Scene 5 shifts back to the present. Willy goes to Charley's office where the secretary, Jenny, overhears him talking to himself. Willy is still enjoying his reverie from Scene 4. Willy is taunting someone about Biff's impending football game and the touchdown he has promised to make for Willy. Willy's daydream ends when he sees Bernard. Willy discovers that Bernard is very successful and that he will soon be staying with rich friends who have their own tennis courts. Willy tells Bernard that Biff is closing a business venture with Bill Oliver. Willy also states that Oliver recruited Biff and is paying his expenses.
Willy asks Bernard how he managed to succeed so well, while Biff did so poorly. According to Willy, Biff's life took a turn for the worse after the Ebbet's Field game. Bernard reminds Willy that Biff failed math, and as a result, he did not graduate. Bernard questions why Biff did not attend summer school. Willy is not sure why he did not go.
Bernard remembers that Biff traveled to Boston to visit Willy and talk about his future. He then tells Willy that Biff burned his homemade University of Virginia tennis shoes and got into a fistfight with him when he returned. Bernard asks Willy what happened to Biff in Boston. At this point, Willy becomes angry and resentful.
Scene 5 builds upon the desperation established in Scene 2. Willy has been borrowing money from Charley for weeks in order to pay the bills. Since he has always been jealous of Charley, this is extremely difficult for him to do. However, Charley gives Willy what he needs and does his best not to humiliate him. In many ways, Charley is a much better friend to Willy than anyone else is, even though Willy denies this to himself.
Willy is "genuinely shocked, pained, and happy" to learn of Bernard's achievements. It is difficult for him to talk with Bernard because Bernard has done so well, while Biff has not. Willy cannot help but compare the two men now, since he continually compared them as children. Although Willy is happy for Bernard and certainly does not wish him any ill, it is not easy for him to observe Bernard's success. Willy had always predicted that Biff would surpass the "anemic" Bernard, due to strength and the fact that he was "well-liked." This is yet another example of the failure of Willy's predictions. Not only is Bernard more prosperous than Biff, but Willy is forced to borrow money from Bernard's father, a man that he has always envied.
It is important to note that Willy uses the past to attempt to create order in a present that is no longer bearable. However, Willy selectively chooses and arranges his memories and facts in a way that is pleasing to him. He does not randomly choose memories, nor does he allow himself to remember everything. Instead he tries to carefully edit out anything that could disrupt the order he desires. The conversation between Bernard and Willy is unsettling to Willy because it awakens unbidden memories that he prefers to deny.
Up until this point, Willy blames Biff's failures on laziness and lack of motivation, but after Howard fires him, Willy begins to consider that perhaps he is responsible in some way: "It keeps going around in my mind, maybe I did something to him. I got nothing to give him." Willy has muddled this idea around but has not thought of what he might have done wrong. Bernard suggests that something else is behind Biff's downward spiral since high school, and he hints that Willy is connected to the change in Biff. Once Bernard connects the change in Biff to Biff's Boston visit, Willy knows what he did wrong. He becomes defensive toward Bernard as a way of denying his own culpability. He refuses to admit anything to Bernard, but Willy suspects that he has not only ruined his own life, but his son's as well.