In places where I'm comfortable and know the situation, I can be rather outgoing. (ie. at work, at home, so on) Also when it is something that is someone's job to do (ie. asking for the check, etc.) I have no issues. With one or two friends, it is all good.
If I am in a different area, have more than one person I don't know near me (just one person in non-face-to-face conversation), it is asking for something that is above and beyond the person's normal work, etc. I am increadibly shy.
I believe it is partly because I feel safe in comfortable areas, people I know already know I'm weird (and actually like that fact, go figure), and if I am to ask anyone for something that has to do with thier job... well, it is something they are supposed to be doing. Less chance of rejection perhaps?
I am getting better, but it is something I have to keep working at. I don't think I'll ever be to the point where I can go up to a random person (in a place other than home or work, if you are in either of those places, you will learn of my strangeness anyways, may as well throw it on you right away) and start up a conversation. I am hoping to get to the point where I can go up to extended family or friends of friends this way however. *Crosses fingers*
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Humm, guess I should put something witty here, huh?