Once I went up to a beauty I had a crush on and asked her to autograph one of the pictures I had taken of her through the window of her house and she freaked!! What the hell? I thought she would be flattered.
And don't ever crawl through her bedroom late at night and say "you know I have had my eye on you for a while and think your cute. Wanna go out sometime?"
That actually used to work in high school. Girls would laugh their ass off if you said it the right way and then play it off like you're totally kidding.