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Jamie
With stays under $250 a night.
Jeffrey
VRBO makes it easy to celebrate sweater weather. You could book a cabin stay with.
Jamie
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Jeffrey
A walk away, or a lakeside home with a fire pit for cozy nights with friends. Or if you're not a sweater person, we can call it corduroy weather. More flexible and with stays under $250.
Jamie
A night, you can book a home.
Jeffrey
That suits your exact needs.
Brooke
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Jeffrey
Okay, I will admit I was a little judgy today in the second date update.
Brooke
Just today, huh?
Jeffrey
But seriously, what is she thinking? I really like your new comment quote, waste your pretty. I'm going to start using that. Yeah, don't waste your pretty. 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. Yalls laughs and antics are the perfect thing to drown out the construction noises while at work.
Brooke
You thought you found it late so you can binge, huh?
Jeffrey
Yeah. Yeah. There it is. How loud you have to have us to not hear construction noises. Yeah.
Brooke
Like jackhammers.
Jeffrey
Yeah. Yeah. Or which one gives you a headache first? Yeah. You know, honestly. Hey, your brand new episode starts right now.
Brooke
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.
Jeffrey
It was this show that had to teach you that. Not high school, college.
Brooke
No, I.
Jeffrey
Personal experience.
Brooke
No, I was very much in the Disney mindset. You go out to fall in love.
Jeffrey
I know. That's so cute. I just want to pat the top of your head.
Brooke
I learned some people date for just the free meal. Some people date because their horoscope told them to. Yeah, 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.
Jeffrey
Why are you at the Rainforest Cafe? Have you had their volcano dessert, bro?
Brooke
Sorry, those mango tango daiquiris 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 onto the dating apps, and I'd like to find out what that is. Jamie, welcome to the show.
Jamie
Hey, how are you?
Jeffrey
Are you ready to shock Jeffrey? Yes.
Brooke
My whole world is about to be rocked. What is it that made you or who is it that made you get on the app?
Jamie
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 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.
Jeffrey
Okay, that feels normal.
Brooke
Emotions just to, like, get back in. You're like, let's go on a day. Let's see what happens.
Jeffrey
I don't know. That confidence thing. Are you just waiting for enough compliments to come through before the confidence kicks in?
Jamie
Yeah, exactly.
Brooke
Okay, so did it work? Were you able to grab some confidence from somewhere?
Jamie
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.
Brooke
All right, what did you do for your date?
Jamie
See, here's the thing. So the first date almost never happened, basically.
Jeffrey
Uh. Oh.
Brooke
Oh, no. Why?
Jamie
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.
Brooke
Why?
Jamie
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.
Jeffrey
Just by coincidence, you don't like moving stairs?
Brooke
Well, hey, I got my foot stuck in an escalator as a child. It was traumatic. So I understand.
Jeffrey
And you see those stories of, like, I'm sorry, I shouldn't add. Shouldn't add. My bad. But I know what you're saying. I've heard Crocs are really dangerous on them, too. That gets really.
Brooke
Oh, yeah. See that in the way. Sorry, Jamie. Hopefully we're not triggering you with all these horror stories. We're really not trying to.
Jeffrey
Sorry.
Jamie
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.
Jeffrey
Oh, my God. That sounds so painful.
Brooke
Ye. I'm sorry to laugh. It is kind of a funny image, but I understand.
Jeffrey
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?
Jamie
Right. 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 him to think I was weird immediately or.
Brooke
No.
Jeffrey
What a weird situation. And it's your very first interaction. I know.
Brooke
So what did you do?
Jamie
I just had him hold my hand while I sat on the elevator step and kept my eyes closed and we rode up.
Jeffrey
Oh, good idea. Okay. Worried about falling.
Brooke
If you can't see it, it can't hurt you.
Jeffrey
Wow. Shame on that bar for not having a handicap entrance with. I bet there Was somewhere there.
Brooke
But you made it to the top of the escalator, right?
Jamie
Yes, I did. He helped me off. 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.
Jeffrey
I don't mean to rush things, but I'm so worried about you getting back down. Yeah.
Jamie
Yeah. I ended taking the stairs down, so.
Jeffrey
Oh, there were stairs? Yeah.
Jamie
The escalators are much more visible. Found the stairs later, thank God.
Brooke
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. Yeah, you said it was. You were having a good conversation. Like, what did you two bond over?
