Problematic Summer Romance: Essay Prompts for In-Depth Analysis

This page offers twelve analytical essay prompts for Ali Hazelwood's Problematic Summer Romance. Each prompt is designed to explore specific character arcs, thematic tensions, and structural choices within the novel. For every prompt you will find a justification of its importance, a defensible sample thesis direction (not a full essay), and three to five evidence leads from the chapter outline and key scenes. Use these prompts as starting points for your own critical reading.

1. Maya’s Emotional Growth from Avoidance to Vulnerability

Why it matters: The novel traces Maya’s arc from deflecting her feelings to honestly demanding reciprocal love. Analyzing this change reveals how Hazelwood ties emotional maturity to romantic resolution.

Sample thesis direction: Maya’s journey from hiding behind jokes and self-deprecation to confronting Conor with raw vulnerability mirrors her broader recovery from grief; the turning point is her angry rejection of his scrunchie keepsake in Chapter 36, which forces him to admit his self‑loathing.

Evidence leads:

Prologue: Maya lies to Eli about an MIT interview to delay arrival; she uses ice‑skating as emotional release.
Chapter 9 (stargazing): Maya confronts Conor about other women, but still deflects her own feelings.
Chapter 25 (flashback phone calls): Over two years, Maya gradually shares anger, fear, and desire, laying groundwork for vulnerability.
Chapter 36: Maya finds the scrunchie and erupts, accusing Conor of hiding behind grand gestures; she declares her own freedom.
Chapter 38: Conor confesses love at sunrise, and Maya accepts his vulnerability in return.

2. Causality: How Conor’s Father’s Death Reshapes His Reluctance

Why it matters: Conor’s refusal to act on his feelings is partly rooted in his family history. The revelation of his father’s death in Chapter 12 adds a causal layer to his emotional shutdown.

Sample thesis direction: Conor’s guardedness is not only about the age gap but also about the unresolved trauma of a cruel, controlling father; learning of Finneas’s death in Chapter 12 triggers Conor’s confession in Chapter 38, linking grief to the release of love.

Evidence leads:

Chapter 11 (Edinburgh flashback): Conor tells Maya about his father’s illness and his own self‑worth struggles.
Chapter 13: Conor reveals his father is a cruel bully and his stepmother is younger than him; this shapes his fear of repeating patterns.
Chapter 12: Conor tells Maya his father died months ago; Maya offers congratulations, a darkly comic pivot.
Chapter 22: Conor and Tamryn discuss legal disputes over the estate, showing ongoing family friction.
Chapter 38‑39: After the sunrise wedding, Conor confesses his love, finally separating himself from his father’s shadow.

3. The Age‑Gap Theme as a Barrier and a Mirror

Why it matters: The age gap is the central obstacle, but the novel complicates it by showing both characters’ perspectives. Comparing scenes where Conor invokes it versus Maya challenges it reveals the theme’s function.

Sample thesis direction: Hazelwood uses the age gap as a deliberate structural barrier that forces both characters to articulate what they truly want; Conor’s use of it as a shield (Chapter 19) contrasts with Maya’s insistence on agency (Chapter 14), ultimately leading to a redefinition of power.

Evidence leads:

Chapter 3: Conor asks if Maya is high, dismisses her as childish; later she taunts him about Avery’s age.
Chapter 15 (Greek theater): Ticket seller mistakes Maya for Conor’s daughter; Conor gives an “I told you so” look, but Maya jokes “Daddy” to reclaim the moment.
Chapter 19 (Edinburgh): Conor stops kissing Maya citing the fifteen‑year gap; Maya argues age is a construct.
Chapter 27: Conor brings Maya to orgasm but refuses to let her reciprocate, citing age as a barrier.
Chapter 39: Conor admits he wanted to marry her from the start, but wouldn’t rush her – a reversal of his earlier stance.

4. Contrast Between the Edinburgh Flashbacks and Sicily Present

Why it matters: The dual timelines allow direct comparison of Maya and Conor’s relationship at two moments. Contrasting scenes highlight what has changed and what has remained unresolved.

Sample thesis direction: The Edinburgh flashbacks establish a foundation of selfless care (Conor tracking Maya down after her breakup), while the Sicily present shows that same care has curdled into protective self‑denial; the contrast underscores that their issue is not lack of feeling but Conor’s refusal to let feeling lead.

Evidence leads:

Chapter 11 (Edinburgh): Conor pretends to be Maya’s romantic interest, fakes sex noises, and offers his hotel room – protective kindness without romantic claim.
Chapter 19 (Edinburgh): Conor stops a kiss but then gives Maya an orgasm, refusing reciprocity.
Chapter 4 (Sicily): Conor ends their conversation calling Maya a “childish brat,” a sharp contrast to his earlier patience.
Chapter 26 (Sicily): Conor orders Maya to her room with a low growl, treating her as someone to command rather than partner.
Chapter 36 (Sicily): Maya confronts Conor about the scrunchie, forcing him to admit he kept it for three years – the Edinburgh care has turned into fetishized distance.

