I'm pretty good at taking portraits of my family and friends; I know who they are and what they "really" look like. But if I'm asked to make a portrait of someone I don't know so well, I'm often unhappy with the results.
I know some tricks for getting people to be comfortable and to drop the cheesy smile, and for getting serious expressions. But beyond that, a portrait is supposed to capture the personality or essence of a subject. How do I get more than just a technically fine "picture with a person in it" when I've only got a short time with that person?
I imagine that this is something serious working photographers come up against all the time. When it's Winston Churchill (or someone else famous), one might research beforehand, or have the luck (and chutzpah) to do that cigar-stealing trick, but what about just normal strangers that I want to photograph in a single short sitting?
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