I was talking with a friend of mine when she told me that "pretty sure" means something like "more or less sure". I've always known that it meant "totally sure" and was astonished to find this out.
Thinking about it, I could not remember why or how I learned the wrong meaning and looking on the Internet I found more people that thought the same before being corrected.
Edit: I do know that there is a question answering the meaning of the expression. What I'm trying to find out with this one is the reason why some people like me learned the wrong meaning and was sure it was correct. Sorry if I wasn't clear enough.
What could be the origin of such misunderstanding?