I met a girl in my last year of high school. I really started to like her, but wasn't sure how she felt about me. Things dragged on with little interaction between us until finally one of MY friends told one of HER friends that I was interested in her.
(That girl is my wife now.)
It's hard to put yourself out there when you're not sure how receptive the other person will be. And these days with everything so "politically correct" it's extra scary.
If you feel comfortable with it, maybe you can be gently encouraging to help give him the signals that he's looking for. It's a give and take from both sides, but it helps the guy to have even some idea that the girl is receptive to him.
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