Charley has a love/hate relationship with Willy. Although the two neighbors bicker about things, Charley evidently sincerely cares for Willy. He tries to get him to stop obsessing about Biff, to be honest with himself about his career, and to take the job that he is offering him. Willy, who is in a precarious mental state during the play, insults Charley, rejects his advice, rejects his job offer while accepting his handouts, and swears at him. Charley asks, "When the hell are you going to grow up?" He feels Willy is clinging to the past, such as his relationship with his current employer's father, when Willy should be able to change with the changing times. Charley also asks him, "Why must everybody like you?" This indicates that Willy is stuck in an immature mindset of needing approval. He should have come to terms with who he is, his skills and...
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his shortcomings, long ago. But because Willy cannot face the truth, he remains immature, still struggling with issues of identity and self-worth even though he is nearing retirement age. Willy stands in stark contrast to Charley's son, Bernard. Willy has always mocked and belittled Bernard, and now Bernard has an excellent career as a lawyer, has a family, and moves in impressive social circles. He is even arguing a case before the Supreme Court. When Willy asks Charley why Bernard didn't mention the Supreme Court case to him, Charley says, "He don't have to--he's gonna do it." Willy, on the other hand, is constantly bragging about things he is going to do or lying about things he has done. This also shows Willy's immaturity. Charley, because he truly cares for Willy, points out to him his need to grow up. Unfortunately, Willy ignores Charley's attempted intervention.
In Act II of Arthur Miller's Death of a Salesmanwe find Willy Loman and his friend and neighbor, Charley talking to each other during one of Willy's hallucinatory memories.
During this particular flashback, Willy is getting ready for Biff's biggest game in Ebbet's Field. We know how Willy lives vicariously through Biff's personal accomplishments in football. To an average person, this game should be about seeing Biff accomplish the goal of playing in a big field. To Willy, judging from his extremely agitated mannerisms, we can tell that this event signifies the beginning of Willy's own American Dream.
However, in the flashback, Willy's high spirits are being subdued by Charley's composure. This makes Willy very mad, since in reality Willy is absolutely secure in the idea that this night would be legendary for Biff, and that he will become a famous football player from that moment on.
This is the reason why Charley, in view of Willy's ridiculous, and almost out of control behavior, finally asks Willy
Willy, when are you going to grow up?
To which Willy answers:
Yeah? Heh? When this game is over, Charley, you'll be laughing out of the other side of your face. They'll be calling him another Red Grange. Twenty five thousand a year.
Charley: (Kidding) Is that so?
Willy: Yeah that's so
Hence, we can see how Charley downplays Willy's behavior and basically laughs at Willy's immature behavior practically to his face. Willy, far from recognizing himself and his behavior, continues the childish talk with his annoying, almost bratty and catty behavior toward Charley. It really makes us agree with Charley and question ourselves as to when Willy will grow up. We realize, until the end, that Willy really never does.