To My Sweet Boy, For The Day You Drop Mommy Off

by Mary Katherine
first day of preschool sad mom
Mary Katherine / iStock

“Mommy, come with me? Mommy, no leave?”

I put on your tiny shoes and your hand reached up to hold mine. We pulled your blue doggy backpack over your shoulders, and I smiled reassuringly, but my heart frowned. In the parking lot of your new preschool, there were already tears in your eyes. Your feet shuffled toward your classroom and you gripped my finger like a vice. Your lips were turned down.

If this is a good thing, why does it feel so hard?

On your first day of preschool drop-off, you reached your arms out and cried my name. Big ole tears streamed down red cheeks. I gave you a kiss and walked back to my car, literally turning my back on your cries. The whole thing wrecked me. I wish you were old enough to understand why, but at 2 years old, you aren’t.

You’ve already gone back inside with your friends. You’ve probably stopped crying. Well, I’m just getting started. While these feelings are fresh and achey in my heart, I am sitting in the car, writing you a letter. Because when you get older—when you can finally understand—there is something I want you to know about preschool drop-off.

My sweet boy,

By the time you are able to read this, these preschool drop-offs will be a distant memory. Truth be told, you probably won’t remember them at all. You won’t remember the screaming or the tears or the way your teacher calmly held you as I hurried my way back to the car (in case I lost courage and ripped you away from their arms). You won’t remember all the panic on my face or the redness in your cheeks. You won’t remember, but I promise I will.

You won’t know how Daddy and I agonized over which little school would enrich you, protect you, and encourage you to grow. How it took us six months in our new town to finally gain the courage to sign you up. How after visiting 12 schools—twelve!—we settled at the quaint Jewish temple with colorful paper on every wall. The teachers were all so kind and had been there for years. We wanted you to trust these adults. To make new friends and play in confidence without Mommy hovering nearby. You’ll never remember how we fretted over this decision, losing sleep and tears. You couldn’t possibly remember, but your parents certainly will.

You won’t know how guilty I felt at home, cleaning the carpet for the third time. How the dishes were done, the bed was made, and how I was certain that by 10 a.m., your confidence in me was officially crushed. While you were wondering where Mommy was, I was on the phone with Ms. Joanna, getting an update on how you played with that brown plastic donut and laughed when the teacher blew bubbles during circle time. By now, you couldn’t possibly remember these details. But sweet boy, know that I will.

Maybe you’ll be 7 years old when you read this, rolling your eyes because this letter only proves how ridiculous Mom truly is. Maybe you’ll be a teenager, embarrassed by this emotional trainwreck of a confession. Or maybe, I like to imagine, you’ll be packing up a safe four-door sedan with blue jeans and polo shirts. There will be a college bumper sticker on the back, a tank full of gas, and you will smile at me assuringly as I grip your hand like a vice.

And maybe as you pull out of the driveway, you’ll find this letter folded neatly in the passenger seat.

There will come a day when Mommy is the one at drop-off. Perhaps I’ll put on a brave face. Or there will be big tears streaming down red cheeks. Either way, it will be your turn to hurry back to your car and leave me sniffling in the rearveiw. And when that moment comes, you’ll be looking ahead to some new adventure—not looking back.

You won’t be remembering the lunch boxes, the tiny socks, or your 2T Mickey Mouse T-shirt. That I woke up an hour early today so we could make wild-berry muffins before preschool. You won’t remember that I dropped you off at this quaint preschool, and sat in the car to write you this letter (while sobbing like an idiot). You won’t know all of the pride and love and joy and sadness that simultaneously consumes a parent’s heart when they see their child take a step, or leap, toward independence.

You won’t know how that feels. But I will.

Mary Katherine