Alex (Luke Wilson) is an author whose writer's block and gambling debts have landed him in a jam. In order get loan sharks off his back, he must finish his novel in 30 days or wind up dead. To help him complete his manuscript he hires stenographer Emma (Kate Hudson). As Alex begins to dictate his tale of a romantic love triangle to the charming yet somewhat opinionated stenographer, Emma challenges his ideas at every turn. Her unsolicited yet intriguing input begins to inadvertently influence Alex and his story and soon real life begins to imitate art.