Some­times I feel like I must be wear­ing some sort of a sign, like a “kick me” on my back, or invis­ible ink on my fore­head that says “gull­ible.” I talk to a lot of strangers, and most of the time I enjoy it. In fact, I am try­ing to make talk­ing to strangers my work. Some­times, how­ever, try­ing to be open and enga­ging puts me in com­prom­ising situations.

I was hanging out in the lobby of my hotel on Christ­mas night, and this young guy comes up to me and says “hey, are you from around here?”  Obvi­ously not, oth­er­wise why would I be in this hotel on Christ­mas?  And then he says “I need some help man.” That’s when I flipped on the recorder. Have a listen to the rest:

We were sit­ting no more than twenty steps from “the Mag­ni­fi­cent Mile.”  The fancy stores had been packed with shop­pers buy­ing hand­bags and gad­gets the night before. The street was all but vacant now. It felt like we were the only two people left in a world that had been deserted.

He made his case. It was a scam, and I knew it from the start, but I bought it anyway.

We set out alone through the empty canyons of steel and glass. Around one corner a drunk was yelling at a cop; “fuck you, I ain’t scared of you or nobody!” The cop yelled back “you bet­ter be scared! Scared I don’t put you in a men­tal asylum!” Merry Christ­mas. We marched on, talk­ing, through Grant Park, past the bean, towards the train sta­tion. It was start­ing to get cold. When we finally reached the sta­tion the train had already left.

“Where’s the hostel?”  I said. He was look­ing like crap, slur­ring his speech, stum­bling here and there. I was start­ing to get wor­ried. As we roun­ded the corner head­ing back down­town, he star­ted to tell me a story:

“Once, when I was a kid, my par­ents took me to Navy Pier (where there is a Fer­ris wheel) for the day. My dad gave me ten bucks, for rides and stuff. There was this guy, sit­ting there, beg­ging. I gave him the money. My dad gave me hell, said I was an idiot, that I wasted his ten bucks. But I didn’t feel bad. I fig­ure that that guy must of really needed it.”

When we got to the hostel he didn’t want to stay. I knew he would have to get rid of me. “There’s an all night diner around the corner,” he said, “the sub­way is in the other dir­ec­tion.” I don’t know why I gave him the money. I said good­bye, and we shook hands.

As I turned the corner, I watched him go back into the hostel and make a phone call. In a moment he was back on the street, cross­ing over in the wrong dir­ec­tion. I fol­lowed as he went in to a corner store, and watched as he bought lot­tery tick­ets and an ice cream cone. When he came out of the store the stag­ger was gone. The slur in his speach had cleared up. Back on the side­walk he said to me “hey, be care­full,” and then he was gone.