NOTE: This was originally answered on Quora and is saved here as part of a Quora classics series.
Sometimes yes, sometimes no. There isn’t really any way to know. More importantly: who cares?
I have heard some make a straight pitch, “Ladies and gentlemen I ain’t out here selling these candies for no baaaaasketball team. I’m selling these chocolates for a dollar so I don’t need to sell anything else, and to keep me and my friends off the streets.”
It’s called the hustle, and it’s what everyone is doing here: whatever it takes to make that almighty dollar. Besides which, too many of those stories are true: too many sick people, too many psychologically unwell people, too many embarrassed parents asking for money with one hand and holding the hand of their kids with the other, too many lonely, quivering veterans and stories about the VA. A man in a wheelchair, who you wonder how he got down here. A man with a face sanded down to the nubs, saying he was burned with acid, holding out the newspaper article that describes his story. A man with no legs, who stinks of shit and piss and drags himself along the floor of the train, his military pant legs tied in a knot and black with the grit of the train, shaking a coffee can filled with change, silently looking at the floor in hope, and humiliation. I’ve seen all of these people, again and again and again. I don’t actually care if their stories are precisely true. I’ve seen enough truth for a lifetime, down there.
This isn’t how a society is supposed to work. This is why New Yorkers expect to pay for social services—we don’t think this kind of thing should be outsourced to the momentary generosity and caprice of individuals—we expect government to play a part, here. Things have gotten worse.
I don’t usually buy the chocolate, but plenty of times I’ll just give them the dollar, if I have it.
I also don’t generally give money out unless I have change or loose dollars to part with, but I always try to give someone money if they have a good pitch.
There are some people who have some kind of fear: what if they are lying, and don’t have a basketball team? What if they are just going to use it to buy drugs? What if they are trying to get one over on me?
Relax. In the wealthiest city of the wealthiest nation in the history of the world, this strikes me as a pretty shitty perspective. They need it, you don’t, and it’s an incredibly cheap way to help someone. You think they’d be out here if they had a ‘real’ job? Sure, some might. Most wouldn’t.
You don’t have to give money to everyone on the train who asks for it—who could afford to do that? But don’t tell yourself bullshit stories about other people’s imagined moral failings in order to make yourself feel better. Tell yourself a story about their awesome basketball team, instead.
And remember to tip your waiter.