The first short story in Tell Me a Riddle, "I Stand Here Ironing," is a monologue spoken by Emily's mother. The narrator has been asked to help an unidentified figure from Emily's school, who wishes to better understand the girl. Pregnant at a young age and abandoned by Emily's father, the mother had to work hard to provide for herself and Emily, and she as a result often neglected the girl. Later, when the mother married a new man during the Depression, Emily had to serve as a second mother to her younger siblings. As a result of this, Emily has become a shy, introverted girl who has trouble in school. All this changes, however, when she discovers her talent for clowning and begins performing publicly. Ultimately, the mother believes Emily will be okay, but hopes she will find a way to define a identify for herself in the face of pressures that otherwise limit a woman's agency in the world.
The second short story in the collection is "Hey Sailor, What Ship?", the story of an old sailor named Whitey who visits his friends in San Francisco while on leave. Whitey suffers from severe alcoholism, so while the family's young children still love him, the older daughter Jeannie despises him, and the parents (Lennie and Helen) worry about him. Helen loves how Whitey has always helped her and shown sympathy, and Lennie has always relied on him to provide news of the wider world. Whitey's condition grows worse, until the family confronts him and he leaves the house. He wanders off into the night, friendless and alone.
The third entry, "O Yes," tells the story of Helen and Lennie's daughter, Carol, and her experience with racial inequality. Twelve-year-old Carol attends the baptism of her African-American friend, Parry Phillips, and faints because of the extreme emotion in the church. As Parry's mother Alva tries to explain to Carol the freedom that many people feel at church, Carol again becomes overwhelmed and shuts her out. Helen and Lennie struggle to understand the pressures Carol faces at school, though her older sister Jeannie cynically insists segregation is a fact of life. Later, when Carol one day stays home sick from school, Parry brings her homework. The friends realize that they have grown apart because of being treated differently, but they cannot express it to one other. Helen tries to comfort Carol when she cries over the situation, but they cannot find words to speak.
The final story, "Tell Me a Riddle," is considerably longer than the first three. It follows an aging couple whose repressed problems have bubbled up to the surface in their old age. Eva and David are an immigrant couple who moved to American from revolution-torn Russia. They had seven children together, and Eva ignored her own desires in order to mother them. Now, in the present, David wants to sell the house and move to a retirement community, but Eva likes the freedom and quiet she has finally earned. They bicker constantly, alarming their children, but David drops the intensity when he learns that Eva has terrible cancer. Though he does not tell her the truth, he brings her on a trip to California to visit one of their children and her new baby. Eva has difficulty connecting to her grandchildren there, and insists they leave. Instead of bringing her home, however, David takes her to Los Angeles, where they get a small apartment thanks to their granddaughter Jeannie. Partly because of old friends they reconnect with there, Eva begins dreaming of her past, and discovers the truth of her illness. In her final days, she finds a strange joy, and David comes to understand the isolation in which she has lived.