Penny Draws Books in Order

The Penny Draws books are Sara Shepard's warmest stories, aimed at middle grade readers who might recognise their own worries in Penny Lowry. Penny is a fifth grader who writes letters to her dog Cosmo and fills her notebooks with funny doodles whenever her anxiety starts to spike.

In Penny Draws a Best Friend, she returns from summer break eager to see her longtime best friend Violet, only to discover that Violet has changed. Suddenly Violet thinks Art Club is for babies and prefers hanging out with Riley, the meanest girl in school, leaving Penny feeling abandoned and convinced she must have done something wrong.

As Penny navigates awkward lunches, confusing social rules and a big secret her parents are keeping, she finds help from a new group of friends and from Mrs Hines, the school's feelings teacher. The book mixes strange classroom details, fart jokes and simple black and white cartoons with gentle explanations of panic and intrusive thoughts.

The sequel, Penny Draws a School Play, finds Penny halfway through fifth grade and facing even more change. Her family is moving to a new house, her mom is about to have twins and everyone in class is required to take part in the school play, which is Penny's worst nightmare. Once again she leans on Cosmo, doodles and counseling to try to be brave.

Taken together, the series shows that worry can be managed with practice and support rather than magically cured. It is a good fit for readers who are not ready for Shepard's darker thrillers but still like stories about friendships, family surprises and figuring out who you are.