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Content Warning: This section of the guide contains cursing and sexual content.
The Prologue takes place before Part 1, “Seven Days Before the Wedding.” Maya laments to a friend that she doesn’t want to go to her brother Eli’s destination wedding in Sicily because she doesn’t want to see Conor Harkness—Eli’s best friend who Maya’s been in love with for three years. Ten months ago, Conor stopped talking to her, and Maya is still hurt. After everything Maya and Eli have been through as siblings, Maya says, “[I]f my brother wants me at his wedding, I’m going. End of story” (3).
Maya manages to arrive in Sicily a day later than Eli wanted by offering to fly with his oversized dog. During the flight, Maya mentally prepares herself to see Conor again, but all her preparation dies when she shares a ride to the wedding party’s villa with Conor’s girlfriend, Avery. Maya wants to hate her on principle, but she can’t because Avery seems nice, and she “like[s] nice people” (11). Avery can’t believe the resemblance between Maya and Eli, stopping just short of admitting how handsome she thinks Eli is.
When Maya was a teenager, her parents died suddenly, and she was sent to live with Eli, whom she barely knew. This motivated her to graduate high school early and attend college in Scotland, where she coped with her mistakes of lashing out at the people she loved. At age 20, she moved back to Texas to live with Eli. After healing her relationship with him and her friends and finding activities she enjoys, she feels like she’s “built a nice adulthood over the ruins of a shitty adolescence” (16). After getting her master’s degree in physics, she was offered an opportunity to study at SERN in Switzerland, which she took, even though it partly felt like she was running away again.
The wedding villa is in the town of Taormina. On the ride there, Maya desperately searches for a reason to hate Avery. They have the same guidebook of Taormina, complete with annotations and cracked spines, which makes Maya fear there’s no avoiding the friendship.
When Maya arrives at the villa, she sees Eli and Conor laughing. Eli, Conor, and their friend Minami are the owners of the fastest-growing biotech investment firm in the world. Conor is on the phone, chewing out an employee. To distract herself from Conor, Maya takes in the view of the ocean and Mount Etna, which rises to a majestic dark peak and takes her breath away. Finally, she’s forced to interact with Conor, who immediately starts subtly reminding her that he’s 15 years older and not a romantic option.
Eli accidentally grabs Avery’s suitcase and starts to leave, thinking he’s showing Maya to her room. When he realizes his mistake, he asks Conor to grab Maya’s luggage, and Maya finds herself alone with Conor. As they walk, she babbles about the villa’s architecture in an attempt to come off as casual. In her room, Conor asks if she’s on drugs because she’s speaking rapidly. Maya is offended and argues she’s being easy-going. Conor scoffs, and Maya decides that “if he’s going to play this game, I’m going to give him difficult” (28). Before he can leave, Maya asks if Avery is the reason Conor stopped talking to her.
In their last conversation 10 months ago, Conor told Maya he was seeing someone and was worried she would get the wrong idea about him and Maya. Conor confesses he and Avery are no longer together. Being intentionally cruel, Maya asks if the two hope the trip will fix their relationship. Avery is around Conor’s age, and Conor has made it clear he thinks “a nonexistent age gap [is] the core requirement of a successful relationship” (30). Conor doesn’t understand why Maya hasn’t moved on. Maya argues there is no moving on for her, and Conor storms out, telling Maya to stop acting like the child she tries to say she isn’t.
After Conor leaves, Maya stares at the closed door and replays her falling out with Conor in her head. After her parents died and Maya went to live with Eli, Conor and Minami helped Eli take care of her. The three also started their company, and when Minami had a baby, Avery joined the company so Minami could pull back to be with her family.
After a nap that doesn’t make her feel any better, Maya goes to the pool, where she runs into her friend Nyota. Nyota’s biggest goal for the week is to have sex with a hot guy. When she decides Conor is the one, Maya hisses that he’s hers before immediately retracting the statement and feeling foolish. Nyota is intrigued, and Maya details her feelings for Conor, as well as his objections to their age difference. Nyota thinks this is ridiculous and urges Maya to pursue him because they’re both adults, and “there’s nothing wrong with having a little problematic summer fling” (41). When Maya hesitates, Nyota asks if Conor knows how Maya feels. Maya reveals her past with Conor.
