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- New York City playboy and professional charmer Jack Frost is rocked to discover that his one true love is engaged. As the news send him spiraling into a self-destructive cycle of reckless behavior, redemption comes from an unlikely source.
- 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. With his best friends, Nicholas Pinto, Raul Pinto, Valerio, a chain-smoking, nunchucking, grandiose artist; and Nick, a cynical, foul-mouthed, jokester, Oliver struggles through attacks of mania, drunkenness, first love, betrayal, migraine-inducing masturbation, virginity, and the loss of an imaginary friend . . . hoping to survive this uniquely-New-York baptism by fire.