At the opening of The Well of Loneliness, Lady Anna is a 20-year-old Irish virgin whom many regard as nearly the “perfect woman.” When she marries Sir Philip, she is said to be “a goddess” who possesses “quiet pride” and “promise.” With the birth of her only child, Stephen, Anna’s darker side is revealed. She resents Stephen for not being feminine, and though she feels guilty about these feelings, she does not feel so guilty that she can bring herself to accept her daughter as she is. Additionally, she feels jealous of Stephen because she feels that Stephen stole Sir Philip from her.

While she remains physically lovely even at age 40, her “dislike of the unusual, a certain deep-rooted fear of the unknown” mars her personality, keeping it from being anything but short-sighted and cruel (57). When she discovers that Stephen is attracted to women, she wishes death on Stephen and refuses to allow her to stay in their home. Even when Stephen becomes famous for her talent as a writer and has successfully established her own home in a different country, Anna refuses to acknowledge her as anything but a business partner. Anna’s bitterness eventually eats at her beauty, and she spends her days pale, ill, and devoid of any relationship she doesn’t have to pay for.