Guy talk and it's a girl thing

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How far are you willing to go when it comes to getting the girl's attention? And how do we know when you're actually exerting much effort? I mean, girls and guys encounter some relative problems but they react to it quite differently. All I know is that we both don't want someone who associate meanings to plain kindness. Unfortunately, this is where problems arise. Because the tendency is that it's never easy to deal with the thin line that separates kindness from the other thing, if you know what I mean, especially if you're never really buddies. Since we're not, I am doomed. :) He's never really the flirty(wrong word, i guess) kind. And then all of a sudden, he began acting like a man. Okay, he's always been a gentleman but he's doing it a little bit too much lately. The thing is, I didn't respond to them. Was that bad? I usually smile at him and you know the usual thing and he's like that too but during that time, I was kind of taken aback because I didn't know how to respond to his actions all of a sudden. I seriously didn't mean any harm. Again, is that bad? :) Bear with me.