1. From The Catcher in the Rye to A Separate Peace, Prep and Skippy Dies, writers have often been drawn to the world of prep schools. What do you think attracts writers to the prep school setting? What attracts you as a reader? How is Bellingham Academy different from any other prep school you may have read about? Why do you think the author chose to set the novel in a school that caters to troubled teenagers?

2. Sailing plays a major role in the novel. Whether you are familiar or unfamiliar with the sailing terms how does Jason’s sailing partnership with Cal help you to understand the closeness of their relationship? How do the language and nomenclature of sailing and celestial navigation serve as metaphors throughout the book?

3. The novel begins with a quotation from Captain John Paul Jones, “I wish to have no connection with any ship that does not sail fast for I intend to go in harm’s way,” and another quotation from a poem by Dan Chiasson, “You know/what you did. You know you know/what you did./No one is hearing your ornate confession.” After reading the novel, how do these two epigraphs inform your understanding of the character of Jason Kilian Prosper? Why does Jason put himself in harm’s way? Is the novel Jason’s attempt at a confession and if so, how do you feel about his confession?

4. Aidan, Cal, and Jason all have questions about their own sense of attraction, their sexuality and desire. What do you think the author is attempting to say about the nature of human sexuality, especially among teenagers?

5. The characters in The Starboard Sea come from tremendous privilege and often squander or take for granted their privilege. Do you know people who are similar to the characters in this novel? Was it challenging for you to empathize with their troubles or did you recognize their teenaged vulnerability?

6. The novel is set in 1987 and there are important references to the Black Monday Stock Market Crash, Baby Jessica, and the Robert Chambers Preppie Murder Trial. Why do you think the author chose to set her novel in the past? Those of you who are familiar with this time period, how well did the author capture the late 1980s? Whether you are familiar or unfamiliar with this time period, how might this setting mirror the current cultural and economic landscape?

7. Throughout the novel, the author references several literary works, O Pioneers!, The Awakening, The Scarlet Letter, Moby Dick, The Sun Also Rises, The Motion of Light In Water. Many of these books are often read in high school. Why do you think the author references these works in particular? How do these books resonate within the lives of the characters?

8. What did you think of the adults in the novel? Are any of them suitable role models for their children or their students?

9. Both Chester Baldwin and Yazid Yazid face different forms of prejudice. How does the novel handle issues of race, racism, and bullying?

10. Aidan, Nadia, and Diana are all anagrams. Why do you think the author gave these characters these names? How might these characters be connected through these anagrams?

11. The novel takes place over the course of a single school year and not all of the questions raised about the characters’ lives are resolved. How does the novel’s ending make you feel?