For me, the start of street was to "shoot from the hip", this was a less intimidating way for both the "taker" and the "taken".
Funny, it is like a drug after that, and you become a little more brazen as you go.
After that it became exciting to get the eye-contact of the "taken", take and move on, chimp later if you like.
Now I find it easier to be "given" an image rather than take it (find interest and ask to have it). This is definitely more social, but not as exciting.
I'm am not weird or pervy, but I find people in their natural habitat really fascinating.
Ultimately, think how you would feel being one of the "taken", it doesn't really hurt, and it's over in a flash.