Tell Me a Riddle

Tell Me a Riddle is a 1961 collection of four short stories by American author Tillie Olsen. All four stories involve deep characterizations of people who make up a complicated family. The stories give a voice to the anxiety, repression, stereotyping, and injustice experienced by women in the twentieth century, primarily through an emphasis on their marital relationships. They also confront the problems experienced by men, racial inequality, sickness, and mortality. Despite their almost unbearable problems, many of the characters learn how to flourish. The collection’s titular story, “Tell Me a Riddle,” is often considered Olsen’s magnum opus.

The collection’s first short story, “I Stand Here Ironing,” is a monologue delivered by the unnamed mother of Emily, a young girl who breaks out of her shell when she discovers a love of clowning. The mother admits that she was not present to care for Emily’s well-being or emotional needs, to the point where she virtually neglected her. When Emily’s mother got pregnant while very young, Emily’s father left her to raise her alone. The stress of working to provide for both of them led the mother to resent her life and try to escape her maternal responsibilities. The mother connects her absence to Emily’s shyness. That is why, when Emily embraces the unorthodox hobby of clowning, the mother supports it with unusual earnestness. Still, she interprets Emily’s clowning passion as another form of escape from the compromising forces on women’s identity that abound in the world. She believes that Emily will find her way, nonetheless.

“Hey Sailor, What Ship?”, profiles an elderly sailor, Whitey, who uses his vacation to visit his old friends Lennie and Helen in San Francisco. Whitey, a longtime alcoholic, is worse for wear. Lennie and Helen are concerned for his well-being. Their eldest daughter, Jeannie, strongly dislikes him, and their younger children love him. Helen and Lennie see the best in Whitey, who has only treated them with warmth and compassion. Lennie has lived vicariously through Whitey’s travels, and Whitey has helped Helen through many trials. One night, when Whitey’s alcoholism worsens, his friends realize they have no choice but to try to intervene. He leaves the house and enters the darkness, alienated by a condition that even his best friends cannot understand.



“O Yes,” follows Carol, the daughter of Lennie and Helen. When she is twelve, Carol celebrates the baptism of her African-American friend, Parry Phillips, in a predominantly African-American church. Carol is so overwhelmed by the churchgoers’ enthusiasm and spirit that she becomes terrified and faints. When she wakes, Parry’s mother, Alva, explains that their church is one of few places for them to experience the feeling of freedom. Carol struggles to understand the experience of blackness, choosing to continue to resist her friend’s efforts to enlighten her. Meanwhile, Lennie and Helen try to speak to Carol about the racism she sees in the world. Carol’s older sister, Jeannie, argues that segregation will always exist. When Carol is home sick one day, Parry arrives with her homework. The old friends interact awkwardly, both realizing that their experiences of race are making it harder to relate as they grow older. At the end of the story, Carol cries to her mother, but Helen doesn’t know how to comfort her.

The last story in the collection, Olsen’s novella, “Tell Me a Riddle,” concerns a couple, David and Eva, who immigrated from Russia while young and are now approaching old age. For most of Eva’s adult life, she has spent most of her energy raising their seven children and feeling unable to follow her dreams. Now that their children are all independent adults, David suggests that they sell their house and transition into a retirement home. Eva, on the other hand, relishes their newfound peace and freedom. For this reason, and several other trivial ones, they squabble frequently, sometimes erupting into anger.

When David discovers before Eva that she has terminal cancer, he quits arguing. Rather than reveal it to Eva immediately, he takes her to visit their daughter and baby grandchild in California. Once there, Eva struggles to relate to her fully American grandchildren, feeling more alienated than ever as a Russian immigrant. When she asks to go home, David takes her to Los Angeles instead, where they used to live and still have old friends. They move into a small apartment provided by Jeannie, one of their granddaughters. The new environment and rekindled connections help Eva remember her past. When she finally discovers that she has cancer, she does not despair; rather, she finds joy in her family and friends and the memories they made together, even after she left her first homeland and made a life in America. Her renewed joy helps David finally understand how her immigrant experience has shaped her. “Tell Me a Riddle,” like the eponymous collection, validates the different experiences of generations, races, nationalities, and genders, showing that people are resilient even as the modern world hurtles forward.