In this dissertation I explore “The Woman Question” in the discourse of Iranian male authors. A pro-modernity group, they placed women’s issues at the heart of their discourse. This dissertation follows the trajectory of the representation of “The Woman Question” as it is reflected in the male discourse over the course of a century. It discusses the production of a literature that was anchored in the idea of reform and concerned itself with issues pertaining to women. These men challenged lifelong patriarchal notions such as veiling, polygamy, gender segregation, and arranged marriages, as well as traditional roles of women and gender relations. This study is defined under the rubrics of “The Woman Question” and “The New Woman,” which I have borrowed from the Victorian and Edwardian debates of similar issues as they provide clearer delineations. Drawing upon debates on sexuality, and gender, this dissertation illustrates the way these men championed women was both progressive and regressive. This study argues that the desire for women’s liberation was couched in male ideology of gender relations. It further illustrates that the advancement of “The Woman Question,” due to its continuous and yet gradual shifting concurrent with each author’s nuanced perception of women’s issues, went through discernible stages that I refer to as observation, causation, remedy, and confusion. The analytical framework for this project is anchored in the “why” and the “how” of the Iranian male authors’ writings on women in addition to “what” was written. This dissertation examines four narrative texts—two in prose and two in poetry—entitled: “Lankaran’s Vizier,” “The Black Shroud,” “‘Arefnameh,” and “Fetneh” written respectively by Akhundzadeh, ‘Eshqi, Iraj Mirza, and Dashti. Chapter one outlines the historical background, methodology, theoretical framework, and literature review. The following chapters examine, the advocacy for companionate marriage and romantic love, women and nationalistic cause, veiling and unveiling, and the emerging figure of the New Iranian Woman as morally depraved.