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A
I have some very exciting news about an ethical phone carrier. I just switched to. This is Chelsea Handler from Dear Chelsea. Forget about all these other phone companies. Forget about Verizon, forget about AT&T, forget about T Mobile. There's this new carrier called Noble Mobile and they actually pay you to stay off your phone. You can earn real money, up to 20 bucks back every month just for putting your phone away. If you're like me and you're tired of feeling controlled by your phone, social media, or just disgusted by those screen time alerts, this is the answer. Go to noblemobile.com and try it for $10. That's noblemobile.com Chelsea.
B
Hey, it's Joel and Matt from how to Money. If your New Year's resolution is to finally get your finances in shape, we've got your back prices, they're still high and the economy is all over the place. But 2026 is the year for you to get intentional and make real progress.
C
That's right, yeah. Each week we break down what's happening with your money, the most important issues to focus on and the small moves that make a big difference and kick off the year with confidence. Listen to how to Money on the iHeartRadio app, Apple Podcasts or wherever you get your podcasts.
D
It's Brooke and Jeffrey and this is the second Date Update podcast. Thanks so much for being here. And today one of our listeners got caught in the car with another woman. But it is definitely not what you think, so wouldn't really raise jealousy in you. Yeah, so you're going to hear that in just a second. We got a brand new one. But. But first we love to highlight you what's on the comments.
B
Alexis.
D
Yes. Jewels of all trades said thank you for continuing to give me reasons to want to stay single. Lmao.
B
Oh yeah.
D
And once you hear today's oh yeah.
E
Oh, man.
D
Yep, yep. Okay, we're just going to get into it. Brand new episode starts right now.
A
Brooke and Jeffrey in the morning.
D
Second date update.
F
We have another listener who believes they already know the reason why they're not getting a call back.
D
I love this. I feel like it's people doing the.
F
Work for us, you know, make us work less. Yeah, we appreciate that. And similar to a previous call we did recently, a parent was involved.
D
What is going on? Why are is everyone bringing their moms and dads to date?
F
Well, I don't know all the details. That's all I got from the email. I don't know which parent it was. What happened? How much tongue Was used. So let's make sure we get all the deets from our listener, Ricky. Ricky, welcome to the show.
E
Thanks for having me.
D
Can we just start with your parents or their parents?
E
Okay. I guess I should start at the beginning.
F
Yeah. Before we get into all the hot parent talk, and I definitely do want to get there.
G
Well said, Jeff.
F
Let's start with the girl that you met. What's her name and how did you meet her?
E
Her name is Annette. I met her on a dating site. This is a new one my friend recommended to me. It's very up and coming. It's. It's called can do Better. It's weird, but I liked it.
D
It's can do Better.
F
Can do better.
E
Yeah.
D
Okay.
G
I don't think I belong on that site.
D
Yeah. Looking for worse is the other.
G
Yeah, that's where I go.
E
All right.
F
What makes this app different?
E
Well, you upload a picture of yourself, which is pretty standard, but what you do is you also draw a picture of the person you're looking for.
F
So you draw it?
E
Yeah, you draw it.
D
Do you have to be. Wait, do you have to be a good artist, or are you just looking at stick figures?
E
Yeah, there's lots of different types. You know, there's good ones, there's bad ones. I'd say mine was pretty in the middle.
D
I want to go outside just to see people's drawings.
F
So you drew a picture of your ideal match, and that turned out to be Annette, it sounds like.
G
And it finds the person, like, in the system that's already registered. Is that how it works?
E
I'm not sure if that's how it works, but she reached out to me and she said that she kind of looks like the picture, and she did a little bit.
D
Can I ask what was in the drawing?
E
You know, it was green eyes and brown hair. And she had green eyes and brown hair.
G
That's actually a great combo.
D
That's rare.
F
Dang. Never see that. So you and Annette, I guess, went out on a date. What did you do?
E
Yes. This is embarrassing to say, but this is where we get to the parent talk.
F
How did the parents come into play?
E
You know, we decided to meet at a restaurant, and I was hoping that she was going to be waiting for me inside, but she was waiting outside, and she saw me get dropped off by my mom.
G
That's where the mom was.
F
Okay. She was just your chaperone. Your mom didn't stick around, did she?
E
No, no, but it would have been a thing that I could have tried to play off, but fortunately, she also yelled out after I got out of the cause. Good luck, sweetie.
