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I prefer Sidney, and on a boy. It really irks me how many fantastic masculine names are being appropriated by the girls. (R.I.P. Ashley, in the US, at least.) Still, I knew an adorable little girl named Sydney which softened me up just a tiny bit, so you will not incur my complete wrath if you do use it. :)

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I'm not sure about the "friendly and caring" image, though. It's all a matter of opinion, really, but I would see a Sydney as being a little more vivacious and edgy, not in a bad way, of course.