How to Fail at Flirting Chapter Forty Summary

⚠️ 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, along with her colleagues, attends a retreat meeting chaired by President Lewis, Jake, and Carlton. The cramped room overlooks a forested path to the lake. Naya’s emotions churn when she sees Jake; she obsesses over his appearance and whether he misses her, fears he slept with Gretchen, and worries he saw Davis touching her. Jill avoids Naya’s gaze. Davis dominates the discussion, repeatedly rephrasing Naya’s ideas and claiming them as his own while belittling her lack of tenure. Naya initially suppresses her anger, remembering the fear and disgust from the van ride, but eventually she interrupts Davis, clearly stating that he repeated her point. Davis dismisses her as “so sensitive.” President Lewis calls for a break and asks Naya to stay behind. Alone, he reveals he knows about her relationship with Jake but expresses disappointment she didn’t disclose it. Despite this, he praises her for speaking up, admits he should have intervened, and offers to speak to Davis. Naya declines, not wanting to give Davis more ammunition. The chapter ends with President Lewis leaving to join the others, and Naya reflecting on her risky stand.

Key Events

Naya arrives at a crowded retreat meeting and spots Jake, causing emotional turmoil.
Davis repeatedly steals Naya’s ideas and talks down to her based on her pre-tenure status.
Naya internally struggles between professionalism and the urge to confront Davis.
Naya finally calls Davis out, stating he rephrased her idea and should think of his own.
President Lewis calls a break and privately confronts Naya about her relationship with Jake.
Lewis shares his personal “Flip” story to illustrate that risky decisions can lead to good outcomes.
Lewis commends Naya’s assertiveness and offers to speak to Davis, which Naya declines.

Character Development

Naya Turner: In this chapter, Naya transitions from fearful, self-doubting colleague to someone who publicly asserts herself. She moves through stages of anxiety, anger, and finally action. Her decision to speak up, even without immediate support, marks a significant shift in her professional confidence.
President “Flip” Lewis: Previously a distant authority figure, Lewis reveals a warm, philosophical side. He acknowledges his own failure to intervene and validates Naya’s voice, showing his capacity for growth and a desire to foster a more equitable environment.
Davis: Remains condescending and manipulative, but his mask cracks when Naya confronts him. His behavior underscores the “old boys’ club” culture Lewis later criticizes.
Jake Shaw: Present but mostly silent; his only reaction is a clenched jaw and averted eyes. He does not defend Naya, leaving her frustrated.

Themes, Symbols, or Motifs Evidenced Here

Sexism and Academic Gatekeeping: Davis’s constant referencing of Naya’s pre-tenure status is a classic tactic to undermine a woman’s authority. The chapter highlights how women in academia are often dismissed or silenced.
The Cost of Silence vs. Speaking Up: Naya’s internal debate about whether to confront Davis mirrors the broader tension between maintaining professional decorum and fighting for recognition. Her eventual stand shows the personal risk involved, especially given her undisclosed relationship with Jake.
Vulnerability and Trust: Naya’s longing for Jake’s acknowledgement and her disappointment when he doesn’t meet her eye reflects her continued emotional vulnerability. The unresolved status of their relationship adds pressure to her professional situation.

Why This Chapter Matters

This chapter represents a critical turning point for Naya. She publicly challenges the systemic condescension she has endured from Davis, and she does so without the protective backing of a powerful ally. President Lewis’s reaction—affirming her voice while gently rebuking her for not disclosing the relationship—suggests that Naya’s honesty and courage are valued more than her mistakes. The chapter sets up potential consequences with Davis, possible reconciliation or distance from Jake, and reinforces the novel’s central question: can Naya find both professional fulfillment and authentic love without hiding parts of herself?

Study Questions and Answers

Why does Naya finally decide to confront Davis despite her earlier resolve to remain professional? Answer: Naya’s anger overrides her fear when Davis repeats her point and dismisses her as “sensitive.” She realizes things cannot get worse and that continuing to stay silent would feel like accepting his condescension. Her decision is propelled by a shift from passive fear to active indignation.
How does President Lewis’s “Flip” story serve as a lesson for Naya? Answer: Lewis shares the story of how a foolish, risky backflip led to meeting his wife and gaining a lifelong friend. He implies that sometimes “dumb, stupid, and dangerous” decisions—like Naya’s affair with Jake or her outburst at Davis—can still lead to positive outcomes, provided she has a good head on her shoulders.
What does Lewis reveal about his own failure in the meeting, and how does this affect Naya? Answer: Lewis admits he should have stepped in to stop Davis’s behavior and promises to do better. This admission makes Naya feel seen and validated, but she declines his offer to speak to Davis, indicating she does not want to give Davis more opportunities to weaponize the situation.