D
Wait, why did your mom drive you? Yeah, because that's what matters.
G
Oh, that's a good point.
E
Look, I've just did a bit of a situation. I don't want to get too into it, but it's just temporary. It's not permanent.
D
And, you know, why do I feel suspended driver's license for some reason.
G
And also, this is, like, temporary for the last 10 years.
D
Ye.
F
Which we all can relate to those things, by the way. Don't feel ashamed.
A
If my mom could drop me off.
D
I'd take the ride.
A
Yeah.
D
So she's just too busy. Were you able to make a joke about it? Because that's a great way to recover.
E
Yeah. You know, we were laughing, and she said she didn't have a problem with it, but the date only lasted about an hour. And this is also a little bit weird, but I'm not really used to going out to Westeros all that much, so maybe. I don't know, I was very excited, and she thought that was weird. But.
D
Can I ask, how did you express being excited at the restaurant?
E
Yeah, I don't know. I was just a little over enthusiastic, I guess. Just saying. They bring it out to you. I just kept complimenting the service and everything. I don't know if I wasn't playing it cool enough there.
D
You're like, wow, they wash your dishes for you.
G
But, you know, genuine positive energy can be charming. You know, like you were being me.
D
I get it. I. You know, you should have seen me in sixth grade. The first time we ever were able to get delivery pizza.
G
Oh, boy.
D
Oh, it was like being at Disneyland.
H
Wow.
D
We all greeted the guy at the door. This is not helping me. I screamed. I couldn't believe that they were gonna bring it to us.
E
No way.
D
I don't know what happens when you grow up in a little town, you.
F
Know, but you're not necessarily painting the best image right here for Ricky.
D
I don't think it's innocent and loving. They're on a quiet, awkward date.
G
That's true, actually, as well.
F
Did you feel like there was a connection happening between you and Annette while you were eating together?
E
I mean, I felt one, but I don't know if it was reciprocal. So, I mean, I think it might have just been maybe me being weird about the restaurant, or my mom dropped me off, but I just want to know why she's not calling me back.
G
It is a little interesting. And Mom's like, bye, honey. Have fun and he's like, I am so excited to be here.
F
How are you?
G
It doesn't seem like she got dropped off for a play date.
D
Wait, was she there when your mom picked you up?
F
Oh, yeah. How did it end?
E
Yeah, my mom was just shopping at Target nearby and picked me up also.
D
But did Annette witness that part too?
E
Probably.
D
Okay, yeah. I mean, here's the problem. It sounds like the middle of the day actually wasn't that bad, but how you start and end a date is probably the most important piece.
C
Yeah, good point.
G
Last impression and first impression.
F
You don't want to bookend it with mom talk, usually unless you play it off good.
D
But I don't know. Yeah, maybe your mom cursed you by saying good luck. She should have said, break a leg, sweetie.
F
Yeah, I don't know.
G
Remember that for when you drop your.
F
Kids off on dates. So when you said you think you know the reason why, is it because the whole situation with your mom?
E
Yeah, she said she was okay with it, but I don't know if she really was.
D
Have you heard from her at all?
E
No. If you can get a hold of her, that would be the first.
D
Okay.
F
Okay, well, let's find out when we call Annette for you and see if your mom is the person who actually blocked you from finding true love when we do. Mom blocks happening way too often right now. We'll do it with your second date update right after this.
A
Brooke and Jeffrey in the morning.
D
Second date update.
F
There is nothing like a mother's love when she helps you take your first steps, reads you Dr. Seuss books at night, and drops you off for your date in her Honda Odyssey while shouting, good luck, honey. Mommy loves you.
D
I think it was actually, sweetie.
G
Oh, good luck, sweetie. I'm glad you said that. I almost asked what her car was, but I was like, I don't want to.
F
That was what I pictured in my mind. Because that's what actually happened to our listener, Ricky. His mom dropped him off and picked him up from his dinner date with Annette.
D
Dude, if she hadn't have yelled, he could have pretended it was his Uber driver. Yeah, that's true for sure.
G
Next time if moms. If you're dropping your kids off, be the Uber driver.
D
Or just stay two blocks away and walk.
B
There you go.
G
That's good too.
F
Your Uber drivers don't shout, good luck, sweetie. When you walk into places you're going.
G
That's a five star review.
D
I really should stop selecting the silent mode.
