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Dave Ramsey
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Caller (Tyler)
I'm in this relationship where I feel like I get leaned on financially pretty well. And I'm very young and I do pretty well. As of right now, I have a lot of money saved up. And I just am wondering the perspective that you guys may have on is that like a healthy relationship or should I be using this time at my age to generate more wealth than what I'm doing?
Ken McElroy
What is the relationship? Is this a marriage? Is this dating? What are we talking about?
Caller (Tyler)
Dating?
Ken McElroy
Okay, how long you been dating?
Caller (Tyler)
A year and a half.
Ken McElroy
Year and a half. How much money do you make?
Caller (Tyler)
135.
Ken McElroy
And you said you've. You've been putting stuff away. Do you have any debt?
Caller (Tyler)
No debt.
Ken McElroy
And what kind of retirement situation are you starting to build?
Caller (Tyler)
I max out my 401k and then I have about in my private savings account just around $100,000, making me about 18% a year.
Ken McElroy
Okay, so tell me about the other person in this relationship. What do they do and how much do they make?
Caller (Tyler)
They are in mental health and they make around $50,000 a year with somewhere near 70, $80,000 in debt currently.
Ken McElroy
Okay, now let's get to the crux of the call.
Caller (Tyler)
Yes.
Ken McElroy
What do you mean by leaned on? Like, let's get real here. Like, we need an example that really bothers you, either hurt you or angered you, or maybe one of each. I'm gathering all this for Jade and I to be able to weigh in here. So give us some examples or one good example.
Caller (Tyler)
I would say like vacations and then like weekend funds, dates, everything along those lines.
Jade
So you pay for the vacation?
Caller (Tyler)
Yes.
Jade
The whole thing?
Caller (Tyler)
Yep.
Ken McElroy
And is it manipulative and how she puts that out there? Like, how is that decided?
Caller (Tyler)
No, it's more of just like she knows that I know and that it's like really not even up for discussion.
Ken McElroy
So who?
George
Who?
Jade
Wait, wait, wait, wait.
Ken McElroy
How does she know that?
Caller (Tyler)
Yeah, well, just that, like, she knows that I know she's not in a great financial situation.
Jade
All right.
Caller (Tyler)
Like, you know, in this young. At day and age, I feel like, you know, females want to do all the fun stuff and just because the situation, they may not be able to. It's just.
Ken McElroy
He just went. He just went. Females.
Jade
Listen when you say females all around the world know something has gone down.
Ken McElroy
I agree.
Jade
That's caused you to be. You're feeling sometimes.
Ken McElroy
I haven't heard yet, Jade, anything where she's leaning on you.
Jade
Well, that's what I'm gonna get to. Tell me how the conversation goes down.
Ken McElroy
Yeah.
Jade
Is it you saying, oh, it's, you know, it's July, we should probably go on vacation. What do you have in mind? Or is it her bringing up, hey, it's July, we should probably go on vacation. What do you have in mind? Like tell me how the conversations go. And, and, and I need that because it's very different if you saying, hey, you know, let's go, let's go down to Fort Lauderdale. And she's like, okay. And, and you' I made the reservation for the Hilton. And she's like, okay. And then you just go versus her saying, where do you want to go, honey? And you're like, well, I don't know. And she says, well, I found this really cute place, I think we should go here. And then you're like, well, okay, right. All of that matters. So I want to know how it goes.
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Jade
All of that matters. So I want to know how it goes.
Caller (Tyler)
I would say it's more of like, oh, we should do something. And then like I'm a very minimalist person. And then perspective on there and gets a little starts that, you know, the standard starts to increase and then it just kind of goes from there.
Jade
Okay, listen, I ain't saying she's a
Ken McElroy
gold digger, but she. I get the lean now, I think. Do you feel that? I want to make sure I get the female perspective. I feel the. Okay, I get the lean. So where, where are you relationally with this gal? Like, is this.
Caller (Tyler)
I don't, I don't live with them. No.
Ken McElroy
Oh, no, no, no. I'm not even, I wasn't even getting into that. I'm saying, what's your on a scale of 1 to 10? 10 being she's absolutely one, I'm going to marry her no matter what, or one being could care less if I'm in this relationship one more day. There's your extremes. Where are you at with her?
Caller (Tyler)
Yeah, I feel like I'm like right in the middle. It's just like a little stuck situation.
Jade
Okay.
Caller (Tyler)
I do care about them and you
Ken McElroy
know what I mean, you care about her, but this is troubling you.
Caller (Tyler)
Yes.
Jade
So what we need to decipher here is the line. And Ken, you're just the man to do this. We need to decipher the line between the classic chivalrous male behavior and I know, I'm choosing.
Caller (Tyler)
I would agree.
Jade
Right?
Caller (Tyler)
I would agree.
Jade
And then what is too much and kind of like the lean as what we called it. So I'm going to start by saying yes. If you take me on a date, especially like, yeah, you're not living together. Like there's no like intent that we are in any way beyond dating. I'm expecting the male to pay every single time.
Ken McElroy
Totally agree. And I would say yes, you should be paying for dates. You guys have been dating how many years?
Caller (Tyler)
Yeah, one and a half.
Ken McElroy
Yeah, yeah. So you're paying for dates. However, when she comes up with an idea, that is an expensive idea and by the way, you get to determine what you feel is expensive. This is a two way shit. Yes.
