To Eat With, Or, Not To Eat With?

"And the scribes of the Pharisees, when they saw that he was eating with sinners and tax collectors, said to his disciples, “Why does he eat with tax collectors and sinners?” Mark 2:16 ESV

    As I have been getting ready to go downtown to minister to the homeless and needy, I was thinking about the fact that we serve them so well with food, once very other month, but we ourselves don't eat the food, mainly because we are busy serving them and we are not sure that there is enough food for us and them. But how does this come off to someone on the streets as we watch them eat while we share the Gospel with them?
   I don't really know what it looks like from their perspectives, but could it look like we are in a separate category than they are in? 
   We have done a program in the church called, 'The Conversation' where we invite people who are interested in finding out about basic Christianity. We start out by eating a meal together and as we are eating and drinking our dinner, we get to talk to the guests and get to know them. There is a unity in our meeting because we are eating with them, not just serving them but actually eating with them. And we find out a lot about the people who attend these classes while we eat with them.
   It is something I am pondering right now. It is not very easy to eat while talking to people, but it can be done. What do you think? Should we eat with them, and if so, would that help bring about a knitting together of us with the people, or, is it unnecessary for us to go through the trouble to make enough food for us and them? I would like to hear your thoughts.

Serving the Homeless Downtown. Should we eat with them?