Stuart, newly hired by a Manhattan law firm, is immediately attracted to his coworker Penelope—a woman who, apparently embarrassed by her beauty, does her best to downplay it with conservative attire, as well as extremely reserved behavior. Regardless of appearances to the contrary, Stuart feels Penelope has a fiery disposition and isn't indifferent to love: he's convinced she's putting on a chastity act, even if he can't imagine why. Increasingly captivated by Penelope and determined to solve her mystery, Stuart sets about gaining her trust; but she, although always friendly, remains inaccessible. His coworkers, convinced Stuart’s blind to the obvious and only seeing what he wants to see, chasing after a figment of his over-hopeful imagination, marvel at his stubborn persistence. But could Stuart's perceptions be accurate? Is Penelope leading a double life, to an extent unimaginable to those at the office? Does she wear the mask of propriety to throw her coworkers off the scent?