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I don't tend to initiate conversations unless I know the person well. I don't mind replying to someone (strangers included) because; since they started the conversation, they already demonstrated a desire to speak with me in some way.

So I suppose I don't start conversations due to a fear of rejection, and a potential inconvenience from an awkward situation. Besides, I don't like to think about me being "that annoying guy who doesn't shut up," or something like that.

As for what I do about it, nothing really. I suppose I just go with my natural tendencies(?) Forcing myself to be assertive and starting a conversation doesn't feel right. Plus, it hardly ever goes as smoothly as I had hoped...


Oh and about this:

This is specifically bad when I'm interested in a girl I never talked to; I get really scared of trying to talk to her. Usually, I don't have any problems talking to girls I like, if the ice was already broken, but I just can't break it on my own.
I relate to it and then some, I would imagine quite a lot of people do as well. But, at least for me, that is a whole different can o' worms.
 
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