Eddie Garrett agrees to watch a duffel bag for an acquaintance who is heading to prison. When he discovers cash in the bag, he's unable to resist the temptation and winds up deeply in debt. When the prison release is shortened, Eddie suddenly has a small window of time to win all the money back.

Irresponsible 20-something Jenny arrives in Chicago to live with her older brother Jeff, a young film-maker living a happy existence with his novelist wife Kelly and their two-year-old son. Jenny's arrival shakes up their quiet domesticity as she and her friend Carson instigate an evolution in Kelly's life and career. Meanwhile, Jenny strikes up a rocky relationship with the family's baby sitter-cum-pot dealer.