1. Joyce McDonald describes the town of Bellehaven as a beautiful bucolic spot: ". . . Victorian homes nestled between ancient oaks and maples . . . the very sight of it could take your breath away especially in the spring when all of Edgewood Avenue was shimmering with crabapple blossoms." Yet the town has a very dark history. What is its secret, and how is the town being punished for it now?

2. The main characters in SHADES OF SIMON GRAY are Simon Gray, Devin McCafferty, Kyle Byrnes, Danny Giannetti, and Liz Shapiro. Discuss each of the characters and their relationships. Who among the people you know are like any of them?

3. Danny Giannetti believes "You don't have to play the game, you just have to know how to win it." Kyle Byrnes lives by the creed "Do anything you want, the trick is make sure no one ever finds out and if they do . . . lie like hell." Even Liz Shapiro, who believes she is an honest person, secretly removes an antique journal from the historical society to work on a report. She rationalizes: "They would never miss it. She would return it in a few days and no one would ever be the wiser." What do you think influenced these kids to formulate philosophies that allow them to comfortably behave so dishonestly?

4. A 2002 study of 4500 high school students across the country by Rutgers University's Management Education Center found that 75 percent of the students surveyed engaged in serious cheating. Common student responses were: "I actually think cheating is good." "A person who has an honest life can't succeed." How is this survey relevant to SHADES OF SIMON GRAY? How do you and your classmates feel about cheating? How does the larger world of politics, business, and media affect your attitudes? Be honest!

5. SHADES OF SIMON GRAY raises questions of ethics and ethical behavior. What ethical dilemmas do you face outside school? Do your friends influence the choices you make? Would you do something unethical to please them?

6. Of all the conspirators, Devin is the only one who rejects the rewards she receives as a result of "the project." What is the turning point for her? Does your opinion of Devin change by the end of the novel?

7. Before Simon's accident, what clues indicate that he might have crashed the car on purpose?

8. "The way Simon was beginning to see it was, there were two ways out of this place: you either pulled yourself up or you let them hang you." Simon knows he has a choice. The visions or out-of-body experiences he has while in a coma help him come to a decision. How do his encounters with Jessup Wildemere help him make his choice?

9. "He found himself outside his room, near the nurses' station, where two doctors were talking. He tried waving his hands over his head to get their attention, but the doctors never so much as glanced his way. Within seconds Simon's ears filled with a strange whooshing sound. He felt himself propelled like smoke through the stem of a pipe, right into his body." The belief that critically ill patients can have out-of-body experiences is a very controversial one. Where do you stand on the issue? Do you believe Simon's experiences are real? Propose an alternative explanation.

10. SHADES OF SIMON GRAY demonstrates that normally honest, law-abiding citizens can be manipulated and corrupted into committing illegal acts, whether in 1798 or in the present. What was it about the people of Havenhill that allowed them to hang a man without a trial and then lie about it? Does it make any difference that they were ignorant of the truth? Simon knew he was being manipulated by Kyle, Devin, and Danny, yet he still chose to get involved in "the project." What was Simon's sin?

11. When they need quiet time and a place for serious thinking, the characters in SHADES OF SIMON GRAY find their way down to the river. What is it about a river that makes it conducive to thinking? Talk about where you go to be alone to think.

12. Joyce McDonald often takes advantage of the multiple meanings of words she uses–for example, the expression a murder of crows and the words shades of gray in the title. Talk about the author's use of language and how it helps to set a tone and to give richness to the novel.


This guide was prepared by Clifford Wohl, educational consultant.

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"A page-turning plot, good characterization, and very convincing setting will have this suspenseful thriller driving up library circulation."

—Kirkus Reviews

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Courtesy of Laurel Leaf

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