Brooke and Jeffrey: Second Date Update - Second Date Update: Escalator Escape

Episode Date: November 19, 2025

The woman on the phone today says she was FORCED to confront her biggest fear in the first 5 minutes of her date. We’ll figure out what she’s so scared of in your Second Date Update podcast!See omnystudio.com/listener for privacy information.

A decade ago, I was on the trail of one of the country's most elusive serial killers, but it wasn't until 2023 when he was finally caught. The answers were there, hidden in plain sight. So why did it take so long to catch him? I'm Josh Zeman, and this is Monster, hunting the Long Island serial killer, the investigation into the most notorious killer in New York, since the son of Sam, available now. Listen for free on the IHeart Radio app, Apple Podcasts, wherever you get your podcasts. On the podcast Health Stuff, we are tackling all the health questions that keep you up at night.

I'm Dr. Priyankawali, a double board certified physician. And I'm Hurricane Dabolu, a comedian and someone who once Googled, Do I Have Scurvy at 3 a.m? And on our show, we're talking about health in a different way, like our episode where we look at diabetes. In the United States, I mean, 50% of Americans are pre-diabetic. How preventable is type 2? Extremely.

Listen to Health Stuff on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts. I'm Robert Smith, and this is Jacob Goldstein, and we used to host a show called Planet Money. And now we're back making this new podcast called Business History about the best ideas and people and businesses in history. And some of the worst people, horrible ideas and destructive companies in the history of business. First episode, How Southwest Airlines Use Cheap Seats and Free Whiskey to fight its way. into the airline is. The most Texas story ever. Listen to business history on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts.

Podcasters, it's time to get the recognition you deserve. The IHeart Podcast Awards are coming back in 2026. Got a mic? Then you've got a shot. Every year, we celebrate the most creative, compelling, and game-changing voices in podcasting. Is that you? Submit now at IHeart Podcast Awards.com for a chance to be honored on the biggest stage in the industry. Deadline December 7th.

This is your chance. Let's celebrate the power of podcasting and your place in it. Enter now at iHeartpodcastawards.com. What do you get when you mix 1950s Hollywood, a Cuban musician with a dream, and one of the most iconics it comes of all time? You get Desi Arness. On the podcast star in Desi Arnaz and Wilmer Valderrama,

I'll take you in a journey to Desi's life, how he redefined American television and what that meant for all of us watching from the sidelines, waiting for a face like hours on screen. Listen to starring Desi Arnaz and Wilmer Valderrama on the IHard Radio app, Apple Podcasts, or wherever you get your podcast. Okay, I will admit I was a little judgy today in the second date update. Just today, huh? But seriously, what is she thinking?

I really like your new comment, quote, waste your pretty. I'm going to say you start using that for that one. Don't waste your pretty. I've heard that out of that. Oh, God, I use that all the time. Don't waste your pretty. All right, you'll understand what's going on here in a second because we got a brand new episode for you.

But first, comments. Alan Jameson said, I'm so glad I found the podcast so late in the game. Y'all's laughs and antics are the perfect thing to drown out the construction noises while at work. Hey, you've got he found it late so you can binge, huh? Yeah, yeah, there it is. I wonder how loud you have to have us to not hear construction noise.

Yeah, like jackhammers? Yeah. Or which one gives you a headache first? Yeah, true. Honestly. Hey, your brand new episode starts right now. Second Date Update. Something I've learned since I started working on this show is not everybody necessarily dates for true love.

Oh, that's for sure. It was this show that had to teach you that? Not high school, college. No, I have a personal experience. No, I was very much in the Disney mindset. You go out to fall in love. I know, that's so cute. I just want to pat the top of your head.

I learned some people date for just a free meal. Some people date because their horoscope told them to That's actually true Some people date because their spouse wanted to try opening up the relationship So now it's a table for three at the rainforest cafe And that always works out Why are you at the rainforest cafe? Have you had their volcano dessert bro?

Sorry. Those mango tango daugries cannot come fast enough But they serve alcohol They sure do One of our listeners Jamie wrote us in her email Saying she had a different reason for hopping on to the dating apps. And I'd like to find out what that is. Jamie, welcome to the show. Hey, how are you? Are you ready to shock, Jeffrey? Yes. My whole world is about to be rocked. What is it that made you, or who is it that made you get on the apps? Yeah. I've just been trying to get myself back out there. I've been in a few relationships that didn't work out recently. And so I'm just trying to get my confidence back up. I don't really assume I'm going to fall in love immediately, but, you know. Okay, that feels normal. You're what they say like going through the motion. Just to, like, get back in, you're like, let's go on a day, let's see what happens.

