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A Letter to My Son on His First Day of Kindergarten

A Letter to My Son on His First Day of Kindergarten

Dear Max,

Tomorrow is your first day of Kindergarten. Your backpack is packed, your new lunch box is set to go and your summer “homework” is in a folder ready to be turned in.  In a way, it feels like it took forever for this day to get here, but in another, I can’t believe you turned five and are starting school. Your dad and I have thought a lot about this day for the past year or more and it prompted a lot of changes in our lives. We want what is best for you and your brother, especially where your education is concerned so we thought a lot about where to live and what kind of school to send you to.

First Day at Bright Horizons

I hope that as you start school, your exuberance doesn’t wane. Your curiosity is going to get you so far and help you move past things that are difficult for you. In the years to come your differences may become evident to others but I hope they never become evident to you.  I just hope you continue to feel comfortable and confident and that this is the beginning of bigger things for you. You are so smart and so charismatic.

I cannot wait to see you get on that school bus, though I’m sure it’ll be through tears…mine not yours. I wonder what you’ll be thinking and feeling sitting in that big seat all alone. You aren’t going to know anyone; not one person. You’ve memorized your address and phone number and you know to sit in the front of the bus. You know to ask the bus driver for help if you need anything. I slipped a note card into your backpack with all your information and you have a new medical id bracelet. We’ve done all we can to prepare, the rest is up to you.

First Ride on a School Bus

So have a great day tomorrow. Eat your snacks and lunch and participate during circle time. Say hello to people when they say hello to you, and do your best to make a new friend. Know that your dad and I are thinking about you (and most likely your brother too). I’ll be waiting for you when you get off the bus in the afternoon so be ready for a big hug and probably more tears from your mom. The first day of Kindergarten is a big deal for me too you know. You’re my little boy, but this is the beginning of your big boy life and even though you are ready, I’m not sure that I am.



  1. MediaMom August 28, 2012 at 2:30 pm

    Tears are streaming down my face. I can’t believe our kids are heading off to new places with new people. I am not ready. I am glad they are.
    Just know the circle of life goes on. Benjamin was wearing the shirt in this picture just yesterday. 🙂

  2. Profile photo of Kate

    Kate August 28, 2012 at 3:07 pm

    Made me cry too and I’m years away! Beautiful post.

  3. EricaB August 28, 2012 at 4:32 pm

    Posts like this should have a tissue disclaimer at the top. Maybe an icon that tells me to be ready for a good cry.

    You have prepared him for this moment for so long and now he will spread his wings and fly. It is amazing to see how Max has grown and all that he has accomplished in his 5 years. It is because of you and Ian that he is the wonderful boy he is. Congratulations as you both begin kindergarten too.

  4. Heather August 28, 2012 at 5:20 pm

    Beautiful letter!

  5. Bridget August 28, 2012 at 7:40 pm

    Oh, this is so sweet. Can you imagine that they let them get on the bus like this?? Next week, I’ll put Teagan on the bus and I know I will be crying my eyes out. As a second child, she has a little more freedom but I remember when Ceara went to school, I kept thinking, I barely even let her play upstairs by herself and now she is getting on a bus, on her own! Good luck. It sure is hard, especially when you are so used to getting daily info from the center. But it is also a lot of fun and truly amazing to see how they change and thrive.

  6. Nr. Happy September 7, 2014 at 2:38 am

    Wait until they’re 26 and reciting back your transgressions..

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