I once gave a guy $5 because he told an interesting tale. He explained how he was so poor that his family only had one light bulb in his house, so at night they'd have to unscrew it and take it from room to room if they wanted light.
A few months later he came up to me again, this time trying to sell me "his" umbrella because he ran out of "bus fare". I declined, he insulted my appearance, I insulted his and called him on not remembering that he had asked me for money a while ago and giving him a $5. He admitted his umbrella thing was just a hustle and that he was just doing whatever it took to survive.
One thing I've wanted to try when someone asks for money is to start speaking to them in another language and pretend to not understand English. But I just never got up the nerve. Tynan, please try that one time and let me know what happens!