It depends. There was a guy around here that never asked for money, but was obviously homeless. He just sat by the street, waving and yelling out "Have a nice day!" I would have given money if he was still there when I finally had extra cash to spare.

When I worked in the mall, I often got off work at 12:30am. As I waited for my ride, I'd get asked for money 9/10 times. I gave money the first time.. because I gave him the benefit of the doubt. But after a while, I was pretty sure he wasn't homeless. He was always clean shaven, did not have any odor, wore clean clothes (they looked old.. but any thrift store will have old clothes available) and he ALWAYS said he had "two ninety-five". Never a penny more or less. After that, I never spoke to him.. I'd always have my music blasting and I'd just stare at him not saying a word. But one day he asked again, and I yelled out "I @#)$(*&#% gave you money before. You had $2.95 that day too". Ohh.. the look on his face...