A Simple Story`s peculiar portrayal of two generations of women, mother and daughter, has invited many attempts to locate a link between the two narratives. Focusing on the male figure of authority upon whom the two stories hinge together, this paper examines how the novel reveals as problematic the combination of moral instruction with heterosexual love in the conventional courtship plot that assigns the male lover the role of the reformer of the heroine. This paper begins by showing how conventional expectations of gender naturalize the male as a figure of superior wisdom while situating the heroine as an object of reform. The male hero in this novel is portrayed as an authority figure who is inadequate both as reformer and lover due to his susceptibility to excessive emotions and his despotic assumption of authority. The paper then examines how complications arise when the male figure takes on the dual roles of guardian and lover to the heroine and why their romantic and marital relationships are doomed to fail. The two parts of the story are connected when the vindictive father associates the daughter with the mother`s sin and thus compromises his relationship with his daughter. Ultimately, the two narratives, taken together, can be read as a critique of a patriarchal paradigm that reproduces rigid notions of hierarchical gender relations.