Elevator Girl (2010)

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Succesful Boston lawyer Jonathan McIntyre is a fatherless workaholic, who only dates girls recommended as career boosts by his colleague and buddy Nick Sweeney. At Jonathan's festive inauguration as the law firm's youngest full partner, he meets in the elevator Liberty Taylor, the caterer, who still refuses to pick one of her jobs for every day of the week. Encouraged enterprisingly by his secretary Rosemary, they date and start falling in love. As Nick predicted, her lack of ambition and social skills prove rather a big obstacle for his future.