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The Rachel Cruze Show

This Annual “Dream Date” Will Change Your Marriage (and Money)

The Rachel Cruze Show

Ramsey Network

Self-improvement, Education, Investing, Business

4.83.6K Ratings

🗓️ 19 January 2026

⏱️ 28 minutes

🧾️ Download transcript

Summary

🛡️ 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

Transcript

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0:00.0

One thing marriage and money have in common is they both require intentionality.

0:09.6

So today, my husband Winston is here and we're going to explain how we are intentional

0:14.3

when it comes to our planning for the new year.

0:17.1

Be sure to like, subscribe, and share this episode with a friend.

0:38.4

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

1:13.1

with our money? What do we want to do with our schedules, our time, and all of it? We were kind of like

1:17.1

month to month, week to week, versus day by day. Day by day. Probably because we were having

1:22.5

babies and surviving. Surviving. We can actually breathe. We and we're like about five years from

1:27.7

i know so we decide okay let's just we kind of started off the dream date started off with just

1:34.1

dreaming remember that we went to dinner yeah downtown and we like got out a sheet of paper and just

1:40.3

started like running down long term big goals yep yeah from travel the pool came out of this they weren't even goals they were just like they were just started like running 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, yeah. And then they started to become a little more like formalized and like things that we want short term long term.

2:01.1

Yeah.

2:01.8

Yeah.

2:06.9

Being able to prioritize the list to say, okay, what's actually realistic or what parts of this could we actually do?

2:08.6

Yeah.

2:09.1

So that was kind of the beginning.

2:10.1

So it's very like, very casual.

2:11.9

And then now fast forward probably five years.

2:14.6

Now we kind of have a system in place.

2:16.2

So when we meet, we usually do breakfast or lunch in January to look ahead and you usually bring your computer.

2:23.9

Because dinner's a little too ridiculous to bring a computer too. So it's a little more like

2:29.5

casual. Yes. Yeah, yeah, yeah. Bring a writing utensil. You can't really do that at dinner.

...

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