Boarding School Drop-Off and the Unexpected Grief of an Empty Chair

“Table for Five, Please.”

I said it for years without thinking.
Until the first time I didn’t.

After dropping off my oldest daughter at boarding school, I held it together. I did what so many parents do—I focused on the logistics. We unpacked the car, made her dorm bed just right, arranged her desk lamp and books, fluffed the pillow, and stocked the shelves. I smiled and reassured her while reassuring myself. I was so proud of myself that I didn’t shed a tear.

But the unraveling came later. On the drive home, we stopped for a quick bite.

It came out of the blue and frankly shocked that this was the moment the grief hit me - when the hostess asked, “How many?” 

I started to say “Five,” but shook my head and whispered “Four.”

And just like that, the math of motherhood broke my heart.

It wasn’t the goodbye in the dorm room that got me—it was the empty seat at the table. That one missing plate opened the floodgates. I sat through that meal blinking back tears, pretending to be present, feeling the weight of all the things I didn’t know I would grieve.

It wasn’t just her absence—but the little moments that had stitched our days together. The shared dinners, the car rides filled with nothing and everything, and even the sibling fights in the background. I missed it all. The rituals I’d once taken for granted.

When I dropped off my second daughter, I recognized the ache more quickly.
Another proud goodbye. Another neatly made bed. Another quiet drive home. Another table set for one less.

And now, I’m preparing to drop off my youngest. Soon it won’t be five. It won’t even be four. Or three.

It will be two.

Just me and my husband—after years of raising three daughters—returning to a version of ourselves we’ve not known since we first became parents. The rhythm of our days will change once again, but this time it’s not about making room for babies, or adjusting to school schedules—it’s about rediscovering who we are in the quiet.

Sending my child off to boarding school when they are 14 or 15 years old wasn’t a single moment. It’s a gradual unfolding, a loosening of my tight grip that yearns to keep them safe and secure. It’s trusting that what we’ve built—over years of bedtime stories, carpools, traveling, squash tournaments, fights and late-night talks—will carry them when they are on their own.

Letting go doesn’t mean detaching. It means showing up in new ways: through group texts, weekend visits, stalking Life360, waiting breathlessly for random calls while they’re walking to the gym, and those soul-filling reunions at the gate.

So to every parent walking through this season of change:
If your voice catches when the hostess asks, “How many?”—you’re not alone.

And to my husband—after all these years—you’ll have my full attention finally.
At our table for two.

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