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

Episode Date: October 27, 2023

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 brand new Second Date podcast!See omnystudio.com/listener for privacy information.

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then tune in to my podcast, Building One. I speak with some of the best product builders out there. I've always been inspired by frustration. It came back to my own personal pinpoint. So we had to go out to farmers and convince them. Following that curiosity is a superpower. You have to be obsessed with the human condition. Listen to Building One on the iHeartRadio app, Apple, or wherever you get your podcasts. 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. Yeah. Like every Halloween, Brooke forces her husband to dress up in some elaborate homemade costume that he has absolutely no interest in wearing. Yeah, it's true. I don't know. He really liked being the vasectomy doctor that one year. Yeah. 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. Yeah, it was a couple's costume.

Meanwhile, Alexis has a Halloween tradition where she must throw up bright red punch into the cup holder for evil 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. Okay. 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 awkward Tuesday. Bad problems to happen to him every year? Sure.

Okay. Well, one of us 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. It happened the first time last year, but I want to keep it going. Okay. Oh, interesting.

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 5'5", maybe 5'4", and 3 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 not poking fun at him. I tell women all the time to date short men. You work so much harder. I stop listening every time Brooke starts saying this. Seriously, those tall guys, they just, like, phone it in, you know? You want a guy that loves you, you get a short hottie. Yeah.

Someone with low self-esteem. Isn't that right? Right, Andrew? Well, 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 told 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. Wait. Someone who's strong enough to pick you up and carry you around. No, man. Every time they hug, he picks her up and spins her in a circle. He's a grown man, Brooke. He's not a circle. He's a grown man, Brooke. He's not a baby. I'm a grown woman.

Brooke just wee. Sorry about that, Andrew. That's a bold thing to be honest in your message. Did she respond? She did. To her credit, she was like, sure, what the heck, let's meet up. 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, 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 and we, Oh, I like where this is going, my man. Keep going. Come on. He says, go back to my place. 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. But like, at the time, it was Halloween night, and we had a couple drinks. And 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. But 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. 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, and because I felt like we have the same kind of sense of humor and really connected, I thought that she would say yes, 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,

and 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. Maybe you found your person. If she was into this, maybe this is the person for you. How did it go?

It was definitely fun, and we got a good amount of candy. Dude, that's not even the point. Did you go home and spread it out on the floor and do trades? Did you take a photo of that? I can't believe not even the point. Did you go home and spread it out on the floor and do trades? Did you just 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've 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. But 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 like 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 mash-up 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, you should 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 meet honestly the first time he asked her to pretend to be his mother should have been the awkward but that's because you know before we had him on we didn't know the full story but Andrew basically wants to take Kate out on another date

and 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? No, it's fine. You guys wouldn't have had advice anyways. Yeah, 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. Remember, welcome to the show that you've been working on for over a decade well i bet for you i bet you 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 i believe you with that there you go one word answer says yes i don't think he's confident in us but 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 okay okay he's like yeah she said we're doing it. All right. I'm kidding. That's why we're here.

You said something else. All right. No, you're right. You're right. Let's just call her and I'll ask that question and see if we have better luck this time. Okay? Ask a different question, but yeah. All right.

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 uh you're on the radio right now with brooke and jeffrey in the morning oh no did i why oh no oh no welcome to the show kate yeah no this is a good thing kate we're doing something with you called the second date update oh okay 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 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 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's he's know. We don't know. That's why we're asking. Right. So, like, 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 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 it is the turnoff like you acting as his mother or is the turnoff you acting as his mother to not just him but all of all of his friends i'm 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 as you. Then they can, yeah, do the adult parties. Perfect! Halloween is supposed to be so much hotter. Yeah, 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, like, 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 how much fun you had doing this with me.

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 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. And like you have this like group of these little guys. And you want me to be the tall chaperone to you and all your friends.

And it just doesn't make sense to me. It's not sexy. It's not, I mean. Can you guarantee her that it'll be sexy make sense to me. It's not sexy. It's not, I mean. Can you guarantee her that it'll be sexy, Andrew? Gross. 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, right? 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. Now we're talking. Is that worse? Ew.

Okay. Smaller than her daddy. 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. You can someone throw a Halloween party out of your friends. I don't think we're going to make any progress romantically with that as the date, Andrew.

I don't want to do that, just to be honest. All right. So, 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 yeah 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 not alone in this right well maybe to you it. 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. 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. No, hey, we're not trying to do that. She's never dating a short guy again. I know. Brooke tries to stand up for them. I Okay. No, hey, we're not trying to do that. She's never dating a short guy again. I know. That's the experience.

Brooke tries to stand up for them. 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. Shocking. All right, Brooke, put on the stilts. You're up. Yay, Brooke! Brooke and Jeffrey in the morning. You ever played trick-or-treat in the truck stop bathroom

where you go and knock on an occupied bathroom stall and you shout trick or treat and see what happens? Why do you ask these questions? I feel like they should just be inner monologue. I'm tempted to try it because I bet it would still go better than the call that we just had. Wow.

I thought for sure you'd already tried it. Well, no. Shockingly, not yet. Okay. But this Halloween, I'll keep you posted on what happens. Dude, he just really didn't get it. I don't... He just really thought it was romantic, I think. No, no, I think he just wanted to get free candy.

Yeah. I mean, which I feel him for that. You know, I get that. By the way, is there, like, a short guy meetup group? Is that how they're all, like, meeting? I don't know. Me and all my friends are different heights. Maybe there's an app for this.

Yeah. And they, like, measure your height in order to be able to download the app too. So you can't get it unless you are. And when you download it down is the key. Very down. That didn't work out. It was kind of doomed from the start with that idea for

a date. But it doesn't mean we can't help you out. We can always have you email the show. We'll call the person who isn't calling you back and check out all of our podcasts, all of our second dates, wherever you get yours at Brooke and Jeffrey. Brooke and Jeffrey in the morning. Ugh, we're so done with new year, new you.

This year, it's more you on Bumble. More of you shamelessly sending playlists, especially that one filled with show tunes. More of you finding Gemini's because you know you always like them. More of you dating with intention because you know what you want. And you know what? We love that for you. Someone else will too.

Be more you this year and find them on Bumble. Jon Stewart is back in the host chair at The Daily Show, which means he's also back in our ears on The Daily Show Ears Edition podcast. Join late night legend John Stewart and the best news team for today's biggest headlines, exclusive extended interviews, and more. Now this is a second term we can all get behind. Listen to The Daily Show Ears Edition on the iHeartRadio app, Apple Podcasts, or wherever you get your

podcasts. Did you know that 70% of people get hired at companies where they already have a connection? I'm Andrew Seaman, LinkedIn's editor at large for jobs and career development. And on my podcast, Get Hired, I bring you all the information you need to, well, get hired. Landing a job may be tough, but Get Hired is here for you every step of the way with advice on resumes, networking, negotiation, and so much more. Listen to Get Hired with Andrew Seaman on the iHeartRadio app, Apple Podcasts, or wherever you like to listen.