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Andy stays with his mom, and Jen moves in with her sister, Miranda. Andy holds back tears on their weekly phone call as he still hasn’t entirely accepted that Jen ended their relationship. Jen’s therapist suggested that she list everything she dislikes about him to confirm why the relationship didn’t work, an exercise that Andy finds useless because he doesn’t believe that they should have ended it. Jen says that the list “will help you separate the fantasy of us from the reality of us, which I think you know deep down wasn’t working” (12). They’ve both started smoking again, and Jen misses Andy’s mother, to whom she was very close. They agree that the scheduled phone calls may not be healthy and decide to text each other when needed. Jen encourages Andy to tell his best friend Avi about the breakup, but he isn’t ready.

Andy’s mother brings Andy a cup of tea and puts on Frank Sinatra’s In the Wee Small Hours album, which she says brought her a lot of comfort after his father left them. The music fills Andy with nostalgia, and he remembers all the small things he loves about Jen. He watches clothing on the line dance in the wind, which he views as a sign and a reminder of what it’s like to be in love, before collapsing into his bed in tears.

The narrative flashes back to the night Andy met Jen at the birthday party of Jane, Avi’s girlfriend. Jane is pregnant with their first child, and Avi is already very drunk. Avi finds Andy looking for cigarettes and introduces him to Jen. Andy is instantly physically attracted to Jen and offers her a drink. They spend the rest of the party in a booth, laughing and learning about one another. Jen sells insurance for boats, and she learns about Andy’s unique career as a comedian. Since he only does a few shows a year, he uses the rest of his time doing odd jobs and random gigs to make money. When Andy asks Avi if Jen is single, he says, “[f]orever single” (20), which Andy finds strange since she is attractive and fun.

Jen and Andy go to another bar and dance together until it closes. Andy offers to escort her home because he wants to spend more time with her. On the bus ride, they share more deeply about themselves and feel that they’ve known one another forever. At her door, Jen makes the first move and kisses Andy. She wants him to stay over, but she is on her period (Jen later reveals that this is a lie so that they don’t have sex instantly). Andy leaves the following morning for a monthlong stay in Edinburgh for his annual show at The Fringe Festival. Though the Edinburgh show gets terrible reviews, Andy doesn’t care because he and Jen text and talk on the phone daily while he’s gone.

Back in the present, most of Andy’s belongings are still in the flat he rented with Jen. Before leaving for an errand for his mom, Andy scrolls social media and watches Jen’s story multiple times, zooming in on the photo and searching for the answer to his question, “[w]hy did Jen fall out of love with me?” (34). Once he gets to the shops, Andy gets a whiff of the Armani perfume that Jen wears. Andy stops at a bar and orders a bottle of red wine. After his fourth glass, he receives but ignores a text from Avi, wondering where Andy has been. Debbie, a family friend, sees Andy and encourages him to erase everything about Jen from his life. Numbed by the alcohol, Andy convinces himself that he’s okay with the breakup. In Boots, he drunkenly stumbles over several displays and purchases four bottles of Armani, which he tosses into the canal.

Andy goes to a pub to avoid being home alone while his mother is at work. He texts Jane over WhatsApp and asks if he can stay with their family for a while. Jane warmly invites him to stay as long as he needs. However, Andy still avoids Avi’s texts. He finally responds and tells him that he is back home for a while and will see him this weekend. After settling on a place to stay, Andy plans to store his belongings, which he sees as “[a]nother decision made for the funeral of my and Jen’s relationship” (42). Andy remembers his very first breakup with a girl called Nicky, leaves the pub, and uses a pay phone to drunkenly call Nicky’s family home. He awkwardly leaves a message with her mother for Nicky to call him. Desperate not to be alone, Andy stops by Avi’s parents’ home, but no one answers the door, so he leaves a note. Later, Nicky rings Andy’s phone, and he asks if they can meet for drinks or dinner. Nicky is now married and has a family, and she nicely tells Andy that they wouldn’t have much to discuss after all the time that’s passed and suggests that they continue keeping up on Facebook only. Andy apologizes for contacting her out of the blue and blames his behavior on the breakup. Nicky empathetically says that she remembers that he didn’t take their breakup well.

Andy travels by train to London to clean out the apartment. He listens to the new Bon Iver song on the trip and tries to conceal his sobs from his seatmate. When he arrives at the storage facility, he realizes that he accidentally booked it under the last name “Dawson Dawson,” and the attendant forces him to rebook. At the apartment, Andy can see that Jen organized and folded all his clothing, and he imagines her turning the move-out into a party where her friends make fun of his pants. Suddenly, Andy faces the depressing truth that all his belongings fit into a 16-foot storage unit. He sends Jen a text thanking her for organizing his stuff.

