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Urban commuting is dehumanizing. We pass thousands of strangers without even a nod or meeting eyes. Sometimes, when I see a person with a particularly sad or frazzled look, I say, "Hey -- Whatever it is, it'll get better soon, I promise. Hang in there and smile." I usually try to do it in a situation where I can walk away (subway arriving at my stop, or we're going in different directions on the sidewalk) so they aren't forced to give me a response or thinking that I'm going to preach gospel or ask for money. About half the time, they look at me like I'm crazy. The other half, they smile. :) Try it. Say something encouraging to a stranger and walk away with a smile. You might make someone's day.
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