Returning to his Chicago haunts, Augie begins working on getting a teaching certificate, and the school at which he does his practice teaching employs his old neighbor, Kayo Obermark. Augie also buys a used Buick, which won't start on cold mornings without a push. Kayo nags him about not being married and becoming a father. "I seemed to have critics everywhere," Augie reflects, and he tells Kayo "my pride has always been hurt by my not being able to give an account of myself and always being manipulated." In fact, Augie's drift through life has been a series of manipulations: by Grandma, by Einhorn, by Simon, by the Renlings, by the Magnuses, and by Thea -- among others. He asserts that "Reality comes from giving an account of yourself, and that's the worst of being helpless."
Kayo invites Augie home to meet his wife, and while he's there Kayo's brother-in-law offers to buy the Buick. Augie sells it to him for one hundred eighty dollars, paid by check, but then the brother-in-law insists they play poker. Kayo and his brother-in-law's wife play too, but Augie is the only winner. He gives Kayo his money back on the way home, but the brother-in-law stops the check when the Buick stops running, and Augie has to come fetch it.
He resumes his affair with Sophie Geratis, who is married now. But Sophie's husband has turned out to be gay, and she wants to divorce him and marry Augie. Despite Kayo's advice, Augie isn't ready to get married and tells Sophie so. She says, "I'm all right for bed, but not to marry.... Nothing is ever good enough for you to stick to. Your old man must have been some aristocrat bastard." Augie tells her that all he knows about his father is that he drove a truck for a laundry. But he knows that Sophie "would have scolded me for my own good too much."
Another friend, Clem Tambow, has an idea: He and Augie will open a vocational counseling service. Clem is about to get his psychology degree, so he'll give aptitude tests and Augie can conduct interviews. Augie rejects the idea as too much of a scam. He tells Clem that he has had a revelation: "since I've been working for Robey I have reached the conclusion that I couldn't utilize even ten percent of what I already knew.... Anything that just adds information that you can't use is just plain dangerous." So he wants to simplify his life: He wants to buy a little land and settle on it. He'll "get married and set up a kind of home and teach school." He'll get his mother and his brother out of their respective institutions, and he'll get the students for his school from state institutions. He'll teach woodworking and maybe his brother George can teach shoe repair. "Maybe I'll study languages so I could teach them. My mother could sit on the porch and the animals would come around her, by her shoes, the roosters and the cats. Maybe we could start a tree nursery."
Clem scoffs at Augie's little utopia, starting with the students: "You think you'll love them so they'll turn into little Michelangelos and Tolstois, and you'll give them their chance in life and rescue them, so you'll be their saint and holy father. But if you make them so good, how will they get along in the world?" Augie wants to be a king, he says, "You sonofabitch, you want to be the kind goddam king over these women and children and your half-wit brother. Your father ditched the family, and you did your share of ditching too, so now you want to make up for it."
Augie persists in this daydream, however, and even thinks about marrying Sophie. But then Pearl Harbor is attacked, and suddenly his attention shifts elsewhere: "At first I went off my rocker, I hated the enemy, I couldn't wait to go and fight. I was a madman in the movies and yelled and clapped in the newsreel." But when he goes to volunteer he discovers that he has developed a hernia from the fall with Bizcocho. So he goes into County Hospital to have the operation done.
Sophie visits him every day in the hospital, though she thinks he's crazy for having the operation when it could get him out of the draft. Her husband has been drafted, which she sees as another reason for Augie to stick around. "Simon came to see me and threw a bag of oranges on the bed. He bawled me out that I hadn't gone to a private hospital." Padilla has let his girlfriend use Augie's room while he was in the hospital, so he's essentially living there, too. So he lets Augie move into his own place. "It took me many long months to get better, and I was doing very poorly. And about this time I got a letter from Thea, APO San Francisco, telling me that she had married an Air Force captain."
Augie goes to visit his mother, and they go for a walk. On their way back, Simon drives up with a blond woman in the car. He signals to Augie not to let their mother know about the woman. Simon "was making real dough now. A company he had invested in was manufacturing a gimmick for the Army." After taking their mother home, Simon introduces Augie to his mistress, Renée. "It was a hard thing for me to get through my head, after I came to know her, that she could be so important to him," Augie recalls. She seems immature and somehow suspicious and uncertain to him. Though Simon proclaims his love for Renée, "He was romantic about Charlotte too. And Renée had to bear it and know she could never have any exclusive claim on him." Augie reflects, however, that he had treated Stella pretty much the same way when Thea turned up in his life. Renée gets her own by demanding from Simon everything that Charlotte has. They fight about it: "Charlotte has her own money, don't you realize that?" Renée replies, "But not what you want. I've got that."
While waiting to recover from the hernia operation, Augie takes a job as a salesman with a business machine company -- a plum job made available by the wartime manpower shortage. But he remains eager to get into the service, to Simon's disgust -- Simon has been declared 4F because of an ear problem. The Army and Navy continue to reject Augie, so he joins the Merchant Marine. While he's waiting to go to Sheepshead Bay for training, Augie runs into Simon, who tells him that Renée tried to commit suicide -- though he admits that she may have been faking it. Charlotte had found out about Renée and told Simon that it had to stop. After a meeting in which Renée cursed Charlotte and both Charlotte and Simon slapped Renée, Simon paid Renée off and sent her to California. But she had come back and telephoned Simon with the news that she was pregnant. Simon told her he didn't care and called her a crook. "After a silence she hung up. This was when he thought she would kill herself." So he went to check on her and found her unconscious. She is in her fourth month of pregnancy, and he asks Augie what to do.
"What's there to do? Nothing. There'll be a kid now. Who knows but that this is the way you and George and I happened to come into the world."
Augie applies to the Purser's and Pharmacist's Mate School, but has to do training on Chesapeake Bay first. In Baltimore there are letters from friends, including Sophie, who has joined her husband at Camp Blanding. "She said farewell but kept saying it in different letters." They return to Sheepshead, where he studies bookkeeping and "ship's doctoring." Stella Chesney, whom he helped get out of Mexico, is in New York. He learns that Oliver had promised to make her a star in Hollywood, and that they had wound up in Mexico on a kind of side trip. On a weekend leave, Augie and Stella resume their affair, and he falls in love with her.
Was she a vain person, or injurious or cynical, it couldn't make any difference now. Or was I a foolish, uncorrected, blundering, provisional, unreliable man, this was taken away as of no account and couldn't have any sense or meaning.He has to return to the base on Monday morning, and he is on his best behavior for fear that his next weekend leave will be canceled. He hurries back to her the next Saturday and finds her sick in bed, partly because she was worried if he really loved her. He proposes to her, and they decide to get married once his training at Sheepshead is over.