Dolly All the Time

In these chapters, Monaghan expresses The Importance of Accepting Love and Support as the pretense of Dolly and Stewart’s fake dating arrangement is replaced by authentic emotional connection. The shift in their relationship is evident in grand gestures like helicopter rides as well as in private moments, such as when Stewart appears at Dolly’s sleeping porch, unable to stay away because saying goodbye was a “terrible idea.” These actions demonstrate a level of care that allows Dolly to lower her long-held defenses. Her confession to Naomi that she has “jumped off a cliff” captures her willing surrender to vulnerability (254), a stark contrast to her usual caution. For the first time, Dolly is not just performing a role but is actively participating in a relationship where she feels seen and valued. This development explores The Importance of Accepting Love and Support as Dolly allows herself to experience a partnership that is reciprocal rather than one-sided. Stewart, too, sheds his guarded persona, admitting his week away was “torture” and that he’d “change the world” to be with her (278), cementing the mutual vulnerability that makes their bond real. 

As Stewart and Dolly’s bond deepens, he helps to reduce The Burden of Caretaking. Stewart begins to form a meaningful connection with Gus, briefly alleviating Dolly’s solitary parental responsibilities. The Red Sox game becomes a venue for Stewart to integrate into Dolly’s family life. This link is further developed through the sailing lessons, where Stewart assumes a mentoring, almost paternal, role. Dolly observes them, worrying she was “naïve or even arrogant to think that Gus would be fine without a father” (263), and recognizing in her son a flicker of “the confidence that comes from having a second person who completely has your back” (263). The trust between Stewart and Gus is solidified when Gus confides in Stewart about his dream of taking over the family business and his crush, secrets he has not even shared with his mother. This new dynamic offers Dolly a glimpse of a life where she does not have to manage everything alone, momentarily lifting The Burden of Caretaking. Stewart’s genuine involvement with Gus validates the potential for a shared future, raising the personal stakes of their romance and making the subsequent collapse of their relationship all the more destructive.

The contrast between the two primary settings of the relationship, Dolly’s sleeping porch and Stewart’s estate, represent authenticity and performance, respectively. The sleeping porch shows a space of genuine, unpolished intimacy. It is a liminal space, open to the sounds of nature, where Stewart comes to find the real Dolly and admits he wants to know “what it felt like in [her] bed” (256). The space is unfinished, with unsanded spots on the ceiling, mirroring the characters’ own vulnerabilities and the in-progress nature of their bond. In contrast, Eight Oaks represents the suffocating weight of legacy and class. Modeled on the Gilded Age palaces of Newport, it is a stage for social maneuvering where family dynamics are transactional and public perception is paramount. While genuine affection can exist within its walls, as seen in Stewart’s private bedroom, the public spaces demand performance. The authenticity fostered on the porch cannot survive the scrutiny and power dynamics of the estate during the Starlight Gala. This contrast illustrates The Harmful Consequences of Class Division, suggesting that true connection can only flourish away from the rigid structures of inherited wealth and expectation.

The Starlight Gala at Eight Oaks brings these simmering class tensions to a boil, raising the question of whether the social chasm between the Whitfields and the Bricks is ultimately unbridgeable. The romance builds as Stewart kisses Dolly openly and they exchange veiled declarations of love while dancing. However, this idyllic moment is shattered by Grant’s revelation of their contract, a move that weaponizes Dolly’s working-class status against Stewart. In the ensuing confrontation, Stewart prioritizes his family’s corporate legacy over his commitment to Dolly, abandoning her on the dance floor to placate his father. His defense that he “did it because of what happened with Audrey” reduces Dolly to a strategic solution to a family problem (285), erasing the partnership they had just affirmed. This decision emphasizes the destructive power of class expectations; despite his genuine feelings, Stewart regresses into the role of a dynastic heir protecting his position. Dolly’s exit through the delivery entrance, after having been welcomed as a guest through the front, emphasizes her reclassification from partner back to hired help.

In the aftermath of the gala, the relationship reverses from emotional intimacy to a cold, financial arrangement. Stewart’s terse text messages, which use periods (unlike all his earlier communications) to signal a formal emotional distance and describe his actions as “fraud,” strip their connection of all its recently acquired warmth. The final delivery of a check by messenger institutionalizes this break, confirming that their time together has been officially re-categorized as a business transaction. His failure to fight for their relationship after he promised he would “change the world” for her forces Dolly back into a position of defensive self-reliance (278). She immediately resumes her caretaking role by lying to Gus to shield him from her pain. However, the experience has irrevocably changed her. Her subsequent outburst at her father, in which she accuses the family of being “stuck” in time, is a direct consequence of her heartbreak. Having tasted a life in which she was supported and cherished, Dolly can no longer tolerate the stagnation she had previously accepted. The immense pain of the loss leads to self-reflection, exposing the deep personal costs of her lifelong role as a caregiver and igniting a desire for change.