Gertrude Stein is an avant-garde poet and art collector living in Paris. She uses words to mimic the visual techniques of Cubism, deliberately breaking away from linear grammar to create abstract literary portraits of the people around her. She hosts regular social gatherings that attract the era's most prominent artists, actively encouraging them to break with traditional artistic methods.

The narrator of "If I Told Him" is a subjective voice attempting to create an exact resemblance of a person using words. The speaker plays with constant repetition, present-tense declarations, and homophones to capture a fragmented likeness. They abandon traditional logic in favor of sensory, shifting impressions that change line by line.

Picasso is a pioneering Modernist painter who famously paints a portrait of Gertrude Stein during his Rose Period. He spearheads the Analytic Cubism movement alongside Georges Braque, developing a geometric style that heavily influences Stein's writing. As a social upstart, he actively challenges the existing artistic hierarchy by abandoning realistic representation entirely.

Napoleon is a famous historical French military leader and the poem's only proper noun. He serves as a symbolic stand-in for Picasso, representing primacy, repetitive patriarchal history, and the disruption of traditional hierarchies. Artists historically depicted him as physically larger than life to capture his intangible power rather than his literal proportions.

Alice is Gertrude Stein's life partner, editor, and confidant. She supports the lively social atmosphere of their Paris apartment and drives supplies to French hospitals during wartime. She functions as Stein's primary sounding board for new writing and eventually becomes the subject of Stein's best-selling book.

Leo is Gertrude Stein's older brother. He shares a Paris apartment with her during her early years in Europe, a period during which she establishes her famous Saturday salons and immerses herself in the local artistic community.

William James is a prominent psychologist and professor at Radcliffe College. He teaches Gertrude Stein about automatic writing and motor automatism, acting as one of her strongest advocates and encouraging her to pursue medical school.

Braque is a Modernist artist and early practitioner of the papier collé technique. He works closely with Picasso to take apart objects and analyze their individual components, creating an aesthetic that directly influences Stein's literary approach.

Matisse is a prominent Modernist painter and regular guest at Gertrude Stein's Paris apartment. Like Picasso, he is encouraged by Stein to break with artistic tradition, and he serves as the subject for one of Stein's early literary portraits.

Hemingway is an emerging writer participating in the Parisian literary and art scene. He attends Gertrude Stein's salons, where he interacts with other avant-garde figures who influence the Modernist movement.