The Lupo family arrives on Martha’s Vineyard and drive to the impressive Carmichael summer home. After being greeted by Erica’s mother, Peggy, Olivia meets Erica’s charming adult twin nephews, Nick and Charlie. Peggy shows Olivia to her room in a separate wing, where Olivia is shocked to discover that she’s sharing a bunk room with a stranger. Her roommate introduces himself as Connor McCallister, revealing that he’s not a Carmichael but is working as a nanny for the family’s younger children. Despite her surprise at the sleeping arrangement, Olivia has a friendly first interaction with Connor, whom she finds vaguely familiar. She wonders how he already knew her last name.

Olivia joins the Carmichael family gathering, feeling like an outsider. She meets Nick’s fiancée, Sage, and Charlie’s husband, Luke. Dinner conversations with Erica’s siblings, Beth and Jay, highlight the disconnect between Erica and her sister. Family tensions surface after dinner when Nick’s suggestion of a game called Assassin is shot down and Erica is forbidden from vlogging the vacation. Olivia learns that Connor is a recent high-school graduate who will be playing lacrosse at Notre Dame in the fall. Later, Swede insists on sharing the bottom bunk with Connor. Just as they are settling down to sleep, Connor reveals that they have a past connection by asking Olivia if she remembers him.

Olivia wakes up early and, during a run, recalls her conversation with Connor from the previous night. She discovered that they knew each other from a sleepaway camp called Camp Skytop years ago, where they were both part of a homesick group of campers nicknamed “the Homebodies.”

Back at the house, Olivia is impressed by how capably Connor cares for Finn and Teddy, the young sons of Erica’s niece. As he drives them to camp, Olivia has a major revelation: Connor’s Jeep is the same one she mistakenly climbed into weeks ago at Elkins Village.

Later, Olivia goes to a private beach with her cousins and meets a group of their friends, some of whom know Connor well. One friend, Katie, cryptically tells Olivia to be gentle with Connor because he “has a really big heart” (98). Back at home, Olivia has a difficult phone call with her grandmother, whose memory seems to be failing, though a brief moment of her old humor gives Olivia hope. That evening, after finding Connor in their shared living space, he suggests that they hang out on the porch after he uses the outdoor shower, and she agrees.

Connor joins Olivia on the porch, where they share snacks and talk about their past relationships. Connor reveals that he’s a bit of a serial monogamist, while Olivia explains that her last relationship was more casual. The conversation leads to Connor inviting Olivia on a surprise outing the next day.

After they drop Finn and Teddy off at the Edgartown Yacht Club, Connor blindfolds Olivia and drives her to the Jaws Bridge, a popular spot for jumping into the water. Olivia reveals her fear of heights, and though Connor is encouraging, he doesn’t pressure her. She decides to climb onto the railing with him and, spurred by the moment, agrees to jump. As they leap off the bridge together, Olivia grabs his hand.

After Olivia and Connor jump from the bridge, Olivia is caught in a powerful current and struggles to reach the seawall. An older man helps pull her to safety. Later, in the car, Connor admits that he was distracted by her smile before his jump and confesses that he has always liked her. The revelation makes Olivia uncomfortable, as she doesn’t develop feelings easily and worries about leading him on.

They collect Teddy and Finn from camp and go to a local fudge shop, where Olivia sees a picture of the Edgartown Harbor Light on a gift box and recognizes it as the lighthouse from Annie’s painting. The group walks to the lighthouse, and Olivia realizes that Connor’s familiarity with the island could help her trace Annie’s path. At the top of the lighthouse, moved by the view that her grandmother must have seen, she tells Connor about Annie’s visit. When he asks if her grandmother went anywhere else, Olivia offers to show him her list.

Olivia continues her project of recreating Annie’s photos, with Connor taking pictures of her at the Old Whaling Church. Back at the house, she shows him the old Polaroids, and he comments on the striking resemblance between Annie and Olivia. That evening, the entire family participates in a chaotic game night organized by Peggy, which involves teams stuffing balloons into oversized nightshirts. Olivia snaps at Erica when she accidentally pops a few of the balloons.

Feeling guilty about a glare she gave Erica during the game that was caught on video, Olivia apologizes. Erica accepts and confides that she feels judged by her family, forcing her to hide her work from them. Later that night, Olivia and Connor talk in their room, and she confesses that she once accidentally got into his identical car at Elkins Village. Connor explains that he was visiting his grandfather, who lives there and is dating Fliss Williams—a woman Olivia knows from visiting Annie. They end the night by planning to visit the Flying Horses Carousel the next day for Olivia’s project.