I met Roger Blondell around 2 p.m. on a Thursday afternoon in early July. A tall chubby black man, Blondell was dressed in worn-in jeans and a shirt that looked like he'd had it on for a few days. Still, he didn't seem quite homeless. We were standing on the corner of 24th Street, at 7th Avenue, across from Whole Foods. "Can you spare some change?" he asked.

I told him I could.

In big cities, being confronted by panhandlers is a daily occurrence. On street corners, trains, and inside of stores, someone always has their hand out. In those fleeting moments, we're faced with a very important decision—do we sympathize with the person's plight, reach into our wallets, pull out a crisp Washington and hand it over politely; or, do we ignore the requests from the less fortunate and carry on with whatever we were already doing?

According to New York City's Department of Homeless Services, there were approximately 3,180 people living on the street last year and every night 60,000 people seek shelter. The city has desperately tried to reduce this number, but with the scarcity of affordable housing and the cost of everyday living at an all time high, it seems unlikely that someone on the street will ever really get off of it. According to the Cost of Living Index, New York is 47 percent more expensive to live in than the rest of America, which means food stamps, public assistance, and unemployment benefits will only get you so far. You have to be rich to be poor here.

Blondell lives in a small apartment on the Upper West Side and comes down to Chelsea three to four days a week to see if he can scrounge up a few extra bucks while he's job hunting.

"[I] look to see who's hiring, pick up an application, things like that," he explained. "Just keep the faith, you know?"

Blondell is 60 years old. He's divorced and has two children, and up until April he was employed at a place that he describes only as "a store." He worked there for a spell but lost his job when the company downsized. Blondell claimed unemployment benefits for a week that he was actually working—he needed money for a Metrocard, food, normal stuff—and as a result the New York State Department of Labor cut his benefits. He has a hearing in August, but until then he's out on the street, trying to muster up $10 before he heads back to his apartment.

"The money I get now, I use to eat with," he said. "And I have to have my phone on. Because if you get a call [from an employer] and it says the phone is cut off, they're not going to call you back."

Despite the fact he was panhandling—begging for money, essentially—Blondell was congenial. He smiled, spoke in measured tones, and had he been wearing different clothes, he could have been one of the thousands of workers out in the area on their lunch breaks. Still, his easy-going demeanor wasn't helping him much.

"I hoped I could just rely on the kindness of people," he said. "People think you're going to use [their money] to get high. When anyone used to ask me for money, if I had a dollar, I'd give them a dollar. I hoped they'd do the right thing with it."

I often feel the same way, and when I think about the two dollars I typically shell out for a simple cup of coffee, I have no trouble sparing a buck or two. I shook Blondell's hand, wished him luck and handed him $5. We said our goodbyes and walked off in different directions.

Some people may be charitable in private, but on the streets they can be cold. I've seen New Yorkers purposely avoid contact with panhandlers because they were either afraid or just didn't know how to interact with them. After all, it's far easier to stare down at your smartphone than it is to deal with an uncomfortable reality.

"It's that perception of otherness that I think some people have trouble negotiating," says Mary Brosnahan, the President and CEO of the Coalition for the Homeless. "It's like nurses in a burn ward. After a while I think people just shut down and become inured. They want to believe that person has made some bad decisions in their life. Not that there were some decisions that were made—including which household they were born into—that were beyond their control."

The Coalition for the Homeless is the oldest non-profit homeless advocacy group in the United States, and through their feeding program—trucks that stop in locations all around the city—they put food in the mouths of thousands of New Yorkers every night. Not all of them are homeless. Many, in fact, are like Roger Blondell. They don't have drug problems or alcohol addictions. Hand them cash, and they won't smoke it away. They're ordinary people, trying to make it through tough times.

"Most people I see on the street are not homeless, and that presents an odd advocacy dilemma," says Brosnahan. "That is skewing people's view of homelessness. There are 54,000 people in our shelters tonight, and it runs the gamut. People working one and two jobs, and they are still coming to our feeding program. Saving two or three dollars on dinner allows them to make it through the week."

One night two weeks ago I walked around Midtown Manhattan for hours. Up from Chelsea to Herald Square, to Times Square and back down to the Flatiron District. Homeless people flock to this area, presumably, because this is where the money's at.