Chapter 6 takes place three years earlier in Scotland. A few days prior, Maya’s boyfriend of a year and a half slept with her roommate, and Maya’s two best friends in the country are on his side. Tearful and desperate, she calls Eli, only to be redirected to his office and put through to Conor because the receptionist thought it was a business call. Just like the few times she interacted with Conor before she left, he is clipped, distant, and borderline rude. Eli is on a transatlantic flight and won’t be available for several hours, so Maya starts crying again and hangs up.
Conor calls back, sounding put out, but asks what’s wrong. Maya details how her boyfriend broke up with her for one of her roommates; when she got upset, her friends told her she was unstable and blamed her for being aggressive. To her surprise, Conor understands her situation and takes her side, saying she had a right to be mad. Maya isn’t sure he’s right. She knows she tends to get overly angry when the people she cares about hurt her. She wanted Scotland Maya to be a new, easygoing version of herself, to which Conor says, “it sounds like Scotland Maya is more like a plastic doll than a real person” (53).
Conor offers to find Maya a hotel so she doesn’t have to go back to her apartment. Maya thanks him but refuses. She won’t be chased out of her life by this. After a few hours at the library, she goes home, where she finds Conor standing in her kitchen, chatting with her roommate and ex-boyfriend.
In the present, Maya and Nyota arrive to a dinner with Eli, Rue (Eli’s fiancée), Tisha (Rue’s best friend), and the rest of the wedding party—primarily friends from work and school. The outdoor table looks like something out of a fairy tale with twinkling lights crisscrossed overhead and Mount Etna towering in the background. Maya remembers how she feared Rue would take Eli away from her but came to understand that Rue was just shy and awkward, not cold and distant. The rest of the crew includes Minami and her family, Avery, and Conor, who is showing Minami’s daughter the trees beyond the table. When the toddler notices Maya, she fusses until Conor carries her over. As he hands the girl to Maya, Maya looks up at him, which she immediately regrets because his eyes hold “a guarded, hidden, resigned kind of sadness” (65).
The only person at the table Maya doesn’t recognize is a beautiful blonde woman named Tamryn, who sits next to Conor and seems oddly intimate with him. To distract herself, Maya strikes up a conversation with a friend who asks if she’s decided between a job offer in California or a research fellowship at MIT. It’s clear the guy is romantically interested in Maya, but she can’t muster any feelings for him. Instead, her eyes stray to Conor, and she chastises herself, thinking “maybe it’s time you did something to solve this problem, Maya” (70).
After dinner, Maya takes the toddler back to look at the trees and twinkling lights. As she does, she overhears the others talking about how much younger Maya is than them, and she can’t miss Conor’s mumbled assertion that she was a child more recently than the rest of them. Maya pretends not to notice and does her best to enjoy the beautiful night. Later, she hears footsteps and is shocked to find Conor approaching.
Conor sits beside her and starts up a conversation about stargazing. A few years ago, Maya told him she loved the stars because her dad taught her about them. She remembers how Conor used to listen to her vent without offering empty platitudes. Only once, he said that he wished he could carry the hurt for her. Then, Maya believed him. Now, she knows that’s “because I’m a fucking idiot” (74). The memories make her spiteful. She asks Conor why he came to sit with her when there are clearly more mature women back at the table. When she starts to storm off, Conor grabs her wrist. He doesn’t want to fight or have the awkwardness of their past between them anymore. Maya can’t bring herself to let him go and admits she’s missed him. Suddenly, Conor looks like he desperately wants to tell her something. Before he can, someone at the main table throws up, followed by the rest of the group.
Everyone at the table except Maya, Conor, and Minami drank shots of a beverage from a street vender, and now they all have food poisoning. As the three discuss what this means for the wedding, Tamryn stumbles downstairs to ask if there’s nausea medication. She still has an easy rapport with Conor, so Maya is amazed when she finds herself liking Tamryn. Maya helps Tamryn back to her room, where Tamryn asks Conor to come inside. Conor goes, and Maya stands in the hallway, “[r]emembering a time when I pulled Conor inside my room” (85).
