@HopefullyLost1211 Thank you for your input! I guess there's a time and place for everything, except for dangerous begging. Being an analytical and pensive type also features a tendency to overanalyze situations, so only the other person truly knows what they have been through.

@Velvet Lounger Thanks for your advice also. I occasionally feel like a fish out of water where I've gone to school because I grew up in the country, so its great and very interesting to get input from someone who lives in one of the world's most globalized cities. Of course like you I won't give money away so people can get wasted or use it selfishly but it is rewarding to give when it's appropriate. I gave quite a few dollars in the Sydney Harbour and New Orleans' French Quarter for people showing off their musical talent!