
Tis the season for starting preschool! Jack started preschool last year, and we absolutely love our school. However for the first 2 months last year, we had a lot of tears and hard times at drop-off. The teachers were amazing in sticking with him and comforting him during that time, and I researched all the tips and tricks to make drop off smoother.
We bought quite a few books to help with the separation anxiety he was experiencing – a few were hits and a few were misses. So wanted to take a moment to share the books that worked best for us on this topic. These books really help to reinforce the school routine and the idea that grown ups will always come back to get you.
Fortunately this year has been smooth sailing so far as he’s very familiar with the school and his friends. But my heart definitely goes out to those who are having tough drop offs because I know first hand how hard it can be. Here’s our go to books on separation anxiety and getting used to starting preschool:
best Books for starting preschool and separation anxiety
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1. Don’t go

This book is a little harder to find (we bought used on Amazon here), but I’m including since it was one of Jack’s most requested books around the time his separation anxiety started to taper off at drop-off.
Don’t Go is a sweet story about a boy elephant named Daniel and his first day at school. The author does a really nice job of portraying the sequence of events leading up to drop off through pick up, and was a story Jack really related to. He loved helping Daniel find where in the classroom he placed his lovie for naptime.
2. daniel goes to schooL

Jack loves Daniel Tiger and this book and the associated TV show “Daniel Tiger Goes to School” from season 1 is where we got the little tune “Grown-ups Come Back” that we sang time and time again on the way to school to help reinforce that point.
We absolutely love Daniel Tiger, and it was one of the first and only shows we let Jack watch when he was a young toddler. It builds on the pioneering PBS series Mister Rogers’ Neighborhood, which as PBS states is for “a new generation of children telling an engaging story about the life of a preschooler using musical strategies grounded in Fred Rogers’ landmark social-emotional curriculum.”
This book does a great job of validating the feelings a new preschooler is going through, while offering positive reassurance that grown ups will always come back at the end of the day. Unlike a lot of other books on the topic, this one also has Dad Tiger dropping off Daniel, which is a nice change of pace. Click here to buy.
3. THE NIGHT BEFORE PRESCHOOL

Another book that help illustrate and validate feelings at drop off and throughout the day along with the typical preschool activities. The title has fun alliteration for kids too. For some reason, Jack always loves the lunch scene in this book and looking to see what all the friends are eating! He always likes seeing Mama Llama put the picture Llama Llama made at school up on the refrigerator.
Similar to the Daniel Tiger book, this one also helps to reinforce grown ups come back with the line “Mama Llama you came back!” Once Jack had heard the story a few times, I had him recite this line along with me as we were reading. Click here to buy.
4. LLama llama misses mama

Another book that help illustrate and validate feelings at drop off and throughout the day along with the typical preschool activities. The title has fun alliteration for kids too. For some reason, Jack always loves the lunch scene in this book and looking to see what all the friends are eating! He always likes seeing Mama Llama put the picture Llama Llama made at school up on the refrigerator.
Similar to the Daniel Tiger book, this one also helps to reinforce grown ups come back with the line “Mama Llama you came back!” Once Jack had heard the story a few times, I had him recite this line along with me as we were reading. Click here to buy.
5. the kissing hand

This was one of the first books Jack’s preschool teacher read to the class last year. Gives them a tool they can use when feeling sad at school or other separation. In the book, they learn they can hold onto a kiss from mom or dad in their hand, and pull it out and press on their cheek when they are feeling sad and need some love at school. It’s a sweet message to your little one that even if your parents aren’t with you, their love will remain. Click here to buy.
