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This paper investigates the cultural context within Vladimir Nabokov’s Lolita (1955), examining how the setting of post-war America intersects with the plot and themes of the novel. After World War II, the United States went through a phase of sudden prosperity, as soldiers came home to start families and return to the workforce, something which led to the creation of the now-iconic ‘nuclear family’. However, the emergence of new forms of structural misogyny relegated women to the home as wives and caregivers. Lolita functions as a sharp critique of the domestic culture of 1950s America, one that shows in clear detail how women and girls were and still are forced to accept the patriarchal institution of heterosexuality. Using the lens of Adrienne Rich’s theory of compulsory heterosexuality, this paper contextualizes the actions of Humbert Humbert and Dolores Haze, first reviewing the scholarly and critical debates surrounding the novel before relaying the history of the post-war era and Rich’s primary claims, and moving to a close reading of the ways in which Humbert devalues female queerness as well as a review of Rich’s “characteristics of male power”. Finally, it examines Humbert’s aestheticism as a means of control, and Dolores’s inability to escape from a society where patriarchy forms the bedrock. It concludes with the idea that Lolita functions as a twisted version of the American dream, and posits that the truths it exposes still remain pertinent in the modern day.