Learn what "why does he look kind of familiar" means, when people say it, and how to use it naturally in English.

It means the speaker thinks they have seen the person before but cannot place him.
From Rosy Psycho, Episode 15
Someone sees a man who looks familiar and wonders where they know him from.
Use this when someone seems recognizable and you are trying to remember why. It is a natural everyday question and not rude.
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