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A
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.
B
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.
C
It's going to be interesting to see how many fans this guy has from our brand new second date update today. Definitely let us know what you think in the comments. It's Brooke and Jeffrey in the morning because we love reading those comments. And before we get to our brand new episode, what do you got, Alexis?
D
This was from last week on the Brooke breaks you up, but still a funny comment. So if you missed it, Brooke helped break a couple up for them.
C
Of course, unsuccessfully, but go listen.
D
But if you did, then you'll know Mareki said this inspired me to break it off with someone I was dating, and I did. So thank you. Longest 26 minutes of my life. And I wish Brooke did it for me. Next time, I guess.
E
Hey, submit your request.
C
Maybe she will. Oh, my God. I feel like 26 minutes is pretty short. I've had breakup conversations that went on for hours.
F
Oh, yeah.
C
But by the end you're like, oh, my God, just leave.
B
Yeah.
E
Now I see why people just do this through text.
C
Yeah. All right. Hey, thanks for letting us in on your personal life. We love that.
D
And now that you're single, maybe hear you for a second date update.
C
There you go. Full circle. All right, your brand new episode starts right now. Brooke and Jeffrey in the morning Second date update.
F
We've heard from a lot of people on this show who've moved cities and started over that it's not easy.
C
No, I mean, what a challenging thing to do. But so rewarding. So awesome. Good for you.
F
But a lot of stress. You gotta get a whole new driver's license, memorize a whole new address.
C
That's what you're worried about? Not like making new friends and having a community?
F
No, that's easy. But changing your favorite inflatable store location on your app? I mean, where are you going to find your inflatables now? And will they be as sturdy as the previous one?
C
Yeah. Blow ups are us. Is that It.
F
They don't exist here, Brooke. Now you're out. Who knows where you're going to blow up and didn't realize you're going to spend time with lots of headaches and roadblocks when you move. And no one knows that better than our listener, Eric, who's requested our help today. Eric, welcome to the show, man. We appreciate you listening to us in both cities. Your old one and your new one.
G
Yeah, thanks for having me, guys.
F
What was the reason behind the move? Or is it a work thing? A criminal past that you're trying to outrun?
C
What are we working with an ex? An ex is always a good reason to move cities.
G
I mean, I did recently change jobs and.
F
Oh, okay.
G
I work in an office with a lot more people that are my age now. Nothing against older people, but it's nice to have people that are my age now.
F
Yeah, I wish we could have that here, but Brooke just keeps on coming back.
G
I don't know how it happens.
E
I know. We're all like, geez, I am not.
C
That much older than you.
F
No, it's fine.
C
You are also getting older, Jeffrey. It's how it works.
F
No, I enjoy having your presence. It's like a nice, warm wisdom sort of thing.
C
So were you nervous moving to the new place, or did you know anyone there?
G
I didn't know anyone at the time. You know, I'm pretty friendly. I can get to know people. I mean, there's actually this one girl, Anna, and we've been friendly at the office, and we actually just have, like, a naturally good vibe together.
F
Oh, okay. That's a little bit dangerous territory, dude.
C
Right when you come in, you're trying to move somewhere.
A
Yeah.
C
Were you thinking, like, romantically, immediately with this woman?
G
No, not at all. I just like her vibe. And it was her birthday the other day, actually, so I wanted to do something special for her, so I got her a birthday cake. But I also got this coffee mug with a dog on it because she said that she really loves dogs.
C
I'm confused. Is this. Did you go on a date with her?
A
Yeah.
F
Did you hang out outside of the office?
G
Well, she really liked the mug that I got her, and she came to my desk and thanked me, and I was like, you know what? We should grab dinner sometime after work. And she was like, all right, yeah, that sounds great. And so after work, we headed over to this restaurant. It wasn't anything too fancy, just like a diner. And I got to know her some more, and I realized that I really enjoyed her energy. And we Kind of had a funny little moment. We ordered corn dogs and we interlocked our arms. Like when you would drink champagne to eat them. That was kind of funny.
C
Like when you do a big fancy toast with your new bride or whatever, and you interlock arms.
F
Yeah, but with corn dogs, it's a little bit of a different.
C
You mean it's classier, isn't it?
A
Yeah. What do you mean?
F
I feel like you must have been getting a lot of looks from other people in the restaurant. Seeing the corn dog interlock thing, I.
