High school sophomore Lily opens herself to new possibilities when, despite warnings, she becomes friends with "ghetto girl" Hazel, a new student at the private Vaughn School which Lily, following in her elitist mother's footsteps, has attended since preschool.

After the death of Elizabeth Holland, all of New York speculates about her unfortunate demise and wonder what role her mischievous sister, Diana, and notorious cad Henry Schoonmaker played in the events leading up to her death.