I love looking at portraits, especially street portraits done on the fly of strangers. Thomas Hawk has a great collection of what he calls $2 portraits. The concept behind the $2 portrait is that if someone comes up to him on the street to ask for money, he offers to give that person $2 in exchange for permission to take a quick photo. Based on the number of photos in his set I'd say that most people seem to be receptive to this type of deal.

I've thought of doing something similar here in Winnipeg (although I rarely actually have any change) and need to get over my fear of approaching people.

Wired.com has a great video how-to about taking street portraits. After watching the video I think I am ready to try taking some portraits of people I encounter in my neighborhood.