
It really depends on the feeling I get with each individual. Obviously asking some stranger if they mind if you take their picture will affect the outcome of their expression but I usually talk with the person for a while in a friendly way before asking them, camera in hand. There are times of course, I would have missed a good candid shot had I stopped to ask if they objected.
In my opinion, it's how you carry yourself and your camera that allows your subjects to feel comfortable, or not. I've heard you convey your self image through your lens to your subject and it is this reflected image you receive back on a subconscious level from your subject.

My favorite work and what I enjoy the most is photographing the landscape of America, particularly the American West, but I will always enjoy the challenge of shooting strangers and learning something new from all those I photograph. Shoot a stranger, make a friend!
An interesting article by Qiana Mestrich titled "Photography Empathy: How you feel is what you get" about how photographers are like mirrors can be read at Black Star.
"As I progressed further with my project, it became obvious that it was really unimportant where I chose to photograph. The particular place simply provided an excuse to produce work... you can only see what you are ready to see - what mirrors your mind at that particular time." ~George Tice