We feel some sympathy for Willie because of his intelligence and his eccentric lifestyle. Willie's personality is constantly at war with the expectations dictated to him by his upbringing. He is supposed to dislike Jews and Italians, he is supposed to be completely subordinate to his parents, and he is supposed to care for nothing but money and influence. Willie quietly resists these rules, however. Willie becomes more of an individual in response to his military training and his relationship with May Wynn. He likes Marty Rubin despite his religions, and repeatedly defies his parents.
Willie has very complex relationships with his parents, the depths of which are first touched on during the scene when Mrs. Keith drops her son off at Columbia. Mrs. Keith, though well-meaning, tries to shelter Willie from reality. She would prefer to hand him everything that he needs in life, rather than allow him to become independent, as evidenced by her attempts to get money to Willie after he enters the service. At this point in the novel, her efforts appear to come more from a conservative desire for Willie to lead a proper upper-class lifestyle than from fear of losing her only son. Mr. Keith is mostly absent from the events of this part of the book. The only interaction between him and his son comes in a flashback in which Willie considers enrolling in the Navy at the beginning of the war. Showing no opinions of his own, Mr. Keith simply warns Willie that going into the Navy would upset Mrs. Keith. Other than this episode, Willie's father quietly plays his role as the family breadwinner, and does not make up a noticeable part of Willie's support network.
May Wynn is Willie's opposite. She is poor, uneducated, and Italian; she speaks her mind with honesty, perception, and color. She is also more interesting than Willie is, having passed up a free college education, as we find out later, in favor of the money available to her in the lounge singing business because of her talent and figure. It is almost certain that she foregoes college in order to help her family with their financial struggles. She picks up immediately on the impossibility of commitment between herself and Willie, but still allows their relationship to develop. This indicates that like Willie, at least at first, she is solely interested in having a good time.