28 Summers

The chapter moves to the earliest point of the novel’s timeline, 1993. Mallory is 24 years old and living in New York with her wealthy friend Leland Gladstone. She has a dead-end job as a receptionist while Leland has snatched up a desirable job at a literary magazine that both Mallory and Leland applied for. Tension between the two friends is running high, with Leland disdaining Mallory’s demeanor and lifestyle and Mallory resenting Leland’s success.

One day Mallory’s father calls and tells her that her aunt Greta, his sister, has died unexpectedly and left Mallory $100,000 and her vacation cottage on Nantucket Island. The rest of Mallory’s family is estranged from Greta because she came out as a lesbian after her husband died, but Mallory has continued to maintain a relationship with Greta and her partner Ruthie. As soon as Mallory finds out about her inheritance, she makes plans to leave the city, relieved to have free housing and some measure of financial security.  

As she settles into life on Nantucket, Mallory gets a call from her brother Cooper announcing that he’s getting married to his brand-new girlfriend. He asks Mallory if she’d be willing to have him and two friends up to Nantucket for a small bachelor party over Labor Day weekend. Mallory agrees.

Mallory gets a call from Leland, who had mentioned coming to visit on Labor Day, telling her that her friend has booked flights to visit that weekend. If Leland had checked with Mallory, she would have discouraged her from coming that weekend because one of the friends at Cooper’s bachelor party, Frazier, is Leland’s ex-boyfriend who she dated seriously in high school. But since everyone’s trips are already planned, Mallory and Leland decide to “surprise” Frazier with Leland’s presence at the cottage.

As soon as Cooper and his friends get off the ferry, Mallory is attracted to the third member of the group, Jake McCloud, who she’s never met before but heard about from her brother. Mallory and Jake had several flirtatious phone conversations about five years ago during her freshman year of college, when she would call her brother’s fraternity house (which Jake also lived in). Jake is taking pre-med classes at the wish of his parents, who are both doctors, but thinks he’ll end up working as a lobbyist in Washington D.C. when he graduates (which is exactly what happens).

The Labor Day gathering begins, and Leland and Frazier reunite gracefully. Jake tells Mallory that he has a complicated relationship with a lawyer from his hometown of South Bend, Indiana, named Ursula de Gournsey. Mallory is dismayed that her interest in Jake might be for naught.

The group is about to head out to a local bar when Cooper gets a phone call from his fiancée, who is unhappy about the whole bachelor weekend. Cooper ends up staying at the cottage while the other four go out. Leland and Frazier are already kissing passionately in the backseat of the car, which makes Mallory uncomfortable. At the bar, Leland and Frazier disappear while Mallory and Jake dance. At the end of the night, they find Frazier alone in the car, clearly unhappy, and he says Leland ran into some people she knew from New York who invited her to another bar. At the cottage, Frazier grabs a bottle of whiskey and heads off for a walk down the beach alone. Mallory discovers that Cooper has left to catch a ferry off the island to appease his fiancée.

Alone at the house, Mallory and Jake give in to their mutual attraction and begin kissing, but Mallory is worried about Frazier and the two go out after him. They find his clothes abandoned on the beach and Jake heads out into the water after him, telling Mallory to go back to the cottage and call 911.

Search-and-rescue teams arrive, and finally find Frazier passed out on the sand, not in the water as they’d feared. One of the first responders, a man named JD, remembers Mallory from when he saw her working her waitressing job at a local restaurant. He wanted to ask her out at the time but was too shy. He uses the opportunity now to see if she’s interested. She’s shaken from the scare over Frazier but tells JD to call her house in a week or so.

The next day, Leland and Frazier both leave separately, leaving Mallory alone with Jake for the rest of the weekend.

The chapter begins with a flashback to 1993, which relates what happens during Mallory and Jake’s first weekend alone. Jake and Ursula have been dating since they were in eighth grade, and Jake had a twin sister Jessica who died of cystic fibrosis when they were 13. Ursula was good friends with Jessica, and Jake’s connection to her is largely because of his memories of them together.

