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In this modern day romantic tale, Penelope is about a young girl's inspiring journey, a mysterious family secret and the power of love. With all odds against her, in order for Penelope to break the family curse, she must find true love with "one of her own kind" and realize the most important life lesson, "I like myself the way I am." Penelope Wilhern, born to wealthy socialites, is afflicted by the Wilhern spell that can only be broken when she finds love. Hidden away in her family's estate, the lonely girl meets a string of suitors in her parent's futile attempt to break the curse. Each eligible bachelor is enamored with Penelope and her sizable dowry; until her curse is revealed. Lemon, a mischievous and eager tabloid reporter wants a photograph of the mysterious Penelope and hires Max to pose as a prospective suitor to get the shot. The handsome down-on-his luck gambler finds himself falling for Penelope, but not wanting to disappoint her or to expose his surreptitious ways, he decides to disappear. Fed up by his latest betrayal and determined to live life on her own terms, Penelope breaks free from her family and ventures into the world alone. She finds adventure and Annie, her first friend and becomes the person she was meant to be.