Recently, a friend of mine tried to play matchmaker and hook up one of his close college friends with a casual acquaintance of ours. He arranged a time and place for them to meet one another, during a large social gathering that we used to have once a week.

I thought there was a good chance it was going to work out, but my friend did make a critical error: he told both of them what he was doing. Before the meeting, he went to each of them and said, "I have a friend I'd really like to hook you up with. I think you'd be perfect for them."

You probably know how this played out. When my friend finally got both of them into the same room, they never said one word to each other. My friend the matchmaker pointed them out to one another from across the room, but neither of them ever bothered to approach the other. Later, each of the would-be couple said they weren't interested.

Why didn't this work? I think it's because of expectation. When your friends set you up with someone for the express purpose of initiating some kind of romantic relationship, the whole thing has a very difficult time getting off the ground because the interaction between each party is tainted by this thought. From the get-go, each person sizes up the other one's physical attributes. From there, they start scrutinizing every little thing the other person says, all the while asking themselves: "Could I ever actually date this person?"

The problem is that my friend the matchmaker engaged the rational mind of the suitor and suitorette. Most successful relationships I know of didn't start because the two people decided to start actively seeking a romantic partner. They just happened. Two people were thrown into circumstances that made them get to know one another and a relationship happened to develop between them, instead of forcing circumstances to generate the relationship.

If you're going to play matchmaker, start with the situations that bring people together. The people will work it out for themselves.