How to Fail at Flirting: 12 Analytical Essay Prompts

1. The List as a Double-Edged Sword: Agency and Avoidance

Why this prompt matters: Naya’s recurring to‑do lists (Chapters 2, 41, 45) appear as tools for self‑improvement, but they also let her compartmentalise trauma. Analysing the lists reveals how Naya both reclaims agency and postpones genuine emotional risk.

Sample thesis direction: The to‑do list functions as a performative act of control that allows Naya to assert agency over her life while simultaneously enabling her to avoid confronting the deep‑seated trauma that drives her fear of vulnerability.

Evidence leads:

Chapter 2: Aaron and Felicia create a playful list; Naya mentally adds self‑advocacy and trust.
Chapter 3: At the bar, Naya checks her phone to see the list image before deciding to flirt with Jake.
Chapter 41: After the attack, Naya writes a new list that includes “Get Jake back,” showing a shift toward emotional honesty.
Chapter 45: During reconciliation, Naya lists life goals, finally integrating desire with action.

2. The Ferris Wheel and the Dance Floor: Symbols of Vulnerability and Trust

Why this prompt matters: Two richly symbolic scenes—the Ferris wheel date (Ch. 8) and the tango lesson (Ch. 7)—capture the central tension between control and surrender. Examining them illuminates how Williams uses physical space to map emotional risk.

Sample thesis direction: Jake’s fear of heights on the Ferris wheel and Naya’s panic during the dance both externalise their characters’ core vulnerabilities; mastery of these spaces mirrors their growing trust in each other.

Evidence leads:

Chapter 7: Naya freezes during a Latin dance lesson because of past trauma with Davis; Jake guides her patiently.
Chapter 8: On the Ferris wheel, Jake reveals his fear of heights to impress Naya; they trade deep secrets and kiss.
Chapter 45: The lake setting for reconciliation recalls earlier water‑adjacent scenes (pier in Ch. 7), bookending their journey.

3. Reclaiming the Body: From Davis’s Control to Jake’s Consent

Why this prompt matters: Naya’s body is a site of abuse, shame, and eventually pleasure. Tracing her physical arc—from hiding under cardigans to wearing matching lingerie—reveals her reclamation of bodily autonomy.

Sample thesis direction: Williams portrays Naya’s sexual reawakening not as a simple liberation but as a gradual, consent‑driven process that directly counters the objectification and violence she endured with Davis.

Evidence leads:

Chapter 1: Flashback to Davis picking Naya’s revealing gown; she tries to cover herself.
Chapter 6: Naya deliberately selects matching lingerie for her date, signalling openness to intimacy.
Chapter 9: Jake brings Naya to orgasm with clear consent; she cries from emotional intensity.
Chapter 19: For the first time, she takes control during sex.
Chapter 41: Naya uses self‑defense (knee, palm strike) to physically fight off Davis, reclaiming her body’s power.

4. The Power of Silence: Naya’s Erasure in Academic and Personal Spaces

Why this prompt matters: Naya consistently loses her voice—when Davis grabs her, when Jill gossips, when the committee meeting silences her. This motif underscores the intersection of trauma, gender, and institutional power.

Sample thesis direction: Throughout the novel, Naya’s silences are both imposed (by Davis’s threats) and strategic (to protect her career); her eventual public confrontation in Chapter 40 represents a rupture that enables true agency.

Evidence leads:

Chapter 2: Naya has never told her friends the truth about Davis; she hides her trauma.
Chapter 33: At the committee meeting, Davis manipulates the conversation and Naya freezes, unable to speak.
Chapter 39: On the retreat van, Naya remains silent while Davis whispers degrading remarks.
Chapter 40: Naya interrupts Davis in front of the full committee, saying “That’s what I said, Davis.”

5. Contrasting Masculinities: Jake’s Caretaking vs. Davis’s Domination

Why this prompt matters: The novel offers two sharply opposing models of manhood. Comparing Jake’s nurturing behaviour with Davis’s coercive control reveals Williams’s commentary on healthy relationships.

