Live in a major city and you will be forced to confront homelessness and poverty. On a daily basis you will be asked for money, either directly or through plaintive cardboard signs, by some of the most pitiable people you will ever see. Depending on the type of person you are, your reaction will range from sympathy to annoyance, concern to anger, frustration to apathy. Your general attitude will likely vary over time and even from day-to-day.
When I was 18-years-old in Washington, D.C., I met a homeless man named Piotr Lekki who became, really, one of my only friends in that town. I would buy his drawings, take him for coffee, practice my German with him, and mostly lend an ear to his insane and delusional stories about being a doctor, a king, and the Pope himself. As lonely and broke as I was, I empathized with this man and with his desperation and isolation.
When I moved to New York City, I actually had friends and a life, though I was even more broke. The upturn in my social life and my inability to give away any money at all, combined with the sheer overwhelming size of an even more desperate homeless population, fostered an apologetic "sorry, man" response that persisted for a decade. What's the point in sparing my few precious coins when it won't even make the barest dent in an obviously unsolvable problem?
Then I moved to Portland, without question a kinder city, which attracts and fosters a general populace that is friendlier and more considerate. The amount of people on the street asking for money were far less than in New York City, and most of them were of the silent, cardboard sign variety. My income was also more substantial and I started being more willing to give out a dollar here and there. I frequently bought copies of Street Roots, the local paper advocating for (and usually sold by) the homeless population. I started donating to the local mission and asked others to do so as well.
But... with time, as the monotony of the homeless presence persisted and even increased, and after several incidents of being deceived and disappointed, my acceptance and empathy began to wither. If I saw someone sitting on a corner with a sign, I avoided that corner. I started saying "sorry, man" to the Street Roots vendors. I looked the other way, but all the while I kept wrestling with my guilt.