A difficult book to categorize into any particular genre, The Starboard Sea is at heart a mystery and a bit of romance, but it also churns with some coming-of-age and coming-to-terms elements. Dermont has created a complex parable on the nature of love and passion. The summer of 1987 is the year of damaged goods: record-high AIDS, Oliver North and paper shredders.

Demount’s vulnerable hero, Jason Prosper, has just gotten himself banished from Kensington Prep and is about to start his senior year at the Bellingham Academy. Jason will be joining a select group of students who have been kicked out of better schools for stealing, having sex, or smoking weed, “rich kids who had gotten caught and been given a second chance.” Jason’s father--who seems to want to shift the blame for his life's mistakes onto both his sons--is of the opinion that prestigious Bellingham offers a sanctuary with minimal regulations and valuable lessons to these kids in need.

New England boarding schools are notoriously small, incestuous worlds, but everyone is sure that Bellingham is the one to most likely to give safe harbor to disgraced young Jason, who is still reeling after the sudden suicide of his best friend, Cal. From an absence of light to a prickling concealment, Jason’s existence has become “a rough and painful mask.” For months, Jason had looked upon trim, athletic Cal as the more experienced guy, the one most likely to defy convention. Jason was happy to experience his life as an extension of Cal's, and he still harbors dreams of the two of them recreating Magellan’s voyage, even sailing as far down South as Tierra del Fuego.

Jason’s guilt over Cal's death drives The Starboard Sea. A young man with a genius for tying and untying knots, Jason mostly runs around wearing shoes without socks, picking stars out of the sky. When a boating accident nearly kills Race, a fellow crewmate, the incident shakes Jason’s confidence, convincing him that he is a failure and a danger. In a world where there’s little privacy and where retaliatory hazing is quite common, Jason is reluctant to face the truth of what happened that last time he and Cal sailed together.

Instead, Jason hides behind his growing love for delicate Aiden, a girl with a collection of Fred Astaire’s shoes and a past that is strangely calibrated to his own: “I thought of Aiden as a kind of second chance, a distraction from Cal.” The two share gentle nighttime confidences, and like Cal, Aiden soon becomes Jason's "mythical, faithful companion." Jason knows there’s something unspoken holding them close, a strange serendipity that has brought them together. The other boys--Tazewell, Kriffo, Race, and Stuyvie--have branded Aiden as a homicidal maniac and a slut. In their minds, she’s broken every taboo.

Although set in the past, Dermont's novel holds up a mirror, contrasting the inherent claustrophobia of life in boarding school with the ocean’s wild freedom. The tale has a subtle irony, reinforcing the notions of teenage frustration, the privileged demands of family, and the need to fit in to a world where sexuality is still considered taboo. Reluctant to pull apart the loose mess of his life, Jason finds himself at loggerheads with Race. Sensing his friend’s animosity, he doesn’t see Race's unpredictability and the lengths that he and the school dean will go to cover up any whiff of scandal.

From fluid descriptions of the sea to those who inhabit it, the balance of power shifts as secrets are revealed and Jason moves on, learning to confess to his waves of remorse and discovering a new comfort and wisdom in his beloved memories of Cal.