To My Dearest Child: Reflections on Your First Day at Preschool

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“Mommy, will you come with me? Mommy, please don’t leave?”

As I carefully placed your little shoes on your feet, you reached for my hand with a grip that felt like a tiny vice. We adjusted your bright blue backpack, and while I flashed you a reassuring smile, my heart felt heavy. In the preschool parking lot, I could already see tears glistening in your eyes. You shuffled toward your classroom, holding my finger tightly, a frown etched on your lips.

If this milestone is meant to be positive, why does it feel so painful?

On your first day of preschool, you stretched out your arms and cried out my name. Tears streamed down your cheeks, making them appear even redder. I kissed you goodbye and reluctantly walked back to my car, turning away from your cries. The experience left me shattered. I wish you could comprehend the emotions swirling within me, but at just two years old, I know that you cannot.

By now, you’ve likely settled back in with your new friends, and the tears have dried. Meanwhile, I’m still processing my feelings. As I sit in the car, I’m writing you this letter. One day, when you’re older and can truly understand, there’s something important I want you to know about those preschool drop-offs.

My Sweet Child,

By the time you read this, those drop-off moments will be mere echoes of the past. In truth, you probably won’t recall them at all. The distress, the tears, the way your teacher comforted you as I hurriedly made my way to the car—all of it will fade from your memory. You won’t remember the worry that painted my face or the panic I felt inside. But rest assured, I will never forget.

You won’t realize how much thought your father and I put into selecting the right preschool for you, ensuring it was a safe and nurturing environment for your growth. It took us months to summon the courage to enroll you after visiting twelve different schools. We finally chose that charming temple filled with vibrant artwork on the walls and kind, experienced teachers. We wanted you to build trust with caring adults and foster new friendships, all while learning to play independently without my constant presence. You won’t remember these anxious decisions, but your parents certainly will.

You’ll never know the guilt I felt at home, cleaning and preparing everything, thinking that by 10 a.m., your trust in me would be shattered. While you were likely wondering where I was, I was on the phone with Ms. Clara, eager for updates on your day, delighted to hear that you played with the colorful blocks and giggled during storytime. You won’t recall these details, but sweet child, know that I will.

Perhaps you’ll discover this letter when you’re seven, rolling your eyes at how sentimental I can be. Or maybe you’ll read it as a teenager, feeling embarrassed by my emotional outpouring. I like to imagine, however, that you’ll find it as you prepare for college—packing up your car with clothes and essentials for your new adventure, with a reassuring smile directed at me as I hold your hand tightly.

There will come a day when I’ll find myself in the role of the one being dropped off. Maybe I will wear a brave face, or perhaps tears will flow down my cheeks. Regardless, it will be your turn to drive away, leaving me behind, sniffling in the rearview mirror. In that moment, you’ll be focused on your new journey, not looking back at the past.

You won’t remember the little things: the lunchboxes, the pairs of tiny socks, or the 2T superhero t-shirt that I put out for you. You won’t recall that I woke up early to bake blueberry muffins before preschool or that I sat in the car, writing this letter while tears streamed down my face. You won’t grasp the mixture of pride, love, joy, and sadness that fills a parent’s heart as they witness their child take significant steps toward independence.

You may never know how deeply these moments resonate within me. But I will always remember.


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