This article presents an examination of Mark Twain as feminist, or at least as a man (re)considering gender roles, through “An Awful … Terrible Medieval Romance” (1870). More than a hoax, the story discusses gender roles, as well as touching on women's treatment by men, sexuality, bisexuality, homosexuality, and—most obviously—cross-dressing. The work further touches on a relationship that appears incestuous as the author delves into areas then undefined but now designated by the grammatical term “gender.” With a deliberately complicated plot, to convey the dilemma facing women in a male-dominated society, Clemens exposes hypocrisy and unfairness women confront. The absurdity behind and the confusion of sexual roles in his story underscore the bizarre situation, assumed if unacknowledged, which male attitudes have created and maintained that men expect women to accept. The incompleteness and deliberate nonending of “A Medieval Romance” symbolize the woman's unfinished, unfulfilling situation and her continuing status with no resolution in sight.