In this chapter, Holden Caulfield embarks on a date with Sally Hayes, a girl he has previously expressed interest in, yet his enthusiasm is notably lukewarm. As he prepares for the outing, Holden's internal cynicism becomes increasingly apparent, highlighting his feelings of disconnection and disillusionment with the social dynamics of dating. He dresses meticulously, wanting to present himself well; however, his thoughts are clouded by his pervasive sense of alienation.

When he meets Sally, Holden is struck by her bubbly demeanor and preoccupation with superficial concerns. They engage in small talk, but Holden's thoughts reveal a growing disdain for the triviality of their conversation. He perceives Sally as representative of the phoniness he detests in the adult world, which only intensifies his discomfort during the date.

As the evening progresses, they decide to go to see a play. During the performance, Holden's mind wanders. He struggles to focus on the show, distracted by his thoughts about the people around him and his own feelings of inadequacy and isolation. Frustration mounts as he finds himself increasingly irritated by Sally's behavior and her apparent preoccupation with social status and appearances.

After the play, Holden suggests they grab a drink at a nearby bar. However, the conversation continues to spiral into disillusionment for him. Sally's excitement about the social scene only serves to alienate Holden further. He is unable to relate to her excitement and starts to feel trapped in a situation that feels increasingly meaningless. At one point, he even considers how he could escape the date entirely.

Holden's internal conflict culminates during a moment when he tries to express his true feelings to Sally. In a moment of vulnerability, he suggests they run away together and leave their current lives behind. However, this proposal is met with confusion and irritation from Sally, who cannot comprehend his deeper emotional struggles. This reaction only reinforces Holden's feelings of isolation and disappointment.

Ultimately, the date ends in frustration, with Holden feeling more disillusioned than ever. He becomes acutely aware of the gap between his desire for genuine connection and the superficial nature of his interactions with Sally. The chapter highlights Holden's struggle with his identity and the complexities of relationships as he navigates his adolescence, further illustrating his profound sense of alienation in a world he views as largely phony. This disillusionment becomes a recurring theme, emphasizing his internal battle between longing for connection and grappling with the realities of growing up.