Obviously the normal rules go out the window, because she is going to be much more easily freaked out from any kind of involuntary or surprise escalation. And I know how important communication is, but how can I ask her, "Hey, is it okay if I kiss you?" but still do it in an attractive, confident way?

Or... should I not go for necessarily confidence and just try to be sensitive when I ask?

...Or should I not ask, and try to let her make the moves?

It's a really stupid complicated situation, and I'm sure for most of you, you just wouldn't have a date with this kind of girl, but I'm trying to go for a relationship here, and any advice would be appreciated.