
Brooke and Jeffrey: Second Date Update
Second Date Update: Apple Picking For The 1 Percent
Freitag, 23. Oktober 2026 · 18 min
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Daniel was DESPERATELY trying to avoid answering one specific question on his date with Lilly. It got asked, it DIDN’T go well, and now he wants our help figuring out how to put the pieces back together in your Second Date Update!
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All right, we got your brand new episode. Thank you for being here. It's Brooke and Jeffrey on your second day podcast. But apparently we need a little time to reflect.
Yeah, and yesterday's awkward Thursday because mentioning the HOA, people triggered.
I don't think anybody was in defense of the HOA.
No.
In the entire comments and text board, nothing. We got some comments, let's be honest, that freaking lady is using that 250 bucks to buy her own Halloween candy.
I need to think about that.
HOAs appear to be the preferred job of peeping toms and busybodies.
I would play the.
Petty gray area and go the extra mile by getting regular sized bars, vacuum sealing multiple of them into the shape and size of a king size or even bigger.
Yeah.
Yeah. So anyway, there was plenty more of that HOA hate.
Some people were saying that this could be illegal, what the HOA is doing.
I didn't even realize that.
I'm sure our listener is just scanning all the comments, getting all of the, you know, everything he needs.
All the tea, all the comments. King size for the kids. Yeah, for sure.
All right, we're going to get to it. Your brand new second date update starts right now. Oh, and a quick reminder, next week it is Halloweek. on our show yeah it's a full week of halloween just fun and second date so definitely stick around here uh but here enjoy this episode brooke and jeffrey in the morning second date update we.
Don't get this a lot where a guy emails the show and just flat out says i don't get why this girl isn't calling me back i have a ton of.
Money what.
Wow.
I mean, I could say that maybe that sentence has something to do with it.
I'm not sure what you mean, Brooke.
I mean, how important is that to the modern woman, really? Because I know we joke with you, Alexis, a lot about this, but if a guy is financially well off, does it actually make a difference or not really?
I don't know.
I mean, I feel like it's just more about how he spends, like, have his own place, have his.
Own, I don't know.
Oh, like have his own private jet.
Yeah.
That he can fly you places.
I don't think that would hurt you.
Okay. So, okay, it helps a little bit.
But I am curious to speak with this loaded gentleman who reached out to us.
His name is Daniel. So, Daniel, welcome to the show, man.
Thank you. Appreciate it.
Yeah, your email says that you've been frustrated with the dating scene lately because apparently whenever a woman finds out that you're wealthy, it changes the conversation.
That's what you said. Tell us about that.
Yeah.
I mean, it's just kind of been hurting recently because I'm in a part of my life right now where I'm looking for, like, a real relationship. But I feel like I just attract, like, I'm not trying to offend anyone, like, sugar babies. Oh.
Could it be that you list your salary on your dating profile?
I mean, it's... No, I mean, I'm not up front about it every time, but I feel like as soon as they find out, they're just looking at me as a bank account instead of trying to get to know me more.
Okay, and that's not what you're looking for.
But today, are we calling one of those sugar babies, or is this going to be a real love interest?
No, it's not a sugar baby. I'm hoping it's a real love interest. Her name is Lily.
How'd you meet Lily?
On a dating app, like a regular one, not like Raya or whatever.
Oh, nice.
And what's your ATM pin?
I don't remember.
I haven't used that in decades.
Oh, yeah.
Was Lily a type of person?
I mean, I assume if you're looking for a real relationship with a woman who doesn't care about your money, you're going to want to look for somebody who's successful on their own.
Right.
Yeah.
Like what about Lily said that to you?
I mean, she just seemed very confident in her profile. And then we were like texting back and forth and she just seemed like a real person. And we went out.
For a date.
You know, I tried to keep it pretty simple. Something where we can like talk and get to know each other.
So we went apple picking.
Apple picking is a great date.
Yeah. Yeah.
And she didn't know from my dating profile like what I did really because I, you know, I didn't say it in there.
Good. You don't put.
Like CEO or... Yeah, that's smart.
This is kind of fun because then they find out later that you're wealthy and they already are in love with you.
