In 1983, Oliver Nicholas, at thirteen, is well-poised to enter the precocious teenage world of first-sex, vodka and possible-love in New York City when he is traumatized by the stroke of his housekeeper (and only true maternal figure), a sixty-five-year-old Chilean woman named Aida. What was supposed to be an exhilarating and somewhat fearful rite of passage - diving into the exciting, fast-paced world of first experiences - quickly becomes skewed by an incomprehensible depression, and a house of interior horrors. Surrounded by women - his untraditional, Spanish, photographer mother (more interested in the role of confidante than mother) his sister, a comedic, door-slamming tormentor, marked by her parent's divorce; and Aida, his silver-haired emotional focal point on the verge of death in Lenox Hill Hospital - Oliver struggles to maintain his role as "man of the house" and his sanity.

Jack Frost's playboy lifestyle in New York City is rocked by the news that his childhood love is engaged. Amidst his friendships with Scotch Evans, a ribald nightlife correspondent; Ozzy, a troubled but loving heroin addict; and Kate Hardwick, a bewitching, quick-witted reporter, Jack sinks deeper into depression. Haunted by lost-love and his mother's suicide, Jack plunges into whiskey and self-destruction . . . until his eleven-year-old neighbor, Sophie, an unlikely mother figure, leads Jack back into himself, and out of the nostalgia and excess that consumed him.