The Unique Bond Between an Art Collector and his Sugar Baby

My 53rd birthday party at the office was also something of a going-away party. I was about to go on a three-month sabbatical so that I could take a road trip across the US. As an amateur art collector and artist dabbling in watercolors, it was my idea to visit all of the most well-known art museums in the country and attend exhibitions. And of course, I had this romantic vision of myself stopped by the side of Route 66, painting desert landscapes at sunrise along the way.

Of course, working at a tech firm, most of my colleagues didn’t understand that. A woman from the programming department, whom I had always suspected never liked me, had written, “Enjoy your midlife crisis tour,” on the card. Ha. Ha.

My family also didn’t understand. In fact, because the trip was to start on the anniversary of the finalization of my divorce (not my intention, I swear!), my adult son told me that he thought it was good that I was finally getting back out there. I suppose he thought that I was going across the country to find a new wife or something.

Anyway, I tried not to let the outside noise affect me. I had tuned up my car. I had reservations in nice Airbnbs all along the Pacific coast. Art tours of private collections were booked. Gallery openings scheduled. I had a plan. People in a midlife crisis don’t have plans. They go out and buy sports cars. I was definitely not in crisis.

Two weeks into my trip, the exhaustion hit me like a brick wall. I was tired of the endless monotony of the road between cities. My back hurt. I kept waking up after my alarm, so I had missed every opportunity to paint at sunrise. In fact, I wasn’t painting at all. And because the driving was taking so much out of me, any time that I did go to a museum or exhibition, I found that I didn’t want to be on my feet for more than an hour at a time. My back was just too achy.

And that’s when the idea seemed to sink in. This really was my midlife crisis tour. And it wasn’t giving me even a fraction of the satisfaction that I had been expecting. I felt defeated, so I did what any broody, washed-up artist is wont to do: I went to a dive bar.

I was on my second beer and scrolling on my phone when I saw an advertisement on Facebook for a live model drawing session in the city I was in. It wasn’t until tomorrow, but I figured I could rearrange my trip by a day or two.

I was even feeling a little bit good about how whimsical I was allowing myself to be when the person sitting next to me at the bar gave me a nudge. She was a young brunette with a big smile and glasses. I had been so absorbed in my own thoughts that I hadn’t seen her next to me.

“I’m going to that event tomorrow,” she said, shyly, pointing at my screen.

“You are? What a coincidence!” There was a part of me that thought she might just be messing with an old man.

“Yeah,” she said. “I’m an art student. I go to all of the drawing sessions.”

I wasn’t sure what to say to that, so I said something incredibly stupid: “Do you ever go as the model?”

Luckily, she hadn’t heard my sad excuse for a joke as she had grabbed the bartender's attention and was asking for her drink. While the gin and tonic was being made, I jumped on the opportunity to ask some follow-up questions that I hoped were not idiotic.

Turns out, they weren’t. We had some banter back and forth. I learned where she was going to school and what kinds of mediums were her favorite. And when the bartender came over with her drink, I waved her off from paying.

“From one starving artist to another,” I teased. This time, the joke landed.

“Thanks, my name’s Casey,” she said, before taking her leave to go hang out with her friends.

The next night, I was incredibly nervous, but I knew that I had to go to the drawing session anyway. If I didn’t, I would kick myself for the rest of my days.

It was a pretty packed scene, and luckily, I wasn’t the old guy among a sea of young art students. There were people of all ages with their easels and their charcoals and their fancy paper. I suddenly felt kind of foolish that I had only brought a standard sketchbook and some pencils. Still, the atmosphere was pretty welcoming, and I was happy to see that people were chatting with one another and lending each other materials.

Casey was already there, alone, and had saved me a seat.

“Glad you could make it!” She said, and my fears that she had been messing with me melted away.

The session itself was brutal for me. Drawing someone in person is difficult and even more so when you’re sitting next to an in-training artist. I was blown away by Casey’s technique. She was clearly going to be a pro in a way that I may never be.

What made it even worse was how kind she was about it. Every time she looked over at my scribbles, she nodded appreciatively, as if she actually liked my style. I knew she was being nice, and I liked her even more for it, even though I was burning with embarrassment.

When the session was over, I wasn’t sure whether to run or ask Casey to go for a drink. Luckily, she made the decision for me.

“There’s a brewery not too far from here. Would you want to join me for a beer?”

Over our IPAs, Casey told me more about her art and her hopes for the future. She said that she loved being an artist, but was realistic about what her chances were of actually being able to support herself on her art. She said that she was looking into graduate programs to become a high school art teacher in case things didn’t work out.

“Don’t get me wrong, I would be very happy with that outcome. But, you know, who doesn’t want to become a professional full-time artist?”

It pained me to see Casey already thinking about putting her hopes aside before her career had even begun.

“But, enough about me, who are you, traveling artist man? Tell me your story.”

Before I realized it, we had spent two hours at the brewery, and they were getting ready to close for the night. I couldn’t stand the thought of this conversation ending, but I didn’t want to push anything. For all I knew, Casey saw me as some old man in a midlife crisis.

To my surprise, she kissed me as we were saying goodbye. I was thrilled but also taken aback and not entirely sure that I wanted to open this can of worms. I pulled back.

“I’m so sorry,” we both said at the same time. I cut her off before she could say any more.

“No, no. I’m sorry. I’m just right out of a divorce. I didn’t expect…this. And I’m leaving tomorrow, so I would never want to give you the impression that I’m just looking for…you know. Not that I don’t, or wouldn’t want to, you’re beautiful. I’m just, I’m sorry. This is a messy time for me.”

Casey didn’t seem all that phased, actually. We said goodnight and made plans to have breakfast together before I hit the road.

I, for one, couldn’t sleep that night. Between the excitement of the night and the pain in my back and the flashbacks to how poor my drawings looked compared to Casey’s, I was a wreck. But by morning, I knew what I was going to do.

“This is crazy,” I told Casey as we were stirring half & half into our diner coffees. “But I’ve made a decision. I’m cancelling the rest of my trip.”

Casey looked up from her coffee, looking a tiny bit concerned.

“I’m going home. I’m getting the rest of my trip refunded. I’m driving back. But it’s because I’ve thought of a better way to spend that money. I want to cover your expenses for a year after art school so that you can put off going to grad school and really try this thing.”

At first, Casey was just quiet, but I could see a spark in her eye.

“We just met yesterday,” she reminded me.

“I know talent when I see it,” I said.

Not six months later, I visited Casey again (this time, I arrived via plane). She was having her first exhibition of oil paintings. The place was absolutely packed, and I was in awe of seeing her work in a gallery.

When she saw me, she planted a big kiss on my cheek and told me that she had already sold three pieces. It was enough to keep her going for a few months longer and get her some attention from art galleries in the next city over. More than that, I knew it was enough to boost her confidence, to give her the real sense of accomplishment she would need to become a full-time artist.

I took a look around the room.

“If I’m going to be your fourth buyer, I’m going to have to move quickly! Show me what you’re most proud of; it’s coming home with me.”

I still paint from time to time, and my home is slowly filling up with paintings that I adore. But, by far, the most meaningful thing I learned from my sabbatical was how fulfilling it is to help other artists follow their passion. That, I wouldn’t change for anything.