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Willy goes to Charley's office to borrow money meets Bernard, Charley offers him a job and Willy is again furious at the ‘insult’. Willy sees Biff’s admission as a sign that Biff likes him and decides to leave him the money he will be ‘magnificent’. Willy is amazed to see that Bernard has done so well for himself. He is surprised to know that Bernard is a lawyer, that he has a case pending in D.C., and that he knows people who own their own tennis court in their houses. When Willy tries to embellish Biff in front of Bernard, he finds no other choice but to, sort of, give up. Hence, in an act of complete humbleness, Willy asks Bernard
Willy: What- what's the secret?
Bernard: What secret, Willy?
Willy: How- how did you? Why didn't he ever catch on?
Here is when the most important conversation in the play occurs. Both, Willy and Bernard agree that, after that one Ebbet's Field game, Biff ends up flunking Math, and ruining his chances for college, unless he goes to Summer school. It is then when Biff starts his deep disconnect with the rest of the world. Bernard tells Willy that, after Biff flunked Math in High School, Biff was more than willing to go to Summer school and re-do the class. However, right after Biff visits Willy in New England, everything in Biff's life changes. Willy is shocked to hear this revelation.
This is when we find out exactly what happened that day: Biff had gone to New England to vent with his father the fact that he flunked Math, only to realize that his Dad was there with a mistress. The image of "The Willy Loman" that had fed his ego is now, officially, dead. In turn, Biff's own self-perception dies with it as well. After all, he is just a creation of his father's own missing ego. Hence, the encounter with Willy and the mistress is the triggering event that ruins and changes Biff's life, for good.