I don't know, that confidence saying, are you just waiting for enough compliments to come through before the confidence kicks in? Yeah, exactly. Okay, so did it work? Were you able to grab some confidence from somewhere? I mean, I did end up matching with this guy named Matthew on Hinge. Okay. So I was feeling good about that, and he had some really cute photos. He was kind of nerdy, cute look.

He's wearing glasses. like I was into it. All right. What did you do for your date? See, here's the thing. So the first date almost never happened, basically. Oh, no. Why?

Okay, so we were going to meet up for happy hour. We get there. And I realize, I don't know if I can actually coincide or not. Why? Because the bar you picked is on the second floor, and you have to take an escalator there, and I have this phobia of escalators, basically. Oh, no.

Oh, just bad coincidence, huh? Oh, you don't like moving stairs. Well, hey, I got my foot stuck in an escalator as a child, and it was traumatic. It was scary. And you see those stories of like, I'm sorry, I shouldn't add. I shouldn't add. My bad. But I know what you're saying.

I've heard Crocs are really dangerous on them, too, that get stuck. Oh, yeah. I can see them to win. Sorry, Jamie. Hopefully we're not triggering you with all these horror stories. We're really not trying to. Sorry. No, it's okay.

I actually fell down one at the Mall of America when I was a kid. But it was going upward, so I just kind of kept falling. Yeah. Oh, my God. That sounds so painful. Yeah. I'm sorry to laugh. It is kind of a funny image, but I understand.

So what do you do? You're on this date and you have to go to the second floor and you can't find an elevator. What do you do? Obviously, I'm hesitating and he sees me and he's like, what's wrong? And I didn't want to tell him because I didn't want to think I was weird immediately. Oh, I know. What a weird situation. And it's your very first interaction.

I know. So what did you do? I just had him hold my hand while I sat on the elevator step and kept my eyes closed and we rode up sitting down if you can't see it

it can't hurt you well shame on that bar for not having a handicap entrance with us I bet there was somewhere but you made it to the top of the escalator right yes I did

he helped me off and the drinks were great that we had we ended up having a really good conversation after that I thought he was just a really nice guy overall. I don't mean to rush things, but I'm so worried about you getting back down. Yeah. Yeah, I ended up taking the stairs down.

Oh, there were stairs. Yeah, the escalators were much more visible. Found the stairs later, thanks. After you were at the restaurant, you're like, there's the stairs. Got to delay the lane. Yeah, so sorry. Going back to the date, though, with Matthew, you said it was you were having a good conversation. Like, what did you two bond over?

We actually bonded over planes. Well, like the airline JetBlue in particular. JetBlue, why? Because it's our favorite, and they have the best in flight entertainment. So we just talked about traveling and whatever our experiences and stuff like that. You can get bed sometimes on a domestic flight. They fly to like four airports. I know.

It's New York pretty much. Hopefully no airports with escalators in them. Oh. Okay, so you both love JetBlue. You've already been vulnerable and shared a big fear with him, right? Yeah. Yeah, I opened up a little bit about it, and he was pretty sweet about it. And at the end of the night, he even asked me if I wanted to meet up again, and I was like, yes, definitely.

Oh, wow, he went for the second date asked out immediately. Yes, but after that, there's no follow-through, and so I'm just like, what happened. And how long has it been since your date on the second story? It's been about a week or so. And he hasn't reached out at all? No. Hopefully his phobia isn't actually following through with the second dates Or he's just looking for first floor restaurants and having a hard time

Oh, maybe that's possible Or he's scared of elevators and he's like, we could never be together So much could go wrong I can't take the escalator, you can't take the elevator Neither of us can get vertical Oh, what a tough match Hopefully we'll find out what's really going on When we call Matthew and try to escalate this to a second day

I did it, okay One and done, no more. I have one too. No more puns as we continue for your second date update right after this. Hold on. Second date update. If you'd never heard this story before and I told you a young woman sat on an escalator step, holding her date's hand with her eyes shut tight,

you'd probably think, huh, someone's about to get arrested here soon. Some's happening. But why? Why arrested? I'm not going to, I'm not going to, Explain it, but luckily that was not the case here. Our listener, Jamie, has an escalator phobia, but she beat it going to a happy hour with her date, Matthew, and together they bonded over JetBlue Airlines, of all things.

