New York has its fair share of people begging on the streets, in subways, etc. Over the years, the city has tried to clean this up to encourage tourism. When I was in college, some people in my dorm did a social experiment to see how much money they could make doing this. You would be surprised at how much they made that day.
Because of this, I am cautious when it comes to helping those individual(s) and tend to support them by purchasing food for them. In some cases, I have issues with the organized charities that have significant overhead (e.g., executive salaries) that take from the moneys that should be given to those that they were meant to help. As a general rule, I do not give to those that I believe are capable of finding employment. In addition, I also do not support those that exploit children. This is a common practice in Vietnam. Bars and clubs are inundated with children of all ages selling gum or trinkets or outright begging. Their parents are usually across the street and do not intervene when foreigners, etc. are 'petting' their children.
Tony is a kid that I met through someone, who told me how Tony helped him when he was in a bind and got his wallet stolen. One night I struck a conversation with him to find out his name and learned that he goes to school in the afternoons, which doesn't quite make sense given normal school hours. He's probably 11-12 years-old but is in the third grade. At times, I will pay extra for his gum or not even take the gum, knowing that his mother is watching every dong that changes hands. I am still trying to figure out how to help him, such as pay for his education, without his parents taking advantage of the situation. Last week, I saw Tony as I was going into an after-hours club. He found me as we were leaving at 4am and immediately hugged me. When I told him that I had to leave, he said he wanted to go with me.
Despite my general rule, Tony has tugged on my heartstrings. I had another touching moment this morning in Bangkok. Although I am generally conditioned not to pay too much attention to beggars, especially when I peripherally see children, I happened to notice an elder woman, perhaps grandmother, either assisting with schoolwork or teaching a small child (~ 5-6 years-old) spelling and words as they were hunched over sitting on the edge of the sidewalk. She had a small glass jar of coins in front of her, but was entirely focused on the child at the time. Initially, I kept walking, but the image stuck in my mind, and I had to turn around. I gave her what I had of cash (minus lunch and taxi money to the airport), which was not much. Regardless, she was very appreciative. As I left later, I walked by her again, and she thankfully bowed her head once again.
I do not generally have regrets as I believe that we should learn from our mistakes. Having regrets means that one wants to change the past, thus eliminating the lesson that we were meant to have learned. Not exchanging more dollars to baht today is one of those rare regrets I have in life.