In New Hampshire, Charlie Simms (Chris O'Donnell) attends the Baird School, an all boys boarding school with rigorous classes and expensive enrollment. Yearning for cash from a part-time job so he can return to his family in Oregon for upcoming Christmas Break, the innocent Simms accepts a job for "babysitting" at a nearby household. The job is not what he expects, for he is commissioned to watch over an unlikeable, blunt behaved blind ex-colonel named Slade who has a keen ability at selecting his aides. Because of his sympathetic and integral nature, Charlie agrees to the job. Before he can even locate his level of comfort in the job, Simms is unexpectedly taken to New York City with the colonel, where the ex-military man has several agendas of his own.

Waldorf-Astoria Hotel, 301 Park Avenue (btw East 49th & 50th Streets) Manhattan.

The Plaza Hotel, 750 5th Avenue and Central Park South, Manhattan.

East 57th Street and 5th Avenue, Manhattan.

Pierre Hotel, 5th Avenue and East 61st Street, Manhattan.

Plymouth Street and Washington Street, Brooklyn.

817 5th Avenue and East 63rd Street, Manhattan.

Park Avenue and East 54th Street, Manhattan.