Call me an asshole but I never give them money. Don't push this "disadvantaged" stuff on me, because I don't believe it.
You have to make a series of conscious decisions to become homeless. Not only do you actively decide you don't want to work, because I see Now Hiring signs all over the place, but you have to burn every bridge in your life to become homeless. I don't buy everyone was thrown out on the streets by their parents. I don't buy these people were nicest people and simply could not find a friend who was willing to spare a couch for 6 months until they got back on their feet. I don't buy it that these people would spend my money in any way which improves their lives.
They have different priorities, and if those do not involve pulling one's own weight then they can do their thing. I will not, however, encourage said behavior. If a stranger wants to dance around on the freeway, is it generous of us to give them a tutu so they can dance better? Or should we get him out of the dangerous situation? I personally refuse to let my hard-earned money going to allowing them to get drunk/stoned/f-ed up to the same degree which landed them in the situation.
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First, if you give someone something out of genuine generosity, you shouldn't mind how they spend it. If you tie your own conditional restrictions, you immediately reduce generosity to something more akin to a financial transaction where you expect something specific in return.
Second, why should self-medication be the exclusive privilege of those who can hide it behind clean clothes and shiny cars?
Third, I've always considered carrying a roll of quarters with me everywhere to dispense to all who ask me. I get about five or so requests a day during the work week.
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Forgive me, I must not be genuinely generous. I am in full support in giving a man a meal until he has learned how to fish. If, however, he ignores the fishing lessons and walks away he can do whatever he likes, he just won't get anymore meals.
Self medication is available for those with cars because those people with cars have worked, struggled, and improved their lives to afford it (Paris Hilton whores excluded).