Do confident guys ask out girls that intimidate them? Or do they wait for her to make the move?

Been talking to this guy for a while, we have crazy chemistry and an attraction that's obvious to everyone around us, but he will not ask me out! He jokes about kissing me, he tells everyone how pretty my hair is, etc; it's just always intense when we are together. I've been told by others that he seems to be really intimidated by me and that I may have to ask him out myself. I know that he has gone on random dates with other women and it didn't last or work out, so I know he's confident with them; but there's still this constant chemistry and attraction between us and he still hasn't done anything. Should I make the move? Or is he just not that interested?
Do confident guys ask out girls that intimidate them? Or do they wait for her to make the move?
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