"I'm fine".

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I don't understand how many times I've told people "I'm fine" when I'm really breaking inside.

Of course, most people ask how you're doing out of courtesy. In honest truth, they couldn't really care less about all of your little disappointments and problems. If there were something bigger that was wrong, then they might feign interest, but when people ask you how you are doing, they're not really looking for a story. They're basically saying hello.

because we are so used to people not caring about how we are actually doing, we're afraid that even our closest friends would prefer not hearing about our problems. Even worse is that some of our friends don't want to hear about our problems.

I just wish, for once, that I could tell someone "I'm fine" and they'd reply with "don't lie"

It'd be good to know somebody actually cared about the answer, and weren't just asking it out of habit.

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