Alex Sheldon (Luke Wilson) is an author whose writer's block is the least of his problems - he also happens to be flat broke and owes Cuban loan sharks $100,000. After hanging him out the window and destroying his laptop computer, the thugs give Alex an ultimatum: pay up in 30 days or wind up dead. The only way Alex is going to get that kind of money is by finishing his novel, which is currently less than one sentence long. He's got some idea of what he wants the story to be; as he puts it, "It's about the powerlessness of being in love, how it devours the insides of a person like a deadly virus. It's a comedy." He just can't seem to get it out onto paper. Now lacking both inspiration and a laptop, Alex secures the services of opinionated stenographer Emma Dinsmore (Kate Hudson) to help him complete the novel and get paid by his publisher in time to save his skin.