Jamie
We actually bonded over planes. Well, like the airline JetBlue in particular.
Jeffrey
Jet Blue. Why?
Jamie
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.
Brooke
You can get bed sometimes. On a domestic flight.
Jeffrey
They fly to like four airports.
Brooke
I know it's New York pretty much. Hopefully no airports with escalators in them.
Jeffrey
Okay, so you both love JetBlue. You've already, like, been vulnerable and shared a big fear with him, right?
Jamie
Yeah, I did. 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.
Brooke
Oh, wow. He went for the second date ascat immediately.
Jamie
Yes. But after that there's been no follow through. And so I'm just like, what happened?
Brooke
And how long has it been since your date on the Second story?
Jamie
It's been about a week or so.
Jeffrey
And he hasn't reached out at all?
Jamie
No.
Brooke
Hopefully his phobia isn't actually following through with the second dates or he's just.
Jeffrey
Looking for first floor restaurants and having a hard time.
Brooke
Oh, maybe that's possible. Or he's scared of elevators and he's like, we could never be together again. So much could go wrong.
Jeffrey
I can't take the escalator. You can't take the elevator.
Brooke
Neither of us can get vertical. Oh, what a tough match. Hopefully we'll find out what. What's really going on when we call Matthew and try to escalate this to a second date. Okay, I did it.
Jeffrey
Okay, one and done. No more.
Brooke
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. Something's happening.
Jeffrey
But why? Why arrested?
Brooke
Well, I'm not gonna. I'm not gonna 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.
Jeffrey
Jeff. Yeah, I feel like she's just dropping it in case something goes somewhere and they can get sponsored. And a trip.
Brooke
Nice plane.
Jeffrey
That's good.
Brooke
Looking dumb, smart, but it did bond them. And Matthew even asked her out again at the very end of the night. Yeah, great sign. Thing is, there's been no follow through since. So Jamie has now turned to us, asking if we can get involved.
Jeffrey
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, Alexa? My bad. Thirsty?
Jamie
No, I haven't. I was nervous because I was just anticipating him reaching out to me and I don't know, I didn't want to seem obsessive or weird, I guess.
Brooke
What if it's a big game of stalemate? Like you? Totally. I'm not gonna text her until probably is.
Jeffrey
I mean, I feel like that's how a lot of dating fizzles out. Well, good thing.
Brooke
Nothing weird about a radio show. Random calling and asking to cry into his life. That should go over totally. Fine. Smooth it all over.
Jeffrey
He doesn't have a fear of public speaking. I guess we'll find out soon.
Brooke
Let's see if he even answers. I'm going to dial his number right now. Here we go.
Matthew
Hello?
Brooke
Hey, is this Matthew?
Matthew
Yeah, this is he.
Brooke
Hey, man. Thanks for answering. You're on a show right now, a radio show called Brook and Jeffrey in the Morning.
Jeffrey
Hey, Matthew. Hi.
Brooke
Good morning.
Matthew
Hi.
Jeffrey
Kind of weird. Yeah.
Brooke
It probably doesn't happen to you every single day, I'm guessing, but it'd be.
Jeffrey
Wild if it did.
Brooke
Yeah, maybe once a month I could see it happening. But we're doing something called 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.
Matthew
Oh, okay. Yeah, yeah, I remember that.
Jeffrey
Okay.
Brooke
Okay.
Jeffrey
Remember cute Jamie? You asked her out On a date.
Matthew
Yeah, I remember Jamie. Yeah.
Brooke
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.
Jeffrey
Such a formal way to word it.
Brooke
Yeah, I'm working on my vocabulary.
Jeffrey
Brooke. Yes.
Brooke
I'm sorry. I can dumb it down for the Idaho listeners in your hometown.
Jeffrey
Want to.
Brooke
I enjoy your extensive vocabulary.
Jeffrey
We like courtship where I come from.
Brooke
Yeah, 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.
Matthew
I mean, I was having a pretty good time with her. Like, I. I was like 100% in. Like, on. On wanting to hang out again.
Jeffrey
Okay, so when you asked her out at the end of the date, you were being sincere?
Brooke
Yeah.
Matthew
Yeah. Like, she was cool.
Jeffrey
It was.
Matthew
It was a good time. You know, the drinks were good there.
Jeffrey
That was your highlight. The drinks were good there. He was into it. Okay, so what happened?
Brooke
Yeah, something must have changed since then. Well.
Matthew
Well, it was the comment.
