Teacher Writes Tearjerking Letter to Kids Who Won’t Be Entering Kindergarten This Year

RachelKiser_200TallRachel Kiser
Blogger | Mom of Two


Back to school season is upon us, and with it, there are school supplies greeting us at the door of every big box retailer, reminders to enjoy the last few days of summer, and social media posts of adorable, well-groomed children holding chalkboard signs as they prepare to start a new year.

In the middle of all of the excitement and hustle, however, it’s easy to forget that there are people who are genuinely hurting at the beginning of this new school year: nobody more than parents who have lost children. As they watch their peers’ children (and even their deceased children’s friends) grow another year older and enter into a new grade, it is insanely painful to deal with the fact that their own won’t be joining them.

Rachel Whalen, who runs the blog An Unexpected Family Outing, is a Kindergarten teacher as well as mother to a precious daughter, Dorothy, who left earth too soon in 2016.

As Whalen was busy preparing for the new school year and gathering her thoughts to send out a newsletter, she couldn’t help but be moved thinking about those who so desperately wish their children were entering school that year.

Summer is winding down and I'm gearing up for a new school year. Yesterday, I sat down to finish my mailing for my new…

Posted by An Unexpected Family Outing on Wednesday, August 1, 2018

“Then, I thought of them,” She writes. “The children who should be coming to Kindergarten. I imagined the families who should be receiving letters from new teachers, but instead, they are receiving yet another dose of heartbreak at the milestone their child did not reach.”

Touchingly, she writes a letter, from teacher to student, for all of the students who are missing from the smiling photos on their porches, who won’t be marching off to Kindergarten for the first time.

She says,

“Dear ______________,

Welcome to kindergarten! My name is Mrs. Whalen and I will be your teacher. I am looking forward to holding space for you in my classroom this year. Even though you can’t physically attend, I will feel your presence in my classroom every day.

Kindergarten is an exciting place and how I wish you could experience it with me! I want to teach you all about letters, the sounds they make, and how to make words. I wish you could be next to me as we learn lots about numbers, plants, and animals. I’ll be thinking of you when we learn about life cycles and watch as our classroom caterpillars become beautiful butterflies. I just know you would have so much fun studying the work of famous artists, making scientific discoveries, and learning so many other wonderful things.

I know how much your families wish you were here to share the joys of kindergarten with them. They want to walk you to your new classroom, help you hang up your backpack, and hear all about your day. Please know that no matter how full our classroom is, you will always be missed.

So, on the first day of school, please make sure you send a little extra love to the ones who are missing you. They will be doing the same for you. I am so honored to have you as part of my classroom and to hold space for you in what should be your year in kindergarten.


Mrs. Whalen”


When I read this letter, I felt like I had been socked in the gut. I remember after our first miscarriage, all I could do was think about how old my child would be at any given time. Birthdays and other milestones passed, and I grieved, wondering who they were and would be. I watched my friends, whose children were similar ages, raising their babies and pictured my own.

The comment section, unsurprisingly, is full of stories from mothers who have lost their little ones.

One reads, “My daughter should be starting kindergarten this year. I teach 4th grade, but I see the kindergarten classes in passing often through the day. I have really been struggling with seeing those kids this year with one important little girl missing. Thank you for this letter. From the bottom of my broken heart.”

And another, slightly different but with the same amount of heartbreak, “My little guy turned 5 last month. He’s not gone like most grieving here. He’s not mine. I fostered to adopt and gave him back. I grieve him and all the moments I have lost.”

“When my son was stillborn the counsellor we saw told us that what should be his first day of kindergarten would likely be incredibly painful. At the time I couldn’t see how that would be possible considering how much pain I was already in. But when that day came it was like a punch in the heart. I missed the excited, nervous, clingy boy he should have been. She was right. It was unexpected how much it would hurt. And now, this September, he should be starting middle school. And again the thought of what should be tears at my heart.”

I’m constantly reminded that days, or milestones, that are joyous for some are incredibly difficult for others— the first day of school being no exception.

It’s a beautiful thing when teachers, who are already angels in human form, are even more understanding of hardships and can encourage families where they are. Whalen’s great loss has turned her into an even more effective and loving educator. So, whether you’ve lost a child or not, let’s hold space for those in our community who have, and not be afraid to speak about their children by name. It could be just what they need in such a vulnerable time.



RachelKiser_200TallAbout Rachel Kiser

Rachel is a wife and mother living in Raleigh, North Carolina. She’s a fan of good coffee, wearer of gray t-shirts, and is constantly starting books she will never finish. Her family is her joy, and she loves to engage with other moms and dads on matters of parenting. Her blog posts have also been featured on the Today Show Parenting Blog and Scary Mommy.

View all posts by Rachel Kiser here.

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