During her two decades living in Houston, Caroline Oliver, like any urban dweller, frequently encountered people in the streets asking for money. She struggled with how to respond. She wanted to help, but in a useful way.
And so when Ms. Oliver, a consultant and mother of two who recently moved to Austin, Texas, read about the New York police officer who was photographed giving a new pair of all-weather boots to a barefoot man on a cold street, she was moved.
"He saw a need and he provided for that need," she says. "He couldn't just walk away."
And when the story, which went viral thanks to a photograph snapped by a tourist, turned out to be more complicated, as they often do, Oliver admired the officer's gesture just as much. Sure, the man may not have actually been homeless, as many had first presumed. And yes, he turned up on the streets soon after, shoeless again, telling The New York Times he'd hidden the boots because they were "worth a lot of money."
But still, the officer, Lawrence DePrimo, "saw a need and fulfilled it," Oliver says. "Even though from his experience, he probably knew it might not necessarily work out the way he hoped."
One might think that advocates for the homeless and the poor would say the complicated shoeless-man saga shows precisely why people should give money to organizations, and not randomly on the streets. But two prominent advocates for the homeless, interviewed for this article, felt that giving on the street is a highly personal and sometimes deeply rewarding act — something they occasionally do themselves, and would never discourage others from doing.
"I probably am as conflicted as anyone about giving people money on the streets, and I've been doing this for 32 years," says Neil Donovan, a longtime advocate for the homeless and now executive director of the National Coalition for the Homeless. "I give as often as I don't give, and it's not connected to my financial state at the time."
Mr. Donovan applauds the NYPD officer for what he calls "an act of love" — regardless of the complications. "What motivates a person is important," he says. "What we find out later is less important. And I think we can nod to the fact that if someone's sitting without shoes on the street at night, something has gone wrong. If it turns out they have a place to live, it's a longer conversation."
Donovan notes that a number of municipalities across the country have tried to discourage panhandling by setting parking meters to accept donations for the homeless. But there's something important missing in that transaction, he notes.
"There's something very intimate about being asked for money," Donovan says. "The idea of leaving money at a parking meter strips us of the whole opportunity to give and receive, which are both great acts."
Donovan thinks so many have seized on the NYPD officer's story because he did what they hope they would do in the same circumstances. Oliver, the Texas consultant, agrees. "I wish I could say I would have done the same," she says. "I'm not sure, because I'm jaded. But I hope I would have."
She herself struggles to find the right balance. Living until recently in Houston, she encountered many homeless people near an underpass she drove by frequently. She wanted to know the money was going somewhere useful — not to drugs, for example. So she would stop her car and ask people to meet her in front of a 7-Eleven, where she would buy them food.
But often, she says, the food was rejected. "I once reached into my grocery bag in a parking lot and pulled out meat and milk," she says. "But the woman ran away."
Like her fellow New Yorkers, Kathy Zimmer constantly encounters people asking for money on the streets or in the subway — daily if not hourly. And this is the season — the holiday months, as temperatures drop — when she tends to give more.
And yet like others confronted with such a decision, Ms. Zimmer has a litmus test of sorts. She's sympathetic if someone is displaying a talent, such as singing a song or playing an instrument in the subway. "There are people who really have talent to lend," says Zimmer, a musician herself. "And I know how hard it is to make a living as a musician."
What inspires Mirko Todorovic, who owns a tie and accessories shop at Penn Station, is a little different. He feels more like giving when the person isn't asking. There's a guy he's seen for years, over on First Avenue on the East side, sitting near a garage. "He sits in a chair there, with all his stuff, and never asks for anything," says Todorovic. "I've given him something about 20 times" — maybe two or three dollars.
There's a common desire to help people who help themselves, says Nan Roman, president and CEO of the National Alliance to End Homelessness. "A lot of people think one shouldn't give on the street because it's enabling," Roman says. "They're afraid people will make a bad choice about what to do with the money."
But Mr. Roman, like Donovan, would not advise people to avoid giving. "It's a personal decision as to whether you want to help or not," she says. "Most people, I think, make a decision based on how they feel. That's what I do."
Roman understands how some people may have been disappointed at reading of the complicated circumstances of the NYPD case. But she points out that most cases involving people living persistently on the streets are, well, complicated.
"People don't generally live on the streets unless they have complicated problems," Roman says. "The majority of people would enter some program until they got back on their feet. If it's a chronic case, they have other problems too, like a disabling condition of some sort."
But even if the shoeless man had complex circumstances, she points out, he still was sitting on the street with no shoes on, in the cold. "He wasn't making the wisest decision — but he still needed help," Roman says. "What are you going to do, interview him? Ask 90 questions?"
Roman sees the public's response to the NYPD story as a need for simple, quick solutions.
And so she suggests giving to advocacy organizations, which she does herself. "I think that's the longer-term answer," she says. Adds Donovan, of the National Coalition for the Homeless: "Maybe this [NYPD story] will be something that causes people to say, 'Hey, why don't I give to the shelter this year?'"
But still there will be the spontaneous, daily calculations of people like Zimmer, the New York musician who favors giving to musicians like herself. She also tends to be generous, she says, "when I see someone with an obvious physical impairment." If they look healthy and more able to work, she says, she's less likely to give.
When reminded of the NYPD officer's story, she shrugged and smiled. She said it hadn't affected her calculations. It was just another odd story in the big city.
"You never know in New York what the real story is," she said.
• Associated Press writer Verena Dobnik contributed to this story.
• Sign up to receive a weekly selection of practical and inspiring Change Agent articles by clicking here.