Much to Babbitt's dismay, Ted is struggling in school. Moreover, Ted's relationship with Eunice Littlefield, a carefree girl with a deep passion for the movies, is beginning to worry him. In contrast, he happily observes the relationship between Verona and Escott in the hopes of finding signs of a budding romance. Babbitt wants Ted to go to law school, but Ted is interested in girls and mechanics. He even builds a car from spare parts and sells it for a profit.
When Ted throws a party, Babbitt is greatly disturbed to discover that the teenagers are smoking and drinking in secret. Moreover, they exhibit looser standards regarding the relations between the sexes than Babbitt's generation. When Howard Littlefield checks on the party, he is horrified to see Eunice and Ted dancing so close together. He drags Eunice from the party, and the relationship between his family and the Babbitts cools. After the guests depart, the Babbitts argue about the party.
A visit from his mother and half-brother Martin's family increases Babbitt's growing irritation with family matters. Babbitt's mother and his brother do not understand the modern city life that Babbitt leads. Moreover, Myra's parents move into a hotel, so the Babbitts are obligated to have dinner with them every other Sunday. An illness in February gives Babbitt some relief from the incessant demands of his family. Babbitt suddenly realizes that his entire life is "incredibly mechanical" and wishes he didn't have to return to work.
Babbitt uses insider information Prout gave him in return for his campaign work to extort a high price for some land the Street Traction Company needs to build repair shops. The purchasing agent, the vice president, and the president of the company vigorously protest the exorbitant price, but a compromise that benefits everyone is reached. Babbitt's profit comes to three thousand dollars.
Several customers complain about Graff's dishonesty in dealing with them, so Babbitt, horrified to have a dishonest employee, lectures Graff about ethics and fires him. Graff protests Babbitt's hypocrisy and threatens to reveal the details of Babbitt's shady deals if Babbitt tries to make it difficult for him to get a job in another firm.
Babbitt decides to take Ted with him on a short business trip to Chicago. They enjoy themselves immensely while discussing the excruciating pace of Verona and Escott's courtship, but Babbitt feels lonely and depressed when Ted returns to Zenith for school. By accident, Babbitt encounters Sir Gerald Doak, who is feeling just as bored and lonely. At first, Babbitt is intimidated by the British aristocrat, but he finds that they are a lot alike. They go to a movie and spend the night drinking together in Doak's hotel room.