Guys, how do you feel about "The Guessing Game"?

I hardly ever do this, and if I do, my guy will just say "no" if I ask him to guess anything. Now, I'm fine with that, but I know that would piss a lot of other girls off. I think one major reason girls are so indirect, if not because they are a peach, is because they are shy. If your girl still does this to you after she's warmed up to you, maybe it's just her personality. But I know that a lot of girls will do this to "test the waters" and gauge your reactions to see if they can further relate to you. It's a twisted way of getting to know more abut you, I guess. I honestly find that sort of thing more trouble then it's worth, but I've never been typical.