Berrybrook Middle School Books in Order

The Berrybrook Middle School books follow a rotating cast of students through one very busy school, where friendships, crushes, clubs, and family expectations can feel as intense as any fantasy quest. Each volume stands alone, but together they build a shared world readers can keep revisiting.

The series begins with Penelope “Peppi” Torres in Awkward. New to Berrybrook, Peppi breaks every rule she set for herself on the first day and accidentally hurts someone she wanted to befriend. Joining the art club gives her a place to belong, but also lands her in a tug-of-war with the rival science club. Her story sets the tone for the whole series: smart slapstick, quiet emotional beats, and characters who are allowed to make mistakes and grow.

Brave shifts the spotlight to Jensen, a daydreamer who imagines himself as a hero while struggling to see that his real-life problems count. He loves comics and apocalypse scenarios, but has a harder time recognizing bullying, body shaming, and his own anxiety. Through school projects and newspaper interviews, Jensen slowly finds language for what is happening to him and tools to ask for help. The book leans into social dynamics without ever losing its warmth.

In Crush, the focus moves to Jorge Ruiz, the tall, gentle kid other students assume is a tough guy. Jorge prefers to keep the peace and watch out for younger kids, but a sudden crush on drama-club member Jazmine throws him off balance. As his best friend chases popularity and a social media scandal erupts, Jorge has to figure out what a healthy relationship looks like and how to set boundaries without becoming the bully everyone expects.

Diary is a hybrid: part guided journal, part collection of short comics. Readers get sticker sheets, sketch prompts, and space for their own entries, mixed with three new stories that circle back to Peppi, Jaime, Jensen, and a familiar face who has moved away. It feels like a peek inside the characters’ notebooks while inviting kids to tell their own stories alongside them.

The most recent volume, Enemies, centers on Felicity Teale, an artist and gamer who rarely finishes her projects. Constant comparisons to her organized younger sister Letty push Felicity to join an entrepreneur contest at school, hoping a big win will prove her worth. Instead she tangles herself in old grudges, a drifting childhood friendship, and the question of who really deserves the label “enemy.” Her book digs into perfectionism, burnout, and how to repair relationships when you have been part of the problem.

Across the series, Berrybrook feels like a real school: teachers have distinct personalities, clubs actually do things, and side characters wander in and out of different books. The tone stays accessible and gently funny, but Chmakova does not shy away from harder topics like bullying, divorce, or feeling out of step with your peers. Readers can jump in with whichever protagonist speaks to them first, then enjoy spotting familiar faces as they explore the halls from new angles.