"There are programs that they can go to for shelter, work, or help. For most of them, their lifestyle is their choosing. Even the mentally ill have venues to turn to." This so much. Most of the people for whom money could help don't look like your typical cart-pushing homeless person. People who are looking for jobs/a better life through work, will look much better put together (since they are doing their best efforts to look presentable/feel presentable) and are most likely utilizing social programs to help get them on their feet. I avoid giving stuff to people who look like addicts. Sure if you have disposable income you can spare some change to get them a hot meal and make them feel better, but it won't help them in the long run unless they are willing to change, which most don't. If you give money to a random homeless person you've got to be resolved to the fact that they have the choice of using your donated money on things like drugs and alcohol. I have bought groceries for wandering/runaway vagrants before, because they were very young (teenagers), but I did so knowing that giving them food would not really help them in any way beyond giving them something to eat at night when the kitchens were closed.