I realize that the proper way to say this is "I couldn't care less" because you are saying that you don't care at all, and it's supposed to be one of those English mistakes that everyone makes; however, sometimes when I say "I could care less" I actually mean "I could care less".
If you are trying to say that you don't care at all, I agree, saying "I could care less" makes no sense. But, in some situations I have noticed myself say this and then realized that saying "I could care less" is exactly what I meant to say. The reason being is that usually I'm saying that I do care a little but I'm only doing you/it/them a favor by caring as much as I do. As in, "Look, I don't care at all about this, but I am giving it a little concern or thought because I know it's important to you. But remember, if anything of higher priority ever came along and made me choose between this or that I'd probably drop this in a second."
So I'm saying, I care a little bit for your sake, but if it ever came down to it, I COULD care less.
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