To the Class of '29

(Or, what the Class of '99 is still teaching me)

I don’t remember the first day of high school. If I try, I can pull up fragments—stories, faces, flashes of moments—but lining them up by year is tricky.

Usually, I sort them by who I was dating or obsessing over at the time (rarely the same person). That’s my internal filing system.

If I’m honest, most of high school I was scared I was pregnant. Which is absurd, since I didn’t have sex until after high school. But I was high-strung, anxious, always convinced disaster was around the corner.

What I’m learning through this blog, and through this brutal diagnosis, is that even when my head was full of panic, apparently I didn’t dump it all on other people.

(Emily, my best friend, is the exception. But that was different—we weren’t just trauma-bonding. We were building a forever friendship before we knew what that meant. Which is maybe why her dad was one of the first paying subscribers here. Kind, yes. Sweet, yes. But Emily will always remind me he still only calls her pumpkin, so I know my place.)

Now, my son is starting high school. He got into his top choice, Shawsheen Valley Technical High School, and he’s buzzing with nerves and excitement. I am too. God willing, he’ll make a team and I’ll get to sit in the stands and cheer for the Rams.

We’re both nervous. Because it’s high school.

Has high school ever actually been good for anyone? And if you say “those were the best years of my life,” I can’t help but wonder if you ever think about how you treated others in that time.

I don’t remember ever being cruel—aside from the usual sibling battles with Lindsey—but I still worry. I worry that I hurt someone without knowing it, that some kid still carries something I said or did all these years later.

Lately, though, people from high school have been reaching out. They remind me of kindnesses I’d long forgotten. They share memories of me listening, empathizing, floating between cliques without judgment. They’ve offered me support that has been surprisingly grounding in this season.

That’s data. Proof. That even when it didn’t feel like it at the time, kindness lasted. It stuck.

I’m not Gen X, and I'm not really a millennial either. Born in 1981, I’m that blurry in-between. And I grew up in rural New Hampshire, the kind of rural where the grocery store was forty minutes away. Everyone knew everyone. That kind of closeness makes it hard not to see the humanity in people.

It turns out that’s been my best strategy all along. And now, with a son about to start his own high school story, I’ll lean on those reminders.

Because being kind, even when it feels small or invisible, is never wasted. It is always, always a winning strategy.

So thank you, Class of ’99. For proving that to me then, and again now.

I don’t know if all of my former White Sox and Cubs teammates will be Rams, but enough of them that this picture will 100% be submitted to the Class of 2029’s yearbook (they still make yearbooks, right?)