Back to School Books for Kids with Separation Anxiety

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My youngest is now in 2nd grade and has had a full week of school without crying at drop-off. This is a triumph. For both Kindergarten and 1st grade, we spent a good month dreading the morning drop-off.

Through all of it I was told that it’s harder for me than it is for him (once he got into the classroom he usually calmed down pretty fast). Still, it never got easier to walk away while my son was staring back at me crying as the teacher led him through the door. Those days were rough, and we tried all the tips and tricks. For anyone else out there struggling with separation anxiety, know it does get better, even when it doesn’t feel like it will.

Books are a great way to bring up difficult subjects with kids. Children learn through play, and reading time is the perfect time to address their fears while they are safe and snuggled with you!

Here are some of my favorite books for the back to school blues:

School’s First Day of School

by Adam Rex, Pictures by Christian Robinson

Roaring Brook Press (June 28, 2016)

This charming picture book was our favorite of the back-to-school books. It takes a common topic and flips it on its head for a unique and fun look at back to school. In this book, the main character is the school itself, and school is a little nervous about its first day! I loved the unique twist and the playful illustrations. I also think my son was able to have a certain amount of safe distance from a subject matter that made him quite emotional. Because he so closely related to the characters in the other books, he often started crying or getting upset thinking about his own experience. The personification of the school building really allowed him to look from a safe distance while still soaking in the message of the story and really enjoying it.

The Kissing Hand

by Audrey Penn, Illustrated by Ruth E. Harper and Nancy M. Leak

Tanglewood (October 15, 1993)


This one is a really beautiful and sweet book. A raccoon mommy send her baby off to school and gives him a special gift for when he misses her. The illustrations are gorgeous, and I love the fact that the animals featured in the book are going to school at night-time because they are nocturnal! My book came with a set of heart stickers that you could use for your own back-to-school ritual. One of the pieces of advice I was given for my son, was to have him bring something from home that he could look at during the day whenever he missed me. The kissing hand revolves around that same idea, and the actual stickers let you give your child a physical reminder of the book and its lesson.

Llama Llama Misses Mama

by Anna Dewdney

If you’re a fan of the Llama Llama books, this one is a must for your bookshelf. The book is written in rhyme, which kids love, and it follows a little llama throughout his day, leaving mama, getting used to his new school, and going home again. Llama Llama is such a cute and endearing character, and his plight throughout the story will be a very relatable one. In fact, it was a bit TOO relatable for my son. He would get so emotional when Mama Llama left (that’s pretty close to the beginning!) that we hardly ever made it to the end of the book. But when I was going through his bookshelf recently to donate some of our old books, he specifically asked to keep this one. The whole Llama Llama series is beloved in the children’s book world, and in our house.

We still have some hard days, but over all my son is really enjoying his new school year. We hope your little ones are enjoying theirs too! I always recommend these books for anyone transitioning to daycare or school for the first time. Have you had hard transitions? What books do you know and love about the first day of school?

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