Carry the Sky takes an unblinking look at bullying. What’s unblinking about it? Talk about moments where a character makes a bad choice, and the author doesn’t sugarcoat the results.
What are some of the ways “difference” is explored in Carry the Sky? How does the Wyeth mural act as a symbol?
Has the educational system changed since 1983 in terms of accepting or encouraging difference? How has social media changed the way bullies attack weaker peers?
What are the social, religious, and personal forces that made Taylor feel shame about her sexuality? Do you think those forces are as prevalent today for GLBTQ people?
Jack Song is one of the only people of color on staff at St. Timothy’s, although he has an ally in his friend Sam Omura. How are the depictions of race in the book reinforcing and/or resisting stereotypes?
What do you think about the author choosing two teachers as the point-of-view characters? How would the novel change if the headmaster were telling the story? Or Kyle? Does hearing the perspectives of Taylor and Song, as they try to tend these students, change how you think about your educational experience?
Does Taylor’s grief for Sarah affect her ability to teach? How about the conflicted emotions about her sexuality? As a more seasoned teacher, does Song manage his grief and outsider status any better than Taylor? Do you think Song will stay at St. Timothy’s?
Carla is nearly, but not quite, a point-of-view character. How did the author’s use of dialogue and tape recordings, to get her voice on the page, affect your response to Carla’s experiences? Do you wish she had a point of view or were you glad for the distance?
Carry the Sky is about bullying, but it’s also about loneliness, how being different can isolate individuals. What are some of the ways Kyle reached out—or could have reached out—to the people around him? Who tries connecting with him? Are there characters you hold responsible for what happens to Kyle? If so, which ones?
How did it change your perspective on Kyle’s choice to have his fellow dorm mates find him? Where were all the adults?
Honor and shame are two big themes in the book. How does Song act honorably? How does he act dishonorably? What about Taylor? Which characters—adults or students—have positive influences on the other characters?
How does the Cold War backdrop impact the story? Why do you think the author set the book in 1983?
What are some other boarding school books you’ve read? How are they similar to Carry the Sky? How are they different?