"Confessions of a Failed Southern Lady" by Florence King is a memoir about King's years with her grandmother who attempts to rear her as a Southern lady. King is academically gifted in her youth and much of her story details her struggle to balance her education with the behavior expected of a lady. "Confessions of a Failed Southern Lady" is an extremely entertaining and at times, comical relation of King's formative years which details the influences that created King as a woman and a writer.

Since Granny's attempts to raise Mama as a Southern lady fail, she is eager for a second chance to rear a lady when Florence is born about a year after Mama marries Herb, so she moves in with them. Granny attempts to train Florence to become a lady while Herb educates her. When the family takes a vacation to Colonial Beach, Evelyn causes a scene by claiming her womb is falling out, but Florence is relieved when Herb tells her she does not have to be like Evelyn when she grows up. Florence is promoted to Kindergarten A because she is too advanced for Kindergarten B which worries Granny because ladies should not be too bright. Granny and Jensy force Florence to accompany them on their temporal acts of mercy, visiting the sick and such.

Herb tells Mama, Granny and Florence that it is impossible for an American woman to be feminine because they have no defining goddesses. After being threatened by Harriet Mudd when she tries to be friendly, Florence learns not to try to make herself liked. When Granny inherits a house on 14th Street, the family moves in, and Granny insists upon asking Jensy to live with them. In high school, Florence suffers from menstrual cramps and since the doctor has to break her hymen to examine her, he gives her a certificate of virginity so her husband will know he is not getting damaged goods. Florence chooses not to date in high school and she labels the non-academic girls as malkins or women who fear not being like everyone else. She studies French and begins to idolize Berenice.

Florence attends college at American University because she acquires a scholarship, but she is distraught when she learns she cannot major in French and must switch her major to History. She joins a sorority to obtain dates to appease her sexual desires, but she quits the sorority after attending Marine camp one summer when she returns to the sorority and her sisters mock the female Marines as lesbians. Worried about becoming a malkin after graduation, Florence applies for and receives a fellowship to the University of Mississippi. After obtaining a diaphragm, she loses her virginity to Dr. Newton.

At the University of Mississippi, Florence meets Bres and falls in love, though she cannot spend the night because they fear the anonymous phone calls Bres has received in the past. Since Florence wants to be with Bres forever, she agrees to Bres' suggestion that she apply for fellowships, but when she finds a call for confession stories, she writes and submits two stories. Florence is excited when her stories are accepted, but Bres is furious because she wanted Florence to apply for a fellowship, ending their relationship as a result. Soon after, Bres is killed in a car accident, and Florence responds by sleeping with numerous men. Florence finishes her year at the University of Mississippi by ignoring her thesis and writing more stories.

Back in Washington D. C., Florence tells her family about becoming a writer and moves to her own apartment while searching for other lesbians in vain since she is lonely. When Jensy dies, Herb eulogizes her as a lady and soon after, Granny decides to sell the house on 14th Street and move back to the family homestead in Ballston, Virginia with Mama, Herb and Florence. When Granny has to be placed in a nursing home, Florence finally meets other lesbians through the daughter of one of Granny's neighbors, Mrs. Kincaid. After Granny dies, Florence argues with Evelyn that Granny and Jensy were not ladies. Instead, they were viragoes or women of great courage, strength, and stature who are not conventionally feminine. Mama has always known she was different, but now she understands it is because she is a virago.