SizemikGood on you for volunteering for those in need!!!
Usually when I give to a homeless person, I will give money before they ask, or at times when they don't ask, but I can tell that they are down and out. If I see one or two homeless sleeping under an overpass or on a bench, I or my Partner Dave will pull over, I will get out and walk up and hand them some $$$ and tell them to go buy what they want with it. They usually are very surprised and very thankful. It is fun doing things for others when they are not expecting it.
One of the bad experiences I had was walking to Mc Donalds and ordering a few cheeseburgers to bring home. As I was walking home, a guy came up to me and asked for some money, but I instead reached in and handed him a cheeseburger. As soon as I handed it to him, he threw it on the ground and made some comment that was hard to understand and then he walked away. I was more cautious about giving food after that.
One other time when I was in Philadelphia on Xmas eve, I decided to hand out a little $$$ to some of the homeless, as there were a great many at the time and I felt bad that they had to sleep over heat ducts in the sidewalk. I went to a store and got change in $5 bills, and randomly went up to some of the people and gave them a $5 for X-mas. They were all so thankful, with one lady even crying, all except for one guy who decided that $5 was not enough to give him, and would not leave me alone and kept trying to follow me and ask me for more. I told him I had no more and he started yelling, getting irate and calling me a White boy Fa**ot as well as a few other choice names. I started to get scared, and fortunately I was able to make my way to a WaWa convienience store and go inside so he would stop following me. I told the clerk what happened and he told me how uncool I was for doing what I did and how thankful I should be that I didn't get robbed or worse. I was in my mid 20's at the time, and I didn't think that things could turn out badly like it did. I always make sure now that there is someone with me if I decide to go up to anyone I don't know again.