How My Sugar Daddy Helped Me Discover the Joys of Competitive Chess

I had a math teacher in middle school who absolutely ruined my love of math…and chess. Before then, I actually felt like I was pretty good at math. I enjoyed memorizing times tables and doing division equations in my head. I was even good at puzzles, and often found answers to math puzzles before the rest of the class.

But then, Mrs. Clancy, 8th-grade pre-algebra. She was needlessly cruel and impatient. And she would mark certain students as slow if they didn’t impress her within the first few weeks of the new school year. Plus, if you had an older sibling who had left her with a bad taste in her mouth, well, then you were toast before you could even prove yourself.

“Sorry, Jules,” my older sister told me when she saw that I had been assigned to her old teacher. “She hated me from the start, so she’ll probably hate you, too.”

And hate me she did. She constantly called on me when she sensed that I didn’t know the answer. She had me do equations on the board for the rest of the class to criticize.

And perhaps most embarrassingly, Mrs. Clancy had a special rule that if you finished all your work before the last fifteen minutes of class, you could play chess with a classmate. But, if you didn’t (and I almost never did, because I was overwhelmed and confused), you had to spend the last 15 minutes of class one-on-one with Mrs. Clancy. I don’t want to make it sound like it was more dramatic than it was. But is there anything more dramatic to a 13-year-old than being humiliated and put down in front of your peers? By the end of the year, I was moved down from the honors track to the remedial track in math, and would spend the next four years of high school completely bored in the “easy” math classes.

It’s fine, I thought to myself. I’m never going to need to use any of this. Especially not chess.

Fast forward 8 years after graduating high school, and I’m running my own business as a hair stylist. I absolutely love my job, and I get to work with movie and theater actors. It’s high stress and just about as glamorous as you can imagine.

And the best part is that I outsource all of the math to my accountant, a guy I trust to be honest with my money (at least, I hope.)

Now, in my line of work, sugar dating is pretty common. The mid-to-highly paid actors and producers enjoy having more casual relationships with people within the community. And they are super generous with their time and resources if it means that they can enjoy a relationship that is easy-breezy. If you play your cards right (and date the right guy), you can find yourself invited to the most exclusive parties in the city or be treated to dinner at the best places.

I wouldn’t say that it necessarily makes life easier. I still have to pay most of my own bills and maintain my professional reputation. But it does make life a whole lot more fun. And that’s more than I can say for my girlfriends who are looking for a man who will commit to marriage.

Anyway, I was hired as the lead stylist for a play that was set to run for 6 weeks. And during that time, I got to know all of the actors really well, especially Barry, one of the supporting roles.

Barry was one of the most relaxed, zen guys I had ever styled. Most men were antsy when it came to sitting for their wig fittings. I think they think of it as like the least important part of their job. But not Barry. Barry was very present during the entire thing, asking thoughtful questions about the process and how I got into styling in the first place.

We got to know each other quite well during this time, and eventually, Barry asked if I would want to go out for a coffee once the play was over. Which, of course, I did.

Our first date was at a coffee shop that’s known for having a library of table games. Like I said, I was, at one time, very good at math puzzles, and I’ve always liked competitive games. So, when Barry asked if I wanted to play something, I said, sure.

I didn’t know that he would choose chess, the one game that I had never actually learned how to play.

“Oh,” I groaned with polite disgust. “I know I said sure, but anything but chess.”

Barry was taken aback. He feigned as if I had slapped him in the face.

“But, why? Chess is the best game in the world!”

“Childhood trauma,” I laughed. “I had a teacher who made me hate chess, and math for that matter.”

Barry wouldn’t take no for an answer. “Please, let’s just play one game. I’ll walk you through it so slowly, and if you still hate it, we’ll never do it again. But you once asked me why I’m so calm, and I have to say, it’s because I play chess. It’ll change your life.”

Theater actors are known for being a bit dramatic, but it turns out, he would be right about that last part.

We ended up playing for two hours. I didn’t even realize how quickly the time was going by. I didn’t beat Barry that first date. And I wouldn’t for quite a few weeks. But I was hooked.

“How do I get better at this?” I asked him.

And he gave me the following advice:

Start learning strategy

Barry told me that learning how to play chess was a little bit like trying to write a sonnet in another language. First, you had to learn the other language. Then, you had to learn the rules of sonnets.

Likewise, learning to play chess was a multi-step process. I had to learn the basic rules. I had to learn established strategy (as in, the many different gambits), I had to learn the modern terminology, like “forks” and “pins,” and what it meant to “hang a piece.”

There are books and books and books written on the subject, but I preferred to learn the basics from Barry. He would also sometimes send me articles or passages from books he had read.

Play, a lot

Strategies don’t really mean a whole lot to a visual learner like me unless I can see them in action. So, Barry suggested that I start playing often on my own. I would play online with real players or sometimes against a computer. And, of course, whenever Barry and I had a date, it would end up with the two of us at his place playing chess. This happened once or twice a week, so I was really racking up the hours.

Barry also recommended that I try “cross-training” with math puzzles. The skills weren’t directly transferable, he told me, but it was good to get into the habit of thinking creatively and under pressure. He didn’t know it, but this was right up my alley.

Review your plays

Like any professional athlete, at one time or another, you’ve got to watch the game tape. And this was something that Barry encouraged me to do very early on. He said, get a notebook and a pen and take notes as you play so that you can look back and pinpoint exactly where things went sideways.

This part, admittedly, was the hardest for me. It made me think back on Mrs. Clancy’s glaring corrections on my homework sheets. When I told Barry about this, he smiled. “You don’t have to correct yourself in red ink,” he said. “And it’s not to shame yourself. It’s just to help you get better.”

Push yourself

Over the next few months, I definitely improved. And I even beat Barry a few times. Then a few more times.

I thought that he was going to congratulate me (and of course, he was proud of me), but he said that it was just a sign that I was learning his play patterns, not necessarily getting better at chess in general.

“If you really want to improve,” he told me, “You have to start playing other people.”

At first, I thought maybe this was a roundabout way for my sugar daddy to tell me that we should see other people, and he must have seen the surprise on my face.

“I’m not breaking up with you,” he laughed. “I want to invite you to start playing in my chess club.”

And that’s how I started to get involved with more competitive chess. I have to admit, beating some of the players who took me for “just a hair stylist” was pretty satisfying. And it helped to always have Barry at my side, cheering me on.