Keyslost is right, the match is less likely to happen naturally, that's why you need to force it. You remind me of a girl in my class. She has a personality close to yours, an even if she wasn't a ten, I was obsessed by her, but kept my mouth shut for months. It was her who had to say the first words, and it was after thar I finally could speak freely to her.
Well, to sum up, one of the 2 has to make the tremendous effort of saying the first words, even if they are meaningless, and don't expect the antisocial guy in front of you to do it just because he's a man.