Cultural Conformity
Set mostly within the context of the American 1950s - an era of cultural conformity and McCarthyism - Tell Me a Riddle grapples with the individual's struggle against society's overwhelming forces. In "I Stand Here Ironing," the narrator struggles (and almost fails) to create an individuality divorced from stereotypical images of mid-century motherhood. The title story explores a similar situation through Eva. In "Hey Sailor, What Ship?", Whitey struggles because he has chosen an identity considered marginal. In his exploits to Manila and other countries, he sees the rougher lives that many Americans are sheltered from, and he butts up against anti-Communist sentiments in his struggles to organize a union for the sailors. In "O Yes," Parry and Carol bow under society's "sorting" pressures, as they conform to racial stereotypes. Olsen uses these stories to showcase the danger that cultural conformity poses to the individual, while also detailing complicated methods of resistance and change.
Nuclear Family
The nuclear family - and those excluded from it - form central conflicts for Olsen. In particular, "Hey Sailor, What Ship?" explores how a semi-ideal nuclear family grapples against its complicated feelings for an outside force: Whitey. While the family and Whitey share love for each other, they find it harder to understand one another with each passing year. While the other stories do not manifest this theme as explicitly, questions of family arise in each, especially in terms of how women must challenge or conform to social expectations for how they should operate within it. Although the nuclear family was idealized by 1950s culture, Olsen depicts it as something with many problems, from its patriarchal and restrictive values, to its inability to accommodate those outside of it.
Multiple Voices
Not content to merely present instances of conformity and repression, Olsen also depicts how individuals can resist those forces. One form of resistance that Olsen relies upon is the use of multiple voices. While the family in "Hey Sailor, What Ship?" is a semi-stereotypical nuclear family, the short story manages to showcase each member's voice, from the father all the way down to the youngest daughter. In "O Yes," Olsen again uses multiple voices to tell the story, including Alva's interior monologue about her religious visions and Parry's unspoken reflections on the effects of racism. "Tell Me a Riddle" is a story told equally by the husband and wife, giving thereby an honest portrayal of a complex relationship. Through this work, Olsen asserts that the only way to get closer to truth and realization is to privilege all voices, not just patriarchal ones.
Silence
Complementary to the theme of multiple voices is the growing threat of silence that pervades the book. In "I Stand Here Ironing," the mother struggles against years of silence imposed by both difficult living conditions and female marginalization. Within "O Yes," Alva and Parry's monologues are delivered within their minds, meaning that they can only express themselves in silence. The church in that story stands as stark counterpoint, by offering people a chance to break their silence in communal expression. In "Tell Me a Riddle," Eva embraces the silence that she has grown to love, wanting to die quietly and peacefully. However, she only came to know this silence in the first place because of social expectations that have limited her identity. Cultural forces push many of these marginalized characters into silence, and Olsen innovatively depicts the many different responses one can have to forced silence - from uncertainty, to rebellion, to peace.
Community
In response to the restrictive patriarchal values imposed upon them, Olsen's characters seek alternate forms of community. For Parry and Alva, this community comes from the African-American church, where they are free to express themselves, and where they really feel at home. For Whitey, this community used to be in a brotherhood of sailors, but that community has since fallen apart. David seeks to join a retirement community in "Tell Me a Riddle," but Eva prefers peaceful isolation, a community unto herself. Throughout the stories, the importance of community is heavily emphasized, as is the importance of varied types of communities.
Female Complexity
As a woman writer in the 1950s and 60s, Tillie Olsen brings many female issues to the forefront. "Tell Me a Riddle" paints a complex portrait of motherhood as both a positive and a destructive force. As Eva visits her grandchildren, she finds that she cannot hold the young babies. While this reaction may seem unnatural, Olsen gives us glimpses into Eva's thoughts to explore how the all-consuming love of motherhood can both enhance and destroy a person. In "O Yes," Helena and Alva are able to glimpse the complexities of racial injustice because, as women, they understand marginalization. In "I Stand Here Ironing," the narrator urges her daughter to keep her complexity, rather that conform herself to a simple identity. Female complexity is something to be cherished and studied, and is given a voice in these stories to counteract social forces that demand woman limit themselves to domestic roles.
Unconventional Storytelling
Olsen explores many radicalized themes within her short stories, and she uses radicalized forms to fully enact them. Her innovative use of storytelling is more than experimental prose - it reflects the way that humans understand themselves outside of the simple patterns that society usually demands. "I Stand Here Ironing" is a one-sided conversation that jumps back and forth between the present and past, much like the iron on the table. The idea is that memory and insight do not come in linear ways. "Hey Sailor, What Ship?" is a confusion of temporality and location that showcases both Whitey's drunkenness and his increased disillusion from society. "O Yes" uses unspoken monologues of side characters to provide an enriched version of the story, to paint a more expansive picture of its sad themes. Finally, "Tell Me a Riddle" uses two main characters to provide several sides to the story, to suggest the complexity of any relationship and its history. It also moves loosely through chronology, revealing crucial information about the past later within the story. These changes in story form enable Olsen to tell different stories than the traditional ones, thereby suggesting that understanding people is far more complicated than we tend to believe.
