Every March, our elementary school—like many—observes PARP (Parents as Reading Partners) month. It’s filled with literary activities: a book drive, Starry Story Night (the kids go to school in pajamas at night and teachers read to them), Do the Write Thing workshops (I’m always happy to participate as an instructor), and of course, Character Day, when you come to school dressed as a character from your favorite book.

When my boys were little, Character Day was met with Halloween-caliber delight. They’d happily toddle off on the bus in elaborate, head-to-toe Clifford or Pooh Bear costumes, their three clues (for the Guess Who I Am segment) painstakingly penciled on notecards tucked into backpacks that were bigger than they were.

These were the days when I was more stay-at-home Mom than I am now—even though I’m still a Mom and still stay at home most of the time. Back then, I had about as much fun as the boys did, deciding which character they would be.

When my older son was in fourth grade, he was the Mad Hatter from Alice in Wonderland, wearing a ridiculously enormous hat of his own creation. Then came fifth grade. He—the boy who still had his nose buried in a book every waking hour—didn’t want to dress up for Character Day. The rest of us were aghast. What was going on? How could he not be interested in Character Day? He loves books more than anyone. Ah, yes—but he no longer loved wearing silly costumes among his peers. Imagine.

Finally, he grudgingly agreed to stuff a magnifying glass in the back pocket of his Levis and go as Encyclopedia Brown. Turned out most of the kids in his class didn’t even participate to that extent—and needless to say, he wasn’t happy about being one of the few. The magic of Character Day had clearly given way to adolescent angst.

He went off to Middle School shortly after that, leaving us with only one kid to outfit for the next few character days. I was tremendously sentimental. Thank God, I thought, we still had his brother, and a few more elementary school years to cherish.

My youngest is now a fifth grader, in his last few months of elementary school. He brought home a flyer two weeks ago, outlining the PARP events. I’m sure it’s around here somewhere, buried in a pile of unread mail and newspapers. Thus, yesterday morning dawned like any other around here—in a flurry of get-the-boys-up-and-out-the-door-to-school activity. Somewhere in the midst of it all, we realized it was character day.

My fifth grader was all too willing to skip it, but I managed to convince him to participate one last time. We ran through the gamut of costumes we could easily assemble at the last minute—including, I’m sorry to say, Encyclopedia Brown. If only we knew where the magnifying glass was.

In the end, he grudgingly agreed to be a character from the book he’s currently reading and loving: The Westing Game. The boy, it seems, is a runner. He wears shorts and a tee shirt and sneakers. Sweatband? Nope. Singlet? No way. He might be willing to carry a water bottle. That’s pretty much it.

So off he went to the final Character Day of our family history. The Runner. I still don’t know his name—only that it wasn’t Pooh or Clifford or any of the larger-than-life childhood characters who made it all seem magical back in the day.

Or maybe Pooh and Clifford weren’t responsible for the magic after all. Maybe it was two little boys and a mom who still got to hold them on her lap every night and read them bedtime stories.

In the end, I’m guess I’m glad to have this last bittersweet Character Day behind us. Not because life has gotten too busy and we just can’t be bothered—although I’m sure that might be part of it.

But mostly because I finally figured out that it might be harder and sadder to hold on when it’s time to let go than it is to just let go.