This essay analyzes May Welland in Edith Wharton’s The Age of Innocence (1920). Although May plays a minor role in the novel, the reader recognizes her major influence in her husband’s life even after her death. May’s enigmatic nature also gives rise to critics’contradictory views on May as a victor and victim of the patriarchal system. While exploring these contradictory views on May and demystifying the American Girl’s “innocence,” this essay attempts to transform the contradiction into the complexities of paradox. In approaching the paradoxical traits that May holds, I suggest uncovering the feminine that is deeply buried in her with the help of the insights provided by the analytical psychology of Carl Jung and his followers. I conclude the happy marriage and domestic bliss that May achieves are paradoxical because her marriage cannot be a model of matrimonial happiness or companionship.