Connor is the deuteragonist and primary love interest in the novel. He articulates his feelings directly and honestly while Olivia withholds hers, a contrast that the novel establishes in their first conversation. Where Olivia defaults to deflection, Connor is straightforward about his long-held feelings and his desire to know her better, a directness that both unsettles and attracts her. His self-identification as a “serial monogamist” and a “mama’s boy” is a point of fact rather than a source of embarrassment, indicating his comfort with emotional intimacy and his belief in lasting connections. This open-heartedness represents a departure from the noncommittal relationships that Olivia has chosen in the past, prompting her to reconsider what she wants.

Connor’s persistence pushes Olivia outside her comfort zone and forces her to grapple with her own defensive patterns. He recognizes Olivia from their shared childhood experience at Camp Skytop, a detail that establishes a foundation of shared history. He consistently creates opportunities for them to spend time together, from their first jump off Jaws Bridge to a meticulously planned private dinner, asserting that Olivia needs to make her own memories on her trip rather than solely pursuing Annie’s. He respects her boundaries, giving Olivia room to process her feelings on her own terms. He becomes a partner in her quest to uncover Annie’s past, showing genuine interest and providing support that helps foster the trust necessary for Olivia to begin lowering her defenses.

Connor’s own past as one of the “Homebodies” at summer camp, who regularly called his family, creates a subtle parallel with Olivia and suggests an unspoken understanding of her deep familial bonds. He challenges her to move through The Way Fear of Loss Inhibits Love by consistently showing up as a trustworthy presence in her life. Even after Olivia pushes him away, he gives her space to reach her own conclusions.

Annie is a key character whose physical and mental decline due to her dementia drive the novel’s central emotional conflict. Though her cognitive decline renders her a somewhat static character in the present, the narrative reveals her as a round and dynamic figure through memories, photographs, and the discovery of her past. In the present, Annie’s dementia dictates the rhythms of Olivia’s life, creating a painful reality where she’s sometimes a loving grandmother and sometimes a confused stranger who doesn’t recognize her own family. These fluctuations are the source of Olivia’s deepest anxieties and are the primary illustration of The Impact of Dementia on Family Dynamics in the novel, forcing her loved ones to grieve the person she was while caring for the person she has become.

Despite her illness, Annie continues to function as a mentor figure for Olivia, offering clarity and wisdom during moments of lucidity. It’s Annie who gives Olivia the final push to go to Martha’s Vineyard, telling her, “Martha’s Vineyard is a magical place. Go fall under its spell” (44). Later, during a phone call, she perceives Olivia’s feelings for Connor and encourages her to embrace a summer romance, dismissing Olivia’s practical objections by reminding her that “a couple weeks of fun never hurt anyone” (206). These lucid moments provide hints of the sharp, sophisticated woman she once was and guide Olivia toward the experiences that lead to her personal growth. Annie’s secret past on the island, symbolized by her box of Polaroids and watercolors, creates a narrative parallel between her youthful romance with Christian and Olivia’s burgeoning relationship with Connor, suggesting that the island is a place of transformative summer love across generations.

Erica is a dynamic, round character who serves a dual role in the narrative. Initially, she functions as an antagonist from Olivia’s perspective, a disruption to her original family unit that emphasizes The Challenges of Navigating Relationships Within a Blended Family. Olivia initially interprets Erica’s actions through a lens of suspicion and resentment, seeing the gift of a luggage set or the assignment of a smaller bedroom as evidence that Erica wants her out of the house. Olivia views Erica as superficial and unfeeling, particularly in her seemingly detached response to Annie’s deteriorating health. Erica’s comments to friends about Olivia’s lack of ambition confirm Olivia’s worst fears and lead to a painful confrontation, solidifying their antagonism in the early sections of the story.

The narrative gradually reveals that Erica is a caring stepmother. Her actions are motivated by genuine concern for Olivia’s well-being and a deep-seated insecurity about her place in the Lupo family. Her seemingly critical comments stem from a desire to see Olivia thrive, and her struggles with her own family’s judgment of her career make her more sensitive than Olivia realizes. The turning point in their relationship occurs during a walk in Haddonfield, where Erica finally shows her vulnerability. She confesses her own deep grief over losing the close bond she shared with Annie, admitting that she has been trying to “stay strong” for everyone else. This honest exchange dismantles the antagonistic perception that Olivia has constructed for years and allows a foundation of mutual trust and empathy to form. By the end of the novel, Erica has transitioned into a fully supportive maternal role, encouraging Olivia’s relationship with Connor and becoming an ally in her happiness.

Christian is a supporting character who reveals the mystery of Annie’s past romance on Martha’s Vineyard. His characterization as a largely static figure in the present is precisely what makes him useful in that role. The novel introduces him as a kind stranger who helps Olivia at Jaws Bridge before gradually revealing him to be the man from Annie’s secret summers on Martha’s Vineyard and the artist behind her watercolors. His history with Annie, a passionate romance thwarted by class-conscious parents, adds depth to the grandmother whom Olivia thought she knew and inspires her to pursue a romance with Connor. Christian’s lasting, bittersweet affection for Annie creates a narrative parallel to the connection forming between Olivia and Connor, positioning their story as an opportunity to reach the resolution that Annie and Christian never did.

Chris, Olivia’s father, is a steady, supportive presence in the novel. As a pilot, his job often keeps him physically absent, which contributes to Olivia’s feeling as an outsider in his new family. His love for Olivia is unwavering, and he acts as a mediator in the household, particularly between Olivia and Erica, demonstrating a deep understanding of the emotional weight that his daughter carries as a support for Annie. He acknowledges the toll of the caregiving, telling Olivia, “I can see the emotional toll it is taking on you” (33), and adjusts his own schedule to share the burden. His quiet consistency and trust in his daughter provide a foundation of stability as she navigates the complexities of family, grief, and first love.