Postcollege Ennui

College has proved so reliable a setting for fiction that it’s even laid claim to its own literary genre. But what happens after the campus novel graduates? The transition out of college is a much sadder, much less circumscribed, and, despite classic treatments by F. Scott Fitzgerald and Mary McCarthy, much less popular novelistic subject than college itself. The following books tackle (or, in The Rules of Attraction and Privilege, are born of) postcollegiate malaise, each revealing the downside of what Amory Blaine termed “aristocratic egotism”—the darkest hour of the privileged youth.

English, August: An Indian Story by Upamanyu Chatterjee

This 1988 debut novel opens on a summer day in New Delhi as Agastya (who goes by the anglicized name of August) prepares to depart for a prestigious civil-service job. In an ad hoc blend of idiomatic American English and Urdu, his friends playfully skewer him for being an unlikely bureaucrat and make jokes about the small, famously hot town of Madna where he will be trained. Though August continues to indulge his collegiate creature comforts (e.g., masturbating and smoking pot), the radical changes posed by his new job and surroundings trigger an extended spell of loneliness and depression. With his friends scattered across the globe for work and grad school, August acutely senses the largeness of the world and is forced to reckon privately with feeling “in a state of flux, restless.” If his identity crisis is familiar to American readers, Chatterjee suggests that this is not an entirely good thing: August’s friend Dhrubo, impatient with his melancholy, asks, “Just who and where do you think you are, an American taking a year off after college to discover himself?”

A Fortunate Age by Joanna Smith Rakoff

What about 2009 could have inspired two rote adaptations of Mary McCarthy’s The Group? Both J. Courtney Sullivan’s Commencement and Rakoff’s A Fortunate Age traffic in modernized versions of McCarthy’s characters; each book starts from the improbable marriage of a close college girlfriend and spans the fraught decade or so following graduation. In place of McCarthy’s Kay and Harald, Rakoff gives us Lil and “Tuck” Hayes; in place of the “group,” we get the “crowd.” Though Rakoff’s adaptation often feels perfunctory, it is still thrilling to have someone like McCarthy exploring the earlier group’s late-’90s/early-’00s analogues.

All the Sad Young Literary Men by Keith Gessen

Gessen’s debut short-story collection-cum-novel follows the lives of Mark, Sam, and Keith, as they move through early adulthood, burdened by hefty novelistic ambitions, ex-girlfriends, bittersweet memories of college, and a Ph.D. dissertation that seems to refuse completion. The title, a play on Fitzgerald’s short-story collection All the Sad Young Men, prepares the reader for the depressive, referential, masculine, Amory Blaine–ish action that unfolds. Gessen’s braided narrative revels in the three young men’s shared sense of confusion, urgency, and self-consciousness, which plagues them in the years following their graduations. In the search for fulfillment, each character displays an earnest belief in his own importance, which Gessen both critiques and defends. In their sentimentally educated hands, the whole of history—particularly the October Revolution and the Palestinian-Israeli conflict—becomes little more than an arsenal of solipsistic, albeit elegant, metaphors for love and frustration.

The Fundamentals of Play by Caitlin Macy

George Lenhart, a recent Dartmouth graduate, works as a first-year analyst (“the lowest form of post-undergraduate life”) for an investment-banking firm located in midtown Manhattan. Though a tireless worker, Lenhart is ambitionless and adrift, finding excitement only in the company of Chat Wethers, a fellow Dartmouth alum, and Kate Goodenow, their social circle’s flighty lynchpin, with whom both boys nurse quiet infatuations.

At first glance, Macy’s debut novel—released about a year before 9/11, long after investment banking ceased to seem exciting and long before it began to seem evil again—appears hopelessly dated and irrelevant. Yet Macy, poised at the end of the ’90s, uses the epochal blandness of her era brilliantly, creating a delightful, tensionless document of an indistinct leisure class stuck in the twilight of the Clinton years. Even when Macy addresses the timeless anxieties of privilege, she somehow makes them feel rooted in the peculiar moment: “I was school-sick. I missed school, the lovely order and the sense of limitless yet defined forward movement.” (The book is also unparalleled in its exploration of the impulse that drove hordes of college grads to move immediately into hundred-hour workweeks on Wall Street, a zeitgeist not soon to be replicated.)

The Rules of Attraction by Bret Easton Ellis

Published shortly after Ellis’s college graduation, this novel transposes the author’s scathing perceptions of his former Bennington College peers to the students of the fictional Camden College, where Paul, Sean, Lauren, and others dispassionately narrate party after party and hookup after hookup. Though the book seems almost myopically collegiate, it is governed by the fact of Ellis’s recent graduation, a showcase of the biting condescension that underpinned the author’s arrival into the “real world.” His characters’ staccato dispatches could appear in almost any order—the plot is paper-thin, academic progress appears impossible, and their relationships follow a Sisyphean logic of resumption and termination—and he savors this nonlinearity. In the absence of true development, we are left with a clear-eyed deconstruction of a class that refuses to grow up; the novel never mentions life after graduation, and the extent to which the students try to protract their aimless college years is staggering.

Privilege: Harvard and the Education of the Ruling Class by Ross Gregory Douthat

Douthat’s volume straddles the barrier between memoir and polemic: It is at once a chronicle of the author’s undergraduate years at Harvard and a vigorous assault on his liberal peers and their shared alma mater. Published just three years after Douthat’s 2002 graduation, Privilege takes readers on a vivid tour of the university’s grounds, walks them through his first flirtation with the idea of true love, offers an execrable meditation on the significance of 9/11, explains and excoriates the “parlor liberals and street liberals” that populate the campus, and describes a valedictory game of bowling just after graduation.

Douthat’s tone is more sour contempt than existential ennui, but what makes the book interesting is the author’s abiding bewilderment, the disbelief that college is finally over. Like The Rules of Attraction, the fact that Privilege was written too soon after graduation is exactly what makes it compelling: the author’s attempt at ruthless objectivity, his steady moralistic voice, his intermittent sentimentality, and his wish for distance from an experience that remains painfully recent. Beneath the William F. Buckley worship and pat accusations like “Meritocracy is the ideological veneer [at Harvard], but social and economic stratification is the reality” lies a unique, newly nostalgic conjuring of youth by youth.

Daniel Pearce recently graduated from Bard College and is an intern at Bookforum.