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Originally Posted by guccilvr
The best thing you could do is next time just give him a real nonchalant response and go about your day. It'll bug the shit out of him.
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This I totally agree with. When you're reaction to someone like that is that you really couldn't care less, almost as though it's really nothing new to you, then you instantly take away something that they feel makes them unique and different. That will pretty much get to anyone with vague insecurity issues, and by the sound of it this dude has plenty.