Jackson uses multiple perspectives to expand the scope of the novel, giving readers a glimpse of the friend group at the center of the narrative without restricting them to Caroline’s limited perspective. This principle becomes evident in this section of chapters, which frames Bailey as a deuteragonist who goes through her own independent character arc as she deals with the repercussions of her relationship and pregnancy. Though the novel initially presents Bailey as a rival to Caroline for Van’s affections, these chapters elevate her role, emphasizing that she’s more than just a supporting character in Caroline’s life. The same can be said for Fran and Augusta to lesser degrees, though their experiences and subplots complement the thematic tensions that arise from the dynamic among Caroline, Van, and Bailey.

While at the beach, Bailey observes the physical differences between the fathers and the childless men, concluding that the fathers’ slight physical neglect is a “sign of selflessness to have abandoned vanity for the sake of family” (110). This observation introduces a complex examination of parenthood’s demands on identity, which plays out across these chapters with divergent consequences. While Bailey romanticizes the fathers’ self-sacrifice, Fran experiences it as a source of deep resentment. She watches her husband, RJ, engage in the spectacular “buffoonery” of the Gloucester Greasy Pole competition, a performance of carefree masculinity that culminates in a “joyful backflip as he crashe[s] down into the water” (152). This activity emphasizes RJ’s immaturity. For Fran, his antics contrast sharply with her private burdens: her father’s secret gambling addiction and her brothers’ expectation that she and RJ will solve the family’s financial crisis. While RJ performs a harmless, if juvenile, version of manhood, Fran’s father embodies a more destructive and selfish one. Bailey’s idealized view of paternal sacrifice is thus immediately complicated by the reality of male irresponsibility, leaving Fran to “clean up the mess, and to take care of everyone but herself” (152).

Max’s blunt assessment of the friend group as “so incestuous […] So secretive and sneaky” articulates a central tension in this section (114): The insular bonds of youth are fracturing under adult pressures. His comment, delivered with the directness of an outsider, punctures the group’s pretense of normalcy. This secrecy manifests in Augusta’s private torment over the blue underwear she finds in her couch. She’s unable to confide her fears about Colin’s potential infidelity to either Bailey or Fran, showing a failure in the intimacy that once defined their relationships. Their conversations about cheating remain abstract and unhelpful, revealing a collective unwillingness to confront uncomfortable truths that challenge the group’s stability. The established dynamic is disrupted by Caroline’s presence, which forces everyone to navigate a web of unspoken resentments and fragile courtesies. The arrival of Dylan further strains these bonds, forcing a fundamental realignment. These developments illustrate The Reshaping of Friendships in Adulthood, as old loyalties are tested by new relationships and the secrets they inevitably generate.

The pair of lacy blue underwear that Augusta discovers becomes an emblem of her anxieties about The Fragility of Monogamy. For a month, the object torments her, representing a tangible threat to her marriage and family. Her silent investigation is a desperate search for certainty in a relationship where trust has eroded. When she finally learns that the underwear belongs to her babysitter Zoey’s girlfriend, her relief is immense. The resolution, however, is ironic; it allows her to restore her faith in Colin’s fidelity without ever addressing the underlying issues that made her suspicious in the first place. The narrative contrasts Augusta’s desperate desire for a stable, monogamous marriage with other, more transactional partnerships. Bailey learns that her sister Kylie’s marriage began with her now-husband, Jeff, paying her $500 per date. This cynical arrangement, alongside Bailey’s own decision to have a child outside of a traditional relationship, presents a spectrum of modern partnerships held together by compromise, willful ignorance, and unconventional agreements rather than absolute fidelity.

Miscommunication and unspoken assumptions reveal the growing distances between characters, even in moments of supposed intimacy. On the beach, the women’s conversation about the complex prerequisites for female orgasm, sparked by Fran’s story about RJ, humorously highlights a fundamental disconnect between male and female perspectives on pleasure. This gendered gap in understanding recurs in more subtle ways. At the Beekman Prize gala, Van recites the lyrics to Lynyrd Skynyrd’s “Freebird” as his poem, a private joke that Caroline, who takes it at face value, misses entirely. It’s a small but telling moment of cultural and emotional misalignment. Similarly, Caroline’s attempt to be direct with Bailey about their awkward situation is met with a polite but dismissive internal response from Bailey, who’s more focused on her own regrets about Van. This pattern of characters talking past one another demonstrates how their individual anxieties and histories create subjective realities that prevent genuine connection, even when they’re ostensibly sharing experiences.

The birth of Bailey’s son, Dylan, acts as the primary catalyst for change in these chapters, fundamentally reordering priorities and resolving the central romantic triangle. While the event initially seems to bring Bailey and Van closer, as they fall asleep together in the hospital bed, it ultimately drives a wedge between Van and Caroline. Van’s transformation into a father is swift and all-consuming. His focus shifts entirely to Dylan’s needs, from obsessively researching diaper rashes during a formal gala to prioritizing an early train home over brunch with Caroline’s best friend. His identity is wholly redefined by this new role. The breaking point comes during a hike on the Crane Estate, where Van tells Caroline that he “can’t do both” (188). He frames fatherhood as his life’s new, singular purpose, one that leaves no room for his relationship with her. Caroline’s destructive realization that her rival was “Dylan the whole time” confirms that the demands of parenthood have become an insurmountable barrier (189), eclipsing the romantic connection she and Van once shared.