When I was a freshman in high school, our youth group went to Chicago for the Holiday Youth Convention. It was like youth group, but with like 1,000 kids and it lasted for 48 hours. When we weren't sapping youth pastors of their energy at the hotel, we were free to sap it on the streets of downtown Chicago. As best I remember, this was my first encounter with a pan-handler.
I was wearing cheap, faux-leather shoes, a size too small, scuffed and peeling at the creases. They were barely passable as footwear. Some guy stopped me and complimented me on them. He made the transition from complimenting to physically shining so smoothly I can't remember it. I do remember looking up as the rest of our entourage wisely walked away, and looking down as the guy went to town on my shoes, dabbing them with hand soap from a dixie cup. The shoeshiner was going on about how his hand soap was actually a fine, high-end shoe-polish, specially formulated to preserve texture and give unbelievable sheen.
Now, I don't know what makes a naive-looking high-schooler a good mark for a shoe-shiner (except for the whole naive-looking part). Why he expected me to pay him to shine my crappy shoes, I don't know. He finished - one shoe, I think - and waited for me to hand over some payment. It's unspoken, but obvious, that you're supposed to pay people for things like this. Since it was unspoken, to me it remained unheard. I thanked him and walked away, and I didn't look back.
I was in Chicago again this weekend, a bit more seasoned to the wiles of the panhandler. I had to catch an early train to get back to a friend's house, and I had skipped breakfast, so I stopped to buy some apple juice from a corner store. I spent one of the two singles in my wallet, unaware that a trainride would be two dollars, and the ticket machine didn't give change. So when I got to the Lawrence Avenue station and paused in front of the machine to consider my options. The clerk fingered me as a newbie, and stepped out to tell me I'd have to get change elsewhere. So I walked down to a Starbucks to make change.
I was greeted out front by a man who quietly asked me for change. (The door to Starbucks is a great place to pan-handle - There are lots of guilty-feeling yuppies hoping to earn some instant karma.) He had just smoked and I could smell his breath, deep and rotten. I could smell his lungs dying inside of him. I didn't say a word, just handed him my bottle of juice and nodded and felt proud. Now, I had to replace my cheap apple juice with expensive Starbucks apple juice, which was mostly ice. But still tasty. I used the singles in my change to buy my ticket and hopped the train south.
The night before, after an unplanned trek down Michigan Avenue, we went to the Cheesecake Factory for some dinner. Dan was a marked man, tall and grinning, the only one in our group with shinable shoes. Just as had happened to me ten years earlier, a man stopped him to compliment his shoes, and we all moved steadfastly forward hoping to pull him along. I told him we had to get to our table (a lie) but the man rambled on just the same and smoothly went to shine the shoes. A few minutes later Anna went to physically rescue Dan and the two of them came back, Dan flustered and Anna frustrated. Dan had given the man five bucks, a huge fee for an unwanted shoeshine. He told us the guy asked for $9 a shoe.
This guy was smart. He probably wasn't homeless, and I don't know if it's more appropriate to lump him in with panhandlers, scam artists, or legitimate nostalgic shoe-shiners. Maybe he's all three. But I think it's appropriate to realize that not everyone on a street corner who asks for change - even the ones that provide a service or a good excuse ("It's my birthday" once scored a couple quarters from me) is someone in actual need. That's where the difficulty really is: When you hand change to someone on a street corner, are you helping them get back on their feet, or stay off them for just a little while longer? A professional mooch can probably have their needs met just fine, especially if their needs are a bottle of scotch and a pack of Newports.
Better than coins: A gift card to Subway or McDonald's.