F
Yeah, you really should. But yes, that is the reason Ricky is worried that Annette saw it and it could be the reason she's ghosting. Right, Ricky?
E
Yeah.
D
Okay.
F
Yeah, okay.
E
Okay?
F
Yeah.
D
I mean. Okay. If we get you another shot, how are you getting to the next date?
E
I just need to understand what I did wrong, and then I can know.
D
The correct answer is rideshare. That's the correct answer.
F
And Brooke might even be willing to pay for it, too.
D
Yeah, we can cover that.
F
We just have to get a yes from Annette first. So let's dial her number. Hopefully she picks up and we can get some answers.
B
Here we go.
H
Hello?
F
Hi, is this Annette?
H
Yes.
F
Hey, Annette. Thanks for answering. We're a radio show on the other line here. We're called Brooke and Jeffrey in the Morning.
G
Nobody say anything so he sounds like he's okay.
F
No, make it sound crazy. There really are people here.
E
Okay. We are here.
D
I like that idea, though.
H
When it's happening one of these times.
G
We should be quiet.
F
Yeah, yeah. What's happening is you're part of a segment that we're doing now. It's called the second date Update.
D
Welcome to it.
F
Yeah.
H
Okay.
F
I know it's probably weird to getting this call, but it's not supposed to be a scary thing. We're just trying to help one of our listeners who went out on a date with you recently. A guy named Ricky.
H
Oh, seriously?
G
Yeah, that was a reaction.
F
Ricky told us about your hangout and said he had a great time with you.
E
Oh.
D
He even told us about the app that you guys met on that was kind of cool, where you, like, draw pictures of who. Who you're looking for. That's interesting.
H
This is very strange that he's, like, calling you about this and talking about my life.
D
Well, his life, too.
F
Yeah.
B
Yeah.
G
It's a shared life.
H
Because it's not true.
F
Right.
D
You shouldn't have said that.
F
He went on a date with you. And so we wanted to know some of the details about how you met and what you did when you went to the restaurant together. Because he really liked you and felt a connection and wants to see you again.
H
Why would I tell you any of this? I did not feel a connection.
D
So decency for Ricky, because. Ricky.
F
Sorry, but did you say that you didn't feel a connection?
H
Correct.
D
Is there.
F
Is there a reason? Yeah, because we do know a little bit about what happened, but we'd like to hear your side of it.
H
Well, I'm curious about what he told you.
E
We.
F
We know that you met up at a restaurant and his ride was his mother to get there.
D
Yeah, apparently you saw because you were outside the restaurant, and he knows that's not normal.
H
Yeah, that was a little weird.
D
Okay. But that. Oh, that was not weird.
F
We thought that would be the main reason. In fact, he thought that, too.
E
Oh, no.
F
Oh, there's something else.
D
Oh, that was emphatic.
F
Would you mind sharing what else?
H
Okay. There was a lot of clapping.
C
Clapping?
H
He doesn't go out that much, he said.
D
Oh, yeah. He did mention he was maybe too excited about the restaurant because he doesn't go to him very often.
F
When was he clapping?
H
Oh, for everything. Like, every course that came.
D
That's kind of cute, though. Like, he's excited, and, I mean, it's got to make the wait staff feel good. Like, pop stickers are here.
F
My water is being refilled.
H
He's a grown man on a date, y'.
E
All.
H
Like, oh, yeah, that's the thing. He wasn't a grown man on a date. Did he tell you this part? He chooses to live his life as a kid.
D
Wait, what?
B
Huh?
G
What do you mean by that?
H
Exactly what I said. That's what he told me in the restaurant. Like, he has a full time regular job, but he lives with his parents, and he's kind of, like, in denial about actually growing up.
D
What?
H
Because he just wants to, like, shut things out and live as a kid. Because it's more simple.
D
So he was clapping because he was acting like a child on purpose?
H
I. I believe so.
D
Did he order from the children's menu?
H
No, but he got, like, a burger and fries so he could have. You know what I mean?
G
Like, yeah, so that's one thing to be, like, immature and enjoy those things, but to actively maybe act like a kid is different. I don't know where the line is here.
D
I mean, maybe he was talking about, like, childlike wonder, like, he wants to keep that good spin, Brook.
H
But, like, his mom dropped him off. Like, she does his laundry. Like, I don't. That's not what I'm looking for in a. In a partner like, y'.
E
All.
