The Rejected Suitor is one of several works Eilshemius painted around 1915 that resemble theatrical tableaus. Duncan Phillips said that it was like "an unchangeably perfect scene in a grim and dismal play by Ibsen." Its theatrical quality is enhanced by the device of the "self-made frame," a border painted by the artist to enclose and set off the scene. Experts have noted that Eilshemius's theatrical subjects seem to correspond with a shift in his style away from traditional naturalistic representation and toward a more visionary and simplified approach. Using a dark palette in which browns and deep reds predominate, Eilshemius painted figures and settings with a broad, almost caricature-like simplicity. He also stopped using canvas and began painting on scraps of cardboard and cigar-box lids.
It was late works such as The Rejected Suitor that garnered Eilshemius the label of primitive when he was plucked from obscurity by Marcel Duchamp and compared by Duncan Phillips to the French "naif," Henri Rousseau. In contrast to Rousseau, however, Eilshemius had received fairly extensive academic training, and he took issue with the primitive label, suggesting that his interest lay more in the poetic aspects of a painting. Phillips noticed an underlying sophistication of design in The Rejected Suitor, which features the repetition of ovals, the juxtaposition of horizontal and vertical elements, and "modulations of darks and lights--warmer and cooler areas within the melancholy tone and the dominant shapes." He also concluded that in such works Eilshemius "reveals the fact that now and then he could achieve in that last period a unique and intense expressionism of design and tone—in which laughter and despair are fused with a smoldering passion."
In addition to being a prolific painter, Eilshemius was the author of numerous poems, short stories, songs, novels, and plays, none of which found commercial or critical success. He seems to have found an outlet for his narrative imagination in painting dramatic vignettes. While The Rejected Suitor could have derived from a production he had seen or one of his own plays, it may have been based on personal experience. Phillips suggested that "it is perhaps a memory of a deep personal hurt, of a rankling humiliation in that musty room.”