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I've tried and every time I do I get really scared and nervous.
My friend has this same problem. maybe your just worried you wont say the right thing. just relax and act like its just one of your old friends, not a guy, just a girl thats really ugly[: just kidding. but seriously, maybe if you just loosen up, and dont worry and act like you've known him forever, all will be well. hope i could help! good luck with the guys.
errr!! just look at him in the eyes it that easy!!
people are silly