You don't hear that one a lot on the first dates. More of a Delta guy myself, Jeff. I feel like she's just dropping it in case something goes somewhere and they can get sponsored and a trip taking. Yeah. Yeah. That's good looking out. It's not dumb.

smart, but it did bond them and Matthew even asked her out again at the very end of the night. Yeah, great sign. The thing is, there's been no follow-through since, so Jamie has now turned to us asking if we can get involved. Yeah, and Jamie, you said he hasn't reached out to you, but have you called or texted

him? Sorry, not called. That would be gross, right? Alexis. Talk about phobia. My bad. No, I haven't. I was nervous because I was just anticipating him reaching out to me. I don't know. I didn't want to seem obsessive.

weird, I guess. What if it's a big game of stalemate? Like, he's like, I'm not going to text her until she text me. I mean, I feel like that's how a lot of dating fizzles out. Well, good thing, nothing weird about a radio show randomly calling

and asking to cry into his life. That should go over, totally fine. Totally smooth it all over. Hopefully, he doesn't have a fear of public speaking. Yeah, I guess we'll find out soon. Let's see if he even answers. I'm going to dial his number right now. Here we go.

Hello? Hey, is this Matthew? Yeah, this is he. Hey, man. Thanks for answering. You're on a show right now, a radio show called Brooke and Jeffrey in the morning. Hey, Matthew. Hi. Good morning.

Hi. Hi. Kind of weird. Yeah, it's probably doesn't happen to you every single day, I'm guessing. I'd be wild if it did. Yeah, maybe once a month I can see it happening. But we're doing something called a second date update. And we're trying to help out a listener of ours who went out with you.

recently, and she's not heard from you since. A woman named Jamie. Oh, okay. Yeah, yeah, I remember that. Okay. Remember cute Jamie? You asked you out on a day. Yeah, I remember Jamie.

Yeah. Yeah. So the deal is we've heard from Jamie about the night that you two hung out. And Jamie sounded like a really cool girl who really enjoyed your companionship when you went to the bar together. Such a formal way to word it. Yeah. companion.

I'm working on my vocabulary, Brooke? Yes. I'm sorry. I can dumb it down for the Idaho listeners in your hometown if you want to. I enjoy your extensive vocabulary. We like courtship where I come from. Sure.

So that's kind of the situation. We're trying to help Jamie figure out if there's a reason why you two haven't met up again. I mean, I was having a pretty good time with her. I was like 100% in, like on wanting to hang out again. Okay. So when you asked her out at the end, of the date, you were being sincere?

Yeah, yeah, like, she was cool. It was a good time. You know, the drinks were good there. That was your highlight. The drinks were good there. He was into it. Okay. So what happened?

Yeah, something must have changed since then. Well, it was the comment. The comment? What comment? So as we were saying goodbye, I asked her out and I said, hey, this has been really fun. Do you want to meet up again next weekend? And she paused for a second

And she goes, sure, why not? My bar's pretty low anyways. Whoa. Oh, wow. Well, that had to have been a joke, like, it just landed poorly. That's bad. Where's the joke in that? It's not a good joke.

I mean, it's, she should have been very sarcastic when she said. Yeah. Was she trying to be funny? Like, did you respond to that? Yeah, and I was like, what is that supposed to me? Oh, you did. You said that back. Okay.

And then she said, I'm just joking, right? She goes, don't take it personal. I just got out of a relationship with an 80-year-old guy. What? Whoa. Wait. Dang, you're rebounding from an 80-year-old? That must feel good.

Is that also a joke? I just want this all to be humorous. Yeah, true. She could be like top-year-old. It didn't sound like a joke to me. Oh, God. She basically says the 80-year-old broke up with her, so he could find someone who lives closer to him.

What? Wait. She got dumped by the senior? Exactly. Oh, my gosh. What is going on? Good for that 80-year-old for having standards. I mean, it makes you feel better if she wasn't living in the same city as him.

So maybe she didn't seem. I didn't get the impression of the same city. I've got the impression, like, she's three blocks away, and that's too far for his hips. He can't walk that distance. He needs a caretaker. Yeah. Why on earth would she be in a relationship with an 80-year-old man? That's a lot.

