Dolly All the Time

In the novel’s third section, the tense Whitfield family dinner adds nuance to the theme of The Harmful Consequences of Class Division by revealing how these differences weigh on the wealthy Stewart. The scene depicts the intense psychological pressures of inherited wealth, setting them in contrast to the grounded, working-class world of the Brick family. Grant and Henry publicly criticize Stewart’s business decisions and question his leadership, revealing that the Whitfield legacy is a source of anxiety for Stewart. His subsequent panic attack is triggered specifically by his father’s mention of “mansion tours,” a fear of his family’s home becoming a museum to their failure, a Gilded Age relic whose story ends with him. While much of the novel’s exploration of The Harmful Consequences of Class Division focuses on ways this disparity negatively impacts the working-class Dolly, Stewart’s fear offers another perspective on the theme by showing how the weight of maintaining status has become debilitating. Dolly’s comforting response is an instinctive act of care that momentarily shifts their relationship from a transactional agreement to one of genuine emotional support. Stewart’s acute vulnerability and Dolly’s unhesitating care provides a real foundation for intimacy, moving beyond the public performance their contract requires.

The author uses the fake dating trope to show how The Burden of Caretaking has shaped Dolly’s emotional life, making it difficult to accept support for herself. Following their first kiss on the boat, Dolly’s insistence that their passion was merely “method acting” engages with the conventions of the fake dating romance trope. Her attempt to reframe a moment of authentic connection as a performance reveals a deep-seated fear of emotional vulnerability. This self-protective impulse is a direct consequence of her long-held family role, where she has been conditioned to manage crises and maintain control. The irony of her denial is underscored by Busy’s later observation that Stewart seems “lighter” and happier since their “relationship” began; while Dolly retreats into the safety of the pretense, the positive effects of their genuine connection are visible to those around them. Her struggle illustrates a central conflict in her character arc: Her powerful desire for intimacy clashes with a learned self-sufficiency that equates vulnerability with risk. For their fake dating relationship to evolve into something genuine, she must overcome this resistance to connection and allow someone to share in her burdens.

By structuring these chapters around simultaneous family emergencies, Monaghan advances the theme of The Importance of Accepting Love and Support by forcing Dolly into a position where she must depend on someone else. Stewart’s decision to drive to Point Judith to retrieve an injured Gus is an important turning point, demonstrating a form of care that transcends their professional arrangement. This act is a genuine effort to alleviate Dolly’s stress during a family emergency. When she arrives at Eight Oaks to find Stewart and Gus comfortably playing backgammon, the scene projects an image of domestic ease and integrated family life that destabilizes the clear lines of their contract. Dolly’s overwhelmingly grateful hug is an unguarded, spontaneous reaction, a significant crack in the emotional armor she wears. The episode reverses their established dynamic. Whereas she was the one to provide comfort during his panic attack, Stewart now offers her support, balancing their connection and proving their relationship can be a source of mutual aid.

The key business dinner in Boston further complicates the power dynamics between Dolly and Stewart, subverting the expectations of their class differences. Faced with Henry’s public skepticism about the Kramer deal, Dolly leverages her own background to save the negotiation. Her personal story about a local ice cream shop reframes the project’s value, shifting the conversation from pure profit to the intangible worth of history, memory, and community, an argument that successfully connects with Henry on an emotional level. In this moment, her working-class experience is a source of unique insight and persuasive power. The scene demonstrates her value to Stewart as a strategic equal whose perspective is essential. Their hand-holding at the end of the dinner signals a new stage of their partnership, where personal intimacy and professional success have become intertwined.

The consummation of their relationship in Dolly’s Boston apartment marks the final collapse of the barrier between pretense and reality. The choice of location is critical; by bringing Stewart into her personal, authentic space with its handmade quilts and family photos, Dolly is finally letting him see her true self outside of the “costume” of her public-facing role as his girlfriend. The act signifies a deeper level of trust than their previous encounters, moving beyond the performative settings of yachts and exclusive clubs. Stewart’s actions the following morning solidify this shift. In bringing her tea and asking her to “raise [her] expectations for [him]” (247), he explicitly acknowledges her self-protective emotional barriers and asks for a commitment to a real future. His words challenge her fear of abandonment and her tendency to expect disappointment, inviting her to fully embrace the vulnerability required for a genuine relationship. This moment completes the central arc of the fake dating trope, transforming their contractual arrangement into an authentic desire for a shared life.