Problematic Summer Romance: Your Complete Companion Guide

Spoiler note: This guide contains full details of the novel’s plot, including the ending.

Quick Facts

Short Summary

Maya Killgore, a twenty-three-year-old physics graduate student, heads to Taormina, Sicily, for her brother Eli’s destination wedding. She has spent three years nursing a secret, intense connection with Conor Harkness—Eli’s best friend and business partner—who abruptly ended their friendship after their one night together. Confiding in her friend Nyota, Maya decides to pursue a “problematic summer fling” despite the fifteen-year age gap Conor insists makes their relationship impossible. Across a week of wedding chaos—mass food poisoning, a missing dog, and Mount Etna erupting—the two are forced into repeated proximity. Conor’s emotional defenses gradually crack as Maya’s persistence and vulnerability reveal that his refusal stems not from lack of desire but from deep-seated self-loathing. After a sunrise wedding, a love confession, and a separation of weeks, the couple reunites in Austin and Conor proposes. The story balances steamy intimacy with a meditation on emotional vulnerability, agency, and the courage required to accept love freely offered.

Full Summary

Maya Killgore dreads her brother Eli’s destination wedding in Sicily. The prologue shows her confiding in her friend Jade that she considered skipping it, even lying to Eli about an MIT interview to delay her arrival. The real reason for her discomfort is Conor Harkness—Eli’s best man and the older man Maya has been secretly in love with for three years.

When Maya arrives at Catania airport, she meets Avery, Conor’s girlfriend, who is unexpectedly kind. The two bond over the same annotated travel guidebook, setting up an uneasy friendship that develops across the trip. At Villa Fedra, Conor dismisses Maya as childish, and she lashes out, accusing Avery of being the reason he stopped talking to her.

Chapter 2 provides crucial backstory: Maya lost both parents and moved to Scotland at seventeen, acting out destructively from grief. After returning to Austin, she earned a master’s in physics, rebuilt her life through therapy, and accepted a CERN internship in Switzerland. The narrative then returns to Sicily, where Nyota, Maya’s bold and supportive friend, arrives. When Nyota expresses interest in Conor, Maya blurts out that he is “hers.” Nyota encourages her to pursue a “problematic summer fling,” dismissing age gaps as inherently problematic if both are adults.

The story deepens through extensive flashbacks. Three years earlier, a twenty-year-old Maya was dumped by her boyfriend Alfie for her roommate Georgia. She called her brother Eli but reached Conor instead. Conor flew to Edinburgh, pretended to be a romantic interest from the previous summer to save face for Maya, and spent the night in her apartment. They began a friendship built on daily phone calls and texts—a pattern they maintained for over two years despite Conor insisting the age gap prevented anything more.

In the present, Maya’s rivalry with Avery softens when Avery apologizes for the tension. During a sightseeing trip to the Greek theater, a ticket seller mistakes Maya for Conor’s daughter, reinforcing the age gap. Maya suppresses her feelings, deciding to step aside. But Conor’s actions betray his own investment: he wipes sunscreen from her jaw, translates for her with locals, and repeatedly pulls her away from potential danger, calling her “Trouble.”

A drunken night in Edinburgh is retold in flashback: Maya tries to kiss Conor and he stops her, citing the fifteen-year gap and power imbalance. Maya challenges him fiercely, asserting her capacity to consent. Conor admits his desire and they sleep together, though he refuses to let her reciprocate, needing a minute to compose himself. The next morning he leaves without saying goodbye but sends her expensive gifts and establishes their ongoing phone relationship.

Back in Sicily, the wedding party suffers mass food poisoning from contaminated arancello. Maya and Conor are among the few unaffected. Conor reveals his father died months ago, and Maya recognizes his grief mirrors her own. Lucrezia, the villa caretaker, serves Conor makes Maya granita al caffè, and they explore Taormina together.

The central obstacle of the novel is Conor’s refusal to accept his own feelings. Maya overhears him on a call about a legal dispute with his siblings over their father’s estate. Minami, Conor’s former girlfriend and business partner, reveals to Maya that Conor is emotionally unavailable because he treats partners as people to protect rather than share a life with—but that he told Maya everything he never told Minami, proving Maya is the one person he truly wanted to know him.

A flashback montage shows two years of phone calls: Maya’s failed “emotional fluffing” plan (she only wants Conor), a drunk call where Conor listens to her exist, stargazing lessons, and a conversation in which Conor admits he hates himself when drunk. Maya challenges his belief that love requires hiding parts of oneself.

The physical and emotional tension peaks when Conor finds Maya at midnight by the pool and demands to know who she is texting. Maya trades her willingness to stop for one question: why they never met alone in three years. She argues he avoided physical meetings because their emotional intimacy intimidated him. Conor concedes and orders her to her room—an open invitation she follows.

