JoshuaZ comments on How to always have interesting conversations - Less Wrong
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Everyone can find somebody to practice small talk with. The benefit of conversation practice isn't contingent upon doing so in quick succession, but accumulation of conversation experience over time. You can increase your skills very rapidly even without access to the condensed conversational environment of fraternity/sorority recruitment. I don't even recommend participating in that if you can avoid it, since it's a very stressful experience. But it does make you really good at talking to people.
Go to a bar, people are usually there to talk. Interestingness varies considerably, of course. If you work, make small talk with your coworkers. If you're in school, say hello to the person sitting next to you. Make a habit of doing this wherever you go. That's the best way to practice.
I'm not sure this is perfect advice. For one thing, speaking as a person who enjoys conversation, it can often be deeply uncomfortable when a random stranger tries to start a conversation. I made accidental eye-contact with someone on the subway today and then had to have a conversation about the weather which interrupted mildly productive thoughts.
I agree that in the contexts of school and work this sort of thing might be acceptable. One has to think about the fact that the very worst that happens is that the person indicates they don't want to talk.
One thing I do use as a conversation starter is if someone is holding a book that I've read (in which case I'll comment) or a book I have not read (in which case I'll inquire about it).