Jeffrey
The comment?
Brooke
What comment?
Matthew
Oh, 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?
Jeffrey
Okay.
Matthew
She paused for a second and she goes, sure, why not? My bar is pretty low anyways.
Jeffrey
Whoa. Well, that had to have been a joke. Like, it just landed poorly. That's sad.
Brooke
Where's the joke in that?
Jeffrey
It's still not a good joke.
Brooke
I mean, it's. She should have been very sarcastic.
Jeffrey
Yeah. Was she trying to be funny? Like.
Brooke
Like, did you respond to that?
Matthew
Yeah. And I was like, what is that supposed to mean?
Jeffrey
Oh, you did. You said that back. Okay, okay. And then she said, I'm just joking. Right?
Matthew
She goes, don't take it personal. I just got out of a relationship with an 80 year old guy.
Jeffrey
What?
Brooke
Whoa, wait.
Jeffrey
Dang.
Brooke
You're rebounding from an 80 year old. That must feel good.
Jeffrey
Is that also a joke? I just want this all to be humorous. Yeah, true. Back to back. Yeah.
Matthew
It didn't sound like a joke to me.
Brooke
Oh, God.
Matthew
She basically says the 80 year old broke up with her so he could find someone who lives closer to him.
Jeffrey
What? Oh, wait. She got dumped by the. The senior.
Matthew
Exactly.
Brooke
Wow. What is going on? Good for that 80 year old for having standards.
Jeffrey
I mean, it makes you feel better she wasn't living in the same city as him, so maybe she didn't see him.
Brooke
I didn't get the impression the same city I've got the impression like she's three blocks away and that's too far for his hips.
Jeffrey
Yeah.
Brooke
Yeah.
Jeffrey
Why on earth would she be in a relationship with an 80 year old man?
Brooke
That's a lot.
Jeffrey
Don't judge people, bro. I'm judging. Do you want real answers? I don't know.
Brooke
Not from Alexis. Okay, so that kind of explains a lot.
Jeffrey
And how are you lower than that? I am like offended for you.
Matthew
Yeah, I mean I. 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?
Brooke
Yeah, yeah, you gotta wait till you're 80.
Jeffrey
She didn't bring any of that up. Not the 80 year old, not the comment.
Brooke
Yeah, I feel like we should probably ask her about that because you don't know this Matthew, but Jamie has been quietly listening on the other line waiting to talk to you.
Matthew
Oh great.
Brooke
Yeah, Jamie.
Jamie
Okay, so you're putting me down just because I dated an older man.
Matthew
No, I'm putting you down because you dated an ancient man who kicked you to the curb.
Jamie
Okay, he's right.
Jeffrey
Absolutely. You cannot say older man when he's 80.
Brooke
Jamie, how did none of this come up when you were talking to us in the first part?
Jamie
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.
Jeffrey
Now wait, do actually considered the 80 year old your ex? Because it just sounds like a deal that didn't work out.
Jamie
Yeah, 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.
Matthew
Okay, like you went to the club. Did you have to change attendance? Balls on his walker.
Jamie
Okay, that's really mature.
Jeffrey
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.
Brooke
Well, she says he has a great body. She could be an old people.
Jamie
He respond honestly.
Jeffrey
Okay, you could at least go with personality over body. That's more believable.
Jamie
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.
Brooke
Like, yeah, don't come after who she likes. Don't tell us what the old man's religion was because Brooke will go in.
Jeffrey
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 me. But what if it was a joke or not? He didn't take it as one.
Brooke
Well, what if it wasn't a joke? What if he really was a step down?
Jeffrey
You don't say that to people, Joe.
Brooke
Okay, fine. If he was 60 years old, then it would be okay.
Jeffrey
I'm just really not into the dating for money thing, but whatever people need to do.
Brooke
She's not dating for money.
Jeffrey
Was he rich? We didn't ask.
Brooke
Yeah, I never even asked. Did she. Did he have money?
Jamie
No, he wasn't like rich. Like, I mean, he was fine.
Brooke
Yeah.
Jeffrey
Okay.
Brooke
He only had two boats.
Jeffrey
Brooke.
Brooke
Depleted his whole 401k for.
Jamie
Nothing to do with that. Nothing to do with money.
Jeffrey
I mean, I think at the end of this is like, you were rude to Matthew, right? You said that you had already. Why not not go out with them? Your bar's already low. Like, that's a terrible thing to say to someone.
