You're walking north on Dearborn through Printer's Row, portfolio in hand, and you're feeling pretty good about yourself and about the early-morning showing you've just wrapped up. Work's picking up, the lean years are just about behind you now. You feel confident. You take long strides.
Out of the corner of your eye you see a fellow cutting a diagonal across the street; he's walking right toward you. You size him up. He's black, not dressed well, but not too poorly. He's small, probably not a threat. He approaches and timidly requests a moment of your time. A panhandler, then. You're just coming out of many years of cold-shouldering these people, and now you occasionally come up with a quarter or two if they can come up with a good enough line. You're picky. These people took advantage of you when you were young, traveling alone. Your good nature wore thin. After that you were poor, so you were tight with your dough. Now, though, you've usually got something in your pocket, so you've started listening again, trying to discern the genuinely needy from those who just think you're an easy mark.
"Listen, don't be afraid," he starts out. You think, did I look scared? Of you?
"Listen, I'm from Long Island and I'm trying to visit some friends that live around here." The accent is right, so far so good. You'll listen, but you don't slow down. He has to walk fast to keep apace.
"I parked my car over by that big fountain at about three this morning when I got to town. I went for a walk to stretch and check out the city and the police towed my car. I've been up all night. I called my friends and it turns out they live in Lockport, way out west." It's a good story, you can relate. Maybe you'll give him some change.
"Look, all my stuff was in my car, all my money, my clothes, everything. I'm trying to get out to my friend's place so I can get some sleep and get this all straightened out." Your hand is already in your pocket. His story is either true or very imaginative, and by your standards either one qualifies him. Besides, he seems nice. Humble enough, anyway. You're feeling generous. You're not even sifting through the change this time, just grabbing it all, and it feels like the better part of a buck. You're still walking. You wish he'd wrap up his pitch.
"I called the train station and there's a train I can take to Lockport at 9:30. All I need to get on the train is four dollars and sixty-five cents. Can you help me out?"
Five bucks? Man, these guys are getting ballsy. Five bucks, eh? You smile, pull your hand out of your pocket, and reach his way. You drop 79 cents into his palm and for a moment you feel real good about yourself. The guy looks at the change, stops dead in his tracks. His shoulders drop and the hopeful, friendly expression washes out of his face. You think: ingrate.
"Seventy-nine cents?" He whines it at you. You tell him, hey, it all adds up, and you think of the stories you've heard--from cabbies, from friends in New York--about panhandlers living double lives, pulling down 30 thou' a year tax free. But then you hear his voice from 10 or 15 feet back, and he's saying "Thanks a lot" in a sad, lost, sarcastic tone, and something about that tone grabs you, tells you in an instant that his story is true, absolutely every word, right down to the four dollars and sixty-five cents, and you've left him standing cold and alone in Chicago. You know the odds of him getting the five bucks he needs, the odds of him making his train, are very remote, and you realize how little the five bucks really means to you right now. Your gut tells you to turn around, but no, you'd feel silly. But maybe silly wouldn't be any worse than what you feel right now. But then again, you can feel shitty all by yourself, you don't need to share that with anyone, not with this stranger, and so you just keep walking.