When I attended Steve Huff’s Photography Workshop, one of our assignments was to ask someone on the street if we could take a picture of them.  I think most would agree, this is not an easy thing to do.  Once you do it a few times, like most things, it becomes less awkward.  Probably, the best advice when doing this is to tell your subject why your taking their picture and try to carry a conversation with them for a few seconds to get them relaxed and comfortable with you.

This picture was taken of a lady waiting for the bus at Steve’s workshop.  She actually approached me inquiring why we were all taking pictures.  We talked for a few seconds and she allowed me to take this shot of her.

Leica M9 – ISO 250 1/2000 50mm summilux