The Rachel Cruze Show - This Annual “Dream Date” Will Change Your Marriage (and Money)

Episode Date: January 19, 2026

🛡️ Are you protected with the right insurance? Take Ramsey’s five-minute Coverage Checkup. In this episode, Winston and I share how our annual “Dream Date” has transformed our marriage and our money. We share what we do every year to get aligned on our goals, budget and big dreams. If you’re craving clarity and connection heading into 2026, you’ll love this episode. Next Steps:  🎥 Watch my video Money Lessons We’ve Learned in 15 Years of Marriage (With Winston Cruze). 📑 Check your credit report for free. 💵 Start your free budget today. Download the EveryDollar app! 📈Are you on track with the Baby Steps? Get a free personalized plan.    Connect With Our Sponsors: Learn more about Christian Healthcare Ministries. Get 20% off when you join DeleteMe. Go to FAIRWINDS Credit Union for an exclusive account bundle! Turn to Minno for kids shows you can trust. Use code RACHEL for $10 off an annual plan with a seven-day free trial.    Explore More From Ramsey Network: 🍸 Smart Money Happy Hour 🎙️ The Ramsey Show  💸 The Ramsey Show Highlights 🧠 The Dr. John Delony Show 💰 George Kamel 🪑 Front Row Seat with Ken Coleman 📈 EntreLeadership   Ramsey Solutions Privacy Policy Learn more about your ad choices. Visit megaphone.fm/adchoices

One thing marriage and money have in common is they both require intentionality. So today, my husband Winston is here and we're going to explain how we are intentional when it comes to our planning for the new year. Be sure to like, subscribe, and share this episode with a friend. All right, babe, thanks for being back. Oh, yeah, I am back. You are back. Yeah. You've been a couple of times.

I know. It's kind of a new set of. Negotiating that contract. I know. We've not paid you yet. So we'll see what happens. It's okay. We're working it out.

With legal. With legal. Yeah. My agent. Thanks for having me back, though. That means I did something. You did do something. At least neutral.

And they liked you, the people. They, yeah. It's good. Okay, so January, starting off with Dream Date. This is something that we've done four years in a row, five years, would you say? I don't know when we started planning, but yeah, it's just been a part of our rhythm, yeah. Yeah. I'd say in the latter years, though, we've not been doing this for our whole marriage.

Yeah. But we started, again, a couple years. ago realizing that we weren't looking far enough ahead, probably for the year and beyond, of like, hey, what do we want to do with our money? What do we want to do with our schedules, our time, and all of it? We were kind of like month to month, week to week, versus day by day. Day by day. Probably because we were having babies and surviving.

Surviving. We can actually breathe. We're like about five years from now. I know. So we decided, okay, let's just, we kind of started off the dream date, started off with just dreaming. Remember that? We went to dinner downtown and we like got out a sheet of paper and just started like writing down. Long term.

Big goals, yep. Yeah. From travel, the pool came out of this. They weren't even goals. They were just like big. They were just dreams like what do you, what would be fun or out of the box or crazy or whatever. Yes. Yep. And then they started to become a little more like formalized and like things that we want short term, long term. Yep. Yeah. Being able to prioritize the list to say, okay. what's actually realistic or what parts of this could we actually do.

Yeah. So that was kind of the beginning. So it was very, like, very casual. And then now, fast forward probably five years. Now we kind of have a system in place. So when we meet, we usually do breakfast or lunch in January to look ahead. And you usually bring your computer. Because dinner's a little too ridiculous to bring a computer to.

So it's a little more like casual. Yes. Yeah, yeah. Bring a writing utensil. You can't really do that at dinner. Yeah. You know, it ruins the vibe. So yeah, breakfast lunch.

This is what we do. I guess you could do anything. Yeah, but this is us. Yeah, this is what we've started doing. And then we first look back on the year and we look at every dollar and look at that because every transaction that we do from like moving money from our checking to our savings to our giving to literally every like grocery. transaction, I mean, every single transaction that comes out of our account, and that crazy.

