Go alone
Fundamentally, socialization is something you have to learn by trial and error. Some people learn early. Some people learn late. It's great that you want to learn now.
You strongly desire to have someone teach you how to socialize. I used to feel that way too, but I realized lately that this is actually part of the problem. Firstly, it's unlikely you'll find anyone who will do that, so any opportunity you have to socialize, you'll just pass it up by saying, "Well, I would go if I had someone to go with..." Secondly, if you do find someone, it's likely that *they* won't want to socialize with anyone but you. I can't tell you how many times I've been with someone and said, "Hey, let's go over and talk to that group of people," and the person said, "No, you can do that, but I'm going to sit here and nurse my beer." Thirdly, I suspect you would socialize much better with someone else around. It's not that you can't socialize; it's that you can't do it alone and need some safety around you. Safety is cozy, but it's the problem. You have to get outside your comfort zone and learn to thrive in the limbo of the unknown.
Here is what I suggest you do. Firstly, come up with 5-10 topics that are of interest to you... something you are knowledgeable and passionate about. Then come up with a story or anecdote for each one. Then figure out how to invite the other person into the conversation. For example, you like the history of trains. Now, most people don't like the history of trains, but that doesn't matter. You could say, "So I was watching this documentary last night on the American railroad, and did you know that we used to have hundreds of different time zones so the rails would always run on time? When was the last time you crossed a time zone? Can you imagine crossing not one but seven?" That opens up the possibility for them to tell you about their trip to Chicago or whatever. Reuse these. Over and over again.
Secondly, you gotta go where the people are. You should go alone. You should approach anyone you want to approach... man, woman, child. Just do it. Have your canned lines. As others have noted, go where people have a common interest. But also go where you have little to no interest at all but maybe some curiosity. Never been to a drum circle? Sports bar? Gaelic football game? Go. You may like it.
Best of luck.
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