What's the most you've ever given to a panhandler, and why?

No. Why would I? Once I give them money, it’s their money to do what they like with. When I give money (which isn’t as often as I should), I’m not giving them enough to buy a house, get a college education, pay off a few hundred thousand dollars in medical bills and therapy. To (mis?)quote Sports Night: it’s not like these folks are one hot meal from turning their life around.

I’m trying to make their current circumstances a little better, and they’re human beings who get to choose for themselves what makes their circumstances better. We live in a society where a single bad decision, accident, injury, addiction, or illness can put you on the street forever – I can’t fix that, but I don’t believe for a moment that any appreciable percentage of these people deserve their circumstances – no one does. Yeah, I probably get scammed occasionally, but it’s not like street scammers are living fabulously wealthy lives, either.

When I lived in the city I’d ignore most (that city-walk) and drop a few bucks mostly into buskers and good storytellers. Once or twice a year at random times I’d carry around one or two hundred bucks for a day or two until the mood struck. I generally wrapped it in a single so I could make it a bit away.

Being homeless or dirt poor sucks. Sucks bad. Everyone needs a day off every once in a while. Everyone needs a great day, even if it’s fleeting. I’m sure there are some mother stabbers and father rapers out there, but the proportion of miserably fucked to miserable fucks is fairly small, so my odds were good that most people just had a massively shittier life than I.