Tell Me a Riddle is a collection of four short stories written by Tillie Olsen, and first published in 1961. The four short stories, "I Stand Here Ironing," "Hey Sailor, What Ship?," "O Yes," and "Tell Me a Riddle," touch on issues of individuality, conformity, social pressures, stratification, feminism, motherhood, authorship, and racism. Throughout the book, Olsen works to give a voice to the voiceless, and to depict marginalized stereotypes as complex individuals. In particular, as a female author in the 1950s and 60s, Olsen draws attention to the plight of women, both as individuals and as authors.
"I Stand Here Ironing" is a one-sided conversation spoken by a mother at an ironing board. In her attempt to explain her daughter's reticent but clownish personality, the mother delivers a treatise on women's lives during the Great Depression and World War II, as well as on the difficult relationship between an author and their work.
"Hey Sailor, What Ship?" is a discombobulated story of an aging, alcoholic sailor who feels lost in a world where the nuclear family is increasingly valued as the only life option.
"O Yes" is the story of two young girls separated by racial prejudice and implicit "sorting," as well as a meditation on the difficulty and importance of finding a supportive community.
The final (and title) story, "Tell Me a Riddle," tells of an aging immigrant couple and their struggle to love one another after a life of hardship and demands.
An early version of "I Stand Here Ironing" won Olsen admission into Stanford's prestigious writing program for a two-year fellowship, where she worked on many of the stories that ended up in this book. After leaving the program, Olsen struggled to complete "Tell Me a Riddle" while balancing the demands of everyday life. Thanks to a grant from the Ford Foundation, she was finally able to finish "Tell Me a Riddle" (which won an O. Henry Award for Best Story of the Year in 1961) and publish the four stories.
Many of Olsen's stories are so compelling because they draw from real experiences and struggles, like those of Olsen and her friends. Her courageous work to bring a voice to the voiceless helps to mark the beginning of Second-Wave feminism, and many later authors are indebted to the work she does in Tell Me a Riddle.