We have a lot of people like you described where I work. Every day a different one and they usually have a heart-wrenching story about why they need your money. Thing is though, around here an act of kindness is usually interpreted as an act of weakness unfortunately, and conversations with strangers is a good way to get yourself shot or robbed.

Maybe I seem cold or paranoid, but around here it's a fact of life. I wouldn't say anything to him for the same reason I carry a handgun to work with me every day. Too easy to get killed.