1. No it did not feel uncomfortable for me to be photographed. I'm particularly adept at warping awkward or uncomfortable situations into amusing anecdotes to remember. I don't particularly enjoy the emotional feelings of discomfort, so I choose to make it into a different emotion. In many cases it becomes humor.
2. I can think of several ways to make an uncomfortable subject at ease. First and foremost, inject humor into the situation. Laugh with them and joke with them to lighten their mood. One method would to be a photoninja. If the shot allows for it, don't be seen before hand; CAUTION-This is for family members or close friends only. Otherwise it's creepy. Finally, do a little roleplay. Toss them your camera and let them take a picture of you making a silly face. Letting them be in control for a bit will help them come out of their shell.
Humor is a great device in making people comfortable!
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