When you beat around the bush with these things it almost always causes more stress on you than if you go for it. I think if you just suck it up and just ask her out, it is much better than sitting there and wondering. I liked this girl for six months and I never got the courage up to ask her out. I kept talking to her after classes and walking with her... that kind of thing. It was always on the tip of my tongue, but I could never jsut get it off. Then, she comes up to me and says; "Oh Shaun I have wonderful news!!! So and so and I are going out!" So in my head I am thinking "Oh great..." She has been going out with him for about 5 months now
Just go for it, man. It isn't worth it to not say anything it ends up coming back at you.
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I don't know, I think I am 70/40 on this issue. I always give it my 110%.