Families who loved Penny Draws a Best Friend by Sara Shepard often look for books with a similar feel. These 20 recommendations were selected for their similarity in style, theme, and reading level.

A parent would reach for this book when their child is experiencing the painful growing pains of a shifting friendship or struggling with internal anxiety that feels hard to put into words. This illustrated novel follows Penny, a fifth grader with a busy, worrying mind, as she navigates the heartbreak of her best friend suddenly outgrowing their shared interests. The story deals tenderly with the reality that people change, while validating the physical and emotional sensations of anxiety. It is perfectly appropriate for elementary and early middle school readers, offering a comforting reminder that while some doors close, new and more authentic friendships are waiting to be found. Parents will appreciate how it models healthy emotional processing through art and humor.