The story of a young boy in the Midwest is told simultaneously with a tale about a young girl in New York from fifty years ago as they both seek the same mysterious connection.

A crime she committed in her youthful past sends Piper Chapman to a women's prison, where she trades her comfortable New York life for one of unexpected camaraderie and conflict in an eccentric group of fellow inmates.

In this dark, surreal comedy, Cindy Rossberg has apparently killed her fiance on her wedding day. Her psychiatrist encourages her to move forward with her life. However, as she attempts to do so she finds reality too difficult to contend with as she is bound to the events of the past. As she tries to sort things out for herself, Cindy spirals into a wacky world of bizarre situations that become increasingly influenced by a murder mystery she is writing. In the end, Cindy discovers that she must act as her own emancipator in order to free herself from the role she thinks she is expected to play.