Families who loved The Worst Things in Life Are Also Free by Jim Benton often look for books with a similar feel. These 20 recommendations were selected for their similarity in style, theme, and reading level.

Reach for this book when your child is using sarcasm or self-deprecating humor as a shield for their social anxieties or feelings of inadequacy. This installment of the Dear Dumb Diary series finds Jamie Kelly navigating the unstructured doldrums of summer break and the pressure to keep up with her wealthier or seemingly perfect peers. Through Jamie's hilariously cynical diary entries, the story explores the complex dynamics of female friendship and the temptation to take shortcuts to achieve status. While the humor is edgy and the protagonist is often flawed, the book serves as a safe space for middle schoolers to see their own messy, jealous, and sometimes mean-spirited thoughts reflected and validated. It is an ideal choice for 8 to 12 year olds who are outgrowing earnest stories and beginning to develop a dry, observational wit. Parents can use Jamie's antics to start low pressure conversations about integrity, the reality of 'get rich quick' schemes, and why we sometimes feel the need to compete with our friends.