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A floundering college graduate reluctantly takes a job at an upstate New York sex shop while pursuing an opportunity that could help to launch her career as a poet. Wide-eyed Amy (Emma Roberts) may have graduated from college, but lately life seems to be passing her by. An aspiring poet, she still lives with her parents, and longs for independence. In order to earn a paycheck, Amy goes to work at a local sex shop owned by a spirited older couple. With flamboyant transvestite Rubio and charming local boy Alex on staff, life around the store is rarely dull. Still, Amy can't help but feeling like the future has something better in store for her, and she sets out to land an apprenticeship with notoriously withdrawn writer Rat Billings (John Cusack). Meanwhile, inspiration seems to come from the last place Amy ever expected as her professional relationship with Alex takes a surprise turn toward the romantic.