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As a Southern lady, I can tell you there are several meanings to this Southern phrase. 1. If something terrible happens to you, I say it as a way to say "That really sucks! I feel sorry for you." I'll look at you with genuine sympathy. 2. If I look at you with a sardonic smile, I'm trying to call you an idiot without sounding rude. 3. If I look annoyed or mad, that means you've really crossed the line and you're not in good stead with me. It's my way of saying "Go fuck yourself!!!" when I'm in a situation where I can't just say that.
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