I'd like to think that not only would Riddler's riddles be complex, but I'd also like to think he would have an intricate knowledge of many things, history, science, mathematics etc. On top of that, I'd kinda like to see him use famous quotes a lot in his speech, or some sort of odd idiosyncrasy.
So is it a riddle from the Riddler or did you think of it? Was it in a comic book?
Anyway, like i said, its too vague. It could be anything. There are thousands of things we want to win and never lose. It could be money, it could be a trailer full of hookers, it could be a Ferrari, it could be Angelina Jolie.
Oh please no more riddle this or that.