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.