I guess what I'm getting at, is that the example of Jesus in this situation is not to simply ignore and shun Zaccheus for who he was or the shady reputation he held, but rather to reach out to him with openness and warmth. I want to be more like Jesus. I want to recognize hopefulness in a person that feels hopeless. The example of Jesus is that we should ignore societal barriers, and class, and reach out to others. This might mean going against what's comfortable. For Jesus this meant entering Zaccheus' home, eating with him, and experiencing community with him. Jesus never condoned sin, but he loved others deeply. That was more important to him than whether or not the company he kept seemed appropriate or acceptable to others.
I've grown up believing that it is okay to avoid people who aren't like me, or don't have the appearance of being put together. The older I get, the more this paradigm is crumbling. I guess I'm learning and realizing that we are all the same. We all want truth, acceptance, and love, and something to hope for. My prayer is that I will see others as my brothers and sisters first, and not as outsiders. I believe that this is how Jesus saw others. He was drawn in by the humility and brokenness of others, no matter who they were. - Jon.