A guy I used to know writes about a weird idea he has. He wants me to paint one painting for every month him and his lady have been together.

In order to meet him to talk about it, I have to travel to a neighborhood full of memories. I don’t go there often. I have my reasons. Now I have to act like a tourist where I used to live if I want to get out unscathed.

The bike ride takes about an hour. Plenty of time to ruminate. Is it a good idea what this guy has in mind? Will she see it as a grand romantic gesture or a creepy/obsessive token of his neediness? I’m glad I’m not on either the giving or receiving end of this transaction.

When I was in art school we all sneered at Matisse’s wanting his art to be like an easy chair, but now, who the fuck knows? Even the most steadfast purist gets tired of the bed of nails after a time. When someone likes something I make, I don’t question why or how they like it. What it means to them. If it feels the same as their favorite furniture, so be it.

With commissions, this is doubly true. I hardly have any idea why people ask what they ask for. They have their reasons. It’s none of my business. I’m just the implement selected to carry out the operation. A scalpel doesn’t ask what it’s cutting and neither should I.

The meeting is short. He sends me a series of reference photos with short descriptions/instructions. We settle on a price. This is a Christmas present but it’s still early October. Because the timeframe for his monthly memories is this year, he will have to send me November’s and December’s as they happen. I pedal away from there, back to my own neighborhood.

When I get home, I scroll through his photos. It’s all vacation. The Boundary Waters, South Carolina, Michigan, Florida. These are the moments people live for. They toil away month after month for the highlight reprieve. Places that aren’t their home, not the dull old everyday, are what they look forward to all the time.

I can’t remember a single vacation. Not since childhood. And those aren’t very happy recollections. Like the time I didn’t tell my parents I was burning up with fever as we drove from Boston to Disneyworld. I’d looked forward to it so hard I made myself sick. I was damned if I’d spoil it after all that horrible waiting.

When my father turned 70 and a family cruise to Alaska was planned, I wished them a pleasant journey. As an adult, I see vacation as a distraction from my life that I neither appreciate or want. Almost like a punishment. The best part to me about leaving my little corner is coming back.

But here are dozens of snaps of a smiling couple in various environments. Golf courses, beaches, woods, Christmas. I have to withhold judgment, can’t editorialize, otherwise these paintings will be total crap.

I choose ten photos for January to October and get to it. It’s months later now when I write this, so I can’t reproduce my thought process as I painted. This is one of the great saving graces of painting. There’s no retrieving where the mind goes. At it’s best its a relief from thinking of any kind. I’m thankful for the guy and his vacation highlights for letting me check out this way.

With ten paintings done, I frame them up, put them away in a closet and forget them. I have to wait for the last two months’ memories to happen and be frozen in pixels and sent my way so I can complete the cycle.

The big difference between commissions and my “real” work is that the commissions rarely keep me up at night. I don’t think about them when I’m not doing them. The only time I do is when they aren’t going well. Of course, it’s tough to say how they’re going until the buyer sees them. The only metric of success is their reaction.

I do occasionally ponder the guy’s grand gesture. Christmas morning when she spends half an hour unwrapping the twelve flat boxes. Will he wrap them separately or in one giant package? Will she love it or run away screaming?

Back when I used have relationships with women, I was pretty good at giving presents. But I never did anything on the scale of this. The best I could manage was a nice piece of jewelry or a fancy dinner. Maybe I could learn something from him.

The November and December photos arrive and I set to putting this thing to bed.

I rent a Zipcar for a couple hours so I can be in and out of the cursed neighborhood lickety split. I unpack the twelve paintings and he has a big smile on his face. Mission accomplished. The work was worth it. He gets out his checkbook and shakes my hand.

I’m home an hour later. The studio wall is empty. I can start over as if I never knew a thing about that year of someone else’s vacations. I’m happy he’s happy with what I made him, but have no clue what to actually feel about it. Maybe I’m meant not to feel anything about it. Or maybe I’m just not smart enough to know.

After all, I’m just a dumb painter.