At the lowest point in his life, Richie receives a call from his estranged sister, asking him to pick up his eleven-year-old niece from school. What begins as a simple favor turns into a nighttime odyssey through New York City, where the two form an unexpected bond.

A young girl named Dora goes on adventures with her red boot-wearing monkey named Boots.

Over the course of 12 years, and three stages of life, Sidney Hall falls in love, writes the book of a generation and then disappears without a trace.