Sitting outside the entrance to the 1 train on 32nd street, I met William Hall, a 54-year-old black man with his front teeth missing. He had a cup in his hand and he explained that he was trying get $48 together to pay for a replacement I.D. so he could get back into a shelter, which he'd been kicked out of. He was from Newark and, sure, he'd had his share of issues, but in 2009 his boss at the daycare center where he worked suffered a stroke. His boss was deemed unfit to run the center. After 39 years of employment Hall was out of a job. He had strained relations with his family, a longtime girlfriend with a drug problem, and nobody else to turn to. He wound up on the street. Here, he was implementing a two-pronged strategy—begging for money and collecting cans—in an effort to scrape up some cash.

"I'm trying to get on my feet [and] I don't care how long it takes," he said. Most people don't give him anything, though, which he's okay with, but it might take weeks just to scrounge up the $48. "I don't care if I have to go back to the bottom and work myself up. It ain't gonna take one day, but I don't give up. I will keep going until I get what I want. With somebody help, or without somebody help."

On 23rd Street, I met a couple who declined to give me their names, but nevertheless, asked me for some cash. The wife was splayed out on a dirty mattress sandwiched between two buildings, and the husband, dressed in a soiled loose-fitting white suit, said she was sick. It was terribly humid that night, and she was visibly struggling. I asked how they'd landed in that unfortunate position. Their story was like something straight out of The Grapes of Wrath.

"A guy drove us up here—18 guys—promised us work," said the young Tom Joad. "Some were from Charlotte, others from Virginia. We worked for a few weeks and my wife and I stayed in a hotel in Brooklyn. It was $100 a night. We thought we'd have money to pay for the hotel from the job, but then the building failed inspection, and now we're stuck here. We're just trying to get home. Help us."

I gave the man $10 of the $15 I had. He asked for more and I politely refused. He looked angry. I walked off into the night.

"It depends on the look in their eye, and if I have cash on me," a 25-year-old e-commerce worker told me, when I approached her in Madison Square Park and asked what goes into her decision to give to panhandlers. "Maybe a person is using it for food or to find shelter. I try not to think about it and hope for the best."

Another woman, a 48-year-old artist who lives in Kips Bay, says she donates to Coalition for the Homeless, but exercises more caution when she's on the street. "I do give money on the subway, but not to all," she said. "If my heart gives a pitter patter, then maybe I'll give them a dollar or the change in my pocket. People who are really hungry, that breaks my heart. [But] if they're able to work—if they're healthy and strong and able, and they're asking for money—I'm sorry, I have a problem."

A 36-year-old public relations executive who lives in Chelsea says she's aware of the systemic issues that contribute to homelessness, but she still finds panhandlers "oppressive" and "hard to deal with."

"When I used to spend summer holidays in India growing up, the advice was to never give money to any beggar, because then a trillion would come out of the woodwork and you'd be required to give to everyone—like, where do you draw the line?" she said. "Especially those who are young and don't appear to be physically disabled or even mentally ill, I wonder why they are allowing themselves to resort to this. They seem capable. It's almost a choice, or a willingness to accept a certain lot. It's a matter of inner strength."

And a 34-year-old who works in finance and lives in a luxury rental in the Financial District told me that under no circumstances will he ever give money to a person on the street.

"There are other resources for them to use provided by my tax dollars," he said. "Some aren't even homeless, but are scamming people. And I have heard stories about people giving to the homeless and the homeless being rude. They weren't appreciative. So I don't think much about it. I walk by and don't give a fuck. I'm thinking about investments or what I'm gonna do later, not the homeless."

While it's obvious that many New Yorkers have mixed views on whether or not to give money to the homeless, the decision is ultimately yours to make. Maybe giving money to people on the street is enabling them. Maybe nine out of every ten panhandlers are lying. I mean, doesn't William Hall's story have a few holes in it? But even if every dollar you hand out goes toward something it shouldn't, think about it like this: that person isn't asking for your bank account number. They're asking for some change. Change. In New York. Where a dollar and a dream won't even get you on the train, let alone buy you a beer. And even if it did, would that really be so bad?

"Once you give that person that money, you just have to let go," advises Mary Brosnahan. "It's funny, we were all on our way to celebrate someone's birthday—'Oh, you just gave him money, he's probably going to get a drink'—I'm like, well, we just picked up a bottle of champagne. What are the rest of us doing? If I was in that situation, I'd probably be doing something to take the edge off, too."

Paul Cantor is a writer, editor, and music producer based in New York. His work has appeared in Rolling Stone, MTV News, VICE, and Billboard, among others outlets.

[Illustration by Tara Jacoby]