5. Relationships Beyond the Romance: Sibling Bonds and Found Family

Why it matters: Maya’s relationship with Eli is a crucial subplot, and the novel presents multiple forms of family support. Analyzing these bonds shows how romantic love is embedded in a larger network.

Sample thesis direction: The sibling dynamic between Maya and Eli evolves from distant guardianship to mutual pride, mirrored by the found‑family structure of Rue, Nyota, and Minami; Maya’s acceptance of Eli’s support in Chapter 32 directly enables her to trust Conor’s love.

Evidence leads:

Chapter 22 (beach scene): Eli and Maya talk about their parents; Eli admits their parents wouldn’t have liked Rue, and Maya says “fuck them.”
Chapter 32: Maya admits she deferred MIT and took a teaching job; Eli says he is proud of who she is, not her career.
Chapter 8 (cucamelon plant flashback): Rue’s awkward gift builds a bond, showing Maya gaining a sister figure.
Chapter 24: Minami asks Maya to be godmother, formalizing found‑family membership.
Chapter 40: Avery tells Maya that Conor loves her, and Maya feels hopeful about the future despite imperfection.

6. The Volcano and the Sunrise: Symbols of Change and Stability

Why it matters: Mount Etna’s eruption and the sunrise wedding are repeated symbols that comment on the characters’ emotional states. Analyzing their recurrence reveals Hazelwood’s symbolic structure.

Sample thesis direction: Mount Etna represents uncontrollable external forces that disrupt plans (wedding dress, flights) but also mirror the volcanic inner tension between Maya and Conor; the sunrise in Chapter 38, by contrast, symbolizes a new beginning built on honest vulnerability, not explosive drama.

Evidence leads:

Chapter 28: Mount Etna erupts, grounding flights and ruining Rue’s wedding dress; Maya loses Tiny, leading to cave adventure.
Chapter 33: Etna continues to erupt as wedding chaos peaks; Conor admits Maya is his greatest regret.
Chapter 37: Sunrise over Etna at Villa Comunale; Eli and Rue marry in a quiet ceremony.
Chapter 38: Conor takes off his sunglasses, kisses Maya, and confesses love “that will never pass” – the sunrise ends the volcanic disruption.
(Symbolism contrast) – The eruption is sudden, destructive; the sunrise is gradual, hopeful.

7. Foreshadowing: The “Mayageddon” Competitive Side

Why it matters: Maya’s hyper‑competitive “Mayageddon” side is introduced comically in Chapter 18 but later becomes a marker of her agency. Tracing this trait shows how Hazelwood foreshadows Maya’s refusal to accept Conor’s limits.

Sample thesis direction: Maya’s competitive drive, first shown in beach soccer where Eli kicks her out, foreshadows her determination to win Conor’s vulnerability; the same stubbornness that makes her a troublesome player also makes her refuse his protective walls in Chapter 36.

Evidence leads:

Chapter 18: Beach soccer – Maya’s “Mayageddon” emerges, leading Eli to kick her out; Conor wipes sunscreen from her jaw.
Chapter 9 (stargazing): Maya insists on confronting Conor about his “other women”; she doesn’t back down when deflected.
Chapter 21: Maya makes a deal: she’ll forgo other men if Conor offers himself as an alternative; she leaves him to think.
Chapter 36: Maya visits Conor’s hotel room and orchestrates intimacy on her terms; she leaves when he can’t accept her love.
Chapter 42: Maya points a knife at Conor when he returns – a playful but competitive welcome.

8. Power Dynamics in the Intimate Scenes

Why it matters: The novel repeatedly stages sexual encounters where Conor controls the extent of physical intimacy. Examining who holds power in each scene reveals the negotiation of agency.

Sample thesis direction: Across three intimate encounters (Edinburgh, poolside, and hotel room), Conor dictates boundaries and denies reciprocity, maintaining a power imbalance; only in Chapter 36, when Maya takes control and then walks away, does she equalize the dynamic and force Conor to surrender.

Evidence leads:

Chapter 19 (Edinburgh): Conor stops kissing, but later brings Maya to orgasm; he refuses to let her reciprocate.
Chapter 27 (poolside): Conor touches Maya intimately but refuses to kiss her or let her reciprocate; he leaves after.
Chapter 30 (cave): Conor performs oral sex on Maya twice but again refuses reciprocity, citing power imbalance.
Chapter 36: Maya is in control, orgasms multiple times while Conor holds back; she then leaves, breaking his pattern.
Chapter 41: Finally, Conor and Maya have sex of mutual giving; Conor admits he fell for her at twenty.

