The concept is simple: when a person on the street asks me for change, I offer to treat him or her to a meal. My mission is to fill their bellies, to give them temporary shelter without hassle, to share in conversation, and to dig deeper into their stories rather than what I’ve always done: just pass them by or flip a few nickels in their direction. I have no agenda other than to listen and observe so I can later describe what I discover during these encounters.

FEBRUARY 3, 2009 - CHICAGO, Illinois – He stood almost all silent and still on the sidewalk outside a 7-11 on Michigan Avenue. Besides busy eyeballs behind foggy glasses, his only movement came from his left wrist, which delicately shook a weathered 24-ounce Coca-Cola cup filled with what sounded like a big gulp of change.

The evening was the type so frigid I didn’t dare make a phone call outdoors since it meant removing my mitten. Out of boldness, desperation, or feelings I’ll never fully understand, the man held his ground as the sole beggar I had seen in my half hour roaming the northwest perimeter of downtown Chicago’s famous loop. He seemed immune to the whipping winter winds, impartial to the entire scope of his less-than-ideal situation for that matter.

From the time I spotted him to the moment I approached him on the second pass, I was the only person to outwardly acknowledge his presence in the world on this magnificently busy mile.

To my skepticism, he estimates that sixty-five percent of people who pass have contributed to his cup since he began hustlin’ two year ago. I know this because just minutes after seeing the 38-year-old man for the first time, we were sitting across from each other at a cozy table for two, chatting with our mouths full as we wolfed down burritos.

***

It didn’t appear Anthony was familiar with Mexican-American fast-food cuisine as he referred to the salsa as tomatoes. But he said he’d eat ‘anything,’ so I suggested the first place we passed with the same anxiety I’ve had on first dates. I held the door for him as we entered Qdoba. He crammed his cup full of change into his coat pocket.

Customers’ curious stares shot our way as we took our place in line. Maybe it was his severe limp or the skin around his nose, which was chapped and as white as the snow outside. Maybe the workers had seen him in there before. Maybe it had nothing to do with him. Maybe the 24-year-old white guy with the poor college-student vibe had toilet paper clinging to the bottom of his shoe. I can tell you I didn’t because I checked.

When I told him to order whatever looked good, Anthony chose a steak burrito, brownie, and soda pop. He collected the change that spat from the cash register and began to hand it to me. I couldn’t take it from him. We settled on our seats.

“If I wasn’t shaking that cup, you’d never know I was homeless,” said Anthony, now lifting a cold can of Sprite to his lips. “My clothes are clean, and I don’t smell bad. Could use a haircut maybe.” Not any more than me, I thought.

He had yet to make eye contact with me and asked a total of three things throughout the evening: name, hometown, how long had I lived in Chicago. He seemed neither phased nor perplexed as to why this stranger had entered his life and rarely spoke other than in the form of question like a Jeopardy contestant.

I even apologized at one point for the heavy dose of investigation.

“That’s how you get to know a person,” he responded as rice spilled from the gaps in his mouth where teeth had gone missing.

***

Most of what he told me was neither shocking nor fathomable. He didn’t seem fake but, at the same time, he didn’t seem real. Yes, of course people sleep under bridges. I know that. But my dinner guest didn’t really have a sleeping bag prepared for slumber beneath Wacker Drive on this negative-degree night, right?

Anthony’s friends had gotten an apartment, which is why he had recently showered and shaved. He even had the latest NBA insight. “Shaq can’t run up and down the court anymore like you and me,” he commented. I couldn’t help but picture the image of us moving at a snail’s pace down the street due to his mysterious limp.

Anthony didn’t try to earn my sympathy. He didn’t pretend he was perfect. He said he used his money to eat and ride the bus to look for jobs a couple days a week, but he didn’t claim to be doing everything in his power.  Some times were tougher on the spirit than others.

He openly explained the best strategy for collecting change (gently shake the cup at passerby and speak kindly to those entering the mart). He admitted to a few past mistakes, but “not too many,” (61 days in county for trespassing). He described the life of which he dreamed (a warm home, a job as a firefighter saving people’s lives, and a wife and kids when he was prepared to provide).

The police never gave him trouble as long as he kept his space clean. Where he slept there were a few others, including a woman eight months pregnant. This was the only element of his existence that seemed to disturb him.

He prefers the streets to the shelters because it’s easier to make money by staying out at night; he claimed it was tough to get in anywhere after 8 PM without proof of a work slip. The most he ever claimed to make in a day was $50. He proudly admitted, “I gave someone else a dollar that day.”

When he suggested that ninety percent of the city’s homeless was getting drunk or high and the 10 percent who weren’t just didn’t have the money to do so, he didn’t exclude himself from the group.  Said Anthony, “Some people think we’re just gonna use the money for drugs or alcohol, but the truth is, when you give me a dollar, I can do anything I want with it because it’s mine now.”

He made eye contact with me for the first time.

“And you’re never gonna know what I do with it.”

***

Since this was the first time I’ve sat down with a stranger from the street, I hesitated to pry with sensitive subjects, worried he wouldn’t enjoy his dinner.  I finished my burrito well before he finished his. I asked fewer questions, hoping he would eat faster so I wouldn’t need to rip his life apart with my questioning.

I poked at the topics of family and what led to his homelessness, but it didn’t return anything but ambiguity. He had a mother somewhere, but it didn’t seem like he wanted to talk about her. He was homeless because “life ain’t easy.”  In retrospect, I wish I would have asked so much more. If not as a journalist, then as a concerned citizen. The truth is, I was too nervous.

When we parted ways, I didn’t quite know how to conclude the conversation. What do you say? Call me?

“Well I hope you’re full. It was really nice talking with you. Take care,” was the best I could offer.

“Thank you,” he said softly. He then turned around to face the direction of the place where we had met. I watched him as he slowly limped away for two blocks until he was out of sight. I walked up the stairs to the Brown line, placed my convenient monthly pass in the mouth of the toll machine, and waited for the el to take me home.

I felt I knew a bit more than those who ignore him with cold shoulders or donate pocket change, perhaps wondering if they should feel like a sucker or philanthropist. But I knew I didn’t do what I came to do: to figure out how this man had come to ask for change. I was too wrapped up in the situation itself. I found out nothing more than what you might have already guessed. Next time, I thought.

Just as the train slowed to collect passengers, I exited the platform, my curiosity getting the best of me. I walked the few blocks back toward the 7-11 on Michigan Avenue. I crept carefully until I got a glimpse of Anthony, who was delicately shaking a weathered 24-ounce Coca-Cola cup he had pulled from his pocket.

He never saw me. I never got to know him.