Dating Is A Game, So Start Playing To Win


After a particularly disappointing end to a budding relationship, my best friend said to me, “This is a tough one. I guess as we get older, these guys play more complicated games.” Paradoxically, everything seems to get more complicated as we age and mature. One would think that the older we get, the greater our ability would be to discuss feelings and intentions without playing games with each other’s minds and, more importantly, each other’s hearts. The silver lining in all of this is that with the levels becoming increasingly difficult, it makes winning the game at the end that much sweeter.

I know that many of you would disagree with calling dating a “game.” Whether you see this as a good or bad thing, it’s the hard truth, and the sooner you accept it the sooner you can start playing to win. But here’s the thing: winning is subjective. To me, (and I’m oversimplifying here), winning will be when I find someone who wants to be my partner and my confidant through thick and thin. To the 22-year-old college graduate, winning might be sleeping with as many women as possible during his first year in a new city. To the 39-year-old divorcee, winning might be going on a first date and feeling confident in herself and her ability to put herself out there again. You get the picture.

The heartbreaks start when two people think they’re playing the same game because they do what we all do – assume. And at some point, they come to find out they were playing different games all along. It’s like playing Apples to Apples with someone who’s playing Cards Against Humanity. You might be able to play for a little while without noticing something is up, but eventually someone is going to say, “Wait, hang on a second…”

Many of us are in limbo right now, stuck on the same level wondering when the hell we’re going to beat it. We’re trying. We’re using all the tricks we know. We use the cheat codes our friend used only to find out it doesn’t work for us. We might take a break for a while so we can come back with fresh eyes and a new strategy. But in the meantime, how can we avoid the agonizing mental replays during which we second-guess ourselves and the choices that left us stuck?

We start being upfront and honest with each other, that’s how. If you want to play baseball, don’t ask the person who wants to play football if they want to practice together. “But how do I know if s/he doesn’t want to play baseball?” you wonder. You go on a few dates, you use your deductive reasoning skills, and if you still aren’t 100% sure, you ask; that’s how. Stop beating around the bush hoping the other person will read your mind or assuming they want the same things. If things don’t work out after a month because you found out you were playing different games, how can you have the nerve to be disappointed if you didn’t bother asking if they wanted to play the same game in the first place?

Look, if you’re only trying to play a quick game of tic-tac-toe, don’t engage with the person who wants to play Monopoly, and vice versa. That’s just irresponsible, foul play. Sometimes intentions are clear; other times they’re not. If you’re not sure, don’t be afraid to ask. It’s better to find out sooner rather than later. Wouldn’t you rather start playing with someone who wants to play the same game as you instead of wasting your time trying to convince the soccer player that football is better?

Sometimes people make mistakes, and they thought they wanted to play Apples to Apples but decided they didn’t really like it as much as they thought they would, so they try Cards Against Humanity instead. That’s ok. We’re only human, after all. But the sooner you figure it out and let your teammate(s) know, the better. That way, they can find someone else to replace you without causing too much disruption to their own game.

Single people of the world: if you’re tired of games, you’re not playing with the right people. Games are supposed to be fun, remember? If you’re not playing with the right people, it’s because you haven’t established what the game is and what the rules are. Once you do that, you’ll start playing with the right people and you’ll get better and better. Eventually, you’ll win. But what you win and how you win is entirely up to you.


I’m not suggesting that by being clear with each other we can completely eliminate broken hearts. (Adele and Taylor Swift would both be out of a job if there was no more heartbreak, and we can’t let that happen.) Heartbreak is a natural part of life, and we often learn, grow, and become wiser as a result. What I am suggesting is that it might be possible to stop wasting the precious time we’ve been given by not playing games we’re not interested in playing in the first place.