In June, Myra and Tinka Babbitt travel to visit relatives. On one night when Ted and Verona are both out, George has the house to himself. Unsure what to do with this unusual freedom, he again feels a "discontent with the good common ways" (p. 245). As he broods, Chum Frink walks by the house, drunk, calling George a fool and wallowing in self-pity for the writer that he could have been but will never be.
Suddenly, George is struck with the sense that "all life as he knew it and vigorously practiced it was futile" (p. 247). He questions his desires for wealth and social position and falls asleep thinking of pretty young women, sensing that he is making a "terrifying, thrilling break from everything that [is] decent and moral" (p. 247).
The next day, he leaves the office to see a mid-day movie (for which he is teased at the Athletic Club, having been spotted by Sidney Finkelstein). Later that evening, Babbitt attends a Sunday dinner hosted by Eddie Swanson. There, he flirts with Louetta Swanson, who appreciates his compliments and dances with him--but she ultimately rejects him.
Babbitt visits Paul in prison, understanding that he "[is] already dead" emotionally (p. 253). Back at the office, Mrs. Tanis Judique, a pretty middle-aged widow, seeks George's expertise in finding a flat. "Nervously attracted by her smartness" (p. 253), Babbitt offers her a new apartment that he has been holding for Sidney Finkelstein. She decides to buy it. In the car, he flirts with her and pursues her casual offer to give him dancing lessons. Although he senses that he can put his arm around her, he rebukes himself and takes her home with "excessive politeness" (p. 256), later regretting that he missed his chance with such an alluring woman.
George finds himself increasingly attracted to young women, such as the manicurist at the Pompeian Barber Shop, Ida Putiak. He goes there and gets a manicure so that he can talk to her. He finds her enchanting and successfully invites her on a dinner date. That evening, his car breaks dow, so he picks Ida up in a taxi. After dinner, he is able to kiss her in the taxi on the way home, but she refuses to extend their date, so George is left feeling rejected and ashamed.
The next morning, though George sees no sense in his rebellion, he realizes that he cannot "regain contentment with a world which, once doubted, became absurd" (p. 264). He dreads Myra's return in August, and though he feels moments of reconnection with his former identity as husband and father, he still decides to take a solitary trip to Maine in order to "seek Paul's spirit in the wilderness" (p. 265). He takes out more money than he needs from the bank and bids Tinka farewell as though he will never return.
When he arrives at the guide's shack in Maine, he is not received with the warmth and excitement that he expected. He joins in a game of stud poker and asks Joe Paradise to guide him for a few days. Joe arrives at George's cabin the next morning and, after much persuasion, agrees to guide George on a long hike to Box Car Pond. George enjoys the sense of being rugged and manly as they walk. But after supper and after Joe has gone to sleep, George feels extremely lonely and cannot stop thinking about his family, friends, and business back in Zenith. Thus, he realizes that he can "never run away from himself." He returns home, vowing to "start something" (p. 270).
On the train returning to Zenith, George speaks with Seneca Doane, trying to explain why he campaigned for Proust for mayor, defining himself as an "organization Republican" (p. 272). Doane reminds George that, back in college, he used to be liberal, and they talk about being visionaries with ideals. Doane asks for George's help, requesting that he speak to businessmen about being "more liberal in their attitude" (p. 273) toward Beecher Ingram, a preacher banned from the Congregationalist Church. Babbitt agrees, feeling "idealistic and cosmopolitan" (p. 273) in Doane's presence.
Shortly after his return to Zenith, George calls on Zilla, feeling very sorry for her. He is disturbed by her "bloodless and aged" (p. 274) appearance in the boarding house. He asks Zilla to be generous and have Paul pardoned, but Zilla explains that she has recently become very religious and it is God's blessing that Paul is in jail--for him to repent and save his soul.
At home, Verona and Kenneth Escott are finally engaged. Ted enters the State University as a freshman in the College of Arts and Sciences, though he repeatedly proposes to George that he transfer to the School of Engineering to study mechanical engineering or mining engineering.
Until this point in the novel, Babbitt has wavered between a sense of commitment to the value system to which he has subscribed throughout the entirety of his adult life and the growing sense of unrest and dissatisfaction that urges him to seek something new and more exciting. He has approached the edge of the board several times, but he has never made the jump. Now, two conversations have the cumulative effect of propelling him forth into the rebellion that briefly wreaks havoc in his life. (Eventually, though, this rebellion will allow him to return to his former life with greater hope, satisfaction, and assurance.)
The first of these conversations is the one that he has with an intoxicated Chum Frink. Late one night, Frink passes by the Babbitt house, calling George a fool and explaining that he is a "traitor to poetry" (p. 246), bemoaning the loss of his potential and imagining what he could have been. With the words "Could have written - Too late!" (p. 246) he runs off, and Babbitt is left questioning the wealth and social position that he has been striving to attain. For the first time, he is able to identify his longings (for pretty women, for Miss McGoun, for Paul). He suddenly feels as though he has "found something in life, and that he [has] made a terrifying, thrilling break with everything that was decent and normal" (p. 247).
Thus, he follows through with the break the next day, when he not only notices but also obeys his desire to leave work and catch a midday movie. Then, at a dinner hosted by Eddie Swanson, he flirts with Louetta. He also flirts with Tanis Judique and kisses Ida Putiak after taking her on a date. In the span of a few days, he has pursued several women who appeal to him, which is a far more active approach to understanding and doing what he wants than he has ever taken. All of these thoughts, feelings, and actions testify to the complete change that Babbitt feels just on the verge of making.
It is not until he speaks with Seneca Doane, however, that Babbitt is able to make this leap completely. Doane reminds Babbitt of his former potential as a liberal student at the State University, when Babbitt had intended to do work very similar to Doane's. In fact, Babbitt had actually been an inspiration to Doane. This confrontation with his own lost ideals and failed potential (which resonates with Chum Frink's drunken message) is what finally motivates Babbitt to adopt the new lifestyle that he has been seeking since the beginning of the book. Like a young, naive student back in college, he seems to think that nothing but complete rebellion can quench the thirst that he has for excitement and fulfillment.
Not even his solitary trip to the woods could restore him. In fact, he is out of his element in the woods, unable to deactivate his restless mind and realizing he can "never run away from himself." Nature is too natural and not wild enough. He returns home, vowing to "'start something'" (p. 270). In an uncharacteristic moment, he follows through on his decision to act.