The History Teacher - Mr. Shaw
Three and a half years of friendship with my high school history teacher (a.k.a friend #19)

Our first conversation from February 2023 can be found here.
It’s two days before my 29th birthday—a sunny Wednesday morning; Mr. Shaw and I are sitting on a Richmond Hill café patio. We take our usual orders of coffee and a muffin, falling back into routine, despite not having managed to meet over the last year.
I’ve kept him up to date on anything major via text, and he’s done the same. But the chance to chat in person allows for easy banter.
“You’ve promised a book, twice now,” Mr. Shaw reminds me.
“I know,” I say, smiling.
“Maybe write it first,” he says with a grin.
I explain that if I had published what I wrote three years ago, it would have captured one very specific chapter of my life: Miami, the pandemic, a breakup. But three years later, there’s more to the story. There have been new friendships, new experiences, and a business that didn’t exist when I first sat down to write. I could even devote a chapter to the friendships I made through Facebook Marketplace.
“What were you doing at 29?” I ask Mr. Shaw.
“I was in Japan or maybe coming back from Japan. I was single,” he says.
“How old were you when you got married for the first time?” I ask.
“33,” he says, pausing to think.
Nothing in my 20s has gone according to plan, but I’m happy. I felt this self-imposed pressure to find my life partner by my mid-20s, and there was a sense of disappointment when that didn’t happen—but I can’t deny that wonderful things did happen. I made great friends, built community, studied in New York, and created a life I’m proud of.
“The most stressful time in my life was actually when I was a teenager,” I say. “I worried about my grades and what people thought of me. I couldn’t control what happened. Now, if I want to try something, I can. I can book a flight or just go for lunch. And even though life’s unexpected, I feel lucky to be able to play the game.”
Getting older also means becoming more familiar with life’s fragility. In early April, my neighbour and friend Danielle (friend #36) passed away peacefully in her sleep. At 26, she was a brilliant thinker whose gentle presence touched those who knew her.
The start of my friendship with Mr. Shaw in early 2023 coincided with the sudden passing of his friend and colleague, Mr. AppleJohn. We reflect on our friends, people who both lived beautifully and had something to look forward to.
“When did your mom pass?” I ask Mr. Shaw.
“In November,” he replies.
At 101 and five months, Mrs. Shaw lived a long life. She was a Christian missionary who spent years of her life working with women in Nigeria; those years made up my history teacher’s childhood.
“When anyone would ask her how she was doing these last ten years or so, she’d say, ‘Too blessed to complain,’” says Mr. Shaw.
In her final days, surrounded by her family in New Brunswick, she told stories of her younger years. Singing a song from the ship ride to Nigeria about seasickness.
Our conversation, as always, jumps between subjects. My inquiries or thoughts lead us in different directions.
“Did you ever have students who did poorly in your class but whom you liked as people?” I ask.
“Oh yes, of course. I could recognize that they may have lacked interest in the subject or had other priorities. Some become occupied with social dynamics. But we could still have a good laugh, and I saw them as good people,” says Mr. Shaw.
The classroom has changed significantly in recent years. I was never a student in the age of A.I., and Mr. Shaw was never a teacher. I wonder how these changes will shape the friendships students make, too.
In the fall, Mr. Shaw is going on a motorcycle trip through southern Spain.
“I went to a shop and bought a travel guide of the area. It’s fun writing in the margins and making notes of what I should see,” he says.
“That does sound fun,” I say.
There is something reassuring about realizing that the curiosity of youth doesn’t disappear with age. Maybe, like in high school, life becomes more comfortable with each grade. We begin to understand it better and become familiar with its walls. For all the good and all the bad, we learn to understand ourselves within them, and in doing so, we enable our pursuit of happiness.
“We have two lives, and the second begins when we realize we only have one.”
― Confucius