G
Thought we were just having fun and we were just in our own world. And at the end of the night, I walked her back to her car and I asked if she wanted to go on a hike sometime, and she seemed really into that. And now she's just being super cold to me at the office, and I'm not really sure why.
C
Okay, so at any point was it established that. I mean, it sounds like you were feeling romantic vibes from her, but did you ever clearly state, I think this.
D
Is a date, and, like, you know, she's single.
C
Yeah.
G
We didn't talk about anything romantic, and I never. We never brought anything up where I thought we were having fun.
F
Yeah, but Brooke, it still doesn't change the fact that she's acting cold towards him now at the office, because it seemed like for the most part, they were getting along.
C
Think that that's just because she got freaked out. Like, she thought it was a friend situation, and then there was a moment, maybe it was with the corn dogs, where she's like, oh, whoa, this guy thinks that we need to be dating.
E
You went real far down the corn dogs.
F
Whose idea was the corn dog arm interlock? Yeah, who brought that up?
G
It kind of just happened. I. I don't.
F
How does that just happen?
E
I love it. Dude.
F
Just seems so unnatural.
G
Well, for the record, we toasted the corn dogs, and then we.
F
Oh, no. You touched corn dogs. That could be unsan y.
E
They touch tips and then they interlock.
B
I love this.
E
I want to do this with somebody.
C
So is there any awkward moments that stand out to you where you're like, whoa, maybe we're not on the same page.
G
Not in my mind. I thought we were just having fun. I thought we had a good time.
E
All natural, all genuine.
F
I will say, I did buy coffee mugs for some of my friends here at the office, and I have been reamed endlessly about how horrible the mugs are.
D
Started a fire in my home.
E
I can't wash it.
F
But the thought behind It. That was pretty nice. And yet you are all obsessed with, oh, I nearly lost my life, and.
C
You stood at an ABC wall of mugs and then picked out our first initial.
F
The fact that I remembered what your name start with should say wonders about how much I care about each and.
A
Every one of you.
D
I'm surprised you went into anthropology to buy those. That was impressive.
H
Okay, wait, wait.
C
I want to know. Is there any office gossip that you've heard of? Because somebody's got to be talking like, oh, did you hear the new guy went out to dinner?
G
I mean, I'm not a gossip myself. I try to focus on my work. I mean, I'm still friendly with people, but I haven't heard any nastiness. No one's tried to, like, pull a prank on me or anything else. Maybe. Should I be looking over my shoulder?
E
She doesn't know anybody yet. To hear the tea, like, that's what I realized.
F
I mean, in the few minutes that we've spoken to, you seem like a really nice, pleasant guy. But who knows? We could be totally wrong, and you might be a total nightmare. So let's find out. You might be the worst person we've ever spoken to.
C
So wait, we're gonna call someone that's in his office with him?
F
I mean, is that what you want here?
G
I would like to find some answers why she's being cold to me now because I was nothing but a gentleman, I thought.
F
Yeah, we'll figure it out. We'll reach out to Anna, hopefully find out if you're the best or the worst guy to work with when we come back and do your second date update right after this.
G
Thank you.
C
Yeah, that's the correct response.
F
We will help you. We'll try. Hold on.
C
Brooke and Jeffrey in the morning.
H
Second date update.
F
We've had definitely, like, tense second date calls before, where things get surly between people. Yeah, but this could be a first where we're calling a woman who went out with a guy from the same office. Our listener, a guy named Eric. And our producer has asked Eric if he would stand up above his cubicle and look across the office down into her cubicle as we make this phone call, just to make it even more juicy and dramatic.
E
Oh, my gosh.
F
And Eric has selfishly refused to do that.
E
Don't let them make you do that.
F
Not much of a team player, are you?
G
It would be a little weird. And I might get fired for something like that.
C
I mean, I thought you'd want to alienate everyone in your office space. Before, you know, you really got to know him.
F
Yeah.
C
Is that not how it works?
F
I mean, it works for us on our show. I don't know if it would work for him and his career. But just to recap real quick, Eric just moved to a brand new city. He was liking the vibe he was getting from his co worker Anna while they were working together.
C
There's even presents exchanged.
F
Yes.
C
Well, not exchanged. He gave one way.
E
Okay.
F
For her birthday. So he took her out to dinner. They toasted corn dogs, interlocked arms while eating them. And now all of a sudden, it's weird. Not sure how that's possible.
