building AI tech asking where this is all going. They come from places like NVIDIA, Microsoft, Amazon, and plenty more. So if you want to be smart with your wallet, your career choices, and at dinner parties, listen to Big Technology Podcast on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. You don't need another podcast. You've got too many already. But if you're looking for one that actually changes something, a way to take control of the chaos and find meaning,

well, then maybe the one you feed is for you. I'm Eric Zimmer, and I bring real conversations with real people to help you feed the best part of yourself. No hype, no fluff, just wisdom that works. Listen to The One You Feed

on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Calling all Yellowstone fans. Let's go to work. Step into the Yellowstone universe with the official Yellowstone podcast, hosted by Bobby Bones. From exclusive cast interviews

to untold behind-the-scenes moments, Bobby takes you on a journey through five unforgettable seasons of TV's most talked-about series. I look forward to it. Listen to the official Yellowstone podcast starting January 23rd on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Had enough of this country?

Ever dreamt about starting your own? I planted the flag. This is mine. I own this. It's surprisingly easy. Here are 55 gallons of water, 500 pounds of concrete. Or maybe not. No country willingly gives up their territory. Oh my God.

What is that? Bullets. Listen to Escape from Zakistan. Inhale! That's Escape from Z-A-Q-istan. Binge the whole season on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.