Where I live, it's illegal ("panhandling") but we still do it. When we lived in Houston, Texas there were several homeless that we saw but one lady in particular that stood out to us....she broke my heart!! It was getting cold in the evenings so we went to buy her a sweatshirt, heavy socks, new tennis shoes (had to guess her size), sweatpants and some other things. My husband parked and walked under the bridge (it was under a major highway).....she started screaming at him.

Makes me tear up just thinking about it....feel so sad for her!!!! So my husband just set the bags down for her and walked away. She ran to get them, picked them up still running and yelling at him then threw them in a drainage hole next to the road. So, I guess she never got to ues these things and this is okay....we just wanted to try. We still saw her from time-to-time and never with the other group of homeless people....she was always by herself. She wore a huge, heavy, thick wool type of sack and she was such a mess. She looked like she was an attractive woman and young (40's). My heart always went out to her and wondered if she just needed medication, but no one would even be able to help her because she seemed to avoid other people.
I won't give to just anyone standing and holding a sign for food or work, but there is a man here that we have given food to. He looks like he DESPERATELY needs help! My heart aches for him.... We will go through a fast food restaurant and get him food and water. He has a difficult time talking but he ALWAYS thanks my husband and ALWAYS makes a point to look directly into my eyes and says, "Thank you so much ma'am!!" He is VERY thankful and he definitely needs the help. I want to help him because he does need it and it is VERY, VERY obvious. I haven't seen him for a couple of months and I do worry about him.
*sigh*.......