I do not understand exactly how this is relevant, why would a woman care about such things?
... unless you're unsure about when to feel creeped out or not ... which would indicate other issues ...
anyways, I digress, and perhaps say too much.
So, on to the Q:
I would say, what creeps me out is more of who is doing the asking, not how they are asking it.
In other words, if they look like someone I might be interested in, cool. If they make me think
As if ... 
... then i'm kinda creeped.
sometimes it's black and white, but there are grey areas too. And I know I can't expect them to figure out all the grey areas. ..
/me shrugs