G
What do you mean?
E
Is, they were having fun. Like he thought it was a genuine thing.
F
We've worked together for over 10 years. Has any of it been fun? No.
A
No.
F
That's why this is so strange.
C
We actually have a lot of fun. When you are in the other room. Yeah, yeah.
F
When I'm doing all the work.
C
Yes, yes.
F
Sure. Okay, well, fun for you guys. Let's continue to do our work and call Anna here. Hopefully she picks up the phone and we can get some answers.
E
I just realized. This is your fun, huh?
F
Yeah.
E
When you're on the air, this is the only fun.
F
This is all I get.
C
That's sad.
D
Look at our hitting Starbucks after this.
G
Well, good for you.
C
Thank you, Alexis.
F
All right, I'm just gonna dial Anna. Maybe she could be my friend. Here we go.
I
Hello.
F
Hi, we're looking to speak with Anna.
I
May I ask who's calling?
F
Yes, you may. You're so polite.
C
It's business call, Jeff.
F
Oh, yeah, I forgot. We're a morning radio show. We're called Brooke and Jeffrey in the Morning.
I
Hi, good morning.
F
Let's keep it casual over here and do a segment. You know, not the business stuff. Sorry.
E
You're so weird.
C
This is why we don't let him out of his room.
F
Okay, I'm just saying, sorry to interrupt your day, but we're doing something that's called a second date update. And we're trying to help out one of our listeners that you went out to dinner with recently. A guy named Eric that you work with.
I
Yeah. No, thanks. I wish I hadn't gone out with that guy.
C
Oh, wait, okay, so there's regret there.
F
Yeah, that's a little bit unexpected, honestly, because we talked to Eric and from what we heard about your hangout, it sounded like it was a really fun time.
I
I mean, this is kind of awkward.
C
Yeah, but we know that.
G
Yeah.
I
This guy Eric, he puts out this, like, really nice Guy energy. But he's involved with a lot of other people that I didn't know about.
C
Wait, wait, wait, wait. What do you mean? Like, you're saying he has other girlfriends?
I
Well, I know he has one girlfriend.
F
Oh, wait, just one?
C
Wait, how do you know that? Like, I thought he was brand new to the city. How could he already.
I
Well, for one, like one of the girls in my office, he flirts with her all the time.
G
Okay, okay.
C
Are you sure he's not just being friendly?
I
No, he asked her out, too. Oh, he asked her out? Yeah, and luckily she didn't go out with him. But we looked into this guy, we did some research on him, and we found out that he has an actual girlfriend that's not someone in our office.
C
Wait, really? So he's asking out multiple women in your office with. While being in a relationship?
D
Like a distance relationship maybe, or something?
A
Yeah.
E
Is it long distance?
I
I mean, yeah, I don't know if it's long distance or what. It is.
C
What kind of. I'm sorry, it's just so weird always to have, like, a cheater like that call in to a very public radio station and.
F
Okay.
C
Risk outing himself.
F
Like, what alleged cheater?
C
Well, that's what I mean.
E
Like what an allegedly popular.
C
What did you see? Did you see something online where he said, I have a girlfriend?
I
Yeah, I found his Instagram, and trust me, it just shows everything.
F
Okay, well, people can say anything on Instagram. It doesn't mean it's true.
E
Wouldn't put out lies about themselves on their own.
D
Happy Anniversary, my girlfriend.
F
Yeah, it might just be like, you know, for cloud, for looks. It might not be real.
C
See, he doesn't get how. Yeah, I'll say this, A better argument would be it could be old photos from an ex. Right? Like, maybe he hasn't taken that stuff down.
I
The last one that he posted was, like three or four days ago together.
C
Oh, isn't that like, the same time frame of when you guys are out together?
I
Yeah, I went out with him like, five days ago.
E
Oh, wow.
C
This is going to be awkward for not the reasons I thought.
F
Yeah. So clearly you're not into guys who already have girlfriends, which.
C
And good observation, Jeff.
F
I'm saying good. Good for her. But we didn't know about a girlfriend or anything like that when we talked to Eric. And you should probably talk to him too, because he's on the other line right now waiting to speak to you. He's probably actually across the office too, but it'd be more fun if we could hear the phone conversation.
G
I'm confused because I don't understand what the issue is here. I really.
