The Day My Sugar Baby Inspired Me to Pursue My Long-Lost Hobby

I think if I had grown up in today’s generation, I would have felt freer to pursue my artistic side. But that just wasn’t the reality for me as someone born in the late 60s. All of the men in my family had been war veterans. All of the women in my family had been housewives or secretaries. There was a deeply instilled sense of duty and responsibility to the family.

Like every family, there were outliers in mine. The uncle that no one talked about because he went “off the deep end” and had to see a therapist. The long-lost cousin who moved to San Francisco to join the free love movement and be a muralist. Even my own father seemed to have moments of emotional overwhelm from time to time, and he would retreat to the basement with a six-pack of beer and an artist’s easel with a look on his face as if he was going to do something shameful. When I was a kid, I never saw what he painted, and I had an underlying suspicion that it was somehow depraved and embarrassing.

I, myself, was obsessed with doodling as a kid. I had a hard time focusing in class and would draw in the margins of my textbooks, always in pencil so that I could erase my sketches before returning the book at the end of the year. When I was around 10, my mom found my drawings and made me erase them in front of her. Then she sent me to bed without dinner and treated me coldly for the rest of the week. I got the message. Art, creativity, and any kind of behavior that was out of the norm were not accepted.

I will say, it was a good time to fall in line, to comply with the status quo. When I graduated from high school, I was able to get a good job where I could work up the corporate ladder and make a good living. I used my savings to create a business that I knew would be safe and lucrative. I made good investments in property.

As a good son, I made my mother proud by marrying a good girl. We had three children who went through quite a rebellious stage, but ultimately came out with successful jobs and children of their own.

Suddenly, I was at retirement age, and my wife decided that she wanted to start her life over. We got a divorce, which was painful at the time, but ultimately for the best. When I asked her where things went wrong between us, she told me that things never went wrong, and that was the problem.

“Aren’t you even a little bit bored with your life?” she asked me. I had never thought to be bored, so I couldn’t come up with a good answer.

Shortly after the divorce was finalized, my father passed. When I went to clean out his home, my mother gave me a box of his paintings, saying that she didn’t want to see them. I guess she had never reconciled the man who was her husband with the man who was a secret painter.

When I got home, the first thing I did was look through the paintings. There were some landscapes and still lifes. Some of them were quite good. But the overwhelming majority of work was of a woman who, I realized immediately, was not my mother. No nudes, but somehow even more intimate: her profile, her hands, her hair in a ponytail as seen from behind. Clearly, my father was in love with this woman, and I suspected that my mother knew and decided that banning art was her way of banning this other woman.

Maybe it’s a weird takeaway, but what struck me most about seeing my father’s art wasn’t that he wasn’t faithful to my mother. I decided to set my judgment aside on that front because being disappointed in him didn’t seem like a useful emotion. Instead, what stuck out to me most was realizing that I had never seen my ex-wife the way that my father saw this woman. I loved my wife, and I still feel very fondly about our years together. But this was something different. And I wanted to explore it for myself.

And, maybe I wasn’t ready to tap into my artistic side, but perhaps I was ready to open myself up to connecting with someone that I could be really happy with.

I had no idea how to start that journey, so I asked a few divorced friends over drinks. They told me that dating was all done online these days, and they wrote down a few websites that I could try to meet someone.

For the better part of a year, I tried a few different dating apps that were for older people. And I didn’t find myself connecting with anyone. I don’t want to be rude, but a lot of the women spent our dates complaining about their ex-husbands or letting me know that I would never live up to the love of their life, who had passed away. It was bleak.

Again, a friend of mine came to the rescue and told me that he had a friend of a friend he wanted me to meet. He was honest about the fact that it was a sugar baby, but he told me not to freak out.

“Just meet her first,” he told me. “And then you can decide if you want to be a sugar daddy. If you don’t get along, it’s one bad date. You’ve been on plenty of those lately.”

When June walked into the restaurant on our first date, I was completely gobsmacked. She wasn’t at all what I thought a sugar baby would be like (I’m sorry, but the picture I had in my mind was Julia Roberts in that one movie.) She was in her early 30s, dressed as she had come from the office (and I mean that as a compliment; she was elegant and confident), and had a smile that just about electrified the entire room.

I expected that I would have to be the “adult” in this dynamic, doing everything for my sugar baby, but as soon as June sat down, I felt totally under her command. It made me sweat through my clothes in the first five minutes.

She asked me what had made me interested in calling her, and because I was suddenly unable to string together coherent sentences, I blurted out the story about my father’s box of art.

She hesitated, not understanding my answer. “Oh, so, you’re an artist? Are you looking for a model?”

“No, no no. I mean, I wanted to be, at one point in my life. But no, I was 9 the last time I drew anything for fun. I meant that I wanted to find something that made my life feel like it had a spark, the way that my father clearly had a spark for this woman.”

I was making things worse.

It was obvious that June was used to having this effect on men because she didn’t seem phased at all by my awkward answers.

“I get that,” she said. “So many people live their lives doing what they think they should, and they forget to, you know, live.”

I was speechless. It was like she had taken the jumbled mess of my mind and untangled the exact thing that I wanted to say.

“Have you really not drawn since you were 9? That’s so sad! I draw all the time; it helps me stay focused during meetings. Look,” and she rummaged through her bag to show me her notebook, which had drawings in the margins.

When I tried handing her notebook back, she stopped me.

“Nope, not so fast,” she said playfully and handed me a pen.

“Don’t draw me, that’s too much pressure. Draw that plant over there. You don’t even have to show me afterwards, but you’re not going to go another day of your life without making some kind of art. I’m serious about this.”

June and my first date was the start of a relationship that would change the way that I saw myself. Every time we saw each other, she would bring a notebook and a pen for me to draw. Eventually, I did start drawing her, and I took lessons so that I wouldn’t be embarrassed for her to see my drawings.

When the anniversary of my dad’s passing comes around, I always feel sadness, but also gratitude that his art inspired me to make this kind of change in my life. I feel grateful that I can display my drawings of June without secrecy or fear. Maybe I found that spark late in life, but hey, I found it.