Don't judge people, Brooke. I'm judging. Do you want real answers? I don't want to know. Not from Alexis. Okay, so that kind of explains a lot. And how are you lower than that? I am, like, offended for you.

Yeah, I mean, I felt pretty bad. I didn't know how to respond. And then also, why would I want to go out with her after that? Yeah. Yeah, you got to wait until you're 80. She didn't bring any of that up. Not the 80-year-old, not the comment. Yeah.

I feel like we should probably ask her about that because you don't know this, Matthew, you, but Jamie has been quietly listening on the other line waiting to talk to you. Oh, great. Yeah, Jamie. Okay, so you're putting me down just because I dated an older man? No, I'm putting me down because you dated an ancient man who kicked you to the curb. Oh, wow. He's right.

He's different. Ancient. Absolutely. You cannot say older man when he's 80. Jamie, how did none of this come up when you were talking to us in the first part? I don't know. I didn't think about it. I wasn't talking about my exes. I was talking about the person I wanted to date now. Wait, do you actually consider the 80-year-old your ex? Because it just sounds like a deal that didn't work out. No. Okay, listen. First of all, he was in great shape. Probably better than you, actually. And he was very active.

And he liked to go out and do lots of things. Okay. Like, you went to the club. Did you have to change incentives walls on his walker? Wow, that's really mature. Yeah. I mean, honestly, Jamie, the optics are you're just doing it for money. That's the only reason anyone would date an 80-year-old at your age. She says he has a great body. She can be an old people.

He was fun, honestly. Okay, you could at least go with personality over body. That's more believable. I don't know why I'm getting judged for who I'm dating. Like, it doesn't matter. It shouldn't matter age or religion or whatever, you know, like, I don't come after who she likes. Don't tell us what the old man's religion was because Brooke will go in.

But I don't think it's very fair to compare and say that the current date is worse than the 80-year-old that you just dumped by. Like, I'm sorry, that was just mean. I don't care if you think it was a joke or not. He didn't take it as one. What if it wasn't a joke? What if he really was a step down? You don't say that to people, Joe. Okay, fine.

If he was 60 years old, then it would be okay. I'm just really not into the dating for money thing, but whatever people need to do. She's not dating for money. Well, was he rich? We didn't ask. Yeah, we never even asked. Did he have money? No, he wasn't, like, rich.

Like, I mean, he was fine. Yeah. He only had two boats, Brooke. Depleted his whole 401K for it. That's nothing to do with that. Nothing to do with money. I mean, I think at the end of this is, like, you were rude to me. Matthew, right? You said that you had already, why not go out with them? Your bar's already low.

Like, that's a terrible thing to say to someone. Okay, fair. I was joking. Like, I wasn't super serious. Like, I was having fun on that date. I'm sorry. Like, I'd just gotten out of something. I wasn't feeling good about myself. So I made a bad joke. Okay. And yeah, this conversation kind of got off the rails. It turned into like put downs back and forth. And what we really need to focus on is true love. Okay. How can we see? save this right now. Yeah. I mean, Jamie, you said that you were lowering your bar.

Maybe Matthew is also lowering the bar, too. Jamie, you're the one who, you reached out to our show. That's super low in itself. Maybe you're meant to meet down at the bottom of the dating pool. What are you asking? Are you asking if I want to go out with him again? You know, I don't now. She's joking again.

Classic humor. I don't think she is. I don't think she is. Okay, so Jamie has now rescinded her desire to go out with Matthew again. Yeah, I'm good as well. She can have that 80-year-old man hold her hand up the escalator. Oh, okay. They're definitely going to have to take the elevator.

It sounds like he would carry her up the stairs based on how fit she described. I can see both of them in a forever fall up an escalator. How sweet. Brooke and Jeffrey in the morning. A decade ago, I was on the trail of one of the country's most elusive serial killers. but it wasn't until 23 when he was finally caught. The answers were there, hidden in plain sight.

