The Last First Day of Kindergarten

By Claire Mullen | Family Matters | August 2022 Issue

I’m not quite sure how it happened, but it did. This month, my baby is off to kindergarten.


I’m certain that he’s ready. And I’m pretty sure that I’m not.


He selected his brand new, “big boy” Star Wars backpack and matching lunchbox before I’d even had a chance to clean the crayon nubs, Animal Cracker crumbs and handprint art masterpieces out of his Pre-K bag that I’d noticed around Christmastime occupied much less space on his back than it did when I watched him get out of the car and walk toward his classroom, hand-in-hand with his teacher, for his first day of his last year of preschool.


He’s visited his new school and proclaimed that it is awesome. He knows his ABCs and 123s, thanks in large part to his preschool teachers who have, over the years, taught him those but, more important, instilled in him the things kindergartners really need to know. Things like how to share. How to listen. How to include others. How to help a friend who is hurt or sad. How to say “please,” “thank you” and “I’m sorry.” How to not stick marbles up your nose. How to open a yogurt tube without causing a volcanic eruption at the lunch table. How to wash your hands properly (“Go back and try again with soap this time, please”) and long enough (sing the “Happy Birthday’’ song twice).


He’s officially earned the long-awaited rite of passage of making the special, solo “back-to-school” trip to Target with Mom to carefully comb the aisles, list in hand, in search of items like chubby pink erasers, blunt-tip Fiskars, #2 Ticonderogas pencils and wide-ruled paper. He’ll get to pick out a fun keychain for his backpack, and we’ll throw in an extra tub of Clorox wipes for his teacher for good measure.


After that, we’ll stop by the shoe store for a new pair of high-top Nikes to replace his favorites that grew too small too quickly over the summer. After all, according to my boy, “kids need fresh kicks to go to kindergarten, Mom.” These shoes will be a splurge and a consolation to offset his khaki pants and collared shirt school uniform that I already know he will say is “too itchy” and “too fancy.”


When back-to-school eve is upon us, he’ll have the skills and knowledge he’s learned at home and preschool over the past five years. He’ll have his supplies organized and ready to go. He’ll have his uniform neatly pressed and folded. He’ll have a lunch packed with all his favorites and a special note tucked in. And he’ll have his fresh kicks. About all of that, I am not worried one bit.


What does weigh heavily on my mind (really, my heart, if I’m being honest) is the thought that maybe I let all the days between Nov. 9, 2016, and Aug. 17, my boy’s first day of school, fly by without savoring every one of them. Did I rock him enough? Did he spend too much of his babyhood strapped in his car seat, being hauled all day long from big sister’s school drop-off to a series of mundane errands and after-school activities?


Did he suffer any ill effects from the lack of all the luxuries that I was easily able to provide for his big sister, who had me all to herself until she was almost 3: homemade baby food; long midday crib naps in a quiet house; afternoons spent sprawled together on the carpet in her bedroom with picture books, colorful toys, and nowhere else to be?


What about all the hours that I parked him on the couch with an iPad and a cup full of fruit snacks so that his sister and I could get through a day of virtual, pandemic-era kindergarten? Did I pull out Play-Doh or finger paint for him often enough? How many times did I say “not right now” to his invitation to jump on the trampoline or battle action figures? What if I simply just did not do enough?


I would imagine that if you polled all the mamas and daddies, just about every one of them would say they oftentimes feel this way, too. And, when I really think about it, I bet that if you asked the opinions of their sons and daughters, including that of my 5-year-old, they would say that Mama and Daddy are doing A-OK. Maybe this is just how you feel when you send your littlest boy and a big piece of your heart to kindergarten.


And so, on Aug. 17, I’m going to let go of all that worry and self-doubt. I’m going to embrace the excitement of this big day. After all, it is the last first day of kindergarten in our family.


I’ll wake up early and make everyone a big breakfast. I’ll tuck in my kindergartner’s shirt and try to tame his cowlick. I’ll take a picture of him standing on the front porch, proudly holding his chalkboard sign. I’ll drive him to his new school and remind myself that even if I’m not ready, he is. And then, on the ride home in my empty car, I’ll say a special prayer. “Dear God, please help my son remember to wash his hands. With soap.”