H
He got out of the car. I sincerely believe he was wearing a pajama top.
D
What? He definitely didn't act like a child when we talked to him. And he didn't mention any of this?
H
Of course he didn't mention any of this.
F
Well, he did. He did tell us that he was excited. We just didn't know there was, you know, happy clapping every time food came to the table.
D
It sounded like we were talking to an adult man on the phone when we talk to him.
H
Well, that's what I thought going into it.
F
I mean, if you don't believe us, you can definitely hear it straight from Ricky because he's on the other line right now listening to this call. Like walkie talkies clapping and waiting to speak to you.
H
Are you serious?
D
No.
F
Yeah.
D
Yeah.
F
Ricky, you there?
E
Hi.
H
Hi.
E
I didn't think this was such a problem for you. I thought that you liked the fact that I'm happy and I try to keep a childlike, like you said, sense of wonder and excitement about things, but I just.
H
There's a difference between like a boyish energy and a being in denial about being a grown up.
E
Yeah, I know. I'm a grown up. I have a job. You said that I'm an accountant.
D
You're an accountant. You're a child accountant.
F
You told her, Ricky, like, I choose to live my life like a child. She said those were your words.
D
Maybe she missed misunderstood what you were saying. Like, maybe re. Explain it so she gets it.
E
Look, I understand. I'm fully grown. I'm not in denial about that. It's just that being an adult sucks. Everybody hates it and Amen to that. Yeah. I have the opportunity to just not pay when not pay mortgage and just.
D
Oh, okay. That makes it sound more like you're freeloaded of your parents.
E
No, I haven't.
H
What are you working for then?
E
Like, I save money for things that I like, you know, like big Lego sets or.
D
Hey, no, Legos speak to adults too.
G
Yeah, that's true.
D
That's probably not the best example of what you spend your money on right now.
G
But it's not impressive to be like, this is $1,000 Lego set. Still not as.
H
Not if you don't have a real house to put it in.
F
But financial planning is financial planning, and that's an adult skill set.
E
I told you that this is just temporary and that one day I will get my own place and I'll be able to afford it. Because this whole time I've been choosing to live like a child. And again, it's because people are so stressed out, people are so upset, and I'm a happy person and I choose to be.
F
Well, that's good. I have a hard time arguing with the logic.
G
You're right, buddy.
D
Ricky, you can be happy and still be a man. You need to prove to her that you're a man to get another chance.
B
What?
F
Brooke, he's happy. Why are you trying to take away his happy child childlike happiness?
B
Children?
F
Brooke, come on. It's not your kids.
E
Brooke, look, just because Society tells you you need to live a certain way doesn't mean you have to. Society's been warned about a lot of things.
D
Hey.
G
Society has been won about a lot of things.
D
He's wrong. Did you just drop your art? Because you're talking like a child.
F
I kind of been hearing that, the whole call.
D
Have you?
E
Yes.
G
He's been doing it the whole time. You haven't noticed?
H
No, I mean, I've been wondering that, too. Like, are you doing that on purpose?
E
I mean, I can talk normally if you prefer this.
H
Oh, my God.
G
Oh, my God.
F
Ricky. Are you kidding me?
D
You're talking like a child.
G
That was it.
D
I was wondering, do you tell people your name is Wiki?
E
Oh, my God. I mean, I'm not cartoonish about it. It's just. I like speaking that way. It just makes people expect less of me.
D
And again, I hate it when women do baby talk, too. I just. That's my line. I was with you, Ricky.
F
Until then, it's not baby talk, it's child talk. It's one step above gross. And you're just jealous because Ricky is the happiest boy in this whole universe. And we would like to set you up, Annette, with the happiest boy if you're willing to go out with him one more time. We would pay for that date.
H
Absolutely not.
F
Uber ride. No mothers anywhere in sight.
D
Yeah, they have Uber Teen now.
F
Oh, they do love that. Maybe a coloring book in the back seat.
H
Yeah, at this point, that would feel predatory. I'm not.
F
Thank you.
D
Ricky.
E
I don't know what's wrong with you. I'm a man.
F
Okay. I think, Ricky, it's gonna be a no from Annette today. I'm sorry, bud.
E
Back to the data naps and Legos.
G
Back to the good life.
F
Yeah, he's gonna have a good day.