I
You don't see the issue? Eric, you already have a girlfriend.
G
I never said that I didn't have a girlfriend. Oh, my God.
I
You took me on a date.
G
No, no, it was not a date. It was dinner so that you and I could become better friends.
E
Now you're backtracking.
G
What?
F
Wait, what?
E
It was totally a date.
D
This is a second date update.
G
Yeah, you call it that? I didn't call it a date. It was a dinner.
C
So what were you wanting to do, just be friends with her? Like this whole thing is a big misunderstanding. Is that what you're trying to.
G
Look, here's what happened. My girlfriend and I were talking about how my new job, I don't know anyone, and so she suggested. My girlfriend suggested I should try and make more friends, and she was supportive of that. So then I go to work after our hangout, and you've been treating me so cold. I was just doing what my girlfriend told me to do, is to make friends.
F
Wow.
A
Yeah.
I
Well, I mean, Eric, I'm treating you cold because you're also hitting on another co worker and flirting with everybody.
F
Yeah, that's a little suspicious.
G
I'm not flirting with anybody. I'm being nuts. Not hitting on anybody. I'm just being friendly and playful.
C
You're only being friendly to the attractive single women in the office.
G
Those are the people I vibe the best with you.
F
They are friendly and fun. So you say that your girlfriend is supportive of you meeting new people and making new friendships at work. Does she know the full extent that you're, like, asking these women out to dinner with you?
G
She knows that I'm going out with people from work. She doesn't need to know specifically how they look or their attractiveness level or what we with our food.
C
Does she know you're riding into radio stations for dating segments and not you.
D
Have a girlfriend at all?
F
Defense. He says he's not. He's not after that.
I
I guess I think that Eric is just trying to completely spin this because he was definitely into me.
A
Yeah.
B
Yeah.
G
I'm sorry. I think you're flattering yourself a little bit.
E
So now he can play though. That is a girlfriend lady.
G
Yeah, and she wasn't even my type anyway.
F
Well, that should be reassuring. Anna, he's not attracted to you. Even if you wanted him, he couldn't.
C
Yeah, I mean, man, this is a new work environment for you.
D
What are you doing?
G
Well, I'm sorry you got the Wrong impression. That's what I will.
F
I will say Brooke tries to buy me dinner all the time and it is a huge turn off to me. She's always like Jeff, can I get you lunch? Jeff, can I buy you meals? Whatever.
E
She's direct. She says I'm attracted to you, Jeff.
F
I know.
C
The only turn off. The only turn off is when I ask you to pay me back.
H
Yeah.
F
Oh, okay. So you want this to be a date then?
C
No, I want.
F
You want to go havesies.
C
I buy Ledger, everybody.
F
Brooke, your husband listens to this.
G
Well, you guys sound just as dysfunctional as this situation has been. You're really making it worse. I want you to know that I do still like you as a friend. And if you are interested, I would hang out with you again in a non romantic way.
I
So this whole time all you wanted to do was to be friends with me?
G
Yes. I mean is coming around the corner. Maybe we can go bikini shopping sometime. Right? My treat. What the heck?
F
Yeah, that's friend.
C
Is that a joke? Are you joking?
G
Yeah, like how Brooke and Jeff do. I think it'd be nice.
C
But we're shopping for his bikini.
A
Oh, that's right.
C
Yeah.
E
Jeff gets the tiny ones because we.
F
All know who looks better.
G
I'm being serious. That's what friends do. They go shopping together, they have a laugh, they give each other their opinions on their bikini.
C
On their bikinis. You know, that is the creepiest.
F
Yeah, I was skeptical at first, but I'm fully come around on Eric and his desire.
E
He's our friend for sure.
F
For deep passionate friendship with you, Anna. And if you agree to see him one more time, we would pay for your hangout. Your non romantic bikini hangout.
C
I'm starting to understand why Eric had to move cities to find a new job.
F
You don't know that. Anna, what do you think about giving Eric one more shot?
I
I think I'm gonna pass on Eric at the office.
A
Oh no.
E
Just co workers, huh?
C
Yeah, I just say try not to get yourself reported over there, Eric.
I
Exactly.
G
You know what? That's the last time I make friends in the office.
E
O. I have a feeling that's not true.
F
Your girlfriend's gonna be so disappointed.
B
Brooke and Jeffrey in the morning, New year, new goals. And in this economy, a better money plan is more necessary than ever. I am Matt.
