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AnnaSalamon comments on Use curiosity - Less Wrong
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My experience has been similar, and I'll also add on a related note that probably one big reason why I'm not better at casual conversation is that if I'm not genuinely curious about the answer to a question I'm asking, I often won't have anything interesting to say as a followup to whatever answer I get (e.g. maybe I'll ask "So, where are you from?" or "What school do you go to?", and they'll answer, and then I'll say, "...Ah, um, okay" and not have anything else to say). It seems to me that a lot of advice on conversation (of the type prepared for people with Asperger's syndrome, or social anxiety, or general awkwardness) teaches mostly superficial aspects of conversation, and I suspect that there's a deeper art to it that can't be conveyed so easily. Probably the best way to develop such a sense is to be the sort of person who is naturally actually curious about other people, but for those of us to whom social curiosity doesn't come so naturally, learning to fake it well probably requires a much deeper understanding than can be attained by memorizing standard small-talk questions and such. I expect it's possible to learn to successfully simulate social curiosity, but not if one only understands it at that superficial level.
Rather than simulating social curiosity, have you considered trying to develop such curiosity? For example, you might right now pick a social situation that's coming up in the next few days, and set a five minute timer, and, during the next five minutes, write down as many questions as you can about one of the people who will be there. ("How is X's job going? Why does he tell those stories -- is it because he feels good about himself when people laugh? Because he feels awkward and doesn't know what else to say? Simple habit? ....")
Good advice.
Definitely should be carefully applied by those listed in the previous comment... after all, you don't want to go to the complete opposite and turn into an obsessive, grilling another person about their private life.
I tend to find people don't like that any more than no interest at all. :)
I've been able to turn non-social curiosity into good social interaction. Dale Carnegie says that if you want to be a good conversationalist...if you want people to like you... you need to talk about what the other person wants to talk about. And often the other person wants to talk about themselves, if only for a second. But, what happens if 2 Dale Carnegie followers talk? "Enough about me, lets talk about you". "No no, enough about me, lets talk about you."
I find a better application is, ask a question, or 2, and then rather than asking more questions, make a comment. Doesn't have to be perfect. More knowledge (from basic-research-curiousity) gives you more comments you can make. What little thing do you know about what the other person just said? About fishing, or the university of x, or the story they just told. People don't want to answer questions, they want to relate. "How's the job going?" "Oh yeah I know what you mean...I had a boss who used to do the same thing."
Obviously that can get too banal, which is why the basic-research-curiousity pays off: you can elevate the "we relate" by having something more to say, about things.