George Mason economist Bryan Caplan has some excellent advice on how to increase your "social intelligence." As a teenager and for years thereafter, I had many of the same problems as Bryan and partially overcame them in much the same way. As Bryan puts it, I "at least managed to claw my way up to mediocrity" in this important aspect of life. If you have similar shortcomings (and I suspect many intellectually oriented people do), his advice is well worth considering:
My social intelligence is a lot higher than it used to be. I still wouldn't say that I'm "good with people." But in my youth, I was truly inept. In junior high, I had one real friend, and many overt enemies. Since then, I've at least managed to claw my way up to mediocrity.
A lot of social intelligence is in details and practice. If I could travel back in time and spend five minutes advising myself, though, here are the principles I would try to teach myself.
1. Good conversation is an exchange. The most basic form of social ineptitude is to say what's on your mind, even though you have no reason to believe your listeners are interested. Even more cloddish: Saying what's on your mind, even though you know that your listeners are not interested.
In a useful conversation, in contrast, there is a double coincidence of wants. You have to be interested in what I have to say; I have to be interested in what you have to say....
2. Be friendly. It's not just good advice for libertarians; it's good advice for people. A strong presumption in favor of kindness and respect almost never hurts you, and often helps you. Note that I say "presumption." Don't "wait and see" if people deserve friendly treatment. Hand it out first, no questions asked. You will make friends (very good), avoid making enemies (good), and occasionally show undeserved kindness and respect (only mildly bad).
3. Keeping friends is more important than getting your way. You should think twice before asking anyone for help. If you still think it's a good idea, try to make your request easy to refuse. "How would you feel about..." is much better than "Please, please just do me this one favor!" In the short-run, of course, the pushy approach is often effective. But life is a repeated game, pushing leads to resentment, and your relationships are more valuable than almost any specific victory.
There is a complication, of course. Part of the reason why young intellectuals make these mistakes is that they often don't realize they are doing so. But another part is often the result of having a strong preference for expressing your own ideas and little interest in the things other people want to talk about - especially social chitchat and small talk. If you place a really high value on "hearing yourself talk" and a relatively low value on social popularity, it could be rational to reject Bryan's advice. But if your goal in expressing your ideas is to persuade other people that you are right (or at least worth taking seriously), following the above advice will still be useful. Thought it may be irrational to do so, people tend to discount your ideas if you act like a jerk and give them more credence if you seem friendly and personable. Even if you are the kind of deep thinker who doesn't care much about making friends, you should still make nice if you want to influence people.