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First, become friends with him, spending time hanging out for instance. Make it obvious that you like him and ask how he feels about the two of you together. If he is comfortable with it, ask him to go out and do something fun, such as going to the mall. When you feel really comfortable with him and he feels the same, then ask him on a "real" date. If he is already your boyfriend, just ask him if he'd like to go to a movie, or whatever you like doing together, sometime. You'd be surprised at how easy that is. And if he rejects you be silent for an while, but try to be close friends with him. He might just ask you out!

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