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1.Compliment him. The rarer the compliment the better. Pick a feature he seems to be, or should be, proud of. If he pays careful attention to his hair then compliment that. If you know him well, then compliment a strong, positive personality trait. Say something about how confident, kind, or humorous, etc he is.
2.Touch him. Just reading that probably made you blush, right? Imagine what would happen if you were to touch his arm, especially if he works out. He'll appreciate the physical attention. Pinch his cheek, he won't be able to help blushing and there's something incessantly cute about doing that.
3.Playfully tease him. Pretend that his hair is a mess as an excuse to stroke his hair out of his eyes. Use an adjective like sweet, adorable, or lovable to describe him. Say the color of his shirt is so last year and then follow it up with "just kidding!" and how you actually like it after a pause.
4.Whisper to him. This works best if you whisper something special that you two share like an inside joke or a secret interest that you can only talk about together. If you've just met tell him an ear-catching fact. Leaning in and whispering is sure to make him blush if he's interested in you.
5.Smile and wink at him. It may be a cliché, but it will probably make him blush. It doesn't matter whether you know him or not. Wear lipstick, mascara, eyeshadow, or even fake eyelashes for a more dramatic effect. You want him to notice that you winked at him, it helps if he's the one who looked your way first. Don't break eye contact immediately!
As usual this does not work 100%
Taken from: http://www.wikihow.com/Make-a-Boy-Blush
