It's kinda funny, but I have never considered myself to be pretty. That's not to say that I think I'm unattractive - any of you who actually know me know that's absolutely not true. It's just that pretty is not the way I would choose to describe myself.
Pretty is just a small step above cute, an adjective which I absolutely abhor. Both terms suggest a lack of sophistication. Pretty is pleasing in a simple way, kind of standard. To be pretty is to be attractive, but not in any special way.
Cute should be reserved for puppies, kittens, and shoes. If you want to get on my bad side, tell me I'm cute.
Much better adjectives to describe attractiveness:
I'm not saying that all of those apply to me, but I'm not saying they don't either. My point is that I'm certain there is more to my beauty than just prettiness. I'm not a traditional beauty, and that's part of the appeal.
Or maybe I'm giving semantics way too much weight. But, since we have the tools to be precise with our descriptions, why not take advantage of them? There's so much subtlety and art in language (less in English than some others, but it's still there) that most people simply ignore. It makes me sad. I urge everyone to really think about how you articulate your thoughts and utilize all the tools at your disposal.