Like the show Joe Millionaire.
He wants to find someone who doesn't care, Jeff. Yeah, and then tell her. That's the whole point. There's a lot.
I would say the majority of women, it's not important to them. It's great to find a successful person.
Yeah, it's a bonus. Alexis rolled your eyes when you said it wasn't important.
I mean, I'm serious, though.
Did it ever come out on the date with her? Daniel?
Oh, yes. Yeah.
I mean, we, you know, we're hanging out for a while and eventually, you know, she was like, what do you do?
Which, I mean, I knew that question would come up. I was honest with her. I was like, look, I'm retired at this point, more or less.
That's why you can go apple picking on a Wednesday.
What did you tell her about your previous work?
Well, I was honest. I was, I'm a flavorist.
Flavor, sorry, what?
What is that? Yeah, it's like a food spice chemist.
Food spice chemist.
You could retire doing that, huh?
I don't even know what that means.
Well, as part of my work, I came up with some signature spices.
Did you invent lemon pepper for Wingstone?
No, we're actually talking to Colonel Sanders.
Oh, you invented original.
Yeah.
Okay, that's interesting.
Yeah, that's a cool job to talk about, though. Like, I don't think anyone would think that's pretentious. I think they would think that's fascinating. What was her reaction?
She seemed into it.
You know, the retired thing threw her for a loop. I mean, she had the same questions you do.
Like, what is that?
What's retirement?
Well, I don't get it, though, because you told Jeff, I guess, in your email that when you told the girl that it was your job that changed everything.
Yeah.
Well, I mean, it was kind of at that point when things did change. Like, you know, we're getting to know each other.
It's kind of exciting. But then after that, like the conversation.
Just felt like hard, you know, like things were just not coming as easy. And you know, we're in an apple orchard, right?
Like it was a pretty big space. Yeah.
But it felt like she was trying to like keep a distance from me.
Oh. Or maybe I'm reading into it, but it just felt like.
She's like, you pick this tree.
I'm going to go pick this tree over here.
Yeah.
What else happened on the date?
I mean, toward the end when I, cause I drove us there cause it's a little bit out of town.
Yeah.
You mean your chauffeur drove you, but yeah.
He's retired. He's got to watch his money a little bit.
Oh, that's fair.
The helicopter picks us up.
And then just like, there was no vibe.
I mean, as much as I liked her and I was feeling it, I didn't even go for a kiss.
I just was like, you know, I didn't shake her hand or anything.
It's good you didn't shake her hand. That's a friend zone activity. Yeah, but it is weird.
Every time I've saw someone do an apple press, immediately I feel turned on.
So I think it's odd that she's not.
Cider gets him going.
That's the non-alcoholic one.
Squeeze that juice out, baby.
Do you think that it can be revived, though, your chemistry at this point?
I mean, I hope so, because she does feel different.
She feels not like the people that are just looking to me for my money.
You're right.
From the sounds of it, she's not even into you at all. And I understand that you may not be willing to bribe your way to love, but we are not above that.
We will throw all of the gift cards that we have in her direction.
I was going to say, we don't have cash. We may have a BOGO coupon in the back.
But we do have another rich person, Brooke Kimberly.
So we'll call Lily and see if there's a reason why after your apple picking date, she suddenly.
Isn't picking you.
Is he the bad apple?
We'll change her mind when we do your second date update right after this.
Hold on.
Brooke and Jeffrey in the morning.
Second date update.
If you're just joining us, super quick recap. Our listener Daniel, retired food spice chemist.
That's a good way to put it.
I like that.
He meets Lily, cool girl next door type.
They go apple picking, chemistry's there, till he brings up retirement and suddenly.
chemistry.
Gone and you know we didn't ask him if he flashes aarp card and maybe that was part of the problem.
It's possible but no amount of honey crisps or golden delicious apples could get that early spark back so she's definitely not acting like a typical sugar baby who's only after him for his money but something is definitely giving her pause and we need to find out what that is Brooke, any theories?
I feel like next time, instead of saying retired, because it's not a very sexy word.
No.
If I'm going to be honest. It's not sexy.