After intense encounters where Conor brings Maya to orgasm but refuses to let her reciprocate, Maya’s frustration grows. The search for Eli’s missing dog, Tiny, on Isola Bella forces them into a sea cave during a storm. They share an intimate encounter where Conor performs oral sex on Maya but again refuses reciprocation. Maya realizes his protective self-denial prevents a full relationship.

The eruption of Mount Etna disrupts the wedding: flights are canceled, the dress arrives wrong, and the officiant cancels. At a wine tasting, Conor admits he stopped drinking months ago because he hated himself drunk, and he calls Maya his greatest regret. Avery catches them slow dancing on a balcony and feels betrayed.

Eli confronts Maya about Conor but surprises her by worrying Conor might get hurt. He reveals Conor has secretly done caring things: building bookshelves, donating to her university, and obtaining a graduation gift. Maya admits she truly likes Conor and reveals they maintained two years of daily contact.

The novel’s emotional climax occurs when Maya confronts Conor in his hotel room. She discovers he kept her scrunchie from Edinburgh for three years. She erupts in anger, accusing him of using grand gestures to avoid genuine connection. She declares she is free and has chosen him freely, but he cannot accept her love due to his self-loathing. She leaves, and he breaks something behind her.

At sunrise, Eli and Rue marry at Villa Comunale. Maya cries, recalling her family’s lonely past. Rue hugs Maya and calls her family. Conor and Maya stay behind at the park; he removes his sunglasses and confesses his love, saying it will never pass.

After spending a day in Ortigia, Conor reveals he has been paying for Maya’s music subscription and listening to her playlists for three years. Maya feels secure. The group celebrates the early marriage with a gelato feast. Avery privately tells Maya that Conor said he was in love with Maya last summer.

Conor and Maya have sex for the first time since Edinburgh. Conor invites Maya to come with him to Ireland to deal with his brothers’ estate fight. She jokes about being his girlfriend. After sex, Maya sees the flood of work notifications and Conor promises to be more present.

Maya returns to Austin with Paul. Conor stays away for sixteen days, then admits he needs to be in the same country. Maya moves into his house. When Conor arrives early, Maya points a knife at him—a comedic moment—and they have passionate sex. He says “Welcome home.”

At a dinner with their friend group, Minami acknowledges their relationship, and the friends tease them. Conor and Maya reveal their history. That night, he proposes while naked, presenting a vintage ring he bought in Montreal. He says the ring can be a reminder of his love and that Maya can take years to decide. She accepts immediately.

The author’s note reveals Ali Hazelwood’s love for Sicily and confirms that Villa Fedra is a fictional composite of her favorite Taormina elements. She notes taking poetic liberties with Isola Bella’s caves and exaggerating Mount Etna’s flight disruption.

Main Characters

• Maya Killgore: The twenty-three-year-old narrator, a physics graduate student and figure skater who struggles with grief, family obligation, and a long-hidden crush on her brother’s best friend. She is fiercely articulate about her own desires and repeatedly asserts her agency as an adult capable of making her own romantic choices.
• Conor Harkness: The thirty-eight-year-old biotech co-founder and Eli’s best friend. He maintains emotional distance from Maya despite a three-year secret connection, citing the fifteen-year age gap and power imbalance. His protective self-denial stems from deep self-loathing and unresolved family trauma.
• Eli Killgore: Maya’s older brother, whose destination wedding in Sicily serves as the narrative frame. He grows close to Maya across the novel and ultimately supports her relationship with Conor.
• Nyota: Maya’s supportive and bold friend who encourages her to pursue a “problematic summer fling” with Conor. She serves as Maya’s primary confidante throughout the wedding week.
• Avery: Conor’s ex-girlfriend and a fellow biotech partner. She forms an unexpected friendship with Maya during the wedding week and later reveals she has known about Conor’s feelings for Maya.
• Rue: Eli’s fiancée who struggles with social anxiety. She becomes close family to Maya through small gestures of kindness, including a memorable cucamelon plant gift.
• Minami: Conor’s former girlfriend and business partner whose pregnancy and personal revelations help Maya understand Conor’s emotional unavailability.
• Tiny: Eli’s dog whose escape on Isola Bella forces Maya and Conor into a transformative adventure together.