Pretty convicting. It's tracked. It breaks into percentages of like, here's how much you're saving. Yeah. Here's the percentage of income you spent. Yes. It's very revealing. You're like, oh, wow.

So with every dollar, you can look back at the whole year and it gives you this pie graph and it's color coded. So you can see out of the income you've made, what percentage did you give, save, spend. And then even in the spending, like you're saying it's like lifestyle, food, it goes very specific. So you see, oh my gosh, this is what. where all of our money is going. So as the money expert,

do you ever look at that and think, oh my gosh, that's a reflection of like me? Who I am. Of who you like. Well, yeah. Well, our savings, I kind of panicked. I think it was two years ago because I was like, oh my God, our savings.

That's a reflection of me. It doesn't look as, well, no, it didn't look as big. It wasn't. It wasn't. And then I realized I didn't track in, I know, then I realized I didn't track in every dollar. like probably six months, that transaction I never put in the savings line item, so it didn't show up. So then I went back and corrected it.

Problem solved. And I was like, oh, thank gosh. Because it wasn't big. I was like, oh, no, what did we do? Yeah. Yeah, I would say, but from like the giving is always good. I feel like we always, we're pretty consistent on that. Right.

Like when we see that pie chart. But the lifestyle. Yeah, the look back is just like a gut check. Yeah. I don't know. Do you think we spend too much on lifestyle when you look? And we have a stupid category. We do.

We do have a stupid category. Which is just where you got faked out or something. Yeah. Something that was stupid. By whatever. Just stupid it didn't count. Stupid. It's like the kids go to the doctor and they're not sick.

You know, like that was stupid. Oh, okay. I don't want to pay that stupid category. Just put it in there. Say no to the kids. Oh, yeah. But I'd say, from a pulse check, though, I think we're, we felt good. Would you say the past couple?

Like when you look at. at our look back, what's your emotional reaction to it usually? It's pretty good. Make some adjustments here and there. But overall, it's like it was intentional what we wanted. We meant to do what it shows at the end of the year. Yep, yep. By and large.

Yeah, so that's like the first thing we do. Kids sports is crazy. That's one that I'm just like, oh, okay. Yeah, and we don't even do travel. It's like YMCA. Yeah. Like, it's not even that. But it's just, not just that.

It's like every year their feet grow. And so you're like, yeah. You can't pass pink cleats to Charles. Yeah. I mean, could. I guess people do. But it's not worth it. Not worth the every dollar reflection.

Yeah. We'll buy new cleats. Put it in the stupid category. Stupid. Yeah. So yeah, I feel good about to look back. Yeah. So we just...

That's not where we spend. We spend a little bit of time there. Yeah. But that's kind of. like the first thing we do. Look back on the year. Okay, how does that feel? And then we move into planning. First thing we do is get coffee. That's fair. Okay. Yeah. And then we go and say, okay, let's look at going forward. So we have this Excel sheet. And there's like, maybe like six different categories. First is income. So we kind of assess every single month. It's divided into 12,

like by the calendar. And we kind of say, okay, what are high, high months, low months. We kind of just predict, okay, what do we think we're going to make in these months? And again, this is not like set in stone. This is more just to get a high level guesstimate, if you will, to see here's what we're going to make. Yeah. And so we're able to plug in those numbers. I think I was, I think I pulled up the Excel sheet and I was like, we've got to be able to like see this. Yeah. Somehow, that feels new to me. We've only done that for like the past couple of years. Yes. Yeah, to the Excel level where we're breaking down months. Yeah. Yeah. Yeah. That's so helpful, though.

Playing trips. Yes. So, yeah, so the first line item is income once. What? Well, I just, in the course of our life, like this past year, I remember you being like, hey, how much? Like, I memorized the Excel sheet and you're like, how much it do we have for this trip in March? You know? Yeah, for spring break. And I was like, I know, we put it down.

