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Krista writes: "To pity him is to judge him. "

I must say I don't understand this. Pity is something that initiates from a feeling or believing of separateness...which in this case is a fact, perfectly understandable to your "boys in the back seat." A "spiritual" response would be compassion - an active form of pity? - actually doing or not doing something to help the homeless. So not sure where judging another comes into play here.