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 10th 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.
I’m glad we had time to chat. From our early school days to the devastating hurricanes last year. I feel we are two friends that can pick up our conversation every 10 years like yesterday.
I am looking forward to your next book. I may even buy one this time. 😀
So great seeing you! I know, I feel the same way. I’m awaiting word if my first fiction is getting picked up as I write this. I should find out in the next few weeks.
Wow. What a great piece. You really captured what the 40th feels like in a way thar I wished I experienced my 40th, but failed to go as deep in the conversations.
Thanks Andrew. I didn’t go to the bar after the game on Friday, and I regret that now. I also had an amazing time talking to people just setting up on Saturday morning. I didn’t write it in the piece, but I have felt quite isolated since I started caring for mom 24/7 back in 2023. And I’ve been at the island house most of the time, so I’m here locally, I just don’t make a point to see people here. This weekend made me realize I really need to change that.
This was beautiful, Kathleen! I love it when you write posts like this. I went to my 40th in May. It was exactly how you described it – no one seemed to care anymore about the superficial stuff, they just wanted to talk. I’ve kept in regular contact with several friends I hadn’t talked to in 20 years since.
Thanks, Clare. Yes, I’ve decided I’ll be trying to post an essay at least a couple times per month. I’m at work on another memoir, but I can’t finish it yet because I’m living it. I’m curious to see how it turns out.
Wow. I cannot believe that you didn’t think you were pretty in high school. I had such a crush on you.
Well, you could have told me then.
That was beautiful, Kathleen!
I read it out loud to my daughters and choked back tears. My eldest daughter said, “that was well written.”
We stayed at your lovely place in 2023.
Thanks so much, and I’m glad you could share it with your daughters.
What a beautiful story. I saw in your newsletter that you are writing another memoir and finished a novel, I can’t wait for another one of your books.
Hi Jenna,
Thanks so much. I don’t know which will be first. I am also looking at releasing Sakana Lesson in English. So far been only released in Japanese in that market. So I think I should have something out in 2026.
How wonderful of you to share this. I am headed to mine in two weeks, and now I am so excited about it. Love your books.
Beautiful. Thank you. I feel so much better about my high school insecurities and I will go to my next reunion.
Your words captured the essence of our 40th reunion so perfectly—what many of us felt but couldn’t dream to express so well. I’m truly impressed by the way you brought the experience to life. Thank you for sharing your reflections and helping us all relive such a meaningful time together
I went to my 40th reunion in NC and told the story of my life… A mean girl wrote me the summer that I was in Alaska visiting my father before my sophomore year in high school that the most popular boy in school said I had “little beady eyes “ … I was so traumatized that I allowed my father to talk me into getting my Mother and little sister into moving to Alaska… my father’s brother and many family members ended up in Alaska and we’ve had a fabulous life there…
My classmates were outraged that she’d said that, as he was the kindest guy in our class and he NEVER would have said that… he was the first of my classmates to die in Vietnam 😢
Our lives were enriched by our move to Alaska but it just shows what one mean girl can do to a family…high school can be a bitch !!!
Having known you since time immemorial, I can confirm what he said was inaccurate. And yes, you’re right, the power is strangely lasting.
Glad yours went well. Went my 30th after not having attended others. In HS, I was part of many groups of friends but didn’t really fit in with any one clique. Same thing happened at the reunion. “I paid for this?” I thought.
Passed on my 40th. Perhaps I missed out on the softened edges you described.
Maybe I just love my life now too much to go back and rehash. Maybe the 50th will be different, God willing.
You should definitely go, Jeff. If not, crash some other high school reunion party. Have fun with it. 🙂
Beautiful. I found the same thing at my 40th. I hadn’t gone since my 10th, and debated whether to go and it was a wonderful weekend. People seem to just be so happy to see one another, and had let their guards down.
Beautiful post, and insights, Kat!
Wow Kathleen!
This was amazing. It clearly describes the chapters in so many individual lives and the personal growth as the years accumulate. I can’t believe it’s been 40 years already.
We never know what challenges people face; whether a child or an adult. It is so important, to always remember, to be kind.
This post rang a lot of truth in my world growing up as well. I had my challenges to but nobody really knew it. Reading this brought tears to my eyes.
I’m sorry you never felt pretty. You were so sweet and kind.
I wish I had the opportunity to talk more with you Saturday evening. We will catch up at next meet up hopefully or reunion.
God bless!