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". 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 parents' 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 cannot bring himself to give her what she wants. Fed up by this 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 goes on a journey to discover the world and who she wants to be.