One of the many highlights of boarding school was the first night of snow, junior year. With all that snow outside—pristine, untouched—evening study hall was quickly forgotten. Soon the entire dorm, from the youngest freshman to the oldest senior, was playing gleefully in the snow, despite ongoing study hall. The dorm faculty, who were supposed to be enforcing it, instead watched from the sidelines, smiling begrudgingly.

I remember thinking at the time that this was what boarding school meant—what I would remember for the rest of my life. These spontaneous moments of joy that, though sometimes silly, illustrated the sense of community that boarding school (living with people 24/7) foments. Today, I think the very same thing.

But, to be honest, at first, I didn’t look forward to boarding school at all. Two separate summer programs that I had taken in the two years prior (one at a prep school, the other at a university) had me braced for tons of schoolwork, tons of homesickness, and virtually no fun—only this time it would be for four years instead of several weeks. 

But after the trials and tribulations of the application process, the agonizing weeks of waiting for the result, the brief burst of joy that followed, and one fifteen-hour flight to Boston later, I found myself at Milton Academy, attending the Transitions Program specifically reserved for international students as well as local students of color. 

The happiness and gratification at my (thankfully) successful admission had faded somewhat, making way for the dread that summer school had imbued in me. Little did I know that my expectations would be completely subverted… 

…because they didn’t do justice to the two-week horror that was my experience at the Transitions Program. I discovered just how different things were, compared to CIS (where I had come from). 

The thing was, so many of the students at the Program had come from the Milton Academy Lower School; cliques had already been formed and closed off, friendships had already been established, etc. International students congregated via common language, which might have been a reasonable course of action for me if both my Cantonese and Chinese weren’t so catastrophically bad. The groups of athletes were also out of the question for me. 

So, in summary, I was alone. I was alone among this super-diverse group of individuals with whom I would, in theory, be able to connect with the most easily; who knew what the real school year would be like? Going from being socially secure (back at CIS) to almost complete social isolation had hit me like a truck.

The first and only time I spoke to my Transitions roommate was when we wandered all over campus together on the first morning, looking for the dining hall that ended up being right beneath the dorm we were staying in! For the rest of the two weeks, he pretended like I didn’t exist, which made living in the same room pretty awkward. Anyways, each night I would think to myself: What have I gotten myself into? Four years of this?

Oh, classes were fine, I guess. Though the social aspect of things still leaked into the classroom (friends sitting together etc.) the academic environment seemed new to everyone, leveling the playing field somewhat. But for every eight hours of solace I spent in classes, I spent sixteen more out of them; this daily insight would turn out to be strangely prophetic in an unexpected way, which I’ll get to in a moment. 

So, when Transitions finally ended, I couldn’t even breathe out a sigh of relief; the school year (and my career at Milton) had officially started. 

Duly moving into my room in a different dorm (Forbes House, where I would be staying for the rest of high school), I met my advisory group (the six freshmen in the dorm) with whom I’d be living for the rest of the year. And this meeting, the very first of many, many to come, was like sunlight breaching the clouds. I honestly don’t know what made the difference, but this seemed like the first real conversation that I’d had since arriving at this school. We played a card game until lunch, at which point we went together. I felt like I belonged. 

Over the course of the first year, the sense of comfort and belonging that I felt in that small group would propagate as I got to know others in the dorm—lowerclassmen, upperclassmen, even faculty—through dorm activities, dorm dinners, and more. My fondest memories include, but are by no means limited to, dressing up in ridiculous costumes and yelling our heads off as we sprinted to the gymnasium for the annual dorm dodgeball tournament, sledding down the slope behind the Observatory until our clothes were soaked with melted snow, practicing our dorm Christmas carols in off-pitch preparation for serenading the campus… the list would go on, and on, and on. 

The lesson I learned was that these things—forming bonds and trust—take time (at least for me); no three-week summer course, no two-week Transitions Program could match the familiarity I acquired from living with the same people day-in, day-out for months upon months. There was no room for deception; you got to see other peoples’ true selves, and you got to show others your true self. That was also the biggest difference, I think, between boarding school and CIS. 

Being part of this core group of people gave me the confidence to make other decisions—joining the freshmen soccer team, writing for the student-run newspaper—that let me meet so many new peers, new friends from all around the world: friends I could sit with in class, say hi to on the way to lunch. These became new places (outside of the classroom) where I finally fit in. All the while, Forbes House itself was rapidly becoming a second home, its denizens becoming a second family. The house head was the “mom” of the dorm in all but name, and we boys had no qualms at all about calling each other “brother.” Like a family, we relied on each other, each person playing a part in a collective responsibility. Like a family, we had arguments, though these were often easily hashed out. And I should emphasize the idea of second family as opposed to replacement or surrogate; the relationships I formed and the roles I played within it were completely novel, as well as distinct from the affairs of my immediate family. 

Now, even though classes had become ever more enjoyable as I adjusted academically, I looked forward to the end of the school day, when I could finally be at home again. In a dramatic turnaround, those eight hours—that had ironically once been a sanctuary to me during Transitions—had quickly become a still engaging affair whose end I nonetheless looked forward to each day. And, living that lifestyle—that ideal lifestyle—day after day, week after week, month after month, for years, I got used to it. I started seeing it as the norm. I took it for granted. 

Because when COVID reared its ugly head just as Senior Spring was about to begin, everything went kaput. School was suspended (“temporarily”), and everyone had to go home.

• 

We saw each other off, clapping each other on the back, saying: “See ya in a month!” Way back then, in those naïve, innocent times, that’s how long everyone thought it was going to take for the pandemic to blow over. One month became one month and a week. Then two months. Then three. The eventual arrival of summer heralded the loss of all hope. Graduation was online; it was lukewarm. 

In the end, the thing I regret most is not being able to say goodbye. The thing I regret most is how things just stagnated into oblivion. The thing I regret most is not seeing what I had for the blessing that it was. Like with many things, when I had it, I took it for granted, and when I didn’t have it anymore—when I realized that those experiences were over for good—only then did I understand its true importance. 

Ultimately, that is what boarding school meant—means—to me: meeting people and enriching my life through fostering genuine, genuine, genuine relationships (that I would not have found in any other situation) in this boarding school environment that is tailored for such things. I will fondly, sorrowfully, remember this social element as the essence of boarding school. 

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By Calvin Cheong

Published 10-08-2021