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About The Book

Destiny takes a detour in this “wickedly witty and offbeat novel” (Kirkus Reviews, starred review) that was nominated for the National Book Award.

Finn Easton sees the world through miles instead of minutes. It’s how he makes sense of the world, and how he tries to convince himself that he’s a real boy and not just a character in his father’s bestselling cult-classic book. Finn has two things going for him: his best friend, the possibly-insane-but-definitely-excellent Cade Hernandez, and Julia Bishop, the first girl he’s ever loved.

Then Julia moves away, and Finn is heartbroken. Feeling restless and trapped in the book, Finn embarks on a road trip with Cade to visit their college of choice in Oklahoma. When an unexpected accident happens and the boys become unlikely heroes, they take an eye-opening detour away from everything they thought they had planned—and learn how to write their own destiny.

NYTBR Notable Children’s Book of the Year
NPR Best Book of the Year
NYPL’s Best Book of the Year for Teens
ALA Best Fiction for Young Adults
Chicago Public Library Best Teen Fiction of the Year
A Texas Tayshas Top Ten Selection

Reading Group Guide

A Reading Group Guide to

100 Sideways Miles
By Andrew Smith

About the Book

After losing his mother at a young age in a bizarre accident that left him with a broken back and epilepsy, Finn has been coping but never quite feeling up to meeting life’s challenges. With the help of his charismatic best friend, Cade, a heroic rescue in which the two boys ultimately rescue themselves, and the risk of romance with Julia, Finn begins to see everything differently.

Prereading Discussion

Read Maya Angelou’s poem Caged Bird. Pay particular attention to images of clipped wings and shadow. Why does the caged bird sing?

Discussion Questions

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. What 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.

About The Author

Photograph by Kaija Bosket

Andrew Smith is the author of several novels for young adults, including WingerStand-Off100 Sideways Miles, and the Michael L. Printz Honor Book Grasshopper Jungle. He lives in a remote area in the mountains of Southern California with his family, two horses, two dogs, and three cats. He doesn’t watch television, and occupies himself by writing, bumping into things outdoors, and taking ten-mile runs on snowy trails. Visit him online at

Product Details

  • Publisher: Simon & Schuster Books for Young Readers (September 2, 2014)
  • Length: 288 pages
  • ISBN13: 9781442444973
  • Grades: 9 and up
  • Ages: 14 - 99
  • Lexile ® 890L The Lexile reading levels have been certified by the Lexile developer, MetaMetrics®

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Raves and Reviews

*"A wickedly witty and offbeat novel...a breathtaking read."

– Kirkus Reviews, starred review

"John Green fans will enjoy Smith’s newest novel."


*" Finn’s musings about the universe’s constant dispersal and recycling of atoms, along with his habit for measuring time in the distance the Earth is forever racing around the sun, provide a memorable perspective on human (in)significance."

– Publishers Weekly, Starred Review

"I’m not sure I’ve ever laughed with, cried with, and rooted harder for a character than Finn Easton. His voice is so strong, so real, that his triumphs and failures felt like they were my own. I seriously loved this book."

– Len Vlahos, author of The Scar Boys

Finn Easton has lived his life in the shadow of a book. As a child, Finn was severely injured and his mother killed in a freak accident: a dead horse landed on them when it fell off a truck that was traveling over a bridge. After the accident, his father took many of Finn’s unique characteristics (his name, heterochromatic eyes, propensity to measure time in miles traveled by the Earth in orbit, struggle with epilepsy, and a particular scar along his back) and made them into a character in a Robert Heinlein–esque novel, The Lazarus Door. The novel has attained cult status around the world and made Finn’s life a nightmare. The only person who treats him as though he is not the character in the book is his best friend, Cade Hernandez, the tobacco-chewing, sex-obsessed, teacher-baiting hero to their classmates, beloved for his pitching skills and his ability to get most people—especially girls—to do whatever he wants. Late in their junior year, Julia Bishop moves in and Finn falls in love. She is creative and funny. When she announces that she is moving back home to Chicago shortly after Finn’s birthday, he is heartbroken, but decides to continue with his planned road trip with Cade to Dunston University in Oklahoma, a school they plan to attend unless Cade is drafted by the major leagues or is given an athletic scholarship to another university. The trip is the first time Finn has been out of California or away from home, and Cade helps him cut the cord by throwing away his cell while on the road in Arizona. While driving in a deluge in Oklahoma, they witness an accident and risk their own lives rescuing a little boy, a dog, and a grandfather from a raging river. More than a bit wandering, this will appeal to teens who like novels that with a bit of an absurdist edge.–Suanne B. Roush, formerly at Osceola High School, Seminole, FL

– School Library Journal, July 2014 *STARRED REVIEW

*"This will appeal to teens who like novels that with a bit of an absurdist edge."

– School Library Journal, starred review

"Finn and Cade are a tag team for the ages. No one does male friendship (or vomit and accidental nudity) better than Andrew Smith."

– S.A. Bodeen, author of The Compound

"An unusual and memorable novel."

– Horn Book

*"This unpredictable story of love and friendship is close to perfect."

– Booklist, starred review

"The current of genuine warmth that runs through it ensures multiple revisits and enthusiastic sharing."

– BCCB, starred review

*"A mosaic of recurring motifs, subtle symbolism, wonderfully funny bits, and the best birthday present ever make this a book that repays close attention; the current of genuine warmth that runs through it ensures multiple revisits and enthusiastic sharing."

– BCCB, starred review

"If you're a young boy and a dead horse falls off a bridge, kills your mother, and leaves you with deep scars — and you're prone to epileptic seizures — you'd come to expect the unexpected. Still, it doesn't mean you have to like it. In the shadow of his best friend, the popular and athletic Cade, and forever tied to his fictional namesake in his father's best-selling sci-fi novel, Finn has trouble figuring out who he's supposed to be. Then he meets a new girl and for the first time writes his own story. Hilarious and heartbreaking, you'll be rooting for Finn all the way."

– recommended by Lisa Yee, author, most recently of Warp Speed

Awards and Honors

  • CCBC Choices (Cooperative Children's Book Council)
  • Lincoln Award: Illinois Teen Readers' Choice Master List
  • Kansas NEA Reading Circle List High School Title
  • NYPL Best Books for Teens
  • Virginia Readers' Choice Award List
  • California Book Award Finalist
  • ALA/YALSA Best Fiction for Young Adults - Top Ten
  • MSTA Reading Circle List
  • National Book Award Longlist
  • TAYSHAS Reading List Top Ten Title (TX)
  • Louisiana Teen Readers' Choice Award Nominee

Resources and Downloads

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More books from this author: Andrew Smith