Chapter summaries How to Fail at Flirting Denise Williams

Chapter Six Summary – How to Fail at Flirting

⚠️ 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 calls her best friend Felicia for last‑minute date advice after Jake (the man she threw up near) asked her out. Felicia teases Naya about the unusual first meeting and Naya admits she’s anxious about the date, specifically about what Jake might expect. Felicia reassures her, suggesting she take deep breaths and reminding her that Jake is only in town for the weekend, so the date carries low stakes. Naya picks out a mint‑green top and black skirt, and Felicia’s daughter Emily jokingly calls Jake a “sosopath.” Naya decides on Navy Pier for the date, a public location. She also selects matching lingerie, acknowledging she is open to the possibility of sex. The chapter closes with Felicia’s parting advice: try not to throw up on him again.

Key Events

  1. Naya and Felicia talk on the phone while Naya frantically prepares for her date with Jake.
  2. Felicia teases Naya about having thrown up near Jake, but Naya insists it was not on him.
  3. Naya reveals her anxiety about the date and considers the possibility that Jake might expect sex.
  4. Felicia advises Naya to calm down and points out that Jake leaves town soon, so the evening is consequence‑free.
  5. Naya chooses a mint‑green tank top and flowy black skirt, and deliberately selects matching lingerie, indicating she is prepared for intimacy.
  6. Emily overhears and mispronounces “sociopath,” adding a touch of humor.
  7. Naya suggests Navy Pier as a public meeting spot, and Felicia approves.
  8. Felicia’s final quip warns Naya to avoid another embarrassing incident.

Character Development

  • Naya – Her anxiety about dating is front and center. She second‑guesses her wardrobe, worries about sexual expectations, and seeks reassurance from Felicia. The moment she chooses matching lingerie shows that she is trying to reclaim control over her own desires and is willing to see where the night goes—a small but meaningful step beyond her usual caution.
  • Felicia – Acts as Naya’s blunt, loving confidante. She cuts through Naya’s panic with humor (“Candy is sweet, but dick is better”) and practical advice. Her role underscores the importance of a trusted friend in navigating romantic uncertainty.
  • Emily – Though a minor presence, her misheard word “sosopath” lightens the mood and reinforces Felicia’s role as a mother and a friend.

Themes, Symbols, or Motifs

  • The “list” – Felicia references “that list” from earlier in the book (implied to be a list of goals or experiences Naya wanted to try). Naya’s willingness to “try” suggests the list is a catalyst for stepping outside her comfort zone.
  • Preparedness vs. spontaneity – Naya’s meticulous choice of clothing and underwear contrasts with her desire for “consequence‑free fun.” The lingerie symbolizes her internal permission to be both cautious and willing.
  • Public spaces as safety – Choosing Navy Pier, a busy tourist spot, reflects Naya’s need for a low‑pressure, public environment where she can feel secure.
  • Physical embarrassment – The running joke about throwing up near Jake is a motif that highlights Naya’s vulnerability and her fear of being judged.

Why This Chapter Matters

This chapter is a turning point for Naya’s romantic arc. It takes her from the aftermath of a humiliating first encounter to actively preparing for a second date. The phone call with Felicia externalizes Naya’s internal battle between fear and desire, and the choice of lingerie signals that she is willing to embrace physical intimacy on her own terms. It also sets up the evening’s setting (Navy Pier) and establishes the low‑stakes framework that allows Naya to relax—or to face disappointment if the date goes badly. The chapter’s humor and honesty deepen the reader’s investment in Naya’s journey.

Study Questions and Answers

1. How does Felicia’s advice reflect the theme of risk in dating?
Felicia tells Naya that Jake is leaving town soon, so the worst outcome is an “awkward, sexless date.” This reframes the risk: instead of focusing on potential rejection or long‑term consequences, she encourages Naya to see the evening as a low‑stakes experiment. This aligns with Naya’s earlier “list” and her desire to be more adventurous.

2. What does Naya’s choice of lingerie reveal about her character at this point?
By deliberately selecting matching satin underwear, Naya shows she is open to the possibility of sex—not as a surrender to Jake’s expectations but as a decision she makes for herself. It marks a shift from her earlier panicked “What if he expects sex?” to a more empowered readiness.

3. Why does Naya suggest Navy Pier as the date location?
She wants a public, crowded space to feel safe. Being a tourist destination, Navy Pier reduces the pressure of a private, one‑on‑one meeting and allows Naya to maintain a sense of control. Felicia’s approval (“That’s definitely public”) confirms it was a wise choice.

Navigate