Mallory and Jake follow a routine that they will repeat every year during the rest of the book. They go for drives and walks on the beach, order Chinese food, and watch a movie from the 1970s called Same Time Next Year that mirrors their own one-weekend-a-year scenario. In the movie, both main characters are married but cheat on their spouses once a year with each other. Jake wants them to figure out how to be in a relationship long-distance, but Mallory isn’t interested, having done something similar with her last boyfriend. She tells Jake about JD asking her out, which makes Jake jealous, and jokingly says that Jake needs to come see her every Labor Day weekend. Mallory gets a call from the local high school asking her to substitute teach English classes for a week—she’s hoping for a permanent teaching job and is delighted that she secured teaching work, even temporarily. Jake leaves wistfully and reluctantly at the end of the weekend, promising to return for the same weekend the next year.

Cooper’s wedding brings Mallory and Jake back together before the following Labor Day. Jake and Ursula are back together in spite of a seemingly relationship-ending fight before he visited Mallory. That argument was centered over Ursula’s commitment to her law career, which she unambiguously says is the most important thing to her, even more important than her personal relationships. Jake tells her that her own parents are ashamed of her relentless focus on work, which Ursula brushes off.

That Thanksgiving (the storyline is still relating the events of 1993), Jake is surprised to run into Ursula back in South Bend. She tells him that his comment about her parents made her realize she needed to come home and be present with them more often. Jake is touched by this seeming gesture of selflessness, and the two resume their relationship. Ursula ends up being Jake’s date to Cooper’s December wedding, and Mallory accepts the fact that Jake is back together with Ursula. However, she flirts with another groomsman to make Jake jealous, and sneaks off with Jake at the end of the evening to kiss in a supply closet when Ursula is out of the room.

The rest of the winter, spring, and summer (spring and summer take place in 1994) pass with Mallory and Jake being separated. Despite the problems in their ongoing romantic relationship, Ursula continues to drop hints about wanting to get engaged to Jake. They take a week-long vacation in Paris, an unusual break for her, and at the end of it she blatantly asks Jake what his intentions are for their relationship. Jake says that he doesn’t think they’re ready to get engaged yet, and the trip ends with them both being angry.

Back in Washington D.C., Jake finds out that Cooper’s wife was secretly a drug addict and has left the marriage. The two decide to visit Mallory on Nantucket, where Cooper meets up with a flight attendant he flirted with on the way to the island. Because Cooper doesn’t know about their surreptitious relationship, Mallory and Jake can’t be open about their feelings for each other. Jake jealously notices that there’s a pair of men’s swimming trunks at the cottage, suspecting that Mallory has a boyfriend. Over dinner, the three talk about love, and Mallory says she’s currently in love. Jake doesn’t know whether she’s referring to him or the potential boyfriend.

The three go out to the local bar, and Cooper disappears with the flight attendant, warning them that he probably won’t be back at the house if he decides to sleep with her. Jake takes advantage of being alone with Mallory and asks her about the swimming trunks. She says she’s casually dating JD and that the swim trunks are his. Nonetheless, she and Jake decide to indulge in their annual weekend together. 

Mallory has a full-time job teaching high school English and enjoys her work. She’s well-liked by the students and is friends with the school’s guidance counselor Apple, who waitressed with her during her first summer on Nantucket. Mallory and JD are still dating, but she’s concluded that they aren’t compatible with each other, after a week-long vacation to a tropical island near Puerto Rico in which JD sat in the bar all day drinking instead of exploring with Mallory. She also refuses to let JD do any maintenance around her cottage and is leery of JD’s persistent jealousy over any other male who comes into contact with Mallory. However, JD is invested in the relationship and wants to move in with Mallory, an idea she resists.

Mallory takes an interest in her students, who relate to her well because she treats them with consideration and respect—and because she’s younger than many of the other teachers, helping them see her as a peer rather than an authority figure. She tries to form a mentoring relationship with a senior student, an intelligent, thoughtful boy whose Quaker family will not allow him to visit the mainland or go to college. The rest of the senior class goes on a multi-day trip to Boston, and Mallory offers to take the student for a drive during a free period. Her car becomes stuck, and JD “happens” to be in the closest car that can help them (Mallory suspects he was following her). The mishap attracts the school’s attention to the fact that Mallory took a student, alone, off school grounds, but she isn’t reprimanded. Embarrassed by her poor judgment, she breaks up with JD and keeps a low profile on the island all summer.