But I feel like go get it, you know, like get my computer, find where I saved it. Yeah. But it does work. we put it down in a 12-month calendar, and you remember it, like, at least the- Because I'm planning the trip, and I'm like, I want to spend everything that we decided that we were going to spend. Yeah, yeah, yeah. So it's not like, oh, let's just see what the trip is, and then we'll balance it out with what our budget was. You're like, how much do we have?

What do we have left? Yes. To do this thing. Yeah. So, yeah. So the first category is income, and then we do, we'll go to travel. travel is a category we have. So we look at months and say, okay, what trips are we probably?

I thought we did operating expenses. Next? Yeah. Okay, well, I'm trying to flow with what you just talked about trips. Oh, well, don't, no. In accounting, you don't go straight to. You got to do cost of good sold first. Fine, fine.

Income and then what? Operating expenses. Like your life. Yeah. So that's where we look. That includes giving. It's our. Every dollar budget, basically, for the month.

Okay. We look and say like, okay, what do we spend every month? We're about to do this. We are about to do this. If you jump straight to travel, you're going to lose me. I know, I know. Okay, we are adults and we cover our expenses. Exactly.

We are mature. How else you know what you got left? I know. I know, yeah, I know. So we do that. And then. And then it's like these big items. Are we saving it for a car that year?

is there like a, it's not just travel, but it's like, well, travel is its own line item because we do look through and say, okay, we have spring break. That's right. Yeah. Spring break, summer, fall break for the kids. Kids never go to school anymore. Do we want to do any trips? I have Thanksgiving break, winter break, spring holiday break.

Spring break, spring holiday break and spring break are two different breaks now, apparently. It's a lot. Yeah. So yeah, so yeah, so there's travel. And then there's like whatever else we can think of, which is important. Yeah, so then we do kind of that dream category, which is like the big stuff of like, okay, do we need to replace a car? We built a pool two years ago. So I feel like we had money in each month of what was going to be owed as we're building the pool.

Like that was a thing. Yeah, and if you're doing a construction project and they don't give you a payment schedule and ask for that so you can plug it in. I know. I want to, I'll just reveal to you what I'm going to talk about in January with you. Oh. Oh, this is happening right now. Yeah, I do, I do want to do some updates to the house. Insert, insert, row.

Yeah, insert row. No, it'll be in the stream row. Oh. But update some furnishings in our house. There you go. Because it's been like five years and our couches are just kind of sad now. Six years. Six years, yeah.

The couches are kind of sad. I don't know. There's a couple of pieces, furniture pieces. I think I want to. Replace. Yeah. And the playroom, the kids' playroom needs. It's been used.

It's been loved. It's been loved. And it needs a little, another little love. So that's going to be in our category for 2026. Okay, great. We'll figure out what month we can do that. Yeah, furniture. Insert.

Insert furniture. So we got that. Okay, giving. That's another line item. So above our tithe, what we do month to month, and we change this up. We sometimes, we've done years where we like give to. specific organizations. So we'll talk about that. This past year, 2025, I had the great idea of saying, let's give, I just have a line item for giving, like a good amount of money every

single month that we can just spontaneously give, like give a big tip or see something or hear about something and we can just spontaneously give. So we pulled back from like one or two organizations that we were kind of, yeah, it's unsettled from our giving to do this like more spontaneous giving and I don't know if it worked. I think it worked some months. Some months it didn't. Yeah, I mean, it's just intentionality. Yeah.

You gotta work on it, remember it. Yeah. And be like looking for it and aware of it. I feel like we were good at the beginning of the year because it was new, kind of this new idea of like, ooh, let's like find something. And then it kind of like fades, I feel like, or it did for us. Yeah, that's a fun category, though. So that was fun.

