Lee Holloway, portrayed by [Maggie Gyllenhaal], is the youngest daughter in a dysfunctional family, struggling with her socially awkward and emotionally sensitive nature. Following a troubling incident of self-harm that lands her in the hospital, Lee strives to reintegrate into everyday life. She takes typing lessons, begins dating an acquaintance from high school named Peter, and manages to secure a job as a secretary for the notably eccentric attorney, E. Edward Grey. Despite her unpolished demeanor and the fact that she is far overqualified for the position, Edward hires her, insisting that the work is tedious and devoid of modern conveniences like computers. Lee assures him that she can handle the job as it is.
In the beginning, Edward seems exasperated by Lee's missteps, yet it quickly becomes clear that her submissive tendencies ignite a spark of sexual interest in him. Confronting her about her self-harming behavior, he sternly commands her to refrain from hurting herself anymore, which marks the beginning of a complex BDSM relationship between them. Through this dynamic, Lee undergoes a profound sexual and emotional awakening, falling passionately in love with Edward. However, complications arise as Edward grapples with insecurities surrounding his feelings for her, feeling both shame and disgust about their unconventional sexual practices. Their evolving relationship reaches a breaking point after an intimate encounter in his office, leading to Lee's abrupt dismissal.
Throughout this tumultuous time, Lee attempts to engage in a more traditional romance with Peter, even sharing lackluster intimate moments with him. After being let go from her job, Peter ends up proposing, to which Lee hesitantly agrees. Yet, during a pivotal moment when she tries on her wedding gown, she realizes her heart belongs to Edward and rushes to his office, professing her love. In an effort to test Lee's dedication, he instructs her to sit in his chair without moving her hands or feet until his return. Unwavering, Lee complies, even as Peter, family, and friends visit her, alternating between discouragement and encouragement, all while Edward observes her from a distance, increasingly captivated by her submission.
After three intense days that garner media attention, dubbing it "The Lee Holloway Hunger Strike," Edward finally returns to claim Lee and brings her to his apartment, where he tends to her with care. Ultimately, Lee and Edward exchange vows and embark on a blissful journey together, thriving in their unique dominant and submissive relationship, a testament to the unconventional love they discovered.