Jade
Money bags.
Ken McElroy
Yes, that's right. And you're the money. So when she brings that up, you should feel free to say that feels like it's too much and you can explain why.
Jade
I agree.
Ken McElroy
And I think it's incumbent on you to explain why. Then if she follows up and goes, well, why, why, why? Then you start to go, you know what? Some of this is on me because in the past you've suggested stuff that I would not normally pay for given my views on money. And I've got a formula in place, I don't want to spend this one. You lay it all out so she knows where you're coming from. She shouldn't be guessing.
Jade
On a vacation.
Ken McElroy
Yes, on a vacation.
Jade
What's the chivalrous behavior? I'm thinking half and half.
Ken McElroy
It's half and half. But, but I'm saying he has to take that stand and, and think about it ahead of time and then say no. He has to feel comfortable going, yeah, I'm not comfortable going on a six thousand dollar vacation.
Jade
I, I, I, I agree with that.
Ken McElroy
And then she goes, why? You explain it. And let's say you go, and I'm making this up. You go, I'm comfortable with a $2,000 vacation. Okay, great. So then you explain to her, but I think you should be paying for half of it. Well, I can't right now. So then we aren't going.
Jade
Or we pick something more in your budget.
Ken McElroy
Yeah. And then go and let this bleed into. And I probably the wrong word. Let this lead into a bigger conversation about money so that you, my friend, can go from being a 5 to. To a 8, 9, or a 10 on whether or not we stay in this relationship. You're looking for certainty right now because, Jade, I'm gonna bring it back to you. You're in the weeds on this and the data. And you coach people because he's dating right now and he's on a five.
Jade
Yes.
Ken McElroy
If this doesn't go to some certainty on whether or not they're a good fit from a value standpoint on money, this causes how many issues down the
Jade
line, it's gonna cost so many. I mean, it's the number one. Number two, depending on what piece of research you're looking at. Cause of divorce, money fights, and money problems. So if this is somebody that you're starting to go down that path of. She might be the one. This is, to Ken's point, this is just the type of scenario where you can start these conversations to really see what are each of your philosophies on money. And now's not the time to try to change somebody. Now is the time to try to go, who are you for real?
Ken McElroy
Great point.
Jade
You know, I want to see who you are for real.
Ken McElroy
Yeah.
Jade
And. And vice versa.
Ken McElroy
Yeah. Now, if she says, okay, I. She needs to feel the weight.
Jade
Yes.
Ken McElroy
Of this. And we hope, Tyler, that this goes one of two ways. My hope is, is that she reveals herself. Jade's absolutely right. And so once she reveals herself, and what we mean by that is how she views money, at which point we now get to have a very serious conversation about how you view money. And is there a bridge to where we meet in the middle? And middle being. I'll help you and guide you and teach the principles that I've been living by. If you're willing to do it. That's meet in the middle here. And then you're gonna find out really quick whether or not she values you enough to change her values about money.
Jade
Yes. But the key strategy to what Ken is saying, and this is key, and this is for anybody listening. When you bring up the money conversation, the first question, you don't say your philosophy first.
Ken McElroy
Good.
Jade
You let them say first. Because if they really like you and you say, oh, debt. Yeah, I don't do debt. They're going to go, oh, yeah, me too. Yeah, me too. If they really like you. And they think that. Right. People tend to kind of shape shift, especially in those early stages. So you first say, what's your philosophy on debt? And just shut up, Let them talk. Don't influence anything they're saying. You need to see this. You need to hear it. Then you go, okay, well, would you like to know mine?
Ken McElroy
It's a great point. So, Tyler, this feels like this is a massive, massive moment in this relatively young relationship. So step into it and let's see how this plays out. But you got a great head on your shoulders.
Dave Ramsey
Create your free every dollar budget today. The simplest way to budget for your life.
Date: March 3, 2026
Host(s): Ken McElroy, Jade Warshaw (with Dave Ramsey intro/outro)
Caller: Tyler
This episode of The Ramsey Show Highlights centers on a young caller, Tyler, who feels financial pressure in his dating relationship. Tyler seeks advice from Ken McElroy and Jade Warshaw on whether covering most expenses for his girlfriend constitutes a healthy relationship dynamic, or if he should focus more on building his own wealth. The conversation explores boundaries, expectations, and communication around money in dating relationships.
Jade (02:40): “Listen when you say 'females,' all around the world know something has gone down.”
Ken (06:08): “You should feel free to say, 'That feels like it’s too much,' and you can explain why. She shouldn’t be guessing.”
Jade (07:53): “If this is somebody that you’re starting to go down that path of ‘she might be the one’, this is just the type of scenario where you can start these conversations to really see what are each of your philosophies on money. And now’s not the time to try to change somebody. Now is the time to try to go, 'Who are you for real?'”
Jade (09:22): “When you bring up the money conversation, the first question... you let them say first... People tend to kind of shape shift, especially in those early stages. So you first say, 'What’s your philosophy on debt?' And just shut up...”
Ken (09:53): “This feels like this is a massive, massive moment in this relatively young relationship. So step into it and let’s see how this plays out.”
This episode is a practical, honest exploration of modern dating and finance—delivering actionable advice for anyone navigating love and money.