But any, yeah, any, like, fun. creative giving type thing we put in a category. And then... Because sometimes you just don't feel it. Like when you... Yeah. Just write a check or go online now and give to your organization, you get an email receipt.

You know what I mean? Yeah, yeah, yeah, yeah. So it's hard to be, like, personally, like, affected by giving. Yes. In our digital culture. So that one is really fun because you... you can be personal with it. Yeah.

Because you're actually in a moment to say, oh, yeah, well, we can totally do this or that. Like some of the effects of it. It's there. No, it's fun. Any other surprises? One thing my family and I always plan for in the budget and in life is online protection services like delete me.

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That's fairwins.org slash Ramsey. I will say our van was our five-year car, and she's going on six years, but I'm content with her. All right, 2026. Still going strong. Winston loves the van. I love the van too. That thing loves us back.

It gets hammered. I know. Poor thing. And I don't want to put another car through that right now. I know. Not worth it. Don't mess with that relationship. Yeah.

She's been good to us. There's nothing wrong with her. It's just the vanity of having the minivan. I know. I said it. I said it. I admitted it here. Did you catch it, though?

What? The vanity of the minivan? The vanity. Oh, van. Oh, good job. Thanks. Jeez. So on purpose.

I thought you would have picked up on that dad juggle. No. Quick. Okay, what else? You got those covered. Then what? Okay, and then the last line I am for us. And again, you create your own, but this is our real estate. We have for flipping houses. We have one rental. And then, yeah, then I do some side flipping. Yeah. So every month we put. With a friend. We put. It's a little more affordable that way. That's fair. 50-50 split. Yeah. And that's, that's its own thing, because you're buying a property, putting money into a property, selling property, the money comes back. Right.

That one gets complicated. It's difficult to track. Yeah, but we do. Especially in this market. But we put it out there to say this is how much we want to invest towards flipping, hopefully to make money when you sell it. So that, yeah, that is one. That was a category for us. But you could have, that could be whatever side business you have, if you have a side hustle.

Yeah. How much money do you want to put towards it? Yes. And I also bring the income back into it as well that I'm hoping for as the year rolls on. Yep. Hopefully like around spring break. Why to make some money to pay for? Because you're like, how much was that one?

How was it was that one? I'm kidding. But yeah, that's like, I think that's, those are all the, I think those are all the categories in the Excel date. And then. Date breakfast. Long term? Oh, yeah. And then we still dream.

And then we will take a moment just to say, okay. what's like big things in the next three to five years, what would we want to do, right? Yeah, and I think if you're not asleep by now, I hope you're not. But it can be real tactical and like a financial planning meeting with a writing utensil and Excel sheets and all that stuff. But I like the dreaming part because that's the part that it reveals kind of like the desires of each of us. Yeah. And I get to see you.

Mm-hmm. You know, it's not just money, but it's like, what do you really want? And because you want or dream or desire that thing 10 years from now, then it reveals, you know, a part about you that would give you something. And I'm like, whoa, what is that? Yeah. What does that give you? And why does that feel good or whatever? Yep.

Or if you're scared about something or you don't feel like we're doing this well. Like, there's a connection piece that is the umbrella for this whole breakfast, lunch, brunch thing. Yes. In January, that is the reason I like to do it. You know, I like having a plan, but a plan with connection is even better. Yeah, for sure. And that's what the thing is. It's just to be like, where are we?

Yes, totally. Well, because you end up talking about life through it all anyways. of like, okay, I mean, and everything from like. Charles can't have pink shoes or whatever, you know. Or you want to save up, you may want to retire with a second home or something. Right. And I'm like, where did that come from? I didn't know that.

Yep. Let's talk about that. What do we want to do? Yeah. Is that what you want to do for when the kids are gone? And then you start to be like, you know, start to learn things about each other. Yes. That are helpful that you just don't talk about day to day.