9. The Role of the Confidante: Nyota as Catalyst

Why it matters: Nyota is the first person Maya confesses her true feelings to. Analyzing Nyota’s function shows how external validation propels Maya toward action.

Sample thesis direction: Nyota’s role as the non‑judgmental confidante who encourages a “problematic summer fling” epitomizes the supportive female friendship trope; her insistence that Conor wants Maya (Chapter 16) directly counters Maya’s self‑doubt and propels the romantic plot.

Evidence leads:

Chapter 5: Maya blurts out that Conor is “hers”; Nyota dismisses concerns and encourages a fling.
Chapter 16: Nyota insists Conor wants Maya, not Tamryn or Avery; she “I told you so” after Tamryn’s identity is revealed.
Chapter 40: Nyota is part of the found‑family group that celebrates the marriage; she was right all along.
Chapter 17: Nyota defends Maya’s terrible pasta aggressively, showing loyalty beyond romance.

10. Structure of the Dual Timeline: How Flashbacks Delay and Deepen

Why it matters: The novel intercuts Sicily present with Edinburgh flashbacks. Analyzing the placement of these flashbacks reveals how Hazelwood controls pacing and emotional payoff.

Sample thesis direction: The flashbacks are strategically placed at moments of maximum tension in Sicily (e.g., after Conor calls Maya childish, after the intimate cave scene) to provide backstory that recontextualizes present behavior; this structure forces the reader to reassess Conor’s coldness as delayed grief and self‑sacrifice.

Evidence leads:

Chapter 4 (Sicily) ends with Maya confronting Conor; Chapter 5 immediately flashes to Edinburgh three years earlier (Chapter 6 flashback sequence).
Chapter 10 (Sicily): Tamryn flirts, Maya feels excluded; Chapter 11 flashes to Conor waiting at Maya’s apartment in Edinburgh.
Chapter 18 (Sicily): Maya sees Conor rescue Avery; Chapter 19 flashes to Edinburgh where Conor stops the kiss.
Chapter 30 (cave intimacy) leads to jellyfish sting; Chapter 31‑32 shift back to character reflection, not a new timeline, but the emotional weight relies on the established Edinburgh origin.

11. The Ending as a Subversion of the “Grand Gesture” Trope

Why it matters: The novel ends with a proposal in Chapter 43, but only after Maya rejects Conor’s grand gesture (the scrunchie, the secret donations). Analyzing the ending shows a critique of conventional romance.

Sample thesis direction: Hazelwood subverts the grand‑gesture trope by having Maya angrily reject Conor’s hidden acts of care (bookshelves, graduation computer, music subscription) as evasions of true intimacy; the proposal succeeds only after Conor verbally confesses love and accepts Maya’s terms, proving that vulnerability, not heroics, is the real romantic currency.

Evidence leads:

Chapter 34: Eli tells Maya about Conor’s secret donations and bookshelves; Maya is unsettled.
Chapter 36: Maya discovers the scrunchie and calls it a way to avoid real connection.
Chapter 39: Conor admits he paid for her music subscription; Maya feels secure not because of the money but because now he is honest.
Chapter 43: Conor proposes with a vintage ring, naked, saying she can take years to decide; Maya accepts immediately, showing she values the verbal commitment over the performance.
Ch 44: The proposal is intimate and private, not public; the friend group only learns later.

12. The Orpheus Myth Allusion and Maya’s Backward Glance

Why it matters: In Chapter 26, Maya compares herself to Orpheus when she walks inside without looking back, trusting Conor to follow. This allusion frames her agency within a myth of doomed love.

Sample thesis direction: Maya’s self‑identification with Orpheus inverts the myth: she is the one who risks looking back (trusting Conor will follow), and by not looking, she secures his pursuit; the allusion suggests that the novel is consciously rewriting a story of loss into one of earned connection.

Evidence leads:

Chapter 26: Conor orders Maya to her room; she walks inside without looking back, thinking “Orpheus.”
Chapter 27: Conor follows, and they have an intimate encounter (though he still denies full connection).
Chapter 38: Maya watches Conor at the sunrise wedding, and he removes his sunglasses to confess love – she finally has visual confirmation.
The myth: Orpheus loses Eurydice by looking back too soon; Maya deliberately does not look, and gains Conor.
(Foreshadowing) – The myth also hints at the underworld; Conor’s difficulty with vulnerability is his own underworld.

Use these prompts as springboards for your analysis. For more discussion questions, see the Questions and Answers page.