Ask YC: Best ways to become socially adept?

A few months ago I went down the same road that you did because of my frustrations with social interactions. I read "How to make friends...", tried to talk to people on the street, tried social lubricants like alcohol and caffeine. To my dismay, nothing seemed to work or stick. Then I read the book "The Game" and started getting into the "pick up" scene. While I felt (and still do) uncomfortable with the sometimes negative views of women and social interactions, I have to say that many of the "whys" and "hows" that they teach have helped me a great deal. The one that has helped me the most is http://www.pickuppodcast.com.

Well have you read "How to Make Friends and Influence People"?

If you haven't, the advice in it sums up to: be honest, respect others, respect yourself. That's really all there is to it.

The important thing about how to make more friends is to know how to BE a friend. Think about what you can offer other people, think about how to make the law of comparative advantage work for you.

I also highly recommend Eckhart Tolle's "A New Earth" .. which will not directly talk about how to make friends, but will dig into the root causes of why you have issues with making friends.

Also I would say, one thing that helped me a lot, is I have recently been watching the latest season of "Beauty and the Geek." observe closely the character of "Joe," and instead of laughing at him or thinking how much better you are than him, think about how you are, how all of us are, so very much like him and so very much unwilling to admit it.

I couldn't agree more. During Y Combinator, there were two guys sitting behind me. They said something along the lines of "Not to be sterotypical but I am suspicious of any girls here. They're probably just project managers and not really hackers."

Not a very "social" tactical move to do when there were about two girls around the area who heard his comment and some hackers wonder why girls don't talk to them.

But just observing isn't enough; it can be tempting to use observing as an excuse not to practice and talk.

I agree with jdavid - books on gender-related issues can be helpful. [The Game] is hysterical. Read the ones for guys and girls. Some others:

[How to Succeed with Women] - Sounds cheesy, but goes over the basics that "geeks" often miss, including dressing appropriately, grooming, and polite conversation.

[He's Just Not That Into You] - Manual for women on how to tell if a guy doesn't care about them. Useful for learning about behaviors to avoid and their underlying reasons.

[Self-Made Man: One Woman's Journey into Manhood and Back] - Can't recommend this one enough. Norah Vincent lived for a year as a man, and reports back on the challenges and successes she had. Invaluable for understanding both men and women.