A
Brooke and Jeffrey, in the morning. I have some very exciting news about an ethical phone carrier. I just switched to this is Chelsea Handler from Dear Chelsea. Forget about all these other phone companies. Forget about Verizon, forget about att, forget about T Mobile. There's this new car called Noble Mobile, and they actually pay you to stay off your phone. You can earn real money, up to 20 bucks back every month just for putting your phone away. If you're like me and you're tired of feeling controlled by your phone, social media, or just disgusted by those screen time alerts, this is the answer. Go to noblemobile.com Chelsea and try it for $10. That's noblemobile.com Chelsea New Year, New goals.
C
And in this economy, a better money plan is more necessary than. I am.
B
Matt and I'm Joel.
C
We are from the how to Money podcast. And every week we help you to spend smarter, save more, and make sense of what's going on out there.
B
If you want 2026 to be the year you finally feel in control of your money, we're here to give you the tools and advice to help you make it happen. Listen to how to Money on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.
F
God, I just hope Ricky's mom was not listening to that call because he is definitely going to be put on timeout for raising his voice and speaking like a grown man.
D
That one was so hard.
F
Yeah, you struggled the most out of anybody in the room, for sure.
D
I didn't want to say they mean, but also, like, let's not do this.
F
Yeah, yeah. You know, listen, the good news about Ricky is he makes the rest of the male population look way more dateable in comparison.
D
Well, that's true.
G
Barely.
D
And it makes even you look manly, Jeff.
F
All of us, we all the men listening, totally appreciate Ricky. So, ladies, if you're ever getting frustrated with the options available on the apps, just remember you could end up with a man who colors his menu with crayons at Applebee's.
G
Now follow me on my video game stream at Hilarious Jose.
F
Yes, a true man.
E
There we go.
F
And you can also follow along with our show wherever you get your podcasts on Apple, Spotify, just look up Brooke and Jeffrey and hit that subscribe button.
A
I have some very exciting news. I am always looking for companies to support that are ethical. And let's be honest, the phone companies we've all been stuck with are not that. This is Chelsea Handler from Dear Chelsea. You know, I travel constantly and supposedly I have international free roaming on Verizon, yet my phone bills are still 300, 400, and even $500 a month. It makes zero sense. So I switched to a company with actual ethics, Noble Mobile. And they pay you for staying off your phone. The more you unplug, the more money you save each month. And the most you'll ever pay is 50 bucks. Unlimited coverage when I need it, cash back when I don't. It was started by people I know and trust. So if you trust me and want to join my mission to stop being a phone addicted zombie, come along. Go to noblemobile.com Chelsea right now and try it for just 10 bucks. That's noblemobile.com Chelsea, hey, it's Joel and.
B
Matt from how to Money. If your New Year's resolution is to finally get your finances in shape, hey, we've got your back prices. They're still high, and the economy is all over the place. But 2026 is the year for you to get intentional and make real progress.
C
That's right. Yeah. Each week we break down what's happening with your money, the most important issues to focus on, and the small moves that make a big difference. Kick off the year with confidence. Listen to how to Money on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.
Release Date: January 16, 2026
Host: iHeartPodcasts
Segment: Second Date Update
This edition of "Second Date Update" dives into the unusual aftermath of a first date gone awry. Listener Ricky enlists the team’s help to uncover why Annette hasn’t called him back after their outing. What starts as a classic ghosting scenario quickly spirals into a hilarious but cringeworthy exploration of mismatched expectations, childlike wonder, and... public clapping at dinner. The episode’s main theme is unpacking the difference between harmless quirkiness and red-flag-level immaturity—and whether a “child at heart” approach to adulthood is ever dateable.
The exchange is light, humorous, and cringeworthy in classic "Brooke and Jeffrey" fashion, striking a balance between empathy and playful mockery. The hosts are supportive yet candid, and the guest’s quirks make for standout podcast entertainment, especially as the real reason for Annette’s ghosting comes to light. The team uses their signature banter, with Brooke trying to mediate, Jeffrey playing devil’s advocate, and the rest of the crew riffing on Ricky’s “childlike” lifestyle and its broader implications for modern dating.
The episode delivers high entertainment as promised—shedding light on why second dates sometimes don’t happen. Ricky’s story becomes both a cautionary tale and a comedic highlight for listeners. The hosts wrap up by declaring Ricky a “hero to all men” for making everyone else look more dateable by comparison and encourage listeners to celebrate their own (hopefully grown-up) dating wins.