Avi and Jane live in the London suburbs with their two sons. When Andy arrives, Jackson, their eldest, and Andy and Jen’s godson, excitedly answers the door, but Avi half-jokingly pretends that he doesn’t know Andy. Andy apologizes for his silence and explains that he and Jen broke up two weeks ago after returning from a trip to Paris. Jane and Jen are best friends, and Avi is upset that Jane kept the news from him, but she explains that she is trying to remain neutral. Andy says that Jen gave no reason for leaving him except that she felt they had grown apart, though Andy suspects that she just doesn’t want to be in a relationship. Avi conjectures that she might be seeing someone else, and Andy agrees that it’s the only plausible explanation. Jane interjects that maybe Jen wants to be single, claiming that women are better at being alone than men. Avi promises to help Andy grieve by planning a night out with their friends. Andy helps with dinner and puts the boys to bed; he goes to bed in the attic room, remembering all the fun memories that he and Jen shared with Avi and Jane, and he realizes that he must grieve not only the loss of his partner but also how it will change all his relationships.

Jen responds to Andy’s text in the middle of the night with just “X,” which Jane says means “kiss,” but Andy wants to read more into it. He wonders why she sent the reply so late. He combs through the socials looking for signs and hates himself for using technology to deal with the uncertainties of his relationship ending. Avi’s youngest son, Rocco, pokes fun at Andy’s emerging bald spot, something that he hadn’t noticed until then. He and Avi laugh it away, but despite Andy’s assertion that he’s still young, Avi says that 35 is old since they are closer to their fifties than their twenties. Andy privately photographs the bald spot, creating a folder in his phone called “BALD” to monitor its progression.

Avi thinks that Andy should stay off the dating apps and pick a hobby to help him recover. Andy agrees but can’t think of much that would interest him. Avi creates a WhatsApp group text with their friends to plan their night out to help Andy forget his problems. The narrative shows the back-and-forth messages from all the friends who were once single but are now in committed partnerships with families, and they provide various excuses for not being able to go out at night. While Andy reads the texts, he combs through the depressingly few options for living accommodations online. Reading the text thread, Andy thinks, “I feel like my singleness may end up being a bit of an inconvenience for everyone” (75). He responds that they should forget it and he will stay in. Avi interjects by chiding the friends for not being there for Andy in his time of need and sets the date for the gathering. Later, Andy overhears Avi speaking with his parents about a strange note that someone left for them (the note that Andy left).

Andy travels with his comedian friend, Emery, to his first stand-up comedy gig since the breakup. Emery says that Andy’s in “The Madness” phase (79), and the best way to begin his recovery is to stop using Jen as his masturbation fantasies. The comedy gig is a marginal success as Andy is neither the headliner nor the closer but performs in the “sagging middle” to keep the show moving (81). However, the crowd responds to Andy’s jokes, and he admits that performing helps him feel better. On the way home, Emery suggests that Andy mine the breakup for content, channeling his pain and grief into humor, but Andy says that he doesn’t use his personal life in his act. Emery encourages Andy to harness the freedom of his singleness and get out and enjoy the adventure, but Andy says that he longs for stability. Avi is still up when Andy arrives home, and Andy asks him if he misses the adventure of the single life, but Avi is content being settled and caring for his family. He reminds Andy that even though they had a few wild, memorable nights, most of their adventures ended in disappointed rides home alone. Andy tells Avi that he is genuinely happy to see him settled down, which makes Avi emotional, but he rebukes Andy’s attempt at sentimentality.

On the day of Andy’s get-together with his friends, he learns that Jane is spending the weekend away at a spa with Jen and her friends to help her get over the breakup. Andy doesn’t understand her need for respite since she was the one who broke it off. Moreover, he’s hurt that all her friends can find the time away from their busy lives to spend a weekend with her, but his buddies can barely manage one night out. Avi and Andy meet their friends Rob, Matt, Jay, and John at a pub, and for the first three hours of the gathering, no one asks Andy how he is or speaks of the breakup. He buys everyone tequila shots and breaks the awkwardness by announcing the end of his relationship. However, this only inspires the guys to begin sharing their own stories of painful breakups, which turns into them blaming women for all their problems.

They move on to the next bar, and Avi pushes a very drunk Andy to talk to a woman at the bar, but she brushes off his advance. As the night progresses, Andy feels less comfortable being out in a bar as he feels like an interloper in the late-night scene. Yet, he admits that he also doesn’t want to be at home alone. He wants to be out late with Jen and be back in the comfort that their relationship brings him. Jay leaves to return home to his family, and Andy and Avi take a smoke break, but Andy vomits, and they leave the club. They go to Rob’s apartment since his wife is out and use nitrous oxide to get high. Andy hallucinates that he is dancing with Jen and then passes out.

Andy wakes up the next day severely hungover with no memory of what happened the previous night. After he and Avi lay on the couch all day nursing their hangovers and watching movies, Andy meets up with Emery to attend another comedy gig in Hull. Emery is slightly drunk and asserts that women and men aren’t meant to be together. He claims that Andy is acting like the woman in a breakup, and Jen is acting like a man. Emery performs well despite his drunkenness, but Andy must follow, and his act falls flat with the crowd. On the train ride home, Andy says that he’s considering getting a personal trainer for better physical shape. Emery pokes fun at what he calls “BOURGEOIS” behavior. Andy receives a direct Instagram message from a woman named Tash (who later turns out to be Jen using a fake account to check up on him), who attended his Crouch End show and says that he’s funny and handsome. Andy continues the messaging through the entire train ride, enjoying the thrill of meaningless, online flirting, something he hasn’t experienced since the last time he used a dating app.