Rupert is one of the protagonists and “the Lawrence-figure in the novel” (xxi), according to the introduction by Amit Chaudhuri. He is a county school inspector and is repeatedly described as thin and unhealthy. Having both good and dark qualities, Rupert is called “devilish” (89), as well as “Jesus” (382) and the “savior of man” (384). Rupert often preaches about love and ideals, but he is also very sensual. After having sex with Rupert, Ursula thinks, “Wasn’t it rather horrible, a man who could be so soulful and spiritual, now to be so—she balked at her own thoughts and memories: then she added—so bestial?” (413). The specifics of this sex act are not described, but both Ursula and the narrator point to a startling duality in Rupert’s character.

Rupert is introduced in the first chapter through the eyes of his lover, Hermione, though he soon drifts away from her and becomes more interested in Ursula. Rupert also becomes interested in Gerald after spending time with him on a trip to London. While the women in Rupert’s life both love and hate him, Gerald enjoys his company but keeps him at a distance. Gerald thinks that Rupert is “not to be taken seriously, not quite to be counted as a man among men” (201).