So why did it take so long to catch him? I'm Josh Zeman, and this is Monster, hunting the Long Island serial killer, the investigation into the most notorious killer in New York since the son of Sam, available now. Listen for free on the IHeart Radio app, Apple Podcasts, wherever you get your podcasts. I'm Robert Smith, and this is Jacob Goldstein,

and we used to host a show called Planet Money. Now we're back making this new podcast called Business History about the best ideas and people and businesses in history. And some of the worst people, horrible ideas, and destructive companies in the history of business. Having a genius idea without a need for it is nothing. It's like not having it at all. It's a very simple, elegant lesson. Make something people want. First episode, How Southwest Airlines Use Cheap Seats and Free Whiskey to Fight a Solution.

way into the airline business. The most Texas story ever. There's a lot of mavericks in that story. We're going to have mavericks on the show. We're going to have plenty of robber barons. So many robber barons. And you know what? They're not all bad.

And we'll talk about some of the classic great moments of famous business geniuses, along with some of the darker moments that often get overlooked. Like Thomas Edison and the electric chair. Listen to business history on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. You know, after everything we heard, in that call, I just think it's awesome that 80-year-olds are still trying to put themselves out there and meet people. That's

inspiring. Yeah, dang. It turned into us just roasting an 80-year-old, but really it's really impressive on his part. Half his age I gave up already. I mean, it sucks for his grandkids that they're not going to get any of the inheritance. Yeah, true. You know. Well, that's what I've learned. You're never too old to try and take risks.

Especially when you're sliding into a 31-year-old's DM, shooting your shot with them. That is bravery as an octogenarian. Yeah. And he knows how to use DMs. Look at that. Yeah, you're kind of turned on by him, aren't you, Alexis? He has to hold the phone really far away from his face in order to do it.

I mean, Brooke, if you're thinking about, like, the benefits of it as a young woman dating an old man, just imagine if you're in her shoes combining your rewards card savings with his senior discounts. Oh, no, man. You two could be ruling the world eating dinner at 3.30 every day for half off. I'm telling you, there is not enough discounts or savings in the world. world to waste your pretty on an 80-year-old. It's just not. I mean, honestly.

Unless the 80-year-old's super hot. Let's agree on that. When have you ever seen a hot 80-year-old? I'm pretty sure Tom Cruise is 80. Even the old Golden Bachelor wouldn't date somebody over 60. Oh, yeah. He ended up being creepy, too. You hear about that?

All right. Back off the old guys. That's Brooks territory. Okay, but you can always text in if you want help with your dating life. Older young, we'll try not to judge you. Just email the show. We'll call that person who's not calling you back. A decade ago, I was on the trail of one of the country's most elusive serial killers.

But it wasn't until 2023 when he was finally caught. The answers were there, hidden in plain sight. So why did it take so long to catch him? I'm Josh Zeman, and this is Monster, hunting the Long Island serial killer, the investigation into the most notorious killer in New York, since the son of Sam, available now. Listen for free on the IHeart Radio app, Apple Podcasts, wherever you get your podcasts. On the podcast health stuff, we are tackling all the health questions that keep you up at night.

I'm Dr. Priyanko Wally, a double board certified physician. And I'm Hurricane de Bolo, a comedian and someone who once Googled, Do I Have Scurvy at 3am? And on our show, we're talking about health in a different way, like our episode where we look at diabetes. In the United States, I mean, 50% of Americans are pre-diabetic. How preventable is type 2? Extremely. Listen to health stuff on the IHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

I'm Robert Smith. And this is Jacob Goldstein. And we used to host a show called Planet Money. And now we're back making this new podcast called Business History about the best ideas and people and businesses in history. And some of the worst people. Horrible ideas and destructive companies in the history of business. First episode, how Southwest Airlines use cheap seats and free whiskey to fight its way into the airline is. The most Texas story ever.

Listen to business history on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Podcasters, it's time to get the recognition you deserve. The IHeart Podcast Awards are coming back in 2006. Got a mic? Then you've got a shot. Every year, we celebrate the most creative, compelling, and game-changing voices in podcasting. Is that you? Submit now at IHeart Podcast.

Podcast Awards.com for a chance to be honored on the biggest stage in the industry. Deadline, December 7th. This is your chance. Let's celebrate the power of podcasting and your place in it. Enter now at iHeartpodcastawards.com. What do you get when you mix 1950s Hollywood, a Cuban musician with a dream, and one of the most iconics it comes of all time? You get Desi Arness.

On the podcast star in Desi Arnaz and Wilmer Valderrama, I'll take you in a journey to Desi's life, how he redefined American television and what that meant for all of us watching from the sidelines waiting for a face like hours on screen. Listen to starring Desi Arnaz and Wilmer Valderrama on the IHard Radio app, Apple Podcasts, or wherever you get your podcast.