Not only is Jake trying to prove to himself that he can posses masculine characteristics, but he also tries to do all these things that he thinks the other men are keen on doing. .
The roots of Jake's insecurities with his masculinity come from his personal struggles with women. Brett is the only woman with significance in Jake's life and is the one woman that is the opposite of what Jake needs to feel like a man. Brett is only interested in a man's sexual performance and Jake cannot supply that for her. Brett defines a man's masculinity based on his physical characteristics and not his personality, leaving Jake to feel that a woman cannot love him if he cannot perform in bed. When Jake begs Brett to live together, Brett tells him, "I don't think so. I"d just tromper you with everybody. You couldn't stand it." (Hemingway, 62). Brett is implying that she would make love to other men while they were living together and she doesn't believe that he could handle this. Again, Jake assures her that he is man enough to handle it but she disregards his plea. Jake has a constant struggle with Brett because he cannot be the dominant person in their relationship, thus downplaying his masculinity and questioning his power to be superior over women, a common stereotype of men.
Jake's drive to become a man sure of his masculinity is attained through fear. Jake is fearful of his impotency and not being accepted by his peers. Because Jake has been injured, he finds himself impotent in more that one way. Jake fears that because he has no sexual purpose, his personality will become inadequate and useless along with his sexuality. Jake drinks heavily to hide this fear and try to escape from the injury that plagues his life. By being drunk alongside everyone else at the fiesta of San Fermin made Jake feel the best because in those moments Jake and everyone else were all equal because they were all drunk and no one seemed to remember or care about his lack of potency.