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Curtis Sittenfeld / Do-Over

An extract from Do-Over by Curtis Sittenfeld

Clay never seriously considered the possibility that Donald Trump would win the election, and around nine P.M. central time, when it seems likely he will, Clay texts his daughter, Abby, who is fourteen and at her mother’s house. He writes, I hope you are not too disappointed. Progress sometimes happens in fits and starts. I love you, Abs. Abby texts back, He’s gross, followed by the poop emoji.

That night, Clay dreams of Sylvia McLellan. He dreams with some regularity of boarding school—the classic dream that he’s unprepared for an exam, plus a more idiosyncratic one that involves a girl named Jenny Pacanowski waiting in her dorm room to have sex with him, while, agitatingly, he’s delayed by the task of putting away equipment for the entire lacrosse team—but he’s never before dreamed about Sylvia. And the dream Clay has of Sylvia isn’t sexual; in fact, within a minute or two of waking, he can’t remember what it was about except that it leaves him uneasy. Yet he’s not surprised when, four months later, he receives an email from her. They haven’t had contact since their graduation in 1991.

Hope you’ve been well, she writes. Super-random after all this time, but I’m coming to Chicago for work in April and I was thinking it would be fun to have dinner if you’re around.

After a few volleys, they have settled on a day, a time, and a restaurant near the downtown hotel where she’ll stay. She lives in Denver, she tells him, she’s an architect, her husband is also an architect but not at her firm, and they’re the parents of twin boys who are nine and a girl who’s five.

You didn’t go into politics, either? Clay types, then he adds the phrase the dirty business of between into and politics to convey that he’s kidding, then he deletes the entire question. Her trip to Chicago is three weeks away.


In the spring of 1990, when they were juniors, Clay, Sylvia, and three of their classmates all ran for senior prefect, which was the fancy term used at Bishop Academy for student body president. Their school was in western Massachusetts, and there were a total of seventy-six people in their grade. After Clay and Sylvia tied for first place, a runoff occurred. The exact results were never disclosed, but apparently they were close, so close that the dean of students met with Clay and Sylvia and proposed the following: Because Clay had been their grade prefect for the past three years, and because no girl had ever served as senior prefect—a fact mostly explained by Bishop having switched from all-boys to coed only a decade earlier—Clay would assume the role of senior prefect, but unprecedentedly, another role would be created for Sylvia, that of assistant prefect. Clay would show her the ropes with regard to running Monday and Friday assemblies and serving on the honor council, and in turn, Sylvia would help raise money for senior class activities, especially since, for the first time in Bishop’s history, there was a movement afoot to hold a prom.

Clay can still remember sitting in Dean Boede’s office, the warm New England afternoon outside the big window, his impending lacrosse practice; he can remember how qualmlessly he accepted this offer and how Sylvia did, too. That night, before everyone was released from Sit-Down Dinner, the headmaster announced the arrangement to the student body, and there was much applause.

Clay had been in a few classes with Sylvia over the years without ever talking to her much, and he thought of her as smart—she had at some point won a prize for an essay written in Latin—as well as quiet and almost definitely a virgin. He’d been surprised when she’d run for prefect. She was tall and thin and had long, straight blond hair, so that she looked hot from behind, but from the front you could see her jutting, rectangular jaw and aquiline nose; and besides that, she just didn’t carry herself like a hot girl. A week after being elected assistant senior prefect, she also was elected captain of the girls’ crew team.

Their senior year played out as Dean Boede had proposed: Sylvia stood on the auditorium stage with Clay during assemblies, she attended honor council meetings, they did indeed hold an all-school prom. The theme was “April in Paris,” and the centerpiece was a thirty-foot-high papier-mâché Eiffel Tower with which Clay personally never had physical contact. By the end of the year, his impression of Sylvia remained favorable. Then again, how much thought did Clay actually give her? He was a reasonably conscientious student, an even more conscientious athlete, and a decent boyfriend to a girl named Meredith Tyler, who was dark-haired and looked hot from both the back and the front; meanwhile, he occasionally had sex with Jenny Pacanowski, who also was hot from the back and the front, whom he’d lost his virginity to his sophomore year, who took Ritalin, who’d told him that in first grade she’d repeatedly gotten in trouble for humping the corner of a desk, and who had a boyfriend who’d already graduated from Bishop. Every two or three weeks, Jenny materialized in his dorm room in the middle of the night. There was a rule Clay’s mother had about dessert, which was that she couldn’t seek it out but if it landed in front of her, she could indulge; not that it would have made his mother proud, but Clay had the same rule about Jenny.

When he, along with Meredith, Jenny, Sylvia, and seventy-two other classmates, graduated on a Sunday morning in early June, Clay was handed his diploma not by the headmaster, as everyone else was, but by his father, who was a trustee of the school and also a graduate. In the fall, Clay started at Yale and Sylvia started at Williams, which made it slightly surprising that during college they never crossed paths.

Curtis Sittenfeld is the bestselling author of five novels: ‘Prep’, ‘The Man of My Dreams’, ‘American Wife’, ‘Sisterland’ and ‘Eligible’. Her first story collection, ‘You Think It, I’ll Say It’, will be published in May 2018 (Doubleday UK, Random House US in April). Her books have been selected by The New York Times, Time, Entertainment Weekly and People for their “Ten Best Books of the Year” lists, optioned for television and film, and translated into twenty-five languages. Her short stories have appeared in The New Yorker, The Washington Post and Esquire, and her non-fiction has appeared in The New York Times, Time, Vanity Fair, The Atlantic and Slate. A graduate of Stanford University and the Iowa Writers’ Workshop, she is married with two children and lives in the American Mid-West.
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