How to Get Away With Dating While Married

How to Get Away With Dating While Married

When you get married, as I have gone and done, you assume you are done with dating for good. And thank dog, right? Who needs it. Dating is expensive, making reservations is annoying, it’s difficult to find new activities all the time, conversation can be awkward and’s a chore.

I never enjoyed dating. I liked meeting new people … sometimes, but dating was almost never fun. Maybe that’s just me. I hated retelling my story over and over to women who never seemed that interested. I found myself in too many month long nothing relationships that neither party really cared about. It kind of sucked.

Then I met this lady.

She likes soup and tells hilarious jokes.

On our first date, my wife and I went to a nice restaurant together. We wore decent clothes, had a delicious meal with drinks, appies and dessert, and got to know each other over the course of an hour or so.

I was pretty sure it was just another date and wouldn’t really lead anywhere, but we ended up married a few years later.

Who knew!?

So, it turns out, my wife (to respect her anonymity, let’s call her…Butt Toast) likes to go on dates. Butt Toast likes appetizers, deserts and fancy conversations. She likes getting dressed up and going out sometimes. This behaviour is strange and confusing to me. Doesn’t she know that we have food and chairs at home? And we talk all the time.

"What time will you be home?"
"Do we need eggs?"
"Don't write about me on your blog"

All the time

But, because I want to be a good husband to Butt Toast, I take her on dates.

Every month we plan a date. Sometimes I plan it in secret, sometimes we plan it together, but we’ve both come to enjoy the “what do you want to do for our _______ date?” conversation. Last month we went to a top restaurant, this month another, but we’ve done all sorts of fun stuff on our monthly dates. It’s always something to look forward to, it gives Butt Toast an opportunity to wear something other than her Winnie the Pooh vest (she has literally been wearing this thing for over 20 years) and I’m finding that when you go on a date with someone who you feel something other than indifference towards, you actually have fun!

Monthly Wife Dates.

You should try it, right Kanye?



Want a perfect relationship? Be perfect.

Want a perfect relationship? Be perfect.

For the rest of us, we’ll have to put in a little effort.

No relationship is perfect. They can work long term, for sure, but they aren’t unsinkable. This, however, is not going to be the “relationships take work” blog post that you’ve read too many times. This is just the story of how I started trying in a relationship.

I have no intention to preach, and I’m not going to bless your relationship with any new sort of wisdom, tricks or tips.

In this inaugural “relationships” post, I’ll share some of my relationship history and what I’ve learned over the years. The theme is not trying vs trying. In the end, trying wins out.

Pictured above you’ll see my wife outside of a train station in Taiwan. She wasn’t my wife at the time, but she was sure going to be. I knew it then. I not only loved her, I liked her too. Still do. I feel extremely lucky that she tolerates me, let alone seems to like me back.

Girls didn’t always like me back. But, it makes sense, I never really tried to be likeable.

My first real girlfriend sat beside me in grade 11 math. She was a nice girl. We kissed at a party and, as it happens in high school, we were thus boyfriend and girlfriend from then on. In this relationship my only goal was to maintain. I had a girlfriend! My friends didn’t, but I did. This made me a cool kid. I kept it up as long as she would tolerate me, which wasn’t long. When we went to different universities, we had an amicable breakup. To be honest, I don’t think she was trying too hard with me either. I hear she’s married to a lovely lady now.

My second real relationship was a five year long disaster than ended with me in a different city on the other side of the country, 60 pounds overweight, and reading books on how to survive depression. More on that later. The short story is that neither of us tried to make the other happy. Maybe the opposite.

Because it’s just who I was, I jumped into another disaster almost immediately. I thought I really liked her, but were in our mid 20s, full of ourselves, and didn’t really get along. This one ended after two years of living together when I came home from work with a sore back, opened my email to find her still logged in, and read about how she’d been cheating on me with her best friend, David. I never liked David. David was awful. Probably still is.

And then I was single for a couple of years. That was fun, sort of. Sometimes, anyway.

And then I saw my wife at a charity event. I don’t think I’ve ever told her this, but I genuinely had one of those slow motion, jaw open, romantic comedy moments when I first saw her walk though the double doors and into the ballroom. Wow. She asked me out a week later, and now five years later we are married.

But that took work. A lot of work. More work than I had ever put into a relationship before. I had to do things I wasn’t used to doing. Things like listening, cleaning, changing behaviour when necessary, apologizing when I was wrong, make time to be together, plan things for us to do together, take an interest in someone else’s interests, and be nice.

With all my other relationships, I never really tried. I just figured I’ll do me and if someone didn’t like it, then it was them who was missing out. I had a lot of break ups that definitely weren’t my fault as a result of this attitude.

So, when I met a girl who I really, genuinely wanted to be with. I tried something new –  I tried. 

I wasn’t great at it at first, but I learned. Really, I’m still learning to try, but trying is worth it. It helps that she tries too. We both do, and that’s why trying works.  The trying inspires trying which inspires trying. We both work hard, even when we’re not at our best, to try to be good to each other. It’s not always easy, but it works.

In the future, I’ll try to get into specifics.

For now, how does this fit into the Year Long U-Turn model? Because in 2016, I’m going to try harder, like this, and see what comes of it.