What I Learned From a Year of Intense Dating

In the year before I met the woman who is now my wife, I was dating with purpose. I didn’t necessarily aim to find a wife, but I was pretty intentional about what I was doing. And since I ended up finding an amazing woman and marrying her, I figured I’d share what I learned from it to help men and women looking for something similar.

The biggest mistake I made by far was traveling so much. I wouldn’t do it any differently, but huge gaps between the first few dates torpedoed a lot of relationships that may have otherwise worked. In fact, if it weren’t for my friend Todd pushing me to fly to visit, I probably wouldn’t be married. (“You never like a girl this much. You are an idiot if you don’t see her before your next trip”)

Despite your best efforts, a lot of it will come down to random chance. My wife told me that she only swiped right on me because I mentioned cruises in my profile and she figured we’d have something to talk about since she liked cruising too. There was another girl I was dating earlier with whom it may have worked out if her ex-boyfriend didn’t show up in her life between our first few dates. You just never know.

That said, the key is just maximizing surface area. Figure out what it is you want and spend as much time as possible with potential partners. That also means spending as little time as possible with those who don’t fit. One thing I think I did really well was stop seeing girls once incompatibilities surfaced, even if it was going really well.

It’s important to be who you are on the first date. I see a lot of friends run into trouble when they put on a little bit of a show on the first few dates. I never do that, because I want accurate advertising. So I show up in my only outfit for every date, go drink tea, and try to tell them early about anything that might disqualify me. If you do this, you start a relationship with trust and don’t run into trouble later.

Especially in large cities, I see people paralyzed by choice, always trying to find someone better. But if you keep switching checkout lanes in the grocery store, you never make it out. My strategy was always to look for people who match my criteria, and when I find one I focus on her and act as if she’s going to be the one. Not in a creepy needy way, but basically not allowing myself to sabotage the relationship in search of a mythical “perfect” person.

I was really fortunate to find someone who had a very similar approach. We never talked about marriage or anything like that early on, but both had the philosophy that if we are dating we will put our best effort forward to make it a great relationship.

If I were to boil my philosophy down, I’d say it’s to get out there and meet as many people as possible, but to know what you’re looking for and filter hard for it. Once you find it, give it your best shot, because finding someone you’re really compatible with is hard!


Photo is from a show called Fuerza Bruta that I saw in Vegas. A good portion of it takes place with the cast members on a clear plastic stage a few inches above your head. Really cool!





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