Gabe (JOSH HUTCHERSON) is an 11 year-old fifth grader, living on the Upper West Side of Manhattan with his father (BRADLEY WHITFORD) and mother (CYNTHIA NIXON). Gabe's parents have been separated for a year and a half but still share the apartment. Gabe considers New York to be his city -- well, at least the 10 square blocks that surround his home. Gabe is happy hanging out with his three best friends, playing basketball in the schoolyard and scooting around the neighborhood. He has no time for or interest in girls. But when Gabe joins a karate class and is partnered with Rosemary Telesco (CHARLIE RAY), whom he's known since nursery school, everything changes. Gabe is smitten with Rosemary, even if he doesn't understand the feelings that are both thrilling and tormenting him. And so Gabe begins his bumpy road to first love. When Rosemary reveals she is leaving soon for summer camp and -- even worse! -- may be attending private school next year, Gabe is stunned. With the stakes never higher (at least in his first decade), he must take action to keep his first love -- all in a wonderful, magical world known as the Upper West Side.