BenLowell comments on Behavioral psychology and buying a warranty at Menards - Less Wrong
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When I moved to a larger city with a larger homeless/begging/random street solicitor population, it took me a while to learn the methods of avoidance. I usually like to smile and look people in the eyes when I walk around (at least on a good day) but I find that solicitors---who are looking for that brief emotional connection, are much harder to turn down if I meet their face directly. It took me multiple times of feeling bad before I was able to overcome giving money/listening to somebody's life story/religious ideas. Now I have crowd-scanning-Mormon-avoidance paths similar to most other people.
I found that many street beggars have a story, and if you give it any thought at all it doesn't make any sense. I now have a 'say no first' policy and I figure that if I ever want to run after someone and hear what they have to say they won't mind.