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Thirty-four-year-old Manhattan accountant Cat Connelly has always lived life on the safe side. But after her little sister gets married, Cat wonders if she has condemned herself to a life of boredom by playing by the rules. She decides to take a chance for once, accepting an invitation to spend a month with an old flame in Italy. But her reunion with the slick and gorgeous Francesco is short-lived, and she finds herself suddenly alone in Rome. Now, she must see if she has the courage to live outside the lines for the first time - and to face a past she never understood. It will take an unexpected friendship with a fiery Italian waitress, a whirlwind Vespa tour of the Eternal City with a handsome stranger, and a surprise encounter with an old acquaintance to show Cat that life doesn't always work out the way you expect, but sometimes you have to have fall in order to fly.