The following is another good article about learning how to relate well to those who are homeless: From Beggar to Brother. As the article points out, giving money to those who are panhandling feels problematic. Yet ignoring others is perhaps even more problematic.
I really like what the author had to say as she talks about moving away from fear:
“When I moved to Chicago, well-meaning people concerned for my safety trained me to put on a “Chicago face”—a “don’t bother me” look—to discourage solicitors. . . I put on my “Chicago face” and ignored the man who was sitting in a wheelchair, shaking a McDonalds cup. Meanwhile, at church I was hearing sermons about how Jesus pursued the people society had ignored. . . . I got up the courage to look at the man and nod. Pretty soon saying “good morning” to him became the highlight of my commute. Occasionally I brought him homemade bread or an apple. One day, my friend wasn’t there and I worried about what had happened to him. The next day I told him I had missed him and was glad to see he was okay. Panhandlers are used to people wishing they weren’t there; what an opportunity instead to remind this person that he’s valuable!”
Read the entire article (it’s fairly short) at The Banner.