Chapter 11 flashes back to the past, when Conor came to Scotland after Maya’s boyfriend cheated on her with her roommate. Conor pretends he met Maya at a bar when she was on a vacation with her ex-boyfriend, where she told him she’d get in touch if she ever broke up with the guy. Conor pretends he got a text from Maya, making Maya’s ex and roommate uncomfortable. Before he leaves, he pretends to kiss Maya. When he pulls back, the other two are passionately embracing, so Maya asks Conor to spend the night. She tugs him into her room, where he pushes against the door to make it sound like they’re having sex against it.
Afterwards, Maya thanks him for showing up, even though she still doesn’t understand why. Truthfully, neither does Conor, but when he saw the other two unconcerned with where Maya was, he decided to be rude to them. Conor came up with the vacation story after scrolling through a text-message chain with Eli. Maya looks at the texts, surprised to see how much Eli talks about her and how proud he is of her accomplishments. Maya realizes she wants Eli back in her life. She asks Conor not to tell him she’s in trouble, to which Conor responds, “you’re not in trouble, Maya. You are trouble” (97). Maya smiles.
Conor was in Ireland at a family event when Maya called. He dislikes his father, so helping her was a good excuse to leave. Maya wants to buy him breakfast to thank him for coming to her rescue, though she says she isn’t surprised her ex dumped her for someone prettier. Conor argues the other girl is not prettier and tells Maya she can do better. Surprising herself, Maya believes him.
In Part 1, Hazelwood introduces the main romantic tropes of Problematic Summer Romance: “brother’s best friend” and “age gap romance.” Both tropes play key roles in the changing dynamics between Maya and Conor, as well as in their relationships with Eli. The 15 years between Maya and Conor offer an emotional barrier to the two getting together. This is explored in different ways throughout the book and introduces the major theme of The Meaning of Age. The novel’s alternating timeline uses flashbacks to show how Maya and Conor’s bond developed during her early adulthood, offering emotional context for their present-day relationship. These chapters make clear that Conor was never a parental figure—he supported Eli, who unexpectedly became Maya’s guardian, but hardly knew Maya until she was an adult. The flashbacks also reveal Conor’s heightened awareness of age gaps and power dynamics, shaped by his father’s exploitative relationships with younger women. Rather than presenting himself as above Maya, Conor actively resists the idea that he might hold power over her—a resistance that becomes one of the major emotional tensions of the novel.
Because Maya and Conor barely knew each other during her adolescence, their eventual connection is not shaped by nostalgia, longing, or a remembered hierarchy. Maya never idolized Conor, and Conor had little memory of her beyond her proximity to Eli. This lack of prior intimacy allows their bond to form in real time, rather than being entangled with caretaking or childhood affection. In doing so, the novel sidesteps some of the most fraught age-gap tropes and frames their dynamic as something new—tentative, mutual, and built on present-tense recognition. Since Maya is highly intelligent and has been independent since age 16, this also puts a spin on the “brother’s best friend” trope. Rather than setting up a conflict where the brother tries to shield his younger sister from an older man, the novel foreshadows a different outcome: Maya is already living as an adult, capable of making her own choices. This maturity aims to reorient the reader’s expectations, suggesting that any tension between Eli and Conor will be quickly resolved.
The chapters set in the past offer context to Conor and Maya’s relationship struggles in the present-day main story. Maya unintentionally unloading her problems on Conor is an outlet for her and a realization for him. Initially, Conor comes to Scotland to help her because he sees himself in her situation, but as he gets to know her, Conor understands that Maya is unique. Her ability to roll with the punches at what he perceives as a young age makes it clear she is capable, which allows him to develop feelings for her even as he tries not to. Conversely, after realizing her ex-boyfriend is emotionally stunted and cruel, Maya finds Conor’s easy maturity refreshing and attractive. Their developing friendship again offers context to The Meaning of Age. Though there are 15 years between them, the two have much in common and an easy rapport.
