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Dave: Girls should never be intimidated about asking a guy out. Sure, there is something to all that playing-hard-to-get stuff, but, hey, it’s 2015. Trust me, we know just how hard it is to approach someone for a date—or even to borrow milk money. So any guy worth his salt will sincerely appreciate the effort because he knows just how tough it is. 

A less forward way to take the initiative is by writing a note on your crushes FB wall when he does something cool like the winning run for his baseball team. That might be just the signal that shy boy is waiting for. Keep it subtle though—nothing that begins, “If you ever want to see your dog alive again…”

Bill: One of the most attractive things about girls is their aura of mystery. So if you want to ask that special guy out, do it kind of indirectly. Leave a note in his locker. Send him a photo of a ballpark or something with a fun, casual note on the back. We’re often most attracted to things that are hard to attain. Ask him out, but do it in a way that shows you’re pretty special.