In the early 1900s, Gertrude Stein’s residence in Paris became a gathering place for artists and writers. Some of the visitors who frequented 27, Rue de Fleurus were the young experimental painters whose work Gertrude and her brother Leo Stein had been collecting: Picasso, Braques, Manet, Renoir, Cézanne, Matisse. Beside the more gregarious and articulate Matisse, Picasso, who was new to France and just learning to speak French, was thought of as "the quiet Spaniard" and was not at first understood by the guests at the Saturday-night dinner parties. But as the number of visitors and the frequency of the salon-evenings increased, Stein's friendship with Picasso blossomed. She became more and more certain of his genius. As her brother increasingly sided with the Impressionists, her taste in art became more experimental, and she was among the first major collectors of the Cubists.

In 1905, Picasso asked her to sit for a portrait, and the results (not Cubist, but representational) were dark, brooding, and strange. Picasso famously said, "Everybody says that she does not look like it but that does not make any difference, she will," which was quoted by Stein in The Autobiography of Alice B. Toklas. Stein said later, "I was and still am satisfied with my portrait, for me it is I, and it is the only reproduction of me which is always I, for me." The completion of the portrait marks the beginning of Stein’s interest in portraiture and "resemblance," concepts that would come to influence her writing nearly as much as Picasso’s Cubist philosophies.

Stein’s literary portrait of Picasso "If I Told Him," completed nearly twenty years later and first published in Vanity Fair, is a similarly strange but tender attempt to capture a resemblance of his genius. It begins: "If I told him would he like it. Would he like it if I told him." As a painter might wonder if he is flattering his subject sufficiently, Stein wonders if Picasso will like the "portrait" she writes for him as he hears it told back to him—his own Cubist philosophies translated into language. A later passage addresses how one might create "resemblance" in a verbal passage, which becomes something like repetition:

Exact resemblance. To exact resemblance the exact resemblance as exact as a resemblance, exactly as resembling, exactly resembling, exactly in resemblance exactly a resemblance, exactly and resemblance. For this is so. Because.

In fact, Stein continues to defend the representational nature of Cubism throughout her life, as if one could only get to an exact "resemblence," or image of life, through the distortion, repetition, and altering of the present moment to mimic perception. In her 1938 book Picasso she mentions an incident in 1909 when Picasso, after having completed the Cubist paintings Horta de Ebro and Maison sur la Colline, showed Stein the photographs that inspired the paintings. Stein swore that they were no different than the photographs.

Stein’s most notable experiment with "verbal Cubism" was her book of poetry Tender Buttons, a series of prose poems divided into "Objects," "Food," and "Rooms." In these strange and fractured descriptions of what she sees, the poet works toward the kind of resemblance and portraiture she first saw in Picasso’s work, beginning with a Cubist description of a carafe that seems to alert the world to the exciting changes afoot in poetry and painting:

A kind in glass and a cousin, a spectacle and nothing strange a single hurt color and an arrangement in a system to pointing. All this and not ordinary, not unordered in not resembling. The difference is spreading.