The manipulation of gender in Chaucer's The Canterbury Tales is utterly opaque. While "The Knight's Tale" potentially entices readers to think that Chaucer defines a woman regarding her relationship to man, "The Wife of Bath's Prologue and Tale" suggests that the poet views a woman as an independent figure whose identity has nothing to do with man. This apparently controversial portrait of gender causes some critics to read Chaucer as a pro-woman individual; simultaneously, it inspires other critics to view the poet as anti-feminist. Such debate may cause readers to misjudge Chaucer's multifaceted approach towards gender as well as other hypersensitive topics, thus adding to the atmosphere of complexity and lack of clarity that dominates The Tales.Accordingly, this paper revisits Chaucer's gender-oriented philosophy in The Tales sieving what is conjectured by the poem's critics from what is said by the poet himself regarding gender. The paper concludes that Chaucer has never had the choice to overtly be or not to be the friend of woman but has always adopted a fence-sitting strategy concerning the question of gender due to his sociopolitical status.The paper confirms that Chaucer's viewpoint of women is neither feminist nor anti-feminist but a realistic amalgamation that mirrors the opaque gender culture of England in the fourteenth century.