I seem to get asked for money on the street a lot, so I’ll usually give a dollar or two, sometimes more. Since I don’t donate a lot of money to organizations, though I intend to (I’m looking at you, NPR), I see this as a convenient way to help someone out. But I’ve run into some peculiar situations doing this.
A month or two ago, a man on the street stopped me on my way to work. I reached into my pockets or wallet, making some kind of gesture that indicated I was agreeable to the upcoming request. But the man waved it off and asked instead if I would go and buy him breakfast at McDonald’s. The McD’s was half a block away, and I remembered I had a $10 bill in my pocket, which would cover even the most expensive breakfast sandwich.
So, we went into the restaurant, made our way up to the counter, and I motioned to the cashier to indicate that he would be ordering, and I would be paying. I don’t know what that motion is, but somehow I made it, and she understood it. The man looked at me and asked if he could get the Big Breakfast. I nodded. Go big or go home.
He ordered, and I couldn’t hear what he told the cashier beyond “two chocolate milks.” Ahh, a sweet tooth. When I looked at the cashier, she said, “That’ll be $12.75.” I’ve made some questionable decisions at McDonald’s in my day, but can’t recall racking up a bill over $10. I just hope he enjoyed the meal and his gallon of chocolate milk.
When I lived in New York, I would walk past the same guy outside my apartment every now and then and he would ask for money to tell jokes. I offered to give him money without the jokes, but he insisted. The one I remember was quite raunchy, but also strangely amusing.
After a month or so we began to recognize each other. And one late night, I offered to take him to a diner, so we could grab something to eat. It was probably 3 a.m., and I was hungry. I thought it would be interesting to sit and talk, judging by his taste in jokes. We sat down at the counter, and I ordered a cheeseburger. Then he ordered “two cheeseburger deluxes to go.” Never saw him again. I wonder if he ate both of those burgers the same night.
Once after a concert, a guy asked me for money to get a drink. It just so happened I was on my way to get a drink. So, I asked if he wanted to come along. There was some NFL Films program on the TV, and we sat, had a drink, and talked about Barry Sanders with the bartender. It was quite pleasant.
I figure if you are going to give money to someone who asks for it, take some time and try to get to know them and what they’re going through. They might appreciate that more than the money. The worst that can happen is they leave you eating a giant cheeseburger by yourself at 3 a.m., which really isn’t that bad.