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Troubled by the fact that none of his relationships have lasted, Bart tracks down all of his former loves. He ends up tracking one in particular, Mary Spuckler (voiced by Zoeey Deschanel), all the way to New York City. His former girlfriend ran away from the Cletus family home and set herself up in the big city. Bart and Mary's reunion is cut short when her father tracks her down, and she flees the city in order to maintain her independence. Meanwhile, Marge and Lisa try to enjoy New York City on a budget. Unfortunately, the city's high cost leaves them dissatisfied and unable to experience its culture to the fullest.