Filming of this adaptation of Stewart O'Nan's novel began in Nova Scotia in February of 2006.

In the novel, Arty Parkinson returns one Christmas to his hometown of Butler, Pennsylvania, to confront his haunting past—specifically, the winter of 1974, when he turned 15 and two terrible things happened: his family fell apart, and Annie Marchand, the young neighbor who had once been his baby-sitter, was murdered.

Arty narrates the circumstances leading to Annie's death—the culmination of a string of rash and heedless acts that included leaving her husband, engaging in an affair with her best friend Barb's boyfriend, Brock, and proving negligent in the care of her young daughter, Tara. At the same time, Arty also chronicles his own parents' acrimonious separation, which occurred during those same dreary months of 1974. Annie's decision not to reconcile with her wimpish husband, Glenn, who loves her devotedly and doggedly, is paralleled by Arty's mother's decision to divorce his father, the beginning of the family's downward economic slide. Both sets of adults behave like adolescents, and the effects on their children are grave and irrevocable.

Early on in the casting process it was announced that Amanda Peet would play Barb and Emily Mortimer would portray Annie. Jesse Peretz, the former bass-player for the Boston 'bubble-grunge' band The Lemonheads, was originally slated to direct before the reins were turned over to David Gordon Green, who wrote the screenplay.