I Went to My 40th High School Reunion — Here’s What Surprised Me

I never know quite what to expect at one of my high school reunions.

High school itself can feel like one long audition to fit in. We try on identities, seek out our tribes, and often drift into the tide of expectation, carried along by who we believe we’re supposed to be, how we’re supposed to look, or how to act. The fear of judgment is real and relentless.

In my early 30s, I found one of my journals from 10^th grade in a box shipped to London, where I was working for Microsoft. By then, I was a well-traveled, confident adult with a thriving career, living my best life as a single woman in the heart of an exciting, foreign city.

As I read through those pages, I felt sad for the awkward teenage girl who penned the entries. I never felt pretty. I can still remember the sheer agony of getting dressed for school. One entry read, “Everyone’s going to make fun of my bangs. They’re too short.”

I spent the whole day nervously waiting for some mean girl to mock me. No one said anything.

A surprising shift

Our earliest reunions sometimes felt like performance art, with a “look how great I’m doing!” energy. There was an unspoken scoreboard of who had “made it” versus who was still figuring things out.

The last high school reunion I attended was the 25th. In those 15 years, something softened. This time around, the careful veneers cracked, the pretense thinned to almost nothing. I was genuinely surprised by the candor that spilled out, even while setting up tables for the event.

People talked about the messy and meaningful parts of life: the marriages that didn’t last, the second acts, the kids who are struggling (or thriving in ways we never expected), the careers that looked good on paper but never fed the soul, about parents and friends lost. There was no posturing, no glossy highlight reel, just honesty, humility, and the relief of saying out loud what once would have felt like failure.

At long last, we all showed up as who we really are.

At the after-party in a local bar, in an extraordinary conversation, I learned that one of the most beautiful, most popular girls had been miserable, a prisoner in a powerful clique.

Another, one of the brightest people I’ve ever known, told me how she lost her shot at valedictorian. A bottle of unopened alcohol was found in the hotel room she shared with others on a band trip. She hadn’t brought it, hadn’t drunk any, but the entire group was suspended for the last two weeks of junior year. She missed all her final exams. Just like that, the title she’d worked so hard for vanished. Even after all these years, I could hear the weight of it in her voice, how unfair it still feels, how it shaped her life.

No More Pretending, the Luck of No Smart Phones

Someone shared that she’d told her husband of 30 years she was done being married. But getting a divorce would be too complicated, so she’s simply going to live her life, and he can live his. She was radiant as she discussed chucking her current life to work on cruise ships, or maybe become a Hollywood location scout. I just thought, You go, girl.

Another admitted, “I got exhausted pretending to be happy. It’s so much easier to admit that life is hard instead of covering things up with bulls**t fake happiness.” The conversation began about Facebook. But it struck me as an overall truth, and something I’m guilty of doing in my own life.

Another friend and I toasted our great luck that no smartphones existed to document all of our stupid teenage shenanigans. They live only in memory, and not on r/holdmybeer on Reddit.

A Strange Truth

There’s a strange truth about people you grow up with: no one will ever know you quite the same way. We witnessed each other’s beginnings. From now on, I plan to make a genuine effort to stay connected to them, to keep these conversations alive.

I’d rate my own high school experience as mixed. Yet, I experienced this defining chapter alongside a very specific group of people. They knew me before I had any polish, before I figured out who I was, before life layered on experience, a career, travel, books, a marriage. Before acclaim, loss, and reinvention.

I Wish I Could Talk to My Teenage Self

In a move that would likely surprise my teenage self, I rocked a miniskirt on the first night. I slightly regretted the choice. It wasn’t the best option for navigating bleachers at the Friday night football game in a stiff wind. Still, the fact that I wore it—and felt good in it—says something about how far I’ve come.

I wish I could go back and talk to the girl who penned the journal. I would tell her not to worry, that 40+ years later, she would feel beautiful and confident enough to wear a miniskirt and a short dress to the Saturday night dinner and genuinely not worry what anyone thought.

Maybe that’s the gift of the passage of time. Not to relive who we were, but to finally see each other and ourselves clearly for who we’ve become. I left with a full heart and a head filled with lessons I didn’t see coming. For that, I’m grateful.

Positive experience at a high school reunion? Share your thoughts in the comments.