Chapter summaries A First Time for Everything K.L. Walther

Chapter Sixteen: Dating Apps and a Disappointing First Kiss

⚠️ 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

After returning from Stone Harbor, Madeline tells the bridesmaids she is ready to resume Ready-Set-Date, hoping to stop thinking about Connor. They suggest she create a profile on the student dating app developed by Isa Cruz. Madeline’s parents express concern but allow it after Marco Álvarez vouches for the app’s safety. Unable to finish her profile alone, Madeline meets her friend Natalie at a bakery. Natalie helps her choose photos, including one taken by Connor where Madeline looks especially happy. Madeline admits she still pines for Connor and confesses she hopes going on a date with someone from school will finally make him notice her directly. Natalie reluctantly agrees to help.

Madeline matches with Jacob Bluestein, a wrestler from her school. She tells Connor about the date while they ride horses; he seems perplexed and irritated. Jacob picks her up, and they go to see a Christopher Nolan film. At the theater, they encounter Marco and his Princeton friend Timothy. The date feels awkward: Jacob forgets his wallet, and he does not hold her hand until a jump scare. After the movie, Jacob drives her home and comments that Marco has always liked Madeline, which she denies. Jacob leans in for a kiss, but his technique is sloppy and unpleasant—Madeline’s first kiss is a disappointment.

Key Events

  • Madeline informs the bridesmaids she is ready to resume dating and creates a profile on the school’s dating app.
  • Her parents initially object but allow it after Marco mentions the app is for Council Rock students.
  • Madeline meets Natalie at Little Sunflower Bakery; Natalie helps her select profile photos and learns about Madeline’s lingering feelings for Connor.
  • Madeline matches with Jacob Bluestein and tells Connor about the date while they ride horses.
  • On the date, Jacob forgets his wallet; Madeline pays and is immediately reimbursed via Venmo.
  • They run into Marco and Timothy at the theater; Marco’s presence makes Madeline uneasy.
  • Jacob does not hold her hand for most of the movie; he finally does during a jump scare.
  • In the car afterward, Jacob says Marco has always liked Madeline.
  • Jacob attempts a kiss; Madeline finds it sloppy and unappealing—her first kiss is a letdown.

Character Development

  • Madeline Fisher-Michaels: Madeline’s actions reveal her emotional immaturity. She admits to Natalie that she is using the date to make Connor jealous, acknowledging the strategy is “devious.” Her discomfort during the kiss shows her inexperience and her desire for genuine connection, not just any romance.
  • Connor Matthews: Connor’s reaction to learning about Madeline’s date—a mix of perplexity and irritation—hints at his own feelings. He is dating Lauren but seems bothered by Madeline’s interest in someone else.
  • Marco Álvarez: Marco’s brief appearance at the theater and Jacob’s observation that Marco has “always liked” Madeline add depth to Marco’s character. He is shown as private but observant, and his cameo feels increasingly significant.
  • Jacob Bluestein: Jacob is polite and sweet on the surface (offering to pay, picking her up, calling her “Mads”), but his date etiquette falters (forgetting his wallet, ignoring her hand, an awkward kiss). He lacks the natural chemistry Madeline has with Connor.

Themes, Symbols, or Motifs

  • The Chimera of Jealousy: Madeline hopes to provoke Connor’s jealousy by dating Jacob, a tactic Natalie warns is “messy, painful, immature.” This motif of using a third party to test feelings recurs from Davis’s earlier scheme.
  • First Kiss as Disappointment: The long-awaited kiss is ruined by sloppy technique and drool, symbolizing that rushing intimacy does not guarantee magic. Madeline’s “ew” reaction echoes her internal conflict between her romantic fantasies and awkward reality.
  • Shared Food vs. Separate Orders: Madeline notes that Jacob does not share his popcorn, contrasting with the ease she shares food with Connor. Small rituals of closeness become markers of compatibility.
  • Cameos of Marco: Marco appears unexpectedly at the theater, reinforcing his role as a steady presence in Madeline’s life—almost like a test of her actual feelings.

Why This Chapter Matters

Chapter 16 is a turning point in Madeline’s romantic arc. It crystallizes her strategy of using dating to get Connor’s attention, a plan that Natalie (and the reader) recognizes as flawed. The disastrous first kiss with Jacob confirms that Madeline is not truly interested in him; she is still emotionally tethered to Connor. The chapter also plants seeds for a possible Marco-Madeline connection, as Jacob bluntly points out Marco’s long-held interest. By the end, Madeline’s self-awareness is growing, even if her choices remain questionable.

Study Questions and Answers

1. Why does Madeline decide to create a dating profile on the school app, and what does she hope to achieve?

Madeline wants to stop obsessing over Connor, but she also admits to Natalie that she hopes dating someone from school will finally make Connor notice her. Her deeper goal is to spark jealousy rather than to genuinely find another boyfriend.

2. How does Jacob’s behavior on the date foreshadow the disappointing kiss?

Jacob forgets his wallet (making Madeline pay) and immediately Venmos her back, which feels transactional. He ignores her hand for most of the movie until a jump scare forces contact. These small red flags hint at a lack of natural intimacy, setting up the forced and sloppy kiss that follows.

3. What does Jacob reveal about Marco, and why is this significant?

Jacob tells Madeline that Marco has “always liked” her. Madeline dismisses the idea, but the comment plants a seed for the reader. It suggests Marco’s friendship may hide romantic feelings, adding complexity to Madeline’s relationships with both Marco and Connor.