The problem Biff has with trying to tell his father what happened when he went to see Bill Oliver is symptomatic of the problems Biff has been having communicating with Willy for much of his life. Willy is a good talker but not a good listener. He has an unrealistic picture of his son Biff and consequently has unrealistic expectations of him. Willy wants Biff to be a highly successful businessman to make up for Willy's own inadequacy. Biff has tried to please his father because he loves him and wants his approval. But Biff is finding it harder and harder to go against his own real character. The meeting with Bill Oliver, such as it was, brought Biff's inner conflict to a head. Even though he cannot get through to his father at the restaurant, Biff will eventually force him to listen. Even so, Willy will not agree with Biff's self-assessment or with his son''s assessment of him. Biff says a lot when he says:

I am not a leader of men, Willy, and neither are you. You were never anything but a hard-working drummer who landed in the ash can like all the rest of them.

It is almost comical when, earlier during this climactic showdown between father and son, Willy says:

I am not a dime a dozen! I am Willy Loman, and you are Biff Loman!

Ironically, this statement makes them both seem all the more what they truly are--a couple of nobodies, a pair of losers.

In act 2, scene 5 of Arthur Miller's play Death of a Salesman we find Biff and Happy waiting for Willy for a family dinner amongst the men of the house.

Rather than smoothing their relationship over, this scene is perhaps one of the most eye-opening as many truths will surface when Biff comes to the self-realization that his life has been nothing but a lie.

This self-realization, in turn, comes as a result of an encounter with Bill Oliver, who is a former employer of Biff's. In typical Loman fashion, Biff listens to Willy's idea of going to Bill Oliver, for whom Willy believes Biff was a salesman, to ask him for a business loan so that Biff and Happy can start their own business together.

Willy had assured Biff that Bill Oliver will loan him the money with no problem. However, when Biff goes to see him, Bill Oliver barely remembers him and won't even acknowledge him. This is when Biff realizes that he was never a salesman for Bill Oliver, that such an idea is another one of Willy's self-made lies, and that he was merely another worker of Oliver's. Biff also realizes that his dad has fed him so many fantasies throughout his life that he has come to believe them as deeply as Willy does. This is when he realizes that it is time to tell Willy the real deal.

Biff does tell Willy everything. Albeit with interruptions from Happy, Biff does disclose to Willy what went on. However, it is Willy who tells Biff that he does not want to hear bad news because he has just been fired from his insurance company. The real reason, however, that Biff is not allowed to tell Willy what happened with Bill Oliver is not so much that Biff cannot tell, but that Willy is too involved in his fantasy of Biff being a big shot to accept otherwise.

He lays his last hopes on Biff and Happy even with the knowledge (although he denies it) that both his sons have really not come up to much in life. Hearing Biff say that he failed would be like failing twice over for Willy. It would be the ultimate failure, as a matter of fact. It is this fact, however, that ultimately drives Willy to commit the final act of desperation, and ironically his last act of hope on behalf of Biff, of killing himself to cash in his life insurance so that Biff can start over.