You say you're financially independent.
Oh.
You just moved out of your mom's place, and I'm out on my own, finally.
I mean, you don't need to rely on a job.
For money, right? That's like the doordash people that say entrepreneur. They're still working a.
Lot, though.
I mean, I think anyone wants a partner who has ambitions and goals, and I'm sure you have those, but when you say retired, it doesn't give that vibe.
What do you think about that, Daniel?
Yeah, I mean, I don't put it on my dating profile. It's just something I say in person, but I can definitely tell them I'm like unemployed.
No, that's the opposite problem.
You sound like you're like literally homeless. It's more relatable though.
Before we start changing how you do things and what you're saying to women, let's call Lily and find out what her reasoning is for not wanting to hang out again. Because you seem like a really nice guy.
Oh, thank you. I appreciate it.
And you know what? You're honest. Like, that's the good part. I mean, maybe too honest.
We'll see.
Maybe Lily has a different story to tell, but I'm going to dial her number right now.
We'll see if she picks up. Let's go.
Hello?
Hey, is this Lily?
Yeah, this is Lily.
Hey, Lily, thank you for answering. We're a radio show that you're on right now. It's called Brooke and Jeffrey in the Morning.
Hi, good morning, Lily.
Hi.
Hi.
I like your name.
That's, well, okay.
It's a nice name.
Yeah.
Very pretty name. We know a lot of nice Lillies that are friends of Brooke's.
Yeah.
My best friend who always says, people say they have a dog named Lily.
Well, don't say that to her.
Yeah, we're not saying that to you, Lily.
Oh, no, we're sorry, Lily. It's okay, yeah. I know lots of dogs named Lily, too.
Oh, okay.
We're all on the same page.
Good, good, good.
And we're trying to get on the same page for one of our listeners, a guy that you went on a date with recently named Daniel. Oh, he basically gave us a quick snapshot of the two of you hanging out at the apple orchard. And at the end, he got a vibe that maybe you weren't as interested in him as he wasn't you.
Okay.
Um, was that, can we just start with, is that the correct vibe? Did he read that right?
Yeah.
I mean, I guess that's true.
Okay. Is there a reason why your mood towards him changed?
Well, I mean, I guess he just did some weird stuff.
He what? I'm sorry. He did or said?
Did.
What?
At an apple orchard? What can you do weird at an apple orchard?
Have you ever been to an apple orchard with Jeff?
Yeah.
They have all sorts of fun places. So can I share this with you, Lily? Daniel mentioned a particular moment from your date where he felt the vibe shift when he brought up his early retirement to you.
Oh, no. I don't care.
Oh, what?
Okay.
We, like, pinpointed that moment. He did.
He did. That's true.
He felt that there was a distance between you two after that, but if that's not right.
I mean, the retirement thing was probably just coincidental, but, like, we were... Picking apples and like, so you have a little basket and you're carrying your basket and you're putting apples in it and to go up the step stool, I have to set my basket down.
Right.
And then like, I'd realized that my basket felt lighter, even though I was putting apples into it. I was like, that's weird. So then the next time I went up the ladder again, I noticed him taking apples out of my basket.
What? Daniel was stealing apples from you? What do you mean?
Weird.
He was just getting rid of them. Sometimes he'd just toss them.
That's weird.
Remember he mentioned that he felt that you distanced yourself physically from him after.
He talked about retirement. So you just moved so that he couldn't get your apples.
Yeah.
Oh, my God.
Okay.
Yeah.
But why was he taking apples out of your basket? That's the part that requires a little more explanation. And luckily, we can get some of those answers, Lily, because you don't know this, but Daniel's been on the other line listening to this call the entire time.
The little apple thief is right there.
Daniel? Yes. Hello.
Awfully casual.
That's a guilty hello.
Did you hear what she said?
Yeah, I heard what she said. It's not entirely accurate.
Entirely?
Really?
What's your side?
Is Lily still there?
Yeah.
Why is she under the impression that you were purposefully taking apples out of her basket?
Yeah.
I mean, that part is true. I didn't realize that she noticed.
Oh, wow.