Sample thesis direction: Where Davis uses physical intimidation and emotional manipulation to maintain power, Jake demonstrates that true strength lies in vulnerability, patience, and responsive caregiving—a masculinity Naya can trust.

Evidence leads:

Chapter 1/2: Flashbacks show Davis twisting Naya’s arm and slamming it into a podium.
Chapter 26: Jake draws Naya a bath, buys medicine, and watches Star Wars with her when she is sick, removing all sexual pressure.
Chapter 36: Jake slams a doorframe in frustration but never hurts Naya; he immediately professes love.
Chapter 41: Jake comforts Naya after the attack and threatens Davis, but his priority is her wellbeing, not revenge.

6. The Role of Friendship: Felicia and Aaron as Catalysts for Change

Why this prompt matters: Naya’s friendships are the emotional backbone of the novel. Felicia’s blunt encouragement and Aaron’s perceptive questioning push Naya toward self‑advocacy.

Sample thesis direction: While the romance with Jake provides the catalyst for Naya’s healing, it is her friendships with Felicia and Aaron that sustain her, modelling the unconditional support she must eventually offer herself.

Evidence leads:

Chapter 2: Aaron presses Naya about whether the cocky student reminds her of Davis; he sees what she hides.
Chapter 6: Felicia gives last‑minute date advice and normalises Naya’s anxiety.
Chapter 20: After discovering Jake’s wife, Naya calls Felicia, who advises her to leave discreetly.
Chapter 37: Aaron confronts Naya about pushing people away and urges her to trust Jake.
Chapter 38: Felicia and Aaron lend Naya a sleeping bag, offering practical support before the retreat.

7. Professional and Personal Collide: The Ethics of the Secret Affair

Why this prompt matters: The central conflict of the novel’s second half is the ethical dilemma of Naya’s relationship with the consultant hired to evaluate her department. This prompt explores the intersection of intimacy and institutional power.

Sample thesis direction: Williams uses the affair’s ethical grey zone to interrogate how academic structures—especially tenure—can both empower and endanger women, forcing Naya to weigh professional survival against personal desire.

Evidence leads:

Chapter 12: Naya is shocked to discover Jake is the consultant; she panics about career ruin.
Chapter 13: She invites him to her apartment to end things but instead agrees to a “brief, secret affair.”
Chapter 24: Jake explains that Muriel, the HR director, confirmed the relationship isn’t a rule violation, but they must be careful.
Chapter 36: Carlton inadvertently reveals the affair to President Lewis, triggering a crisis.
Chapter 40: President Lewis tells Naya he knows about the relationship but appreciates her speaking up.

8. The Structure of Secrecy: How the Fake Name “Michelle” Mirrors Naya’s Hidden Self

Why this prompt matters: Naya introduces herself as “Michelle” (her middle name) in Chapter 3. The alias is a small, deliberate secret that symbolises the larger truths she conceals—her identity, her past, her profession.

Sample thesis direction: The alias “Michelle” allows Naya to explore desire without the weight of her public identity; its eventual abandonment marks her willingness to be seen fully, even at the risk of rejection.

Evidence leads:

Chapter 3: Naya gives the name “Michelle” to Jake at the bar, lying about being a tourist.
Chapter 4: After vomiting, she confesses the fake name to Jake.
Chapter 7: At the pier, Naya reveals her first name (Naya) but still withholds her last name and profession.
Chapter 13: When she invites Jake to her apartment, she finally reveals she is a professor.
Chapter 24: They exchange full names (Naya Michelle Turner, Jacob Carson Shaw), signalling full disclosure.

9. Foreshadowing and Threat: The Return of Davis as a Structural Engine

Why this prompt matters: Davis’s reappearance is not a surprise; Williams plants clues (Joe’s warning in Ch. 1, the consulting firm reveal, the anonymous texts) that build suspense. Analysing this foreshadowing reveals how the novel uses thriller elements within a romance framework.

Sample thesis direction: The gradual, almost forensic reintroduction of Davis—through rumours, texts, and the consulting partnership—structures the novel as a siege narrative, where Naya’s happiness is perpetually under threat until she finally confronts her abuser.

