Would you buy me a cup of coffee?

I was just yucking it up on the phone with a friend while walking around downtown in Portland, ME. As I was hanging up, a guy asked me if I would help him get a cup of coffee. I quickly sized him up: cheap blued sunglasses, modest over-the-head headphones around his neck, a modest blue and yellow ski jacket, black pants and black sneakers. The most striking thing was his hair: spiked up, shaved on the sides. A bit of a goatee, pointed and trimmed. I could smell some cologne or aftershave, too.

I got my wallet and said, “Yeah, I’ll give you two bucks. What’s your story?”

He told me he was staying in the shelter and tomorrow he has to be at the Chinese restaurant to try to get a job as a dishwasher. I asked which restaurant; he didn’t know the name, but he described where it was. I know the place.

I told him I thought he seemed to have it together, so I couldn’t help but wonder why he was looking for change. It didn’t seem to fit. I didn’t get an explanation. Instead, he asked if I had any work he could do today so he had something to do until tomorrow. He seemed humble and sincere. Perhaps a bit lost and purposeless.

I told him I didn’t have anything, but to enjoy the coffee and good luck at the restaurant.

As I was walking inside to get my own coffee, he looked awkward as he walked in behind me. Maybe he felt a bit shamed for asking for money and then following me in to buy a coffee behind me. I don’t know. I noticed he tried to stand away and keep a socially acceptable distance.

I ordered my coffee and said I’d get whatever he was getting. I just gave him $2, but bought him a Venti with room for cream, too.

I’m probably one devastating company announcement away from the gutter myself. I’ve been close before. If it all comes crashing down around me, would you buy me a coffee?

Author: Eric Holsinger

Eric Holsinger is a software professional and photography enthusiast in Southern Maine.

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