Honestly, it is hard to stop and give money in the streets, and sometimes is not the best thing to do as it may actually just be giving someone money for an addiction, seems to be the way to go is to give to an organized charitable foundation like Centre Point. Personally, we get approached almost every evening by "Chuggers", (not centre point), these are people who stop you in the street to ask for money for a cause, wearing their organizations coloured jacket with the logo. Mostly annoying, but you do see them stopping and speaking with people in a positive way. Although must be pretty hard work, but great if you want to work on shyness and overcoming rejection.
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