Major Themes

• Age Gap Romance: The fifteen-year age difference between Maya and Conor is a central obstacle, with Conor citing it to reject her advances. Maya insists on her agency as an adult, challenging societal assumptions about age gaps in relationships.
• Power Dynamics in Relationships: Conor leverages his age and experience to deny a romantic relationship, while Maya challenges his control by asserting her own desires. The novel explores how genuine consent and equal footing can exist despite age differences.
• Emotional Vulnerability and Communication: Both Maya and Conor learn to reveal hidden feelings through phone calls, confessions, and small acts of care. Their journey is about overcoming emotional avoidance and learning to accept love freely offered.
• Sibling Bonds and Family Legacy: Maya’s relationship with Eli deepens as they navigate their parents’ death, Eli’s marriage, and Conor’s role as a surrogate family member. The wedding serves as a catalyst for reconciliation.
• Self-Discovery and Identity: Maya grapples with career indecision, anger issues, and self-worth, ultimately choosing a teaching job in Austin that aligns with her authentic desires.

Key Symbols

• Ice skating: Maya uses skating as an emotional release when overwhelmed by grief or family tension, representing her need for a private outlet.
• Granita al caffè: The Sicilian frozen dessert symbolizes Maya’s gradual embrace of local culture and her willingness to trust Conor’s recommendations.
• Tiny the dog: Eli’s missing dog forces Maya and Conor into a wild adventure that deepens their physical and emotional intimacy.
• Mount Etna: The active volcano disrupts the wedding plans with ash clouds and flight cancellations, symbolizing the uncontrollable passion between Maya and Conor.

Ending Explained

The novel concludes with a resolution that honors both Maya’s agency and Conor’s emotional growth. After Conor confesses his love at the sunrise wedding, he and Maya spend a day in Ortigia. Conor reveals he has been paying for her music subscription and listening to her playlists for three years, showing his long-term devotion. He invites her to Ireland to deal with his family estate. Maya jokes about being his girlfriend, and they have sex for the first time since their Edinburgh night three years earlier.

Maya returns to Austin and Conor stays away for sixteen days before admitting he needs to be in the same country. Maya moves into his house, and Conor arrives early, leading to a comedic moment where Maya points a knife at him. They have passionate sex, and Conor says “Welcome home.” At a dinner with friends, Minami acknowledges their relationship. That night, Conor proposes naked, presenting a vintage ring he bought in Montreal. He offers her the freedom to take years to decide, but Maya accepts immediately.

The ending asserts that genuine love requires mutual vulnerability and the willingness to accept love as it is offered—not on terms dictated by fear or self-protection. Maya’s journey from hiding her feelings to openly claiming her desire and receiving Conor’s commitment completes a three-year arc of patience and persistence.

Chapter-by-Chapter Breakdown

Frequently Asked Questions

1. What is the age gap between Maya and Conor? Maya is 23 and Conor is 38, a fifteen-year difference. Maya is an adult throughout the story—she was 20 when they first met in Edinburgh.

2. Is the “problematic” in the title referring to the age gap? Yes, explicitly. Nyota encourages Maya to pursue a “problematic summer fling,” and the central conflict revolves around whether the age gap creates an inherent power imbalance that makes their relationship unethical.

3. Does Maya end up with Conor? Yes. After Conor confesses his love at the sunrise wedding, they reunite in Austin. Conor proposes at the end of the novel, and Maya accepts.

4. How does Eli react to Maya and Conor? Eli initially confronts Maya but surprises her by worrying Conor might get hurt. He reveals he knows Conor has secretly done many caring things for Maya and ultimately supports their relationship.

5. What is the significance of Mount Etna erupting in the story? Etna’s eruption disrupts the wedding by grounding flights and causing the dress and officiant to cancel. It also functions as a symbol for the uncontrollable passion between Maya and Conor.

6. Why did Conor stop talking to Maya for ten months? Ten months before the wedding, Conor told Maya he was going to start dating someone else and suggested reducing their communication, claiming their friendship limited her experiences. Maya confessed she loved him, but Conor deflected. Angry and hurt, she told him to fuck off, and they did not speak until the wedding.

7. What does Maya choose for her career at the end? Maya defers her MIT position and accepts a teaching job in Austin. This decision aligns with her desire for a life that allows her to be with Conor and pursue authentic happiness rather than a prestigious but less fulfilling path.

8. Is there a symbolic object that represents Maya and Conor’s connection? Conor keeps Maya’s scrunchie from their one night together in Edinburgh for three years. When Maya discovers it, she realizes the depth of his attachment, though she initially uses it to accuse him of using grand gestures to avoid genuine connection.

Related Resources

• Chapter summaries for every chapter
• Detailed character pages: Maya Killgore, Conor Harkness, Eli Killgore, Nyota, Avery, Rue
• Thematic explorations: Age gap romance, Power dynamics, Emotional vulnerability, Sibling bonds, Self-discovery
• Symbol guides: Ice skating, Granita al caffè, Tiny the dog, Mount Etna
• Ending explained
• Questions and answers
• Quiz
• Essay prompts