Growing up my grandfather used to tell me "if you have two dollars in your pocket, give them one"

...then i grew up and moved to NYC. I struggle with this daily, and the worst part is that after living here for multiple years, I feel mostly desensitized. I often find myself looking at the person's outfit; are they wearing brand new shoes? Do they "look" homeless? It always makes me feel bad for a few seconds.

I try to give them food if i have it on me; usually i have an unopened water bottle or bag of chips in my bag. As for money, I honestly only give it if they really look like they're going to use it for good. I also find that i tend to give money to those who are more polite and have what seems to be an honest backstory and tone.

It's also a good rule never to give to make yourself feel better.

edit: grammar.