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I think a big part of it is that through your description it sounds like you are wanting to smile for someone, or smile at someone because it would be a good thing to do. The people who smile at every stranger they see aren't doing it for those reasons. They're doing it because they're happy.
When I was younger, I was incredibly shy and had the same difficulties as you describe above. The problem went away when magically I wasn't uncomfortable in groups of strangers, and thereby happy. Because I was happy, I smiled at everyone and everything, really.
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"I'm typing on a computer of science, which is being sent by science wires to a little science server where you can access it. I'm not typing on a computer of philosophy or religion or whatever other thing you think can be used to understand the universe because they're a poor substitute in the role of understanding the universe which exists independent from ourselves." - Willravel
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