One time I went to a Mobil to get some gas in the winter time. It must have been like 10 degrees outside, it was like January in NY. While I was pumping gas, I saw this homeless guy digging through one of the garbage cans between the pumps. We made eye contact and he didn't ask for a damn thing. I went into the shop and bought a drink for myself and when I was walking back out to my car, the guy was pulling some plastic bottles out of the trash can. I walked over to him, handed him a 20 and said "Here, why don't you go grab something warm to eat." He looked up at me and it almost looked like he was ashamed but very grateful. He replied "Thanks buddy..." And I went back to my car.
I didn't mind helping him because he was doing what he could on his own to try to get a few dollars together and he wasn't bothering anyone or begging for cash. I could tell, I definitely made his night. I just hope he made it through that winter, because it was a damn cold one.