Further, Maya’s troubled past means she’s had experiences and emotional struggles other 20-year-olds have not. Her choice to deal with these things in a constructive way allowed her to grow up a lot in a short time span. Conor’s comment that “Scotland Maya” sounds like a plastic doll rather than a person marks a turning point: He becomes one of the first people to validate the complexity of Maya’s emotions instead of demanding palatability. Thus, while she is only 20 during the flashback chapters, her emotional maturity exceeds her physical age, showing how emotional age is determined by more than birth. The Prologue itself is an essential framing device. Maya’s hurt over Conor’s absence and her determination to attend the wedding regardless introduces the theme of What It Means to Love, suggesting that love is persistent, even when wounded. Her loyalty to Eli and her complicated longing for Conor coexist in the same breath, immediately situating love as something capable of holding both pain and grace.
Maya’s relationships with the other female characters of the novel also show the maturity she’s cultivated. Her friendship with Minami is the benchmark for her ability to deal with Conor’s other potential romantic interests. Minami and Conor dated, but it was before Maya thought of Conor in a romantic way. This, coupled with the nurturing role Minami played when Maya was younger, shows that Maya is mature enough to view Conor’s romantic interests as individual people, not simply obstacles to her goal. This is confirmed when Maya meets Avery. Maya initially wants to hate Avery for being the catalyst that took Conor away. Maya’s inner monologue offers up less than complimentary thoughts about Avery, but Maya is respectful and mature in her speech. She even catches herself admiring Avery’s annotated travel book—the same as her own—revealing how intimacy and jealousy are sometimes indistinguishable. Maya is also quick to change her mind about Avery when she realizes the two of them have a lot in common and that Avery is a nice person. Similarly, Maya initially dislikes Tamryn because she’s beautiful and seems to have an intimate relationship with Conor. Though Maya doesn’t learn Tamryn is Conor’s stepmother in this section, Maya is still mature enough to be polite and, as with Avery, able to get to know Tamryn past the feelings of jealousy. This emotional restraint is especially notable given the flashback scenes in which Maya admits to having a volatile temper during her Scotland years—a trait she’s now actively trying to outgrow.
Tamryn’s presence in the novel also introduces third major theme of The Pressure of Expectations on Relationships by offering context for Conor’s character and his view of a romantic relationship with Maya. Conor’s father is a millionaire who seduced Tamryn (who’s a year younger than Conor) to marry him by throwing his wealth around. Conor has always thought the age gap between his father and Tamryn looked ridiculous, and this partly motivates his refusal to get involved with Maya. Thus, Tamryn demonstrates how no two relationships are the same. Tamryn married Conor’s father because she was young, impressionable, and she let herself believe he truly cared about her when he only wanted her as a trophy wife. However, in the time since, Tamryn has grown and come to terms with her poor choices. Her calm rapport with Conor—and his willingness to help her when she gets sick—shows that women who were once “used” can grow into people with agency, complicating the stereotype Conor fears Maya will fall into.
Since Conor fears he is more like his father than he wants to admit, he also fears that he only wants Maya because she’s young, beautiful, and brilliant. Conor uses his father’s behavior as a shield to keep Maya at a distance, which also causes Conor to develop a harmful sense of self-loathing that keeps him from letting himself be truly happy. In this way, Conor’s emotional arc is as much about learning to separate himself from his father’s identity as it is about accepting his love for Maya. This stands in contrast to Maya, who has already done the emotional labor of healing in order to move forward with her life—something that is subtly expected of her as a young woman navigating both grief and ambition. Maya’s job offers from elite institutions like MIT and major tech companies suggest that healing has been, for her, a prerequisite to success. In this way, she and Conor are inversions of each other: She has healed in order to thrive, and he must now heal in order to love.
In this section, Maya’s capacity to reframe her hurt in moments of humor or affection, even while struggling, becomes apparent. Whether through her jokes about Conor’s age or her restraint around Nyota, Maya exhibits emotional intelligence that destabilizes the assumption that she is “too young” to know what she wants. This subtle resistance to being underestimated reinforces the novel’s overarching argument that age cannot be measured in years alone, but in the work of growing into oneself.



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