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A desperate publisher learns that his best author is suffering from writer's block, and devises a plan to make her miserable in order to get her creative juices flowing again. When Jane Lockhart (Karen Gillan) scored a critical and commercial success with her first novel, "Happy Ending", her publisher Thomas Duval (Stanley Webster) was on top of the world. Everyone expected great things to come from Jane, but now as she approaches completion of her sophomore novel, her personal satisfaction is impeding her talent for storytelling. Try as she might, Jane just can't come up with an ending for her book. Convinced that Jane will never finish her book as long as she's happy and determined to keep his career afloat, Tom recruits his best friend Roddy, a caustic high school teacher, to help knock the jubilant author off of cloud nine. All the while, Jane's fictional characters begin to take on lives of their own, Tom begins to suspect that he's falling for the very woman whose spirit he has committed himself to crushing.