Love, Love, Love is part of a group of so-called poster portraits of various artists and writers painted by Charles Demuth between 1924 and 1928. They are all symbolic portraits in which the sitter’s identity is constructed from various words and objects. Demuth embraced a tradition of Modernist portraits established the previous decade by artists and writers such as Marsden Hartley, Marius de Zayas, Francis Picabia and Gertrude Stein herself. Instead of depicting the subject’s facial features, Demuth employs different kinds of emblems and signs, engaging in a kind of play with the viewer. By doing so he furthermore calls into question the notion of identity in portraiture, a complex and controversial theme. Creating an actual likeness was thus not an essential aim.

In the present portrait of the American writer, he uses an enigmatic mask, the numbers 1, 2 and 3 and the word “LOVE” repeated three times, which stand out against the flat background that is divided into two by a marked diagonal separating black from red. Whereas the meaning of the mask is indecipherable, the figures may refer to the writer’s fondness for the number three.