Skip to content

500 Dates

Why you should never stop dating your spouse, and how to do it well.

Sean Johnson
Sean Johnson
7 min read
500 Dates

Last week, as I was reading to my daughter, she asked me how many dates her mom and I had been on during our 15 years together.

We spent a few minutes backing into a number, and arrived at around 500.

I've thought about it a lot since then. The number is bonkers. But it might also be the number I'm proudest of in my life.

It's surprisingly rare to find a couple that still has a routine date night. They know they should do it. But especially when kids arrive, everything else gets in the way.

This is particularly true when both partners work. You have to juggle your profession, your kids, your physical health, your mental and spiritual health, your friend relationships, your relationship with your family, your finances. Romance ends up getting pushed to the bottom of the list.

Why you should never stop dating

I would argue a weekly date night is the most important part of your week, for multiple reasons:

It's the most rational allocation of time you could make.

I talk to my family a lot about the "law of amoratization," which I learned from a college mentor. He once told me:

"You spend an hour a day in your car. You spend all day in your clothes. Invest accordingly."

That idea of investing time and money into the things that matter always stuck. It's why I invest a lot in the quality of my sleep - I spend a third of my life doing that. It's why I think work is an opportunity to practice life - I spend more of my waking hours there than any other place.

Marriage is the same. Your spouse is your most important relationship in your life.

Your job will end, and it will shock you how quickly your colleagues forget about you. Your kids will grow up and leave, and you'll wish they called and visited more.

But this person you're sharing your life with is (God willing) in it for the long haul. They will be there after the company folds. After the exit. After your parents pass away. After the kids are gone.

Invest accordingly.

Dating (or not dating) impacts the rest of your marriage.

When you first were dating and all smitten, you probably were on your best behavior. You were compelled to do things for the other person. You went out of your way to make them happy.

And while it's not practical to expect that your marriage maintains that sense of perpetual excitement, I do think dates rekindle that desire to take care of the other person.

When you are preoccupied with everything else in your life, you literally aren't thinking about the other person's needs. Not because you're trying to be mean. But because your mind can't help but focus its finite resources on the things that have its attention.

Dating forces your attention on your spouse.

It creates the space to truly hear them. When you get bogged down in routine and hurry, communication becomes difficult. When you don't feel connected, simple requests or needs can be interpreted as unreasonable demands.

I've had some of the best conversations of my life on dates. And some of my worst. I've learned more about my wife and her needs on dates than any other time. And I've made material changes to the way I approach our life together as a result of some of those conversations.

You teach your kids how to be a good partner.

Your kids are always watching you, taking mental notes. Just like you did, they will grow up with a bunch of conscious and unconscious conclusions about how to live their lives.

If your marriage is not marked by joy and romance, there's a good chance their conclusion will be that there's no point to marriage. That it's simply a logistical arrangement, rather than a source of deep fulfillment.

Society is deconstructing and questioning nearly every aspect of life these days. And marriage is no exception. There are many people who don't see the point in it.

I wonder how many of these people grew up in households where marriages were lacking in love.

A marriage is almost a statement of values to the world. You are putting a stake in the ground and saying "this is how to live life well."

You make a conscious decision to stick with this person, to do your best to love and serve them. You engage in a process of mutual submission to each others needs. You make one of your life goals to help the other person achieve their own.

But that perspective can be difficult to maintain if you don't create conscious time together to remind yourself why they're so amazing. Why you fell in love with them in the first place.

That desire to serve and love withers. And your kids see it.

How to date well

But there's a good chance I don't need to convince you why you need to date. You might not agree with those specific reasons, but you still see the value in it.

So how do you go about it? Some practical suggestions:

Get a sitter booked on a routine schedule.

Dating wasn't hard pre-kids. But as soon as the littles appeared, it was tough. For the first three months after our oldest was born, we didn't really date at all. Like everyone else we were blindsided by how much work it was, by how tired we were.

