Ask YC: Best ways to become socially adept?

I've heard improv classes go a long way.

If you are a programmer and strongly left-brained (not always the same thing), I'd suggest tricking yourself into thinking you have a logical approach to interpersonal relationships and then going to social gatherings quickly before you over-analyze.

Step 1 - Read most of http://www.amazon.com/Nlp-21-Days-Harry-Alder/dp/0749920300/... - this is NOT a good scientific book, but it seems to be good at convincing you to step outside your comfort zone. Optionally, skip this step and do sit-ups and push-ups instead which will make you feel more confident and comes with a low price tag.

Step 2 - Practice on an opposite-gendered friend whom you have no romantic interest in. If such a person does not exist, skip this step.

Step 3 - Attend social events. These are easy to find: book groups, local music, free martial arts class. Talk to people with no intent to "hook up" or even make friends. And I don't mean "tell yourself you're not interested so you'll have a better shot." I mean just talk to them. Ask something about the event. Ask what time it is (don't wear a watch or carry a cell phone). You don't have to have a conversation. You just have to communicate. Likewise, anytime you eat at a restaurant require yourself to compliment at least one employee while you are there.

Step 4 - Rinse and repeat until you realize you're enjoying all of the events and you talk to random people with more ease. As some of the comments have said, you can have great conversations talking about silly stuff that you don't care about if you enjoy the process of facilitating a good conversation.

Tips:

Don't drink unless you know your limit and have a pre-established track record for staying under your limit. Otherwise, you will end up undoing all confidence building when you get hammered and embarrass yourself once.

Avoid drunk people. They are a pain in the ass and will spill things on you. Both of these tips are easy to stick to if you don't go where people are drinking.

I second the "meet nerds in other contexts" cause. I played some theatre at my university and besides becoming friends with some very cool girls and traveling the world, I strangely enough met a lot of other cs guys there. And those are the ones who are indeed more interesting as they have a life beyond their computer, travel the world and have a broader context in life.

Start by pretending to be genuinely interested in other people's lives, and their problems. If you pretend this for long enough, you'll find yourself actually feeling that way. And then you'll enjoy being around people, because they'll enjoy being around you.

Read "How to Make Friends and Influence People".

Oh you said besides that...well practice what it preaches. Us folk (geeks/nerds/hackers) tend to like to show how much we know about a subject. Some old dude is talking about how his phone can now surf the web...what do you say? Act a bit surprised and ask him a bit more about the subject. Let HIM show what he knows, and get that little feeling of self-importance. Don't squash it by saying you could ssh in to work on your phone 5 years ago and that his phone is garbage.

Also practice, and have someone judge your performance. There are a zillion things to improve on here, it is a difficult art to master. I would also say it is a long road that I wouldn't be satisfied in saying I know well until I can sit in a room with anyone at anytime and befriend them and/or convince them they want to reconnect with me again shortly.

One last thing, I have the most difficulty talking to people I know well and respect. For example, I was recently discussing business and my goals with an old co-worker I really respected, and I found myself a bit flustered. Anyone else experienced this and/or have any suggestions?