Chapter Twenty-Three: 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
Bailey returns from getting printer paper and replays a brief flirtatious exchange with Charlie, feeling flustered and confused. She tries to dismiss it as low blood sugar. Later at home, her mother and Scott announce a surprise fall-break trip to Breckenridge. Bailey panics, imagining Scott forcing a blended family and trying to erase her father. She snaps at her mother and retreats to her room. Her mother follows, and Bailey negotiates bringing Nekesa along. The proposal is accepted, and Bailey texts Nekesa, who agrees to come. The next morning, Bailey thanks Scott for the trip and receives a link to the condo. She feels cautiously optimistic, despite lingering worries about Scott’s intentions and the possibility of a proposal on the slopes.
Key Events
- Charlie flirts with Bailey at the front desk; Bailey internally panics and questions her feelings.
- Bailey’s mother and Scott reveal plans for a three-day fall-break trip to Breckenridge.
- Bailey initially refuses, citing work, then snaps at her mother when pressed.
- Mom offers to let Bailey bring Nekesa; Bailey accepts and texts Nekesa, who agrees.
- Bailey thanks Scott the next morning; he responds warmly and sends a Vrbo link.
- Bailey and Nekesa FaceTime to plan outfits and logistics, leaving Bailey cautiously excited.
Character Development
- Bailey: Struggles with her own emotional whiplash – first from the flirtation with Charlie (which contradicts her loyalty to Zack) and then from the threatened disruption by Scott. Her insistence on “burrowing into” the comfort of her post-dad life shows her difficulty accepting change, yet her willingness to compromise (bringing Nekesa) reveals a fragile openness.
- Nekesa: Off‑page but referenced. Her quick agreement to join the trip and her text (“I thought we hated Scott”) shows she remains a grounding, witty presence who calls out Bailey’s cognitive dissonance.
- Scott: Persistently friendly and accommodating, even after Bailey’s harsh refusal. He offers to teach her to ski and accepts the addition of Nekesa without resistance, subtly proving he is not the villain Bailey imagines.
- Bailey’s Mom: Wears her “I’m the problem” T‑shirt, a telling detail that shows she feels conflicted. She tries to keep peace while pursuing her own happiness with Scott, leaving Bailey torn between protecting their old “us” and wanting her mother to be happy.
Themes, Symbols, or Motifs
- Burrowed comfort: Bailey defines her “comfort” as the life she and her mother built after her father left – a cocoon she fears Scott will destroy. The word “burrow” recurs, contrasting with the “suffocating” feeling of change.
- Change as threat: Every new step from Scott (a trip, a shared condo, talk of teaching skiing) feels like an advance, echoing Charlie’s earlier warning that “he’s only going to advance and take more space.”
- Flirtation vs. loyalty: The opening scene with Charlie sets up an internal conflict for Bailey: she likes Charlie but has Zack, and she fears any change in her workplace dynamic.
- The “us” division: Bailey repeatedly distinguishes between the “us” of her and her mother versus the “us” Scott tries to create with her mother. The language of belonging is central.
Why This Chapter Matters
Chapter 23 is a turning point for Bailey’s personal and relational growth. It sets up the upcoming Breckenridge trip, which will likely test her ability to accept Scott and her feelings for Charlie. The chapter also crystallizes Bailey’s central fear: that accepting change means losing the safety of her past. Her choice to bring Nekesa shows a small but significant step toward compromise without total surrender.
Study Questions and Answers
1. Why does Bailey describe Scott as “the anti-comfort”?
Answer: She views Scott as a threat to the healing, stable life she and her mother built after her father’s absence. He represents change that could unravel that carefully maintained world.
2. How does the flirtation with Charlie affect Bailey’s state of mind for the rest of the chapter?
Answer: It leaves her flustered and self‑doubting, causing her to dismiss it as “low blood sugar.” This confusion pre‑dates and likely amplifies the emotional turmoil she feels when faced with Scott’s trip.
3. What does Bailey’s negotiation to bring Nekesa reveal about her character?
Answer: It shows she is willing to compromise rather than flatly refuse her mother’s happiness. Bringing Nekesa acts as a buffer and a lifeline, indicating that Bailey can adapt – but only under conditions that preserve her sense of control.