I almost pity you but not quite but kind of. There must be a word for this, it's such a common experience.→[More:]

Alice has some trait that Bob considers unfortunate, but Alice does not.

Bob tries to express this feeling. It'd be easy if Alice shared his opinion; that would be pity. And if he believes she does share his opinion, that's what he'll express. "I'm sorry you're X". Pity.

Instead, in order to express his feeling about the matter, he must first get Alice to understand his own problems with the trait in question, which he does not have.

This is often quite awkward. "I've got this problem with your problem... I mean, not that there's anything wrong with it... I mean, it's not your fault..."

Bob knows it's wrong to pity in this situation, but it would also be bad to keep his mouth shut, supposing that Bob's assessment is the correct one. Suppose Alice is depressed, for instance. Depressed people sometimes consider their depression to be an appropriate emotional response to their situation, and they might even be right about that, but Bob contends that she needs to get therapy and medication anyhow.

It's a little like an intervention, maybe? But that's got a specific meaning, for when you stop a person from doing something in order to save them. Or does it? I don't know.