How I did it: I've always wanted a meaningful connection with a homeless person. Instead of giving money...giving company, conversation and sharing a meal.
I was in SF with a friend, when I was approached by a homeless man, asking us for change for food. Instead of giving him money, I told him I'd get him lunch. Carl's Jr was his favorite place. So the three of us walked over there and talked about his background, his past and how he ended up in SF.
It was really nice just having a conversation. He loved the fries!
Lessons & tips: People just need company and someone to listen to them. Just go with a friend! Just do it!