No. So that's why this is super beneficial. Yes. And giving the space for it, because we always talk about how money, it's, yes, the number, to your point, it's like the numbers and the percentages and all of that. But it is so emotional because it so reveals how we want to live life, right? And so as a couple to sit down to yes, being intentional and planning is very helpful from a logistical standpoint, but also to your point, the emotional connection, the conversations that come out of it. You're just like, oh, my gosh, okay, I didn't realize this or that. or I want to do that too, that does sound fun.

And it adds energy and excitement to the future because you need money in order to do things in life, not all things, but a lot of things. And so being able to be in unison and see that together is really big. Do you feel like a lot of couples ask, like if you're on opposite pages on something, like how you come to agreement, if there's something that you're like really disagree on?

And I'm trying to think if there's anything that's come up that we like fully, if there was like a hard stop. I don't think there's been like a specific example, but what would you say to couples? I don't think it has to be that extreme. I think it's going to, I think most people are going to come at this from two different family of origins, two different personality types, two different tendencies, two different ways to see money. And so like our, our pattern is let's take a spring break trip and you throw out a number and I throw out a number.

If we put a number down and we tore off the piece of paper and folded it up, put it in a jar, I think we would all know which one, like, our kids would know. Who put that one? Who put that one? Who put that's a larger number to travel? Mine's just going to be like, I'm good. Like, I'm just, I'm good. Let's just go to Gatlinburg and get a holiday in and put the kids in some chlorine and they're going to love it. And we'll just get created. make some stuff up.

And so that type of... Our low-maintenance man. So that comes, you know, like those conversations are real where you're going to be like, hey, for this, I want to go do this thing. And it's going to be big. And you're going to plan it all out. And we're going to... Should we get first class?

Because we have these credits from American from last year's whatever. And you're just like... We have all these credits. We did have that conversation. See? I already not. See, I'm giving you your script. Should we use it?

Upcreps? This is it. So this happens. And then what I would say, though, there is like a solution that I'm making this up. That's great. Yes. Go. Tell us.

Bringing like my heart and my honesty to the table. Why am I feeling so like insecure about spending money that would be budgeted on an Excel sheet at brunch at the first of the year? What is that about me that feels so insecure about loosening up? having a budget to say, okay, there it is. Now we can spend it to go and do it freely, right? Yeah. And what is the inverse of that? For you, if I want a savings goal or something, you rarely say no, though, to me saying,

like, I want to do this house. If it's spending, it's something. Yeah. I know. It would be not doing something. It would be less about, like, oh, let's, because at least saving for me, there's some kind of movement forward. which is exciting to me.

That's energizing. Even if it is saving, I'm like, oh, well, at least we're like doing this. It would be like, it would be like, we're not going to do.

We're just not going to go. Yeah, that would be like, we're not going to do two trips. Crap. Yeah. During summertime or whatever. Or during the year.

I mean, both of our families are still doing trips. Like our parents are still doing trips. They're still alive and going. So that would be mine. It can become very like overwhelming to me. My would feel suffocated and like if we have the ability to. Freedom's getting squash.

Yeah. I hate that. Yeah. So. So, yeah, so I don't think it's like, oh my gosh, we're on these opposite-based hard stop. We're fighting it out. I would just say bring your heart to the table. Yeah.

And be curious about yourself. Be curious about your spouse. You're not in opposition. Yep. You're at least there together. So that's the first step. Good job. You had to show up and look a babysitter or whatever.

Right. But I don't know any other way except just to bring yourself to the table. and be like, well, this is where I am, and let it happen, let it go at that point. And I would say not every decision has to be decided at that brunch. Like if there are some things that, you know, what? That are. It's very important. We have to, yeah.

You know what I mean? Like if there is a tension point, it's okay to table it and be like, hey, let's come back to this next weekend, right? And so give yourself that freedom too. But yeah, go reflect. Yes. Yeah, yeah. That's good. Yeah.