Lonely and at loose ends, Mallory calls Leland to invite her to come visit. The two haven’t spoken in over six months, and their last meeting felt forced and dissatisfying to Mallory. A woman answers Leland’s phone. Leland can’t come visit because she’s committed to visiting a writers’ workshop in Vermont. Leland reveals that she has fallen in love with a female writer, Fifi. Leland and Fifi have moved in together. Mallory is shocked by the revelation about Leland’s sexual orientation but wishes her friend well. She feels lonelier than ever, having heard from Cooper that Jake and Ursula are still together and are doing things together with him and his new girlfriend (the flight attendant he met on his way out to Nantucket). She starts to doubt whether Jake will really come visit her on Labor Day, even though he promised. She’s relieved when she gets a postcard from him saying that he’ll be there.

Jake and Ursula have moved in together over the course of the intervening year, Jake’s tactic for avoiding the progression to engagement and marriage. Mallory and Jake begin to spend their annual weekend together but are interrupted by Ursula calling the cottage to say that her father has died. Jake immediately flies to Indiana to be with her. He finds that, rather than being the cool, competent organizer of her father’s funeral as he expected, Ursula is distraught and racked with guilt over not being a better daughter. Jake helps her and her family get through it, and his own family comes to the funeral.

On the way back to Washington, Ursula asks Jake about the female voice (Mallory’s) on the cottage answering machine when she called for Jake. He lies and says that the annual weekend is a guys’ trip, and that Mallory wasn’t there.

Jake was bothered, when he saw Mallory, that he didn’t have any pictures to remember her by in their time apart, so he purchased a disposable camera and took candid pictures of her while they were together. Back in Washington, he has them developed and keeps them in his desk at work. He and Cooper meet up for drinks, and he tells his friend about how much more vulnerable and softened Ursula seems since her dad died. Cooper has a new girlfriend after breaking up with the flight attendant. Drunk and thinking about an offhand remark of Cooper’s to just marry Ursula already, Jake leaves the bar and immediately goes to a jewelry store to pick out an engagement ring. He mistakenly tells the saleswoman that his girlfriend’s name is Mallory, however, making him question his commitment to Ursula. Ultimately, though, he buys a ring and proposes to Ursula as soon as he gets home. The moment is lackluster, because Ursula has a headache and doesn’t show much reaction when he proposes, but she accepts.

Jake and Ursula plan a June wedding. Cooper is Jake’s best man, so Mallory gets the details from him but of course isn’t invited. The weekend of the wedding, Leland and Fifi come to Nantucket to visit Mallory. (Fifi is the one who answered the phone when Mallory called Leland in Chapter 3, and at this point the women have been together for almost two years.) Leland tells Mallory that her parents are getting divorced after her mother found out that her father is having a long-term affair with Frazier’s mother, a shiftless woman who was at the fringes of the two families’ social groups while Mallory and Leland grew up. Mallory observes the dynamic between Leland and Fifi during the first evening of their visit and quickly realizes that Leland is jealous of Fifi, who is a literary celebrity and uses her charming, charismatic personality to win people over. Fifi flirts with Mallory when Leland goes to bed, which makes Mallory uneasy.

Mallory is angered the next morning when she overhears a fight between the other two in which Leland insults her, calling her an unoriginal and unsophisticated person. Her feelings hurt, Mallory feigns a change in plans and abandons the other two at the cottage. She goes to the local bar she used to waitress at and gets drunk with a man named Bayer, who’s living on his sailboat on Nantucket for the summer. Mallory tries to spend the night with him, but he refuses to take advantage of her and instead asks for her phone number so they can spend time together sober. She returns to the cottage and discovers that Leland and Fifi are out. She doesn’t see them the rest of the weekend. When she wakes up the next morning, Mallory realizes that Jake married Ursula the night before. Bayer calls her and invites her for a sail.

