Most Helpful Girl
I think flirting/hinting at first can be good, because flirting is fun and exciting. However, because of this flirting she may be expecting something from it (aka you asking her out), so try not doing it for an overly long time where she begins to rethink your intentions, as it may turn her off (like, basically she might start thinking that's just how you are and how you talk). Flirting/Hinting helps her know how you feel (at least a bit) and so if she feels the same, that puts her at ease. But don't make it a prolonged waiting game for her, because it may turn around negatively for you. However, every girl is different, and she may prefer it drawn out or instantly. If you don't know what/when to do it, just do it (: Better getting straight to the point than possibly losing her interest. The flirting can come after asking her out too!
Most Helpful Guy
Hints, I am not scared of asking out, I have done it many times, but I got tired of women that as soon as they know I am interested begin to play hard to get. Now I prefer women to make the first move, then it will just be a cooperation ;)
I have to say that this way the probability of finding a sane woman are much higher ;p