Novelist Alex Sheldon (Luke Wilson) is stuck between a rock and a hard place: He owes $50,000 in gambling debts, and the only way to pay up is to break through a massive case of writer's block. Enter prim stenographer Emma (Kate Hudson). Emma helps Alex work out the plot kinks in his Great Gatsby-esque story, which are explored through fantasy sequences inhabited by the author and Emma -- who is quickly becoming the object of his affection.