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Top 10 Children’s Books: Trying Out New (Bad) Behavior

Top 10 Books of Kids Trying Out New Behavior

I think it’s essential for children to try out new behaviour in a safe place. Like it or not, this probably means at home, on you, the parent.  It’s a child’s way of spreading their wings; trying out new personalities and traits.  A safe way to experiment is important because your child knows that you will always love her or him no matter what.  But a book can also be a safe way to try out new behavior as a reader if you talk about the book in the context of how it makes you both feel.

The Day Leo Said I Hate You is from Robie H. Harris who writes many of the sex ed I posted on previously (It’s So Amazing is an amazing book and highly recommended by moms!) .  I think all my kids went through a phase where I was “The Worst Mommy in the Whole World!”  The power of “I Hate You” is nicely done is this book and much more fun to discuss than when directed in anger at me.

So I built this list around The Day Leo Said I Hate You as my inspiration book, and found 9 other books in which kids are trying out new behavior.  What was really interesting to me was how many of the illustrators from one great book, also wrote their own wonderful book that falls into this category.  That’s kismet!  We start and end with a Bang! (Molly Bang!)

I hope you enjoy these books with your children as well as the joys of your children trying out new behaviors.  Is this a phase or a lifelong endeavor?  Is this what we call a mid-life crisis?  What do you think?  Please leave me a comment!

10. The Day Leo Said I Hate You by Robie H. Harris, illustrated by Molly Bang

My six-year-old son loves this book.  While he has said, “I Hate You” to me many, many times, I usually hear that “I’m the Worst Mommy in the World.”  It was interesting when Leo says this, my son is shocked and says he would never say this to me, his beloved mommy.  So I gently had to remind him that, indeed, he did say this to me.  It made him stop and think about the power of his words. [picture book, age 3-7)

The Day Leo Said I Hate You,, children trying out new bad behavior top 10 picture books

9. Pippi Longstocking by Astrid Lindgren

My middle daughter who is trying at times loves, loves, loves Pippi Longstocking.  She’s the girl who gets to try out any kind of behavior she wants with NO consequences.  So, I guess this book falls in the category of … FANTASY! Nevertheless, this is a classic that endures! [chapter book, ages 6-12]

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8. Curious George by H. A. Rey

Sometimes it’s easier when an animal gets to try out new tempting-but-bad behavior.  And Curious George is so human-like, and frankly, little boy-like that he is the perfect “safe” substitute.  Who wouldn’t want to steal a wheelchair and go down a ramp as fast as possible?  Or climb up a dinosaur skeleton?  Or go to the moon?  This is another classic picture book series that endures.  [picture book, ages 4-7]

pragmaticmom,, top 10 children's books trying out bad behavior

7. How I Became a Pirate by Melinda Long, illustrated by David Shannon

I don’t know any little boy who doesn’t love this book, mine included.  Being a pirate looks fun with no rules or teeth brushing, but it’s not so fun at bedtime!  [picture book, ages 4-7], top 10 best children's picture books trying out new behavior

6. No, David! by David Shannon

The book jacket says that David Shannon wrote this very book when he was a young boy after being tired of being told no all day long by his parents. The initial concept book was a book filled with the world “No!”  It doesn’t surprise me!  He’s such a talented author and illustrator.  My kids all loved this book and though the words are pretty minimal, they loved figuring out from the illustrations what David was doing that was naughty.  p.s.  They especially loved when David walked to school without his pants!  [picture book, ages 2-6]

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5. Two Bad Ants by Chris Van Allsburg

I think that Chris Van Allsburg is another one of those authors incapable of creating a bad book. The artwork alone is enough to buy this book, but the story is great too.  Two ants decide to play hooky after a run for sugar.  They stay behind and have the worst day ever! When the other ants come back that night, are they ever glad to rejoin the line! [picture book, ages 5-8]

trying out new bad behavior top 10 children's books,, pragmaticmom, pragmatic mom

4. Best, Best Friends by Margaret Chodos-Irvine

Sometimes it’s hard to be gracious when your best friend gets all the attention because it’s her birthday so something catty just slips out.  That’s just the way girls roll.  Luckily, at preschool at least, this is all fixable!  [picture book, ages 3-7]

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3. Finally by Wendy Mass

This story has two cautionary themes running thought it:  Be careful what you wish for!  and What Comes Around Goes Around.  [chapter book, ages 8-12]  I have a post on it here.

be careful what you wish for, finally,

2. Lily’s Purple Plastic Purse by Kevin Henkes

Lily is an icon.  At the Wheelock Theater, this book is now a play.  And what is not to love about Lily?  Of all the mice characters in children’s literature, she has one of the strongest personalities and there is some pretty stiff competition:  Mickey Mouse, Stuart Little, and more!  In this book, Lily has trouble waiting her turn to share her new gifts from her grammy.  She has bad day and hates her usually beloved teacher for a few hours, but all is well in the end.  [picture book, ages 3-7]

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1. When Sophie Gets Angry — Really, Really Angry by Molly Bang

This book won a lot of awards and at first I really didn’t get it.  I guess it was because my oldest child does not have an explosive temper.  But my second does as do many kids who need a complete 360 degree head rotating meltdown to center themselves.  I love her illustrations and this book now comes with a CD.  But isn’t it interesting how AFTER the meltdown that the same child who seemed like the devil incarnate is beautifully behaving angel?  It’s very cathartic, a meltdown!   [picture book, ages 3-7]

To check out any book more closely at Amazon, please click on image of book.

By Mia Wenjen, PragmaticMom


  1. All 3 of my kids love “How I became a pirate”. And it’s a real pleasure to read aloud.
    Another book about ‘naughty’ behavior that my 4 year-old daughter just loves is ‘Don’t do that, Kitty Kilroy!’. Unfortunately, I think she can relate to Kitty far too well…
    Great list, thanks!!!

    • Thank you so much! I don’t know Don’t Do That, Kitty Kilroy so thank you for the introduction to that book. I will try to find it so I can add it to the list! Thanks again!

  2. Read Aloud Dad

    Fantastic list indeed. I haven’t heard of some of these books – and they all look smashing, so thanks for sharing.

    Another possible addition is “Harriet, you’ll drive me wild” by Mem Fox.

    Read Aloud Dad

  3. Amanda

    Thank you for compiling a great list! I’m going to check some of these out for my daughter.
    P.S. I loved Pippi Longstocking when I was little! I’m glad she’s still popular.

  4. Jenifer Demko

    Thanks MIa-
    Lots of favorites, but I can’t wait to read Best, Best, Friends. It seems like it would be perfect for CES!

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