It’s the mid-1980s in gritty, vibrant New York City when Francesca “Chess” Varani strikes up a volatile friendship with drama-queen classmate Kendra Marr-Löwenstein. Drawn into the orbit of Kendra’s Salingeresque family, Chess moves into their Greenwich Village home when she graduates from Barnard and takes a job assisting the infamous literary intellectual Clarice Marr. There she receives the sentimental education and emotional roughing up New York bestows on all its young hopefuls—including a doomed love affair with Clarice’s troubled son.

Narrating her story twenty years on, from the winter of the 2008 financial crisis, a sadder but wiser Chess evokes her youth with all the poignancy of time passing—and all the weight of choices made and not made.