Why did you go and notice that thing? Come on.
Oh, boy.
Daniel, love an explanation anytime you're ready.
Yeah, I mean, no, we were having fun and, you know, she can pick all the apples she wants. But when it comes time to pay for them, I thought she like had enough apples. We didn't need to buy the entire.
Oh, my God.
The rich guy is focused on money.
Anybody who talks about how rich they are. I know they are not rich.
Actually, the richest people tend to be the most frugal.
No.
Well, look, I'm sure I have money, but I'm also retired, which.
Is honestly hard.
And if I want to stay above a certain tax bracket, if you will, then I need to stay on budget. And I have a certain amount of budget for the state.
I don't believe anything you say. You chose apple picking.
We're three red delicious over my budget. We can't. You're going to bankrupt me.
Why didn't you just tell her, like, hey, I budgeted this amount for our apples.
Let's get X amount.
Well, that would sound cheap. I'm not going to do that.
Oh, yeah.
But you are cheap.
I mean, there's a huge difference between being cheap and being smart with money.
I mean, like, look, I have three homes. in the state.
I don't really want to hear you talk about your stuff.
Three homes, that is. Three utility bills every month.
Brooke, you should relate to him on that. You're a multi-property owner.
It's hard.
People who have money that are cheap do things like buy used cars because it's senseless to buy a new car.
Things like that.
Brooke bought her husband an old beat-down truck recently.
And then it broke after a year.
They don't steal people's apples that they're on a date with because they don't want to pay for five more Honeycrisp or whatever.
That's right.
They reheat the same lunch at the office every single.
Day for an entire week. Lily? Sorry, we haven't heard from you in a while.
Yeah, I think, you know, my instincts were right.
What was your instinct?
I think that he's too uptight.
Wait, Lily, I think that we were giving him a hard time.
I will say, I think it's ridiculous taking the apples out.
I do.
Unless she has like 200 apples in the basket. That's true.
But I don't know if it's a reason to totally write somebody off.
If he told me that he was doing that, then fine. But like, he didn't tell me. So it just, makes them seem sneaky.
Yeah, sneaky's hard to get past. I get that.
I mean, I would say the word discreet. Oh. Sneaky. That makes it less secretive. Something that people can value.
Uh-huh.
Aw.
What?
Discretion?
And I'll say this, Lily. I have heard this statement before, and if a second date is agreed upon, they usually buy dinner.
Okay. That would really help. One of your houses for some cash. Just one of them.
I don't know that he planned very well for retirement. Yeah.
What do you think, Lily?
Are you willing to give him one more chance and look past the weird apple behavior?
Well, I'll do the second date, but I will say I'm not that hopeful.
Oh. So you also want the free meal.
Maybe you guys have more in common than you realize.
Oh, we can send him to Applebee's. Oh, I don't want to bring up the trauma all over again. Okay, maybe not. But Daniel, are you still up for it? You still want to see Lily again?
Yes.
I mean, that would be great. I think that, I mean, it makes sense for me and I.
Feel Lily, you're very smart and a reasonable person.
And so I, I think there's a lot to connect about.
That poor wait staff is getting no tips.
Brooke and Jeffrey in the morning.
Good Lord, how much you want to bet that dinner's happening before 5 p.m.
On a Tuesday?
They're going to get the early bird special and split a pudding cup, if I have to guess.
They related a lot. At the very end, we realized, wait a minute, they're both a little frugal.
I have a feeling that we're going to give one of them the gift card and the other one is never going to call the other person.
Oh, no.
And they're just going to order extra so they can have leftovers for the rest of the week.
This is one date or it's a couple lunches for me. Let's save $ 3 on this gift card and come back next week for Plinko.
They just both sounded older and older as the call went on and on.
They made retirement sound less and less sexy.
This is why everybody says don't retire because then you lose the spark.
Oh, my dad says because then you die.
Yeah. Well, from the sounds of it, I think he was right.
Yeah.
Don't let your love life die. We won't let it.
If you email the show, we can call that person who's not calling you back and go check out all of our second date updates. They're online wherever you get your podcasts at Brooke and Jeffrey.