A skilled liar and a skilled diplomat use almost identical cognitive machinery — and this should trouble us more than it does. The American pragmatist William James made a distinction that cuts right through this discomfort: he separated 'knowledge-about' from 'knowledge-of-acquaintance.' Knowledge-about is propositional — you can list facts, cite reasons, explain positions. Knowledge-of-acquaintance is direct contact with the thing itself: what it actually feels like from the inside. Most of what passes for empathy is knowledge-about. You understand someone's situation intellectually, you can describe their predicament accurately, and you still haven't touched them. The uncomfortable implication is that you can become extraordinarily articulate about another person's experience — fluent in their grief, precise about their pressures — and use that fluency entirely in service of your own agenda. What James's distinction demands is a harder question than 'do I understand this person?' It demands: am I in contact with them, or am I in contact with my model of them?

Think of someone you consider yourself close to — what do you actually know about how they experience ordinary Tuesday afternoons, as opposed to how you would experience their life?

Drawing from American Pragmatism / Philosophy of Mind — William James