As a high-school student at Deerfield Academy, a Massachusetts boarding school, Hannah Pittard, AB’01, racked up awards for creative writing. After coming to UChicago, Pittard focused on literary criticism, but the impulse to write fiction remained. She brought her grandfather’s Underwood typewriter to campus, on which she drafted and redrafted letters to high-school friends and a then boyfriend living in Thailand.

“I’ve reread these letters,” says Pittard, “and half of them were complete fiction.” One describes a Hyde Park tree that was alive with angry, squawking leaves—an imaginative take on the small black birds that would perch on the branches of a particular tree during winter.

Ten years later, Pittard still finds herself obsessed with all sorts of real-world scenarios—and she still turns those ruminations into fiction. Her debut novel, The Fates Will Find Their Way, published by Ecco last January, explores regret and aching nostalgia for suburban childhood. The book debuted to critical praise; Chicago magazine named it a top four novel of 2011, and the Washington Post’s Ron Charles called it “chilling and touching.” 

A native of Canton, Georgia, Pittard earned her degree a quarter early and moved back to her home state, where she worked as a reporter for the Savannah College of Art and Design’s newspaper. Completing her weekly quota of articles about faculty and alumni artwork and campus events never took long, so she spent her remaining hours in the office writing a manuscript that she calls a “terrible novel-type thing about a girl just like me, only it was third person.”

At first, the manuscript mirrored events in Pittard’s own life, until she began including chapters of completely fictional short stories set on Maryland’s Eastern Shore, where Pittard’s mother and stepfather eventually moved. She noticed the disparity in wealth there: “sprawling farms, old-school money, side by side with poverty that didn’t make sense.” The stories were written by the novel’s protagonist, who was actually Pittard. “The girl who was writing the book, who was me, she was also a writer in the book, so in the book she wrote short stories, and one of the short stories that she wrote—which I wrote for her—I hope readers can see that I know how I sound, that it’s ridiculous—ended up being the first short story I ever had published,” she says with a laugh. That piece, about a group of misfits, appeared in McSweeney’s.

Pittard enrolled at the University of Virginia’s MFA program in 2004, and while there she won McSweeney’s Amanda Davis Highwire Fiction Award. After UVA, she waited tables at the Downtown Grille in Charlottesville and wrote a novel about a man whose wife had left him, eventually placing the manuscript with an agent. “I really thought that all it had to do was be on the market and it would sell. I would have taken anything. And it didn’t.”

The agent took the novel off the market and told Pittard she wasn’t interested in her new effort, The Fates Will Find Their Way. Deflated, Pittard spent the next six months barely writing, until she decided to channel that despondent mood into finishing The Fates.

The novel opens with the disappearance of 16-year-old Nora Lindell from her suburban town on Halloween. The news spreads via phone tree, and the neighborhood boys trade stories on where they saw her last: at the mall, at the riverbank, at the bus station getting into the passenger side of a beat-up Catalina.

The Fates, says Pittard, is not about a missing girl. “It’s about these boys.” Narrated in the first-person plural, the novel moves back and forth in time, the male protagonists remaining obsessed with Nora years after her unsolved disappearance, even as they reach middle age. They concoct tales about her whereabouts—she’s living in Arizona with a Mexican cook and twin daughters; she’s fled to Mumbai and taken a lesbian lover—all while sleepwalking through their own adult lives. Clinging to childhood as they cling to Nora, the characters look back and think, “Well, I guess that was my life,” says Pittard.

To write the male characters, Pittard drew on men she knew who looked back to high school as the best time of their lives. “Part of what makes life precious is that it is short, that it will end,” she says, “so this idea of looking back and being maudlin about a time that can never be recaptured was very depressing to me, but it was also fascinating to me.” She doesn’t imply that wistful remembering is limited to men, but male conversations she’d overheard compelled her to write in a collective male voice: “If my Dad was in a room with ten men and only five of them had gone on a hunting trip to Canada, it would be, ‘Hey, remember when we did this?’ And they’d all sort of nod even if they weren’t there.”

Pittard finished the manuscript in September 2009 and signed with an agent in early October; Ecco landed the deal at auction. She moved back to Chicago in 2010 to become a visiting assistant professor of fiction at DePaul University, and is working on a new novel she describes as an intimate look at a family of four people.

Meanwhile, The Fates is still garnering positive critical reaction. Although Pittard is excited by the response, she also gets a kick out of feedback from those who know her well: “One of my good friends from Deerfield said, ‘Hannah, I don’t like these characters at all. They remind me of the men we went to school with.’ And I thought, ‘Yes, that’s it—only they’re mine; I have soft spot for them all.’”