The Loneliness of the Preppie: The Starboard Sea

Rich New York kid alienated from parents kicked out of several boarding schools for misbehavior gets one last chance at a Massachusetts boarding school specializing in the rejected and expelled; Dad, a big potential donor and friend of the dean, drops son off, gives him a blank check, leaves with hardly a a good-bye. Sound familiar? Have we been there before? Obviously yes, so I have started Amber Dermott's debut novel The Starboard Sea with some trepidation and at least a little sense of literary deja-vu. I honestly have no more tolerance for the sufferings and shenanigans of spoiled brats - and I think Dermott doesn't either; her characters are dislikable to the point almost of parody. What can possibly make this novel work, however, is her capacity to make us care about the protagonist/narrator, as, over the course of the first few chapters, we get to see what's really troubling him: the suicide of his best friend and sailing mate from previous boarding school, and, as we gradually learn, his homosexual relationship with his friend, and his guilt over the suicide that ensued when Dad found the boys entwined. This back story distinguishes Starboard somewhat from its many predecessors: Separate Peace (suicide), Catcher in the Rye (cynical but vulnerable protag), Outside Providence (rich kids misbehaving, new kid falls for beautiful girl on campus), Secret History (though this is college, many of the same themes - though a smarter novel; interestingly, both Secret and Starboard are by women from male POV), Prep (an outsider arrives on campus). Of all of these, Starboard so far has the most worthless and privileged characters - the students are not only spoiled and irresponsible but are actually horrible to one another, to their teachers, and even to the hired help in the cafeteria. I really would have stopped reading sooner - but the suicide back story is drawing me on, and, another strength of the novel, the writing about the sea and about sailing: that's the central trope or theme of the book, as the protag was a star sailor at previous school and now the new school hopes he will lead the team on to victory, but he's unsure he can work with any mate other than his late friend and lover; on first practice, he nearly kills his new mate, making him an outcast in the school. Perhaps there's an echo here of another, quite different prep-school novel: Loneliness of the Long Distance Runner (athletics and both competition and rebellion - who can forget the last scene of Loneliness, in either the novella or the fine film adaptation?). I will give Starboard's Bellingham Academy a chance to keep developing - but I wouldn't want to go there.