On the surface, Terry seems to undergo the most drastic transformation of any character in the novel. At first, Terry seems confident, funny, courageous, a natural leader of men, and, we are told, a charmer of ladies. Later, however, he is shown to be a bully, an abuser, and a fool. Terry hasn’t changed; rather, his true character has been revealed, and Van, the narrator, has come to see him in a new light. Terry arrives in Herland with a theory that men are naturally superior to women and that, consequently, every woman naturally enjoys being “mastered” by her man. This notion is part of the bedrock of Terry’s identity and the source of his self-image. In Gilman’s time, men of Terry’s type were referred to as “blackguards” (as opposed to “gentlemen” like Jeff), and Gilman is saying that one sign of the unhealthy state of our male-dominated culture is the way blackguards such as Terry are viewed as lovable rogues and not seen for the domineering, often violent sexists that they are. The task of a decent society, Gilman suggests, is to turn the laudable energy and drive of men such as Terry in a less anti-social, anti-woman direction.

Though Terry imagines himself a rugged individualist, he is actually just as dependent on women as he imagines women are on men. Without a woman to admire him, flirt with him, and be impressed by his bluster, Terry’s sense of himself as a man is challenged, and he becomes deeply insecure. Faced with a woman such as Alima, who is a match for him physically and intellectually and who has no desire to be subservient to a man, Terry doesn’t know what to do. Unlike Jeff, who is thoroughly converted to Herland’s ways, and unlike Van, who, though cautious, hopes to understand and learn from them, Terry’s response is to reject Herland and to insist ever more stridently on his male prerogatives. Once his fantasies are exploded, he cannot even see the beauty of Herland’s inhabitants, whom Terry sees as unwomanly because of their self-confidence, a society not of women, but of “neuters.” The more strident Terry becomes, however, the more foolish he looks, and the more estranged he becomes from his lover and even his friends.