A
And I'm Joel.
B
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.
A
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.
H
What if mind control is real?
F
If you could control the behavior of.
G
Anybody around you, what kind of life would you have?
H
Can you hypnotically persuade someone to buy a car?
E
When you look at your car, you're.
B
Gonna become overwhelmed with such good feelings.
H
Can you hypnotize someone into sleeping with you?
F
I gave her some suggestions to be sexually aroused.
H
Can you get someone to join your cult?
I
NLP was used on me to access my subconscious.
H
Nlp, AKA Neuro linguistic programming, is a blend of hypnosis, linguistics and psychology. Fans say it's like finally getting a user manual for your brain.
F
It's about engineering consciousness.
H
Mind Games is the story of nlp, its crazy cast of disciples and the fake doctor who invented it at a new age commune and sold it to guys in suits. He stood trial for murder and got acquitted. The biggest mind game of all, nlp, might actually work. This is wild. Listen to Mind Games on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.
F
I had no idea that the number one friendship test to gauge how close you are as friends involved trying on bikinis and rating each other's looks in a totally platonic, non sexual way. Yeah, that's so reassuring.
C
That's normal. I don't even want to try on bikinis with my girlfriends.
F
You must not like them very much. No, Brooke, that's just what normal male and female friends do.
E
Do you even have any friends then? Brooke, if you haven't done this, seriously.
C
I can't stand that guy.
F
He's the worst I know for trying to find friendship at work.
G
Boom.
F
Screw you.
C
He was not trying to find friendship.
E
He's adjusting on the fly.
F
Yes.
C
Yeah, and I'm sorry, but his girlfriend would not be okay with him bikini shopping with other single women.
F
Come on, you don't know it. Relationships look different to everybody.
C
You keep defending him.
G
That's right.
F
I think for our annual show camping trip, we need to scrap that. Do an annual show shopping trip to Pacific Sun. Get all matching swimwear.
E
Dude, I'm down.
D
Somehow that's still better than camping, right?
F
Alexis is in. We're all going bikini shopping this summer. I'm into it, cuz we're friends.
C
Friends.
F
But honestly, if Eric is being serious and he's looking for friendship, he probably should change his approach drastically.
E
Dude, way to set the tone in a new city, too.
G
Yeah.
E
Environment for him. When that gets out.
C
Dude, seriously, I think it's out.
F
Yeah, he's gonna be moving cities again very shortly.
G
Yeah.
E
Honey, good news.
C
I'm moving back.
F
But we're in cities all over the country, so no matter where you need help in your dating life, you can always email the show. We'll call that person who's not calling you back.
A
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. That's right.
B
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 28, 2026
Episode Type: Second Date Update
Hosts: Brooke, Jeffrey (Jeff), Alexis, Jose
Special Guests: Eric (the dater), Anna (the datee)
In this episode, the Brooke and Jeffrey team dive into another "Second Date Update," where they help listeners reconnect (or at least find out what went wrong) after a stalled first date. Today’s case centers on Eric, who recently moved to a new city for a job and “hung out” with his new coworker, Anna. After a quirky first outing involving birthday gifts and corn dog toasts, Anna has been giving Eric the cold shoulder at work. The hosts attempt to untangle whether sparks flew, boundaries were crossed, or if Eric’s intentions (and relationship status) were as innocent as he claims.
The episode is packed with humor, short detours into office gift-giving politics, and one of the show's most memorable food-based “romantic gestures.” Ultimately, it delivers a fresh take on how confusion, assumptions, and social media can complicate modern workplace dynamics.
This “Second Date Update” revolves around workplace boundaries, social media sleuthing, and a hilariously misguided attempt at friendship (complete with corn dog toasts and a disastrously inappropriate shopping suggestion). The episode is a showcase of the hosts' humor and empathy as they attempt to untangle a messy workplace situation—ultimately serving as both a cautionary tale for mixing office and romance, and a reminder to be clear about intentions (and relationship status) in professional and personal interactions.
Key takeaway: Sometimes, a simple "friendly dinner" is a lot more than it seems—especially if you already have a girlfriend. And, never suggest bikini shopping with your coworker as a “platonic” gesture.
Listen to more "Second Date Update" on the Brooke and Jeffrey podcast for more hilarious and cringe-worthy tales of modern dating!