Chapter Twenty-Four: Bailey – The Fake-Dating Plan Takes Shape

⚠️ 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

With the Breckenridge trip imminent, Nekesa calls Bailey in tears: she is grounded and cannot go. Bailey panics at the thought of spending the weekend alone with her mom and Scott. Nekesa suggests taking Charlie instead and, with Theo, has already pitched a fake-dating scheme to annoy Scott. Despite initial horror, Bailey reads their group-chat conversation and, after a phone call with Charlie, agrees to the plan. They will drive out after work the next day and simply show up in Colorado, forcing Scott to accept Charlie’s presence. The chapter ends with playful banter about each other’s appearance and an agreement to pack and rest.

Key Events

Nekesa calls Bailey crying; she is grounded indefinitely and cannot go to Breckenridge.
Bailey worries about the trip alone with her mother and Scott.
Nekesa proposes that Bailey take Charlie and pretend to date him to increase tension with Scott.
Bailey learns that Nekesa and Theo have already been texting Charlie in a group chat about the idea.
Bailey reads the group chat, seeing Charlie’s reluctant agreement and Theo’s enthusiastic support.
Charlie calls Bailey; they discuss the plan and agree to show up unannounced.
Charlie reveals his mother won’t mind him being gone; Bailey feels a pang of sympathy.
They banter about road-trip logistics, music, and Charlie’s beard.
Charlie confesses he thought Bailey was hot when they first met at the movies; Bailey reciprocates.
They end the call with plans to pack and leave the next day.

Character Development

Bailey: Her desperation to avoid a weekend with Scott pushes her to accept an outrageous plan. She shows vulnerability when considering what the fake dating might do to her friendship with Charlie. Her admission that she once found Charlie attractive (before remembering she “hated” him) hints at unacknowledged feelings.
Charlie: He agrees to a high-stakes situation purely to help Bailey, demonstrating his loyalty and willingness to disrupt his own schedule. His comment about his mother being relieved to have him out of the house adds depth to his character—he feels unwanted at home. His playful teasing during the phone call shows his comfort with Bailey.
Nekesa: Although absent