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Saying that they could care less when they mean they couldn't care less.
Like, of course anyone can care less than they currently do.
The way I handle this is to parse them differently. They mean the same thing, but “I couldn’t care less” is sincere and “I could care less” is sarcastic.
Sort of like, “I suppose it’s possible that I could care less about that” reduced to the phrase.
Because both phrases obviously communicate the same meaning, a lack of care, the issue for me isn’t in the understanding but in the parsing. So I had to come up with a way to parse it as sarcasm so it doesn’t bother me.
Like when someone says, “I’ll try and be there” my brain, mildly traumatized by really good English teachers in my youth, screams, “YOU’LL TRY TO BE THERE.” But lately I’ve been making an effort to interpret the “and <verb>” following “try” as an alternate form of the infinitive, since it’s so readily accepted and common in spoken English. We already construct other verbs that way anyway (eg. “I’ll go and do that”).
I…might have a touch of the ‘tism. It wouldn’t surprise me. 😅
I always thought of it as a semi-threat/dismissal. For example, "By your actions I see you don't really care about this serious problem." Then the response, "I could care less." Meaning, it's such a moot point to the person that they could indeed just not care at all about it if necessary.