Book Club Discussion Questions for 100 Sideways Miles by Andrew A. Smith

1. Finn thinks about time in terms of space. He wonders about cosmological concepts and principles that hold the universe together. What does Finn's fascination with the cosmos reveal about him?
   
2. What does it mean to be trapped in a book? Have you ever felt trapped? How so?
   
3. Finn comments, "When you think about it, the universe is nothing but this vast knackery of churning black holes and exploding stars, constantly freeing atoms that collect together and become something else, and something else again." What does Finn mean by this?
   
4. Do you have cosmic concerns similar to Finn's? How are your concerns similar to, or different from, Finn's?
   
5. What qualities does Finn have that have allowed him to endure and eventually thrive despite the tragic and difficult circumstances of his life?
   
6. Finn and Cade are unlikely friends. What is the basis for their friendship? What do their differences reveal about each other? Have you ever had a best friend who was unlike you?
   
7. What do you think compels Cade to be provocative? What does this tell you about him? Have you ever had, or wanted to have, a friend like Cade?
   
8. What does Finn mean when he says, "I generally considered how nice it would be if I could simply stop myself from hurtling through space so fast, if only for a few seconds at a time"? Why was this stopping of movement important to Finn?
   
9. How is Julia's character defined by the author's portrayal of her during Finn's seizure in his living room? What was significant about Finn's response to her?
   
10. What drew Finn and Julia together? What does Finn admire most about Julia? What does she admire most about Finn? Discuss how their relationship changes throughout the story.
    
11. Finn tells the reader, "There was almost nothing about me that wasn't in his book, that didn't trap me into being something invented by someone else." Why does Finn refer to himself as something rather than someone?
    
12. Compare Finn's experiences during a blankout with his usual thought processes. Why is this significant in Finn's understanding of reality in the cosmos? How does Finn respond to his blankouts immediately after they occur? What does this tell you about him?
    
13. Do you think Finn's assessments of himself are accurate? To what extent do labels define you? Discuss ways in which you label yourself and ways in which you and your friends label each other. hat are the results of doing this?
    
14. Images of debris, death, collapse, and abandonment are scattered throughout the novel. Explain the author's use of these images. How do they relate to the concept of the "knackery"?
    
15. Finn says, "I suppose love, which makes atoms sticky, is also in many ways a prison." What does Finn mean by this? How does this relate to the author's use of other images of imprisonment and the desire for release or escape?
    
16. What is Finn's reaction to Julia's shadow play? In what ways does Julia's shadow play help Finn better understand himself? How does it help Finn better understand Julia?
    
17. Why did Julia "continue to insist she did not know how her shadow story might end"? Why did this frustrate Finn?
    
18. Describe the reactions of Cade and Finn during the accident scene. Did Cade and Finn switch roles? How did Finn ultimately grow from this experience? How did Cade?
    
19. Neither Finn nor Cade stayed at the bridge to receive recognition. What does this reveal about them? How would you have reacted if you witnessed a similar accident? Would you have stayed to receive recognition?
    
20. Describe Finn's relationship with his father after the accident. Does he resolve his issues with his father? How does their relationship change?
    
21. In what ways does Finn find his true identity, rather than some shadow of a pre-scripted character?
    

Questions for Further Discussion

1. Why do you think Finn's father chose to name his son after the title character in Mark Twain's great American classic novel about a boy who leaves home to find himself? Have you ever had to leave to find yourself?
   
2. Throughout the narrative Finn refers to his best friends using their first and last names. What significance might this have?
   
3. What does the photo on the inside of the book jacket suggest?
4. What makes Cade eventually decide to read The Lazarus Door? What is his response to the book? What is Finn's response to learning Cade has read the book?
5. When Finn, Cade, and Julia are together, Julia is often in the background taking photographs of Finn and Cade. Why do you suppose the author portrays Julia in this way?
6. How does learning about Julia's reason for moving from Chicago impact Finn? How does it impact their relationship?
7. How does the author present the diversity of cultural and racial differences in the novel?
8. What is Laika's mission in this story?
9. There are several commonly occurring numbers in Finn's life. How and when do they show up? What is their significance?
10. What's the significance of Finn's neighbor, Manuel Castellan, being a former bullfighter? What does Finn's bullfighter name mean?
11. How are the boy and the dog that Finn rescues from the flooding river important to the story?
    

Guide written in 2015 by Judith Clifton, Educational Consultant, Chatham, MA

This guide has been provided by Simon & Schuster for classroom, library, and reading group use. It may be reproduced in its entirety or excerpted for these purposes.
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Unless otherwise stated, this discussion guide is reprinted with the permission of Simon & Schuster Books for Young Readers. Any page references refer to a USA edition of the book, usually the trade paperback version, and may vary in other editions.