How to Fail at Flirting: Chapter Thirty-nine Summary and Analysis

⚠️ Spoiler Warning: This guide contains detailed spoilers for the entire novel. Proceed only if you've finished reading or are comfortable knowing the plot.

Summary

Naya arrives at the parking lot for a university committee retreat, scanning for Jake or Carlton. Instead, Davis intercepts her. He immediately brings up the rumor that she slept with the consultant, mocking her intelligence and suggesting she is trying to save her job through sex. Davis takes her tote bag, brushes against her body, and speaks in a condescending tone. Across the lot, Jill frowns at the interaction, and Jake watches with a cold stare before turning away. On the van, Davis sits next to Naya, spreading his legs to crowd her. While others chat, he whispers degrading comments about her past, including “You can beg, too. I liked it when you begged.” Naya physically recoils, curls into the smallest space, and tries to tell him to leave her alone—but her voice is barely audible. She recalls Wes’s self‑defense instructions but cannot act. The chapter ends with Naya feeling completely stuck, writing “To do: . . . I had nothing. I didn’t know what to do.”

Key Events

Naya searches for Jake in the parking lot but fails to spot Davis’s flashy red sports car with plates reading “NO1DR.”
Davis confronts Naya about the rumor, calling her “calculating” and taunting her for being “inarticulate.”
He takes her tote bag, and his forearm grazes her breast, making her recoil.
Jill and Jake both observe the scene; Jake’s expression turns cold and he looks away.
On the van, Davis deliberately sits next to Naya, invades her personal space, and whispers humiliating references to their past relationship.
Naya retreats into silence and physical withdrawal, unable to speak up or move.
She mentally notes her inability to act, even after self‑defense training.

Character Development

Naya – This chapter highlights her traumatic freeze response. Despite intellectually knowing she should react, her body defaults to shrinking and silence. Her internal monologue reveals shame about her social isolation and regret about not making friends.
Davis – He is predatory and calculating. He uses public settings to intimidate while maintaining a professional facade. His whisper and the detail “I liked it when you begged” show his pleasure in her suffering. The license plate “NO1DR” underscores his narcissism.
Jake – His cold stare and turning away suggest he may misinterpret Naya’s interaction as something consensual. This creates a painful misunderstanding that deepens the distance between them.
Jill – She frowns at the scene but quickly looks away, indicating discomfort or disapproval without intervening, reflecting the bystander effect in the context of workplace abuse.

Themes, Symbols, and Motifs

Power and control – Davis exerts dominance through physical intimidation (taking the bag, crowding on the van) and psychological manipulation (whispering degrading words while appearing collegial to others).
Trauma recurrence – Naya’s body repeats the same helplessness she felt during the abusive relationship, despite her desire to change. The self‑defense class memory highlights the gap between knowledge and action under threat.
Public vs. private abuse – Davis hides his cruelty behind a veneer of professionalism, knowing that others will see a normal conversation. This tactic isolates Naya and makes it nearly impossible for her to expose him.
Symbolism of the red sports car – The flashy car with the plate “NO1DR” symbolises Davis’s egotism and his need to broadcast superiority. It also serves as a warning sign Naya missed when she arrived.
The tote bag – Davis taking her bag is a symbolic act of control, stripping her of autonomy and forcing her to follow him.
The van as a confined space – Davis traps Naya in the back seat, using the close quarters to whisper abuse while others are oblivious, mirroring the isolation she felt during the relationship.

Why This Chapter Matters

This chapter raises the stakes in both of the novel’s central conflicts. Davis’s reappearance tests whether Naya has truly broken free from her trauma, and her regression shows that healing is not linear. At the same time, Jake’s cold reaction introduces a major rupture in their budding relationship, setting up future emotional turmoil. The chapter also underscores the theme of how survivors of abuse are often disbelieved or misunderstood when they try to speak out, and it deepens the reader’s empathy for Naya’s struggle.

Study Questions and Answers

Why does Naya remain passive after Davis whispers the line “You can beg, too” in the van?
Naya is in a trauma‑triggered freeze response. She recalls Wes’s self‑defense advice but cannot translate thought into action. Her overriding fear of causing a scene or being further humiliated keeps her from speaking loudly, moving seats, or physically defending herself.
What does Jake’s cold stare and decision to turn away suggest about his understanding of the situation?
Jake likely misreads the interaction as voluntary or flirtatious, perhaps believing Naya is reconnecting with her ex. His withdrawal indicates hurt or jealousy and a lack of communication, which will likely cause conflict in their relationship later.
How does Davis use the public setting to his advantage in this chapter?
Davis speaks loud enough for colleagues to hear collegial remarks while whispering degrading comments only for Naya. He times his physical touches to look accidental. This double layer makes Naya appear ungrateful if she reacts, and it reinforces her silence, as she knows others around them see only his “helpful” facade.