“Spare anything, ma’am?”

My son looked up at me uneasily, so I left him with my husband and went over to the man, dollar extended. He thanked me and asked my son again for his doggie bag. I motioned him over, nodding my assurances. “I didn’t finish my steak sandwich,” my son told him proudly, as he handed the man his bag. The man thanked him and said, “Be good to your mommy.”

At just that moment a father and his two teenage sons walked past and, without breaking his stride, barked out: “It’d be better if they got a job!”

I was startled by the intensity of the man’s disapproval, but I, too, have had doubts about offering handouts to the homeless. Under the watchful eyes of my child, I chose the action that I hoped would speak to my son about the principles of charity I hold dear, but the truth is, my decision to give has seldom been so clear-cut.

Like most people, I’m more comfortable giving when the people on the receiving end are anonymous. I happily participate in the clothing drives sponsored by my son’s school, and I drop my spare change in the big metal kettle at the mall, where a man dressed like Santa Claus rings his bell and smiles at shoppers.

Giving directly to the street person shambling across my pathway–well, that’s another matter. Hollywood tends to portray the homeless as lovable rogues (think Eddie Murphy in “Trading Places”), but in real life, the person asking for money is often suffering the effects of mental illness or addiction. I’m not proud to admit it, but even the few seconds it takes to look the other person in the eye, extend my hand and offer some change can feel like more of a connection than I want to make.

I’ve heard the intellectual arguments against giving handouts: the money will be used to buy drugs or alcohol, handouts breed dependency, giving money discourages the homeless from going to shelters. I don’t want to undermine the efforts of the mental-health professionals who work to get the homeless off the streets. But what I know in my head doesn’t square with what I feel in my heart. Pretending that people don’t exist and withholding a couple of quarters or a dollar bill feels like the wrong thing to do.

Several years after our encounter with the homeless man in Washington, my son and I visited New York City. As we walked down the street, a thin, drugged-out young man approached us and asked us for change. It was midtown at midday, so there was nothing particularly threatening about the circumstances. Nevertheless, the man was, by anyone’s standards, unsavory-looking with his dirty clothes and unhealthy skin. I passed him by. Half a block later, my son stopped walking and asked: “Why didn’t you give him anything?” I fumbled through a rationale about how we hadn’t had time to stop and why we couldn’t possibly give to everyone. My son interrupted and said, “Yeah, I don’t think you should give money to people like that.”

“People like that.”

In his words and his tone of voice were echoes of the man who told the panhandler to get a job. I had shown my son that it was acceptable to classify people as the deserving and the undeserving poor.

Last spring I traveled to London to do some work-related research. Each day on the way to the library, I passed a group of homeless men lying on the steps of St. Pancras Old Church. Perhaps spending time in one of Charles Dickens’s old neighborhoods set me thinking about his righteous anger at society’s neglect of its poor. Or maybe I finally accepted that I’m in no position–and who is?–to judge another person’s worthiness of a small act of kindness. Whatever the reason, I decided that I would always give when asked, even when it means weathering the sidelong glances of those who think I’m a fool or worse.

My son is now a teenager and will have to decide for himself if and how he’ll give to the poor. For all of my inconsistencies, I hope that I’ve taught him that it’s better to set the needle of his compass to the magnetic pull of kindness than to contempt. But time alone will tell.