I thank God every day in my Shacharit prayers that I didn’t have to go on too many dates in my life. I estimate I went on less than 15 first dates, and I can’t say I actually enjoyed any of them. For some reason, God saw it fit to allow me to cross paths with my wife when I was on the verge of a nervous breakdown near Manhattan’s infamous Upper West Side meat market, one of the scariest neighborhoods for someone like myself for whom being social sucks up a lot of energy.
I never went on a second date with anyone other than my first girlfriend and my wife. Why? Two reasons. Either they didn’t want go out with me again, or I had one of those sinking feelings immediately when I saw the girl and she subconsciously detected it. Women can do that, and negative feelings are very unattractive.
The sinking feeling—that thing is a big misanthropic sin with roots in selfishness and there’s no good reason for it. I only realized this after my dating experiences were over, because after my Jewish dating was done, I was able to sit down with any woman and just talk to her like a human being. I was able to do that because I had no expectations.
I just liked people a lot more, and that made everything more fun.
It’s like the girls always complain, “Why are the good guys always taken?” It’s because when they’re taken, they don’t expect anything from you.
This obviously gives rise to a chicken and the egg issue. If you have to be taken to enjoy dating, how do you enjoy Jewish dating in the first place when you’re not taken? There are generally two ways of accomplishing this. A directed way, and a lucky way, neither of which will work without a basic level of health of mind and spirit.
The directed way involves serious mental exercise. Like going to the gym, except for your brain. The way you exercise your brain is you sit down comfortably, close your eyes, don’t move, and concentrate on nothing but your breath. Focus your mind on only one thing and live completely in the present. You’ll find that your brain will not want to stay anywhere for longer than 10 seconds and it will drift off to either the past or the future immediately. Gently bring it back to your breath.
Do this for 20 minutes in the morning and the evening every day for a month. If you can do this, your mind will be strong enough to focus on the present moment for the whole 20 minutes.
Once you get to that point, you will get rid of that dirty thing called expectation. Expectation is what causes that sinking feeling, and it’s the chief cause of unattractiveness. It’s your brain refusing to stay in the present and wandering into the future. And when the present doesn’t match the future, you lose confidence and you freak out. Without expectations, you’ll find it a lot easier to simply enjoy people’s company for what they give you in the present without worrying about what they can give you in the future.
That’s the way a “taken guy” thinks, at least a happy one. He’s not worried about what the girl can give him in the future. He’s only concerned with the present, because he already has a girl for the future. That’s why he’s more attractive.
To sum it up, the directed way of accomplishing enjoying dating is to exercise your mind. Going into a date with a wandering brain will get you nowhere you want to be. As a matter of fact, going into anything with a wandering brain is a bad idea.
The lucky way is to somehow achieve a basic level of mental calm, have it match up at the right moment at the right time and the right circumstances, and build from there. This is what happens to most people, but there’s no reason to rely on luck when you can prepare in advance.
It’s much more important to strengthen your mind than to brush your hair before a date. Primarily, Jewish dating is about dating a mind. That’s the biggest erogenous zone for both sexes. It has nothing at all to do with how you look. It has to do with how you think.