But when we came up for air we realized this was not how we wanted to live our lives. We saw the need to get a regular date on the calendar. And we knew we wouldn't do it if it was ad hoc.

So we told our sitter to just come. At first every other Wednesday, then every Wednesday.

We said don't call to confirm. Just show up.

There were times when we literally forgot until she arrived. We would look at each other and say, "I guess we're going on a date!"

It's almost like a form of accountability. Someone is physically coming to your house to make sure you go out.

If you are the type that would find a way to bail with regularity, consider pre-paying your sitter at the beginning of each month. If you've already got it scheduled and you've already paid for it, your likelihood of sticking to it goes way up.

Don't create too much pressure.

In the early days, we made the mistake of thinking dates had to be fancy. Which, while fun, created a lot of stress. And was expensive.

We eventually realized we didn't have to drive all the way downtown to some place with a foam course and one of those knives that removes bread crumbs. We could simply go to a coffee shop or get a quick drink at a bar.

You can of course get fancy if you want - we occasionally go all out. But you don't have to. All that matters is there are no kids, and you're talking to each other.

Dress up. Even if you don't go anywhere.

When COVID hit, we started doing date night at home. I got rather good at making cocktails, and we'd light candles and put on a Spotify playlist and just sit in our living room and talk. Honestly those have been some of my favorite dates.

A big part of what makes it special is we dress up. It's super easy these days to just wear sweatpants all the time. But date night is special, and we treat it as such.

Date nights are the only nights in the last few years that I've broken out a suit. My wife loves dressing up, and it's her only real chance lately to get fancy. I love sitting on my couch, drink in hand, and waiting for the tapping noise of the heels as my wife walks down the stairs.

Break out your best clothes, even if you aren't going anywhere.

Make a "date night" list.

One afternoon I told my wife I was taking her to a cafe. And that there was a 99% chance it would be nice, and a 1% chance it would be unforgettable.

She was intrigued.

It looked like any other cafe. It served vegan food, which at the time she was doing so was appreciated. You could tell it had a musical bent to it - there were records for sale, and a big open space with a microphone on one end. But otherwise was nondescript.

But as we sat enjoying our coffee and talking, the owner of the cafe came out.

It was Billy Corgan, lead singer for the Smashing Pumpkins. My wife's favorite band growing up.

I had read about it in a magazine on an airplane a few months prior. And I added it to my "date night" list in my organizational system.

If you've followed me for any period of time you know how vital my organizational system is to my life, and how much I love lists.

My "date night" list might be one of my most important.

Ideas can come from anywhere. If you don't have a good system for capturing them, they disappear.

Spontaneous adventures are great. But let's be real - most of our lives are so busy, so routinized, that there is little room for spontaneous magic with any sort of regularity.

The next best thing is premeditated adventures. Architecting experiences on purpose.

Far from stripping the joy out of date night, keeping lists like this adds to it. I can create adventures and memories far easier because I have a place to capture my ideas.

Set a date goal

We're well into February, and new year resolutions are past us. But that doesn't mean you can't set a goal for the rest of the year.

Consider setting a target for dates. More than you've done in the past. But a number that is reasonable. While I would strongly argue to set a long term goal of a weekly date night, feel free to progress up slowly if that seems unrealistic.

Chat with your spouse about it. Say "I want us to go on a date every month between now and the rest of the year." Block it on the calendar, in advance. Get the sitter booked. Start keeping a list of ideas.

I don't think there's a better investment you can make.


Related Posts

Course: Helping 3s Become 2s - Going Down the Crypto Rabbit Hole

The ultimate introductory guide to crypto and decentralized finance.

Course: Helping 3s Become 2s - Going Down the Crypto Rabbit Hole

How to find the right gift, every single time

7 steps to becoming a more thoughtful gift giver.

How to find the right gift, every single time

The Career Flywheel: 4 Steps to Runaway Career Growth

Don’t build a career ladder. Create a flywheel that builds momentum to dramatically propel you forward. Here’s how.

The Career Flywheel: 4 Steps to Runaway Career Growth