This paper tries to reveal the gender prejudices of the male author in his portrayal of female characters in The Sun Also Rises. As the narrator of this novel, Jake Barnes betrays his anxieties about the emergence of the sexually liberated women. In the past, many critics showed a tendency to divide Hemingway"s female characters into two easily recognizable types, namely either ideal helpmates or bitches. However, Hemingway"s portrayal of Brett Ashley seems to challenge this kind of simple dichotomy. Hemingway"s text is important in that it reflects the cultural struggle of the time, especially the conflict between the old and the modern values concerning gender roles. American women gained the suffrage in 1920, thus having a momentum for expressing their political voices and for participating in many social areas traditionally regarded as men"s. In this novel, Brett is representative of the new generation of sexually liberated women. In contrast, male characters are not prepared to deal with these new types of aggressive women. Despite his critical stance toward the often sexually hypocritical attitudes of the Americans, Hemingway"s upbringing in a middle-class Protestant home seems to prevent him from condoning the sexual freedom of women. In this context, Jake"s war wound needs to be seen as a metaphor for his anxieties about his own masculinity against the threats of Brett and other uncontrollable women in the novel. Being finally unable to problematize the dominant gender and sexual binarisms such as masculine/feminine and heterosexual/homosexual, Jake prefers to maintain the old values, where gender roles are more clearly defined, In addition, this novel is not just filled with homophobic descriptions, but also with prejudiced comments about Jews, African Americans, and foreigners. Wishing to be a successful author, Hemingway seems to have analyzed, and made his novel accommodate to, the cultural codes of his readers.