So, but yeah, but it's been helpful, I think, for us, this new rhythm that we've been in the past. couple of years looking ahead and it's the dream date. Not that kind of dream date, but it's a good date. You know what I'm saying? Yeah. Well, yeah, it's not like, oh, this is a dream. We're going to go to the spa and like. Dreaming. Take me, dreaming date. That's a good way to put it. Make it a verb. It's right. So good. So good. Thanks for having me back. Yeah, thanks for coming back. Talk and Excel and your heart and connection. That's what we love. It's what we love. Okay, so Winston I talked about again when we look back at the past year, kind of where we're at, looking ahead for the next year and planning and then just dreaming in general.

Like, let's talk about when the kids are in high school. What does life look like? So just having fun with those conversations. So those are great ways to kind of plan out if you and your spouse are going to sit down together or just even yourself to say, hey, let's plan out the year. But you have to do the basics if you haven't yet. and this is a crucial first step. So these are things that, again, are not maybe as fun and exciting, especially to all you

free spirits out there, but things that you have to do before you can go and do a dream date. Okay. You first need a monthly budget. Remember once I talked about we know our expenses every single month that we're able to plug in, we would not know those if we were not doing a budget. So making sure you're doing a monthly budget, you're tracking your expenses, and that needs to be a rhythm that you have day in and day out throughout the year. so that way in the next stream date cycle, you have all that information. You also want to make sure

that all of your insurances and wills are in place. So this is really important because, again, this is like the adulting stuff, but making sure that you, number one, have a will. If you don't have a will, you need a will, you guys. This is something that a lot of people skip over in their life. And when something happens to you, it takes like untangling all this information and it's so hard on your friends and family. So creating a will, making sure that's in place. And then also revisiting your insurance. So insurance is one of those things that a lot of people just, they get, they set aside, and they don't revisit it. So there may be insurances that you don't have that you need. You may have some that you have that you can just cancel. And then there's

some that you may be able to adjust what you're paying and actually save money. So here are the insurances that you need. You need homeowners insurance if you own a home or if you're renting renters insurance. Auto insurance, term life insurance, health insurance, identity, left, long-term disability, and long-term care if you're over 60 years old, and I would get an umbrella policy if your net worth is higher than half a million dollars. So those are the insurances. Again, this is like the adult stuff that's kind of boring, but making sure that those are in place, it's really, really important. And you can check in on those every single year to make sure that nothing has changed in your life, right? If you have a kid or you get a different car or you

move, like if something big happens, your insurances may reflect that. So be looking at those every single year. Also looking at your financial goals, which again, you may be talking about in your dream date. I would also say, know your net worth. If you've not added up everything and subtracted your debt to kind of know where you're at baseline-wise, I think it's a great practice to do. Also, pull your credit report. This is something to do every single year to make sure that nobody has stolen your identity and using it. And so again, this isn't necessarily your credit score, but this is just looking to see, okay, if you've interacted with debt or if someone has, when it comes to your name, which would not be good, you're going to know. And you can pull your credit report for free at

TransUnion. You can do Equifax or Experian. Those are three companies that offer it every single year for free. Okay. The truth is, though, you know, depending on where you're starting, you have to be intentional with your money. So for some of you, again, it's going to be going back to the basics, like a budget. So if you are not doing a budget every single month, that is something that is great. Every dollar, Winston, I mentioned it, but we use it. And this is a great baseline in general to start talking about money because if all of this was kind of overwhelming and you're just starting from the beginning and you're thinking, oh my gosh, this is a lot. Just start with the budget. That's going to be plenty for you to do for the next month or two to really get in a rhythm of

doing it. I'll put a link down below for every dollar because it's free and it's amazing. All right. For more conversations between me and Winston, you can check out another episode that we did, money lessons that we've learned in 15 years of marriage with Winston Cruz. You can click right here or if you're listening on podcast, you can click the link below. All right, you guys, remember to take control of your money and create a life you love.