Quoted By:
You really needn't worry about any of these things if you are not being a pervert. I think a lot of the fear of street comes from the fear of rejection, and knowingly indulging in voyeurism.
Practice some social skills first! You'd be surprised how just developing yourself as a person can really help you to take great photos. Look people in the eye as you walk down the street. Obviously, not like some kind of leering psychopath, but just as a human acknowledging another human - you can even throw in a casual nod to defuse any tension that may arise. Talk to people! Strike a conversation with a stranger. Who cares if you say something stupid, or fumble your words? It's an inconsequential little dialogue with a perfect stranger.
Once you feel like you're ready to try to shoot, there is no shame in asking a stranger to pose for a portrait. My approach for this was explaining to the person why I wanted to capture their image, what drew me to them in the first place. This will also help you develop your eye.
Once you build up your confidence in shooting and getting a grasp on the idea of street shoot for years and years, and for gods sake, edit your photos! Most of your photos are going to be shit. Like, really, really shit. But you are going to think they are possibly the best street shot photos ever captured. Get feedback, take it gracefully, be critical of yourself and your work, and continue to research other photographers ( a little homework here wouldn't hurt, maybe trying to articulate why you are drawn to a certain photographer or image. The more you put in, the more you will get out)
Learn your local laws, and don't challenge are person on deleting a photo unless it's a really good image. If it's mediocre or shit, just apologise, delete the image and move on. This is not the hill you wanna die on. However, if you think the image is worth keeping, run away. You can try to debate, but you can't argue with irrational, and sometimes you can be hit for trying.