Pool Shark, I think you should just go for it. You've waited long enough and I'd say if she refuses this time, it's time to move on. By the way, you are absolutely not a sissy. There is nothing wrong with being observant and careful with relationships. I think you treat them as though they are precious and that's the way it should be. I think you maybe should give her a little time just to see what happens though. I would also say that you don't necessarily have to ask her out on a date, just find ways to be around her more and perhaps you'll get some more clues as to whether she likes you enough to bother asking her out for real. If you're super brave you could just ask her to tell you how she feels about you. Be honest and ask her to be honest with you.