Hey, ever notice how a lot of hot chicks have low-cut shirts, with cleavage showing, and that always gets plenty of attention from the guys?
Well, what I do is walk down the street with my fly halfway unzipped, see, and that really drives 'em wild!
But anyway, Xavier, I’ve had plenty of situations like yours, and yes, I’ve always regretted it. Try not to let this possible opportunity slip away.
There are always the possibilities that she’ll reject you, or you’ll look like an idiot, or she has a boyfriend or whatever. The other possibility, that most people don’t forsee, is that she’s merely human–once you talk to her, she might very well turn out to be an uninteresting person. But you’ll never get to know any of that until you find out.
There are many different approaches. You can try something original and clever, or the direct approach of just telling her you’d like to get to know her better, or you can try to come up with some semi-legitimate reason to talk to her and take things from there.
The best tool for learning to do this is simple practice. I’m a naturally friendly guy; I talk to everyone I see wherever I go. You’ll find it much easier to strike up a conversation with an old lady at the supermarket, another guy shopping at the auto parts store, et cetera.
When you do talk to her…
You may be tempted to tell her that you notice her every time she walks by, or something like that. Be careful that when you say it, you don’t sound like you’re stalking her or something.
If you go for the semi-legitimate conversation route, make sure it’s something non-disagreeable. Offering to share your umbrella on a rainy day is a gesture anyone would appreciate. On the other hand, if you walk up with an unlit cigarette asking for a match, and she’s against smoking, you’re already off to a bad start.
If you can, try not to ask her out directly. Ever notice how a good salesman doesn’t sell you stuff, but rather, he “helps” you buy it yourself? Do the same. Try to get chatting for a while, to the point where it’s perfectly natural that you’ll be talking again; that’s much easier than having to ask tough questions.
And as others here have said, you can’t fear rejection, especially when you don’t know her. There is a chance you’ll be rejected, but you know what? Even then, there won’t be regret. You’ll never have to look back on your memory of her and have to say “I wonder what could have been if I’d only approaced that pretty girl?”