Mrs. Willard is the mother of Buddy Willard—Esther’s on-again, off-again boyfriend who wants to marry her. Mrs. Willard is deeply devoted to her son and is extremely protective of him. For example, Esther recalls how Mrs. Willard was a “real fanatic” about virginity and remembers that she gave Esther a “queer, shrewd, searching look” to determine if she was a virgin or not when she came over for supper for the first time. Esther cannot stand Mrs. Willard, owing to her very traditional ideas about the roles that men and women should play. To begin with, Mrs. Willard believes that all men are looking for a “mate” and that all women are looking for “infinite security.” She also believes that men are “arrow[s] into the future” and that women are “the place the arrow shoots off from.” Mrs. Willard’s overview of marriage is distressing for Esther because Mrs. Willard clearly believes that a woman must restrict her behavior in anticipation of pleasing her future husband. Esther rejects Mrs. Willard’s representation of marriage; she desperately wants to forge her own future, not silently support her hypothetical husband from the sidelines. Esther does not want to be a wife or a mother and she feels threatened and judged by people like Mrs. Willard who do not understand that Esther longs for a different path. 

Mrs. Willard represents the traditional gender roles that oppress Esther. Towards the middle of the novel, Esther flirts with a sailor on the Boston Common, pretending she is Elly Higginbottom, an orphan from Chicago. She thinks she sees Mrs. Willard approaching, but is wrong. When the sailor asks what has upset her, she says she thought the woman was from her orphanage in Chicago. The sailor asks if the woman was mean to her and she says yes and cries, momentarily convinced that this horrible woman was “responsible for [her] taking the wrong turn here and the wrong path there and for everything bad that happened after that.” While her fabricated story is clearly false, Esther’s conviction that “Mrs. Willard” caused everything unhappy in her life is not entirely inaccurate. One gets the sense that Esther would have had an easier existence if she had been allowed to make her own choices instead of adhering to traditional 1950s gender restrictions.