Chapter Thirty-Six: Bailey – 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
On the final day of the Colorado trip, Bailey and Charlie join her mother and Scott for breakfast before Bailey decides to spend the day reading by the fire at the chalet café. Charlie takes a call from his mother, then joins Bailey. When Bailey admits she feels confused about their kiss the previous night, Charlie dismisses it as “shit happens.” Annoyed by his casual attitude, Bailey nonetheless adopts that phrase as a new motto: she will stop overthinking everything for the rest of the trip. They spend hours reading Bailey’s historical romance aloud, with Charlie performing the duke’s lines in a ridiculous British accent. Later they hike, and when Bailey’s legs tire, Charlie carries her piggyback. On the trail they find a tiny kitten stuck in a tall tree. Charlie climbs up, rescues the kitten, and cradles it gently. Watching him, Bailey realizes she has developed huge feelings for Charlie.
Key Events
- Bailey and Charlie have breakfast with her mother and Scott at the Blue Moose.
- At the chalet café, Bailey confesses her confusion about the kiss; Charlie shrugs it off as “shit happens.”
- Bailey decides to embrace the “shit happens” mindset to avoid overthinking for the rest of the trip.
- They read Dodging the Duke aloud together, taking turns with character voices, laughing for hours.
- After the café, they go for a hike; Charlie carries Bailey piggyback when she gets tired.
- They discover a kitten trapped high in a tree.
- Charlie climbs the tree, safely retrieves the kitten, and speaks to it in a gentle, soothing voice.
- Bailey watches him and admits to herself that she has deep romantic feelings for Charlie.
Character Development
- Bailey: Her internal shift is the chapter’s core. She moves from anxious overanalysis (“What if I’m too heavy?”) to adopting Charlie’s “shit happens” philosophy as a deliberate coping strategy. This allows her to enjoy the day without second‑guessing every interaction. Her observation of Charlie’s kindness toward the kitten triggers a genuine emotional breakthrough: she acknowledges her feelings for him.
- Charlie: He reveals a softer, more vulnerable side beneath his cynical exterior. His insistence on not analyzing the kiss suggests he may be protecting himself. His willingness to climb a tall tree for a stranded kitten, and the tender way he speaks to it, contradicts Bailey’s earlier assumption that he is a jerk. This is a turning point in how Bailey (and the reader) views him.
- Scott and Bailey’s Mom: Though minor here, their presence reminds Bailey of her parents’ new relationship and her own unresolved feelings about family change.
Themes, Symbols, or Motifs
- “Shit happens” as a liberating mantra: The phrase, introduced dismissively by Charlie, becomes Bailey’s tool for releasing her need for control. It symbolizes a temporary suspension of judgment and anxiety, allowing spontaneity and emotional connection.
- Shared reading as intimacy: Reading Dodging the Duke aloud is not just an activity—it’s a playful, collaborative experience that deepens their bond. The physical closeness on the couch and the laughter create a “perfect date” atmosphere, underscoring that emotional intimacy can grow outside traditional romantic settings.
- The kitten rescue as a symbol of Charlie’s hidden warmth: The kitten’s vulnerability mirrors Bailey’s own emotional state. Charlie’s instinct to protect the kitten, and the gentle, nurturing tone he uses, reveal his capacity for care—a quality Bailey has not fully seen before. The rescue becomes a catalyst for her realization.
- Nature and vulnerability: The hike, the pine trees, and the open trail contrast with the controlled environments (school, hotel) where Bailey usually overthinks. The natural setting encourages physical and emotional exposure.
Why This Chapter Matters
Chapter 36 is a pivotal emotional turning point. Bailey moves from intellectualizing her relationship with Charlie to openly acknowledging her romantic feelings. Her adoption of the “shit happens” mindset is a deliberate rejection of her usual overanalysis, yet it paradoxically leads to the most honest self‑realization of the novel so far. The kitten rescue scene is carefully crafted to demonstrate Charlie’s gentleness in a high‑stakes moment, forcing Bailey to see past his sarcastic armor. The chapter also closes the Colorado storyline with a sense of unresolved possibility: Bailey now knows she wants more than friendship, but Charlie’s casual dismissal of the kiss leaves the future uncertain. This sets up the tension for the remaining chapters.
Study Questions and Answers
1. How does Bailey’s internal reaction to the kiss compare to Charlie’s, and what does her choice to adopt his “shit happens” attitude reveal about her character? Bailey initially feels confused and anxious about the kiss and wants to discuss it, while Charlie downplays it as “shit happens” and refuses to analyze it. Bailey’s decision to adopt his phrase shows her trying to control her anxiety by imitating his casualness. It reveals that she values their friendship enough to suppress her own need for clarity, but it also demonstrates her growing willingness to let go of rigid expectations.
2. What role does the shared reading scene play in advancing Bailey’s feelings for Charlie? Reading aloud together creates a playful, cooperative intimacy that Bailey describes as “perfect date” material. The laughter, the physical nearness, and Charlie’s willing participation in a genre he would not normally choose all break down her defenses. It shows Charlie making an effort to be present and engaged, which contradicts his prickly persona and deepens Bailey’s attraction.
3. Why is the kitten rescue the moment Bailey realizes she has feelings for Charlie? Until the rescue, Bailey has seen Charlie’s kindness only in verbal or humorous contexts. Climbing a tall tree for a helpless creature and speaking to it with unguarded tenderness reveals a vulnerability and compassion that Bailey had not witnessed. This concrete act of care makes her emotional shift undeniable: she cannot dismiss her attraction as just friendship when she sees such a raw, protective side of him.