Gather initial thoughts and broad opinions about the book.

1. Gordon Korman often writes about kids who feel like outsiders, as seen in his books Restart and Ungifted. If you have read other books by Korman, in what ways did Dexter’s “fish-out-of-water” experience feel familiar to Korman’s style, and what felt new or unique about his journey in Old School? Did you find his story ultimately hopeful?

2. What was your experience reading from the multiple perspectives of Dexter, Gianna, Jackson, and others? How did hearing the story from different viewpoints, especially from characters like Ronny or Ms. Napier, shape your understanding of the events at Wolf’s Eye Middle School?

3. What did you think of the book’s blend of humor and heart? Which moments made you laugh, and which did you find genuinely touching? How did Korman use humor to explore more serious themes like bullying, loneliness, and intergenerational connection?

Encourage readers to connect the book’s themes and characters with their personal experiences.

1. Leo Preminger serves as Dexter’s mentor, sharing wisdom that extends far beyond academics. Think about a mentor or an older figure in your own life who has taught you something valuable. What lessons did you learn from them that couldn’t be found in a traditional classroom?

2. Dexter tries to fit in by wearing a T-shirt that says “T-SHIRT.” Have you ever had a similar experience where you tried to fit in but didn’t get it quite right? How was your reaction similar to or different from Dexter’s?

3. Dexter’s practical skills, like fixing a radiator or a coffee maker, come from his “old-school” education at The Pines. What practical skills have you learned in environments outside of school? Do you think they are valuable enough that they should be part of the school curriculum?

4. How did you feel about the “Justice for Dexter” movement that takes over WEMS in the book? Think about a time when you felt passionate about a cause or stood up for someone you believed was being treated unfairly.

5. The novel contrasts the chaotic, rule-bound environment of WEMS with the supportive, community-centered world of The Pines. What kind of environment helps you learn and feel the most connected to others?

Examine the book’s relevance to societal issues, historical events, or cultural themes.

1. The book explores the social gap between younger and older generations. Dexter ultimately becomes a bridge, bringing his classmates and the seniors together through shared activities. Where do you see similar generational divides in our society, and how effective do you think the book’s vision of connection is as a model for bridging them?

2. How does the novel’s portrayal of Dexter’s homeschooling by a community of retired experts challenge or support common ideas about education today?

3. What does the conflict over Dexter’s Swiss Army knife suggest about zero-tolerance policies in schools and other institutions? Given current events in American schools, do you agree or disagree with these policies?

Dive into the book’s structure, characters, themes, and symbolism.

1. The story is told from the first-person perspectives of several characters, which allows the reader to see their internal motivations. How does this narrative choice affect the reader’s perception of the antagonists, Jackson and Ronny?

2. Why does Dexter’s “grandpa” clothing alienate his peers? How does the detail of the logo T-shirts at WEMS help explain their strong reaction? What do the logo T-shirts reveal about the other students at WEMS?

3. The discovery of the bunker becomes the key to saving the school building. Is this ending “earned” through foreshadowing and logical plot structuring, or would you argue that it’s a deus ex machina (a suddenly introduced, convenient plot device that seems to come out of nowhere)?

4. Did you feel that Gianna or Ronny had the more compelling transformation, and what does their development reveal about the nature of friendship?

5. In what way does the contrast between The Pines and WEMS explore different definitions of what makes a place a true community?

Encourage imaginative and creative connections to the book.

1. If you were to design a new class for WEMS taught by one of the residents of The Pines, whom would you choose as the teacher? What would the class be called, and what kind of unconventional lessons or skills would students learn? Imagine what the final project for that class might be.

2. If you took over the Eyeball after the school’s refurbishment, what would be your first headline story about the new and improved school and the bunker museum?

3. What would be an amusing “old-school” problem for Dexter to solve with his newly modified Swiss Army knife?