Second Date Update: Halloween Role Reversal

Published Oct 27, 2023, 3:11 PM

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!

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, Brook forces her husband to dress up in some elaborate homemade costume that he has absolutely no interest in. Weary.

I don't know. He really liked being the vsectomy doctor that one year. Yeah, yeah, yeah, are you no? No? That was the year that I went as before and afterhood.

Interesting that those were back to back years.

It's the same year I got you. Yeah, it was a couple's costumes.

Alexis has a Halloween tradition where she must throw up bright red punch into the couple home or she can't go back into her apartment.

You know, it's a successful Halloween.

Yeah, and those are sacred. And one of our listeners needs help with an annual Halloween tradition he does. It's gonna work acquire 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 where your new Halloween tradition Andrew? Year one. I'm sure next year for problem stopping him every year.

Well, one of us wishes ill on your Halloween. The rest of us will 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, Oh, 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, Broke, don't say that. No, I think it's good with confidence.

I think she's making a state and she's an I.

Tell women all the time to date short man that you got. You work so much listening every time Brooks starts. Seriously, those tall guys they just like phone it in. You know you want a guy that you you get a short hottie with.

Low self esteem? Isn't that right, right? Andrew?

Well, you know self imprecations can go my favorite.

Yea, yeah right here, got her back. Okay, she's how tall?

She's six foot one not short day.

Okay, so you guys are kind of role reversal there. That's cool.

So I called her and 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 five five.

Did I get it? I like to be picked up too. Someone is strong enough to pick you up.

He picks her up and spins her in a circle. He's a grown man, brook, He's not a baby woman.

All right.

Just sorry about that, Andrews. 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 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 thirty first, 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 humoring.

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 keep going.

To 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 head better 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 of drinks.

And Brook, 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. He's using humor to bond with herding me a kid.

Yah.

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 he did.

Oh wow, she's doing it for the plot.

We got into a Halloween cuss she was 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 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.

How did it go?

It was definitely fun and we got a good amount of candy.

That's not even did you spread it out on the floor and like, do Trady just take a photo of that?

I can't believe you 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 gotta tell you, this was the best Halloween I have had since I.

Was like, 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 text or like commenting on me to the social media post. Okay, 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 have six my 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 mashup of second date and awkward Tuesday.

Yeah 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.

Let's 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 up, a kind of thinking.

Honestly, the first time he asked her to pretend to be his mother should have been the awkward yeah after she said yes, it's 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 treated venture 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 relationships.

He's not picking.

He'll take whatever he'll get.

He really does love though, he does know.

But it includes that we're officially gonna switch it up here. No awkward Tuesday anymore. It's a second date update from here on. Now, are you cool with that? Andrew? Is that okay?

Sure? Yeah, I'm cool with that.

That means it's fine advice anyways. Yeah, 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 forever adjective for you, 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, yes, I don't think he's confident in us. 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? For treating thing again or what.

Where you act like her son? Very straightforward. Yeah. Did she respond to that?

No?

Okay, he's like, yeah, she said, we're doing it all right, all right, No, you're right. Let's just call her and I'll ask that question and see if we have better luck this time. Okay, a different question. Yeah, we're going to ask something and something will happen. Here we go and doubt the numbers. 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, no, yes, welcome to the show.

Ok yeah, no, this is a good thing, Kate. We're doing something with you called a second date update.

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 it, 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 were 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 I'm just, yeah, I'm to confuse too, because I'm just kind of like not wanting to go out with him and all of his friends, like his friends. Doesn't understand.

He didn't mention his friends when he talked to us.

He was just talking about do 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.

So much taller than him. Apparently, I can't believe he told you guys that, 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?

No, his adult friends are tall?

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 short as him because he's really short.

So is it is the turnoff like you acting as his mother? Or is the turn off you acting as his mother to not just him, but all of all of his friends both both.

No, I'll tell you this. He didn't make to us anything about wanting to bring other friends along on the trick or tree 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 him.

It would be smart if he brought friends.

They could stack on each other's shoulders and do the trench go thing and then they'd be the same high.

Then they can yeah do the adult parties.

Seems 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 told well yeah yeah.

But going back to what Brooks 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 maskof say.

Hello, Hi, Hi, Kate. Good to hear your voice.

Hey good, yeah you too, Oh Kate, you did say, last like how much fun you had doing this with me, and like you promised at.

The end that we 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.

Says more children, more friends.

God, I it's like if you want me to meet your friends. First of all, we're only go on one date, so it's like, I'm not really ready to go and meet all 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 doesn't make sense to me. It's not sexy.

It's not I mean, can you guarantee her that it'll be sexy?

I suggss.

It's what she wanted last year. You guys were also drinking too. This must be different. Planning at sober and ahead of time.

Just being someone's mom is not high or not.

Maybe maybe Andrew, you could be her dad on this.

Two adults.

Yeah, I think what we want to do is take the trick or treating date off the table completely.

Can someone throw a Halloween party out of your friends? Yeah?

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 you've started dating someone you're not you're not single anymore, that that would be my guess.

Oh she said anything like that.

I am single, but that has absolutely nothing to do with this.

Yeah, she 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 life.

Sounds he's very sold on his own idea.

I think you just go trigger treating without a parental guide, you know, just he promised all.

Of his friends she would chaperone, and now he's freaking out.

You're not lying about that. I mean, 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. 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 Brook.

I'm not tall enough.

I'm so sorry, and I just kind of feel a little creep out about the whole thing.

No, Hey, we're not trying to do it.

She's never dating a short guy again. He tries to stand up for that.

I happened, 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 ancestor.

Anybody who really wants to be a mom for just one night?

Yeah?

I don't think so at this point.

Shocking.

Yeah, all right, put on the stilts, you're up.

It's 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?

As these questions, I feel like they should just be 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 shockingly not yet. Okay, but this Halloween, I'll keep you posted on what happened.

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 it like a short guy meetup group? Is that?

I don't know. My friends are different 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. You downloading down is the key. It was kind of doomed from the start with that idea for a date. But doesn't mean we can't help you out. We can always have you email the show. We'll call the person who was in calling you back. And check out all of our podcasts, all of our second dates wherever you get yours at Brook and Jeffery

Brook and Jeffrey in the Morning,

Brooke and Jeffrey: Second Date Update

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