Tips for photographing strangers, getting past the fear
Approaching strangers for a photo can be intimidating, you wonder how they may judge you and you may have predetermined that they'll already say no, you have to remember that if you don't ask your guaranteed to get nothing.
For the above photo I was tasked with photographing the homeless population in San Francisco's Golden Gate Park for an article discussing resources for the park's residents. I was up against a bit of a wall, what is the best way to go into these peoples squat waving around a fancy DSLR?
In order to be let into a person's space you need to build a rapport and be completely up front about what you're doing. The best thing you can do is just walk up and say hello, talk for a few minutes before you even pull out your camera. Let them know why they would make an interesting subject and ask them basic but relevant questions about themselves.
Your camera is a barrier between you and your subject, going with a small and simple set up will better allow you to capture candid emotion.
Be Persistent, not everybody is going to agree to a photo and some people may even try to insult you. Remember, get up and give it another try.