The novel alternates between two timelines, the early 1990s and 2022, tracing the life of Artie Anderson, a gay man in New York City whose deepest relationships are shaped by the AIDS crisis, loss, and his fear of vulnerability.
In 1992, Artie is a thirty-year-old copywriter at an advertising agency on Madison Avenue. An English major from southern Ohio who entered the field on a whim, he keeps his personal life private. On his birthday, he heads to Julius', a historic gay bar in the West Village, with his two closest friends: Kimberly, a photographer for music publications, and Adam, a charismatic friend. Their bond was cemented five years earlier through Waylon, Artie's former roommate, who has since died of AIDS. At the bar, Artie approaches Abraham Ford, a family lawyer reading alone. Abraham is dismissive, mocking Artie's claim of being a writer, but later follows him home and apologizes. Artie invites him upstairs.
Thirty years later, Artie turns sixty. He lives alone in the West Village apartment Abraham left him and does solitary ghostwriting work. His social world has contracted to his agent Nikki, his elderly neighbor Gina, and Halle, Abraham's twenty-four-year-old daughter with his ex-wife Vanessa. At his birthday dinner, Vanessa announces that she and Halle are moving to Seattle. The next morning, Halle visits in tears and asks Artie to tell her about Abraham, whom she barely remembers. After they leave the city, Artie surveys his life and finds it hollowed out. Nikki urges him to volunteer at Gay and Lesbian Seniors (GALS), a center for aging queer New Yorkers. Shortly after, Gina dies in her sleep.
Back in 1992, Artie's boss reassigns him to a less prestigious account, and Artie suspects homophobia after a coworker spotted him leaving Julius' with a man. Abraham begins attending the group's Saturday movie nights, a tradition continued in Waylon's honor. Adam confronts Abraham about his HIV testing history and lack of involvement in queer activism. On the fire escape, Kim presses Artie about whether Abraham is good for him. Artie reveals that Abraham's encouragement has pushed him to begin writing a novel called
Four Squares, about four queer friends in the Village. Kim asks that Waylon's character receive a happy ending. Artie finishes the first draft by Christmas.
In 2022, Artie volunteers at GALS, where Ali, the blunt program director, runs orientation. He meets Gregory, a warm member in his eighties, and operates a vintage popcorn machine during movie night. A screening of
Philadelphia stirs painful memories, and while tearing down decorations afterward, Artie slips off a ladder and breaks his foot.
The 1992 timeline follows the group's annual New Year's trip to Adam's family home upstate, where Abraham joins them for the first time. Kim interrogates Abraham about his bisexuality and his relationship with Vanessa, whom he has never told about his relationships with men. Abraham admits his failures but insists he is committed to Artie. The trip marks the first time the house has not felt miserable since Waylon's death, and the group cautiously embraces optimism about the coming year.
Recovering in 2022, Artie is barred from volunteering at GALS due to insurance liability but learns he can join as a member instead. At his first dinner, he sits beside Jim Thornton, an older member who introduces him to the regulars. Carson, a retired teacher whose partner died of brain cancer, joins their table, and he and Artie connect immediately. Along with Jim and his best friend Ellis, they form a circle that begins meeting regularly.
In 1994, Artie's book launch draws only five attendees. He confronts Abraham about his continued sexual relationship with Vanessa; Abraham admits it, and Artie walks away in tears. Adam arrives at Julius' with a homemade cake, and the bar erupts in applause. Artie's agent then connects him with Sterling Bismarck, a famous closeted television actor who is HIV-positive and wants Artie to ghostwrite his coming-out memoir after reading
Four Squares. Artie explains his motivation: His estranged parents never read his weekly letters, but the stories need telling regardless. Sterling hires him on the spot.
In 2022, Artie decides to write a sequel to
Four Squares. He retrieves a copy from his storage unit, rereads it, and begins writing with sustained focus for the first time in years. Carson visits the apartment, the first guest since Abraham's death, and reveals he has tracked down a copy of
Four Squares. They attend a party at Annabelle Adams's townhouse, where Artie discovers a photograph of Annabelle with Sterling Bismarck and bonds with her over their shared connection.
The 1992 timeline reaches its crisis in 1996. Kim calls Artie to say she is in love, offering one detail about the person: "Vegan." The group plans their New Year's trip, but Abraham must work first, delaying his and Artie's departure. Kim and Adam drive ahead. On the way upstate, Artie and Abraham unknowingly pass the site of a car accident. When they arrive, the house is empty. Kim and Adam are dead.
Artie tells Abraham he must end their relationship; he cannot risk losing anyone again. They break up. Seven years of isolation follow before Abraham appears at Artie's door in 2004, his marriage to Vanessa ending. They reconcile and spend four months together before Abraham dies of a heart attack in his sleep. At the hospital, Vanessa excludes Artie from seeing the body, but months later she invites him to meet Halle, beginning the Sunday dinners that connect them for years.
In 2022, Halle visits and reveals that Abraham is not her biological father; Danny, Vanessa's current partner, is. Artie is stunned but tells Halle not to apologize. He meets Carson at Julius' and recounts the revelation. Carson asks when Artie last had a new feeling, arguing that Artie spent decades avoiding all emotions to protect himself from painful ones.
Artie's cast is removed, and he returns to GALS to learn that Annabelle has died. Ali reveals a long-held secret: Ali was Kimberly's partner, the vegan Kim was in love with when she died. Kim's last phone call was about Artie; she was furious he would be late for the trip because she and Ali had been planning to move to California together. Ali had wanted to confront Artie at the funeral but, seeing his grief, let the anger dissolve.
On New Year's Eve, Artie finishes his manuscript and titles it
Old Fruits, inspired by Jim's still-life paintings of aging fruit. He attends the GALS party, his first New Year's celebration in over twenty years, and toasts Annabelle's memory with his friends. At midnight, he leans into Carson. They spend the night together at Artie's apartment, where Gina's long-lost cat Walter has taken up residence. In the morning, Artie finds an email from Vanessa explaining that Abraham knew Danny was Halle's biological father and chose to stay, and that she let Artie believe Halle was Abraham's to give him a connection she thought he needed. Artie emails Nikki with the manuscript attached, CCs Halle, and walks out of his building. He crosses the Williamsburg Bridge into Brooklyn and keeps walking for miles, without turning around.