The screenplay by Joyce Eliason and Alev Lytle is based on the 1961 O. Henry Award novella from Tillie Olsen's collection of short stories of the same name.

In San Francisco, Eva draws inspiration from their exuberant granddaughter Jeannie, who lives life to the fullest despite any stumbling blocks it may toss in her path.

To her she reveals the secrets of her soul and shares with her clippings and photos of the literary and philosophical greats – Walt Whitman and Émile Zola among them – who have sustained her in her bleak moments and offered her promise of a better life.

In her review in The New York Times, Janet Maslin called the film "a slow, restrained, dignified effort...so straightforward and so simple that it doesn't prompt anything more elaborate than subjective reactions.

"[2] In 2022 The Academy of Motion Picture Arts and Sciences and The Film Foundation collaborated on a restoration of Tell Me a Riddle with Grant's debut short The Stronger.