Mallory and Bayer fall into a casual, whirlwind romance over the next few weeks. Bayer teaches her to sail on his boat. The two get along well and are sexually compatible, but Mallory senses that Bayer is hiding something. He’s vague about what he does, stating that it has something to do with politics, and avoids public places—although Mallory assumes that that has to do with preferring to be out on the water. When she does convince him to go out to dinner, Bayer runs into someone he knows, who reveals that Bayer is married with children. After they leave the restaurant, Bayer tells Mallory that his wife has given him the chance to have a casual summer fling. Mallory confesses that she’s in love with Jake, and the two end their relationship. Mallory’s confession will have later consequences in the story, notably in Chapter 24.  

During Christmas of 1997 in Baltimore, Mallory goes home for Christmas, disappointed that her family’s Christmas rituals with Leland’s parents have been disrupted by their divorce. Mallory’s parents surprise her and Cooper by inviting Greta’s partner Ruthie to Christmas dinner, which touches Mallory. Jake, who stayed in Washington DC for Christmas instead of going to South Bend, calls Cooper and invites him and Mallory out for a drink while Ursula is busy with her mother.

Cooper notices the chemistry between Mallory and Jake at the bar but is too distracted by reconnecting with an old girlfriend to pay much attention to them.

Ursula takes a higher-paying and more demanding job. Jake quits his own job but schedules a root canal before he leaves. He develops a serious staph infection after the procedure and has to be admitted to the hospital, which Ursula is nearly too busy to arrange. When Jake is released and taken home to recover, Ursula tells him someone from his old office found and returned the photographs of Mallory he’d hidden in his desk, although she has respected his privacy by not looking at them. Jake lies and says that the pictures aren’t his, although he later finds out that Ursula must have known he was lying because his own handwriting is on the outside of the envelope that contains the pictures. He throws the pictures away after Ursula leaves their apartment, knowing that he can’t have them around. He does, however, keep one picture of Mallory, the shells that he found on the beach with her, and fortunes from the fortune cookies in their Chinese dinner ritual.

Jake is offered a job at Johns Hopkins as he recovers but turns it down. He visits Ursula, who’s working on a case in Las Vegas, but angrily leaves after he’s stuck in her hotel lobby because she forgot to add his name to the hotel room. Meanwhile, she’s sitting in a bar with her colleagues. On his way back from Vegas, he runs into an acquaintance who works as a lobbyist for the National Rifle Association (NRA), who offers him a job. Jake looks into the job but decides not to work for the organization after a school shooting tragedy makes the news. After returning from Vegas, Ursula is immediately assigned to a case in Texas that will require her to stay there for the foreseeable future. She and Jake are becoming increasingly disconnected from each other.

On Nantucket, Mallory has taken sailing lessons and gotten a boat of her own after ending her relationship with Bayer, and she takes Jake out on it when he arrives for his annual visit. They sail to a nearby island, more private than Nantucket, where she has arranged to have them stay at an acquaintance’s vacation house. The two have an amazing weekend together, and on the day before he leaves, Mallory and Jake tell each other “I love you” for the first time. 

Cooper is getting married again, and Mallory and Jake meet at his wedding in June, at which they are again bridesmaid and groomsman. They pine for each other across the room at the reception, and in the women’s bathroom Mallory hears Ursula throwing up. Ursula, crying, tells her that she thinks she’s pregnant, and garbles out a sentence that Mallory thinks means that the baby isn’t Jake’s (Ursula has indeed been having an affair with a coworker). The two are interrupted before Mallory can confirm whether she heard correctly, and Ursula goes back to her table afterward. Upset and jealous, Mallory goes outside with Frazier, where they talk and eventually end up sneaking off to have sex. In the heat of the moment, neither of them thinks about birth control.

On Nantucket over Labor Day, Mallory and Jake are subdued when she picks him up. At the cottage, he tells her that Ursula is pregnant, not knowing that Ursula told Mallory at the wedding. Mallory reveals that she’s pregnant too, with Frazier’s baby.