Jamie
Okay, fair enough. I was joking. Like I wasn't super serious. Like I was having fun on that date. I'm sorry. Like I just gotten out of something. I wasn't feeling good about myself, so I made a bad joke.
Brooke
Okay.
Jeffrey
Okay.
Brooke
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 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. You reached out to our show. That's super low in itself. You're meant to meet down at the bottom of the dating pool.
Jamie
What are you asking? Are you asking if I want to go out with him again? You know, I don't.
Jeffrey
Now she's there.
Brooke
She's joking again. Yeah, classic.
Jeffrey
I don't think she is. I don't think she is.
Brooke
Okay, so Jamie has now rescinded her desire to go out with Matthew again.
Matthew
Y. Yeah, I'm good as well. She can have that 80 year old man hold her hand up the escalator.
Jeffrey
Ah, okay. Oh yeah, they're definitely gonna have to take the elevator.
Brooke
Sounds like he would carry her up the stairs based on how fit she described it. I can see both of them in a forever fall up an escalator. How sweet. Crooked Jeffrey.
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Brooke
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Jeffrey
Yeah, it turned into us just roasting an 80 year old, but really, it's really impressive on his part.
Brooke
Yeah, half his age. I gave up already.
Jeffrey
I mean, it sucks for his grandkids that they're not going to get any of the inheritance, you know.
Brooke
Yeah, 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 shot with them. That is bravery as an octogenarian.
Jeffrey
And he knows how to use dms. Look at that. Impressive.
Brooke
Yeah, you're kind of turned on by him, aren't you?
Jeffrey
Alexa, he has to hold the phone really far away from his face in order to do it.
Brooke
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. You two could be ruling the world. Eating dinner at 3:30 every day for half off.
Jeffrey
I'm telling you couple, there is not enough discounts or savings in the world to waste your pretty on an 80 year old. It's just. It's just not.
Brooke
I mean honestly, unless the 80 year old's super hot. Yeah, let's agree on that.
Jeffrey
When have you ever seen a hot 80 year old?
Brooke
I'm pretty sure Tom Cruise is 80.
Jeffrey
Even the old golden bachelor wouldn't date somebody over 60. He ended up being creepy too. All right. Okay.
Brooke
Back off the old guys.
Jeffrey
That's okay.
Brooke
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. Thursday Night Football is on and it's only on Prime Video.
Jeffrey
That is unbelievable.
Brooke
This week, the Bills stampede into Houston to meet the Texans in a showdown under the lights. Are you kidding me with this catch? Coverage begins at 7pm Eastern with football's best best party, TNF tonight presented by Verizon. Not a Prime member, Not a problem. Simply sign up for a 30 day free trial. It's the Bills and the Texans. Thursday at 7pm Eastern only on Prime Video. Restrictions apply. See Amazon.com amazonprime for details. Ah, greetings from my bath festive friends. The holidays are overwhelming, but I'm tackling this season with PayPal and making the most of my money. Getting 5% cash back when I pay in full. No fees, no interest. I used it to get this portable spa with jets. Now the bubbles can cling to my sculpted but pruny body. Make the most of your money this holiday with PayPal. Save the offer in the app ends1231. See paypal.com promoter points can be redeemed for cash and more paying for subject to terms and approval. PayPal Inc. And MLS 910457 okay, only.
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Podcast: Brooke and Jeffrey: Second Date Update
Date: November 19, 2025
Host(s): Brooke & Jeffrey
Guest: Jamie (listener seeking a second date), Matthew (date)
In this hilarious and unexpectedly poignant installment, the team helps listener Jamie discover why her promising first date with Matthew ended in radio silence. What begins as a story about overcoming an unusual phobia quickly escalates (pun intended) into confessions about exes, age-gap relationships, and some unintentional disses. By the end, the real reason behind the ghosting is revealed—and it’s not what anyone expected.
The episode is a classic mix of humor and honest awkwardness. The hosts are playful but push for answers, while Jamie and Matthew’s dynamic oscillates between self-deprecating jokes and raw vulnerability. The show highlights how first-date nerves and jokes can unexpectedly sabotage budding chemistry, and how sometimes the issues aren’t about escalators at all.
Final Note:
If you’re struggling to reconnect after a great first date, make sure your jokes land—and maybe keep the 80-year-old exes out of your punchlines. As for Jamie and Matthew, they’ll be taking separate escalators from now on.