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The key to portrait shooting (for me anyway) is to shoot less and talk more.
I should consider myself lucky for growing up and now working in New York City, the friendliness capital of the world.
It is here that I honed my ability to talk to people. I am curious by nature and a story gatherer and storyteller by vocation (and passion.) So talking and listening to people is a job requirement of sorts. And I don't intimidate or scare easily.

As a photographer constantly honing my portrait taking ability, I find that the more I talk to people in advance the more connected and invested (fascinated, too) I become in my subject (and vice versa.)
So my suggestion to anyone wanting to take better portraits is this: start with a conversation. Camera at your side. Then after a while; and by a while, I mean a while (...sometimes I'll chat for 10 to 15 minutes before reaching for my camera) ask if they mind if you take a picture or two. Then continue the conversation while shooting. The connection you've hopefully already established will make the shooting that much more comfortable and give you something to continue talking about should they get self conscious or feel awkward. Simply ask them to "tell you more about __________"

And remember to share your experience. With them (offer to email a pic) and with us. That's what this here community is all about...the sharing and support to try new and different things.

Now for gawd's sake, stop reading and go take a picture or twenty.

Stay inspired.
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