The Summer of Second Chances (2025) is a young-adult contemporary romance by K. L. Walther, whose debut novel The Summer of Broken Rules was a #1 New York Times bestseller. In this novel, Walther depicts teenager Olivia navigating her grandmother Annie’s dementia, a family secret rooted in Martha’s Vineyard, and a romance complicated by grief and fear. Walther’s portrayal of Annie’s dementia draws on her experiences with her own grandmother. The Summer of Second Chances is also set within the same interconnected literary universe as The Summer of Broken Rules, featuring the Fox family’s Martha’s Vineyard estate and summer-long water-gun competition, Assassin, as recurring elements in the plot.

This guide refers to the 2025 Sourcebooks Fire edition.

Content Warning: The source material and guide feature depictions of illness, death, mental illness, emotional abuse, and cursing.

Plot Summary

Nineteen-year-old Olivia Lupo has deferred her admission to Northwestern University to take a gap year at home, spending time with her beloved grandmother Annette “Annie” Lupo, whose dementia is progressing rapidly and stays at the Elkins Village memory care facility. Olivia is determined to be present for Annie before her memory fades completely, which strains her relationship with her stepmother, Erica Lupo, and makes Olivia feel like an outsider in the family. When Erica announces a three-week trip with her extended family on Martha’s Vineyard, Olivia resists leaving Annie for so long, but when she discovers a hidden box among Annie’s things containing old Polaroids and watercolor paintings of Martha’s Vineyard, Olivia is intrigued since Annie has never mentioned spending time there.

The photos, labeled “Summer camp,” depict a joyful young Annie and hint at a secret past, particularly one image of her posing barefoot beside a green John Deere tractor. During a lucid moment, Annie tells Olivia, “Martha’s Vineyard is a magical place. Go fall under its spell” (44). Olivia decides to join the trip with a new mission: to retrace her grandmother’s footsteps and create a memory book juxtaposing Annie’s Polaroids with new photos of herself in the same spots.

Upon arriving at the Carmichael family’s summer home, which Erica’s family has dubbed “Camp Carmichael,” Olivia is surprised to learn that she’s sharing a bunk room with Connor McCallister, the charismatic nanny for Erica’s grandnephews Teddy and Finn, the young sons of Erica’s niece Ashley. Olivia is surprised when Connor reveals that he remembers her from a childhood sleepaway camp where Olivia was his unapproachable crush. This shared past creates an instant, if slightly awkward, connection.

Connor enthusiastically supports Olivia’s mission to visit Annie’s favorite places on the vineyard, and they begin exploring the island together. They find the Old Whaling Church and Edgartown Harbor Light from Annie’s paintings. At the historic Flying Horses Carousel, they notice a mystery man in the background of one of Annie’s Polaroids, his hand resting on the pole of her carousel horse. As Olivia and Connor spend more time together, including a near-disastrous jump from Jaws Bridge, a romance blossoms. Connor’s directness and open affection make Olivia uneasy, as she habitually enforces emotional distance to protect herself from loss.

The mystery of Annie’s past deepens alongside Olivia and Connor’s burgeoning romance. During a Fourth of July party at the Paqua Farm, owned by the Fox family, the two almost kiss on the roof during the fireworks. Afterward, Connor surprises Olivia with a private dinner at a small cottage on Paqua Farm called the Annex. The evening culminates in a sunset tractor ride, where Olivia is stunned to see the very same antique John Deere tractor from Annie’s photograph. She realizes that Paqua Farm must be the “summer camp” from the Polaroids.

At the end of the ride, Olivia meets Christian Fox, the family patriarch, in his workshop and discovers that he painted Annie’s watercolors. He reveals that he met Annie on the ferry on the way to Martha’s Vineyard one summer when they were in college—him at Georgetown, her at Vassar. He tells Olivia that he initially thought her resemblance to Annie was a coincidence, but then he went to her Instagram profile and found out that they’re related. He shows her one of his paintings of Annie, which he titled Girlhood. Olivia agrees to meet him for lunch the next day so that they can talk more about Annie.

Connor takes Olivia to a special camping spot on the farm where he’s set up a tent with blankets and hot chocolate. They kiss under the stars and have sex in the tent. Connor confesses the depth of his feelings and explains that he can see a future with Olivia. However, Olivia can’t reciprocate his feelings and leaves their relationship unresolved. The next morning, Olivia has a missed call from her father, Chris Lupo: Annie has had a serious fall and is in the hospital, potentially needing surgery. Olivia and Chris plan to leave the Vineyard immediately, which triggers a heated argument with Erica, who suggests that Olivia should stay for the last week of her vacation. Connor overhears and confronts Olivia for being so harsh with Erica; he also reiterates his feelings for her but says that the timing must be wrong.

Back home, Olivia and her father go directly to the hospital to see Annie. The surgery is successful, but Annie is weak and largely non-communicative after the procedure. During one of Olivia’s visits to Elkins, she finds Christian sitting by Annie’s bed. He explains that he and Annie were once engaged, but it was called off because his parents disliked her. Later, Olivia’s father invites Christian to dinner, where he tells more stories about his relationship with Annie. Conner calls Olivia to apologize for their previous confrontation and says that he still wants to see her. The next day, Christian visits Annie one last time, and Olivia gives him the Polaroid with Annie by the tractor. He gives Olivia advice about her relationship with Connor, telling her that timing is malleable.

The reality of Annie’s decline leads to a reconciliation between Olivia and Erica. Olivia apologizes for years of hostility, and Erica confesses her own grief over losing the close bond she once shared with Annie. She explains that what Olivia read as efforts to push her away were attempts to support her independence. She also points out Olivia’s pattern of only dating guys she could never fall for, fearful that everyone she loves will eventually leave her. She encourages Olivia to trust Connor.

A few weeks later, after a particularly difficult visit with a confused and agitated Annie, Olivia spots Connor’s Jeep in the Elkins parking lot and realizes that he’s there visiting his own grandfather. Unwilling to repeat Christian and Annie’s mistake of letting a correctable obstacle end something real, Olivia decides to orchestrate a new beginning for herself and Connor. She gets into his unlocked car and waits, resolved not to let him go. When Connor finds her, she tells him that their first meeting was clouded by her personal struggles and asks if they can start over. Connor gets out of the car and walks away. When he returns, he reintroduces himself and asks her out for ice cream. She accepts, finally ready to embrace their second chance.