Evidence leads:

Chapter 1: Joe tells Naya, “I saw Davis the other day. I think he’s back on campus.”
Chapter 16: Naya spots Davis on campus; later, she receives three anonymous texts referencing her day and his pet name for her.
Chapter 23: Davis sends a nude photo and threatens to sabotage Naya’s tenure.
Chapter 33: Davis arrives late to the committee meeting, touching Naya and manipulating the conversation.
Chapter 41: The physical attack in the woods—the novel’s climax—fulfils the foreshadowed threat.

10. From “Pretty Girl” to “Dr. Turner”: The Evolution of Naya’s Identity

Why this prompt matters: Davis repeatedly calls Naya “pretty girl”—a diminutive that reduces her to a passive object. By the novel’s end, Naya insists on “Dr. Turner” (Ch. 29 with Bertram) and asserts her professional authority. This prompt tracks her linguistic self‑definition.

Sample thesis direction: The shift in how Naya is named—from “pretty girl” (Davis) to “Michelle” (her own alias) to “Dr. Turner” (public identity) to “Naya” (intimate self with Jake)—charts her journey from object to subject, from survivor to thriver.

Evidence leads:

Chapter 1: Flashback to Davis calling her “sweetheart” and “pretty girl.”
Chapter 3: Naya chooses “Michelle” as a protective alias.
Chapter 29: At the gala, Bertram Harrison III leers at her; Naya coolly says, “You’re welcome to just call me Doctor.”
Chapter 40: Naya publicly defends her ideas in the committee meeting, refusing to be silenced.
Epilogue: Naya has earned tenure and bought a house with Jake; she is fully “Dr. Turner” in her professional life and “Naya” in her personal one.

11. The Epilogue as a Promise: Healing and the Everyday Commitment

Why this prompt matters: Many romances end with a proposal; How to Fail at Flirting ends with Naya reflecting on a year of small, hard‑won victories. The epilogue redefines happily‑ever‑after as ongoing, mundane, and communal.

Sample thesis direction: Williams subverts the traditional romantic conclusion by centering Naya’s healing process—therapy, tenure, friendships, and a partner who promises “everyday commitment”—rather than a single grand gesture, arguing that true recovery is cumulative and relational.

Evidence leads:

Epilogue: Naya lists key milestones: Davis convicted (no jail), healing with Jill, tenure, buying a house, expanding her friend group.
Epilogue: Jake playfully talks about cake tasting, hinting at marriage but not proposing; Naya feels comfort.
Author’s Note (Ch. 47): Williams includes the National Domestic Violence Hotline, grounding the story in real‑world resources.
Chapter 45: Jake says he wants to “keep going” rather than start over; Naya confesses she loves him.

12. Consent and Communication: How Jake and Naya Model a Healthy Relationship

Why this prompt matters: Throughout the novel, Jake explicitly asks for consent (“Is this okay?”) and Naya learns to voice her desires. This prompt examines how the relationship serves as a counter‑example to the abusive dynamic with Davis.

Sample thesis direction: Williams uses Jake and Naya’s sexual encounters as a case study in enthusiastic consent, where verbal check‑ins, mutual pleasure, and emotional vulnerability replace the coercion and silence that defined Naya’s past—demonstrating that intimacy grounded in communication is itself a form of empowerment.

Evidence leads:

Chapter 9: Jake brings Naya to orgasm with clear, ongoing verbal consent.
Chapter 14: After sex, Jake asks about Naya’s name and ethnicity; she reveals microaggressions she has endured.
Chapter 15: Jake promises to check with HR about the ethical conflict.
Chapter 26: When Naya is sick, Jake undresses and tucks her in naked, removing sexual expectations.
Chapter 41: After the attack, Jake asks, “Can I stay?” and Naya asks for another chance; they negotiate their reconciliation.

For further exploration of these themes, see our trauma recovery, trust and vulnerability, and consent and communication pages. You can also visit the main book page or the questions and answers section.