Gather initial thoughts and broad opinions about the book.

1. How did Denny’s first-person narrative shape your reading experience? Did you find his unfiltered, literal-minded voice to be a reliable guide through the story’s chaotic events, and how did it affect your connection to him?

2. If you’ve read other books with a neurodivergent protagonist, how did Denny’s characterization compare? What did you find unique about his journey?

3. What was the most shocking or surprising revelation for you in the novel?

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

1. Denny’s mantra is to be a “good guy,” but his good intentions, like trying to return Tom Hanks the goose to Canada, often lead to disaster. Can you think of a time when one of your own well-intentioned actions was completely misunderstood?

2. The relationship between Denny and George is a cornerstone of the story. Have you ever had a significant connection with an animal? If so, what did this relationship teach you?

3. Angus often helps Denny cope with difficult situations. Share a story of a time when a friend helped you during a challenging time.

4. Throughout the story, Denny forms a “found family” with Nori, Theo, and others in his community. Within your own life, who is part of your found family? What are some shared values and experiences that have brought you together?

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

1. The novel illustrates how the national issue of gun violence becomes a source of personal trauma for Denny. Did the story’s focus on his individual experience change your perspective on this broader societal problem?

2. Denny’s interactions with law enforcement repeatedly end in violence and misunderstanding because they misinterpret his neurodivergent behaviors. What critique is the novel making about how the criminal justice system treats people with developmental disabilities?

3. Tesky is a wealthy, powerful man who uses his influence to exploit others. In what ways does his character reflect broader societal issues of power, abuse, and the grooming of young people by those in authority?

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

1. Kennedy uses the frame narrative of Denny writing in a notebook for Dr. Harland. How did this structure shape your understanding of the events and your trust in Denny as a narrator?

2. The Toy Story theme song, “You’ve Got a Friend in Me,” serves as a motif of Mistreatment of People with Disabilities in the Criminal Justice System. What does its use reveal about Denny’s inner world and the ways that the outer world responds to him?

3. The story is a coming-of-age narrative for a 30-year-old man. In what ways does Denny’s journey toward independence challenge typical ideas about growing up? If you’ve read works like Daniel Keyes’s Flowers for Algernon, how does Denny’s development compare to other characters who grapple with cognitive differences?

4. Angus and Lydia serve as foils to each other in Denny’s life. What different aspects of family, loyalty, and betrayal do their characters explore, and how do their personal transformations contribute to the novel’s resolution?

Encourage imaginative and creative connections to the book.

1. Imagine you are casting a film adaptation of The Sideways Life of Denny Voss. Who would you cast as Denny, Angus, and Nana-Jo, and what makes them right for the roles? Which scene do you think would be the most challenging to bring to the screen?

2. Denny’s scrapbook is a key part of his story. If you were to create a scrapbook page for the novel’s final chapter, what images, mementos, or short written entries would you include to capture Denny’s new life with Nana-Jo, Wilson, and his found family?

3. If you could write a letter to one character in the book, who would it be and what would you want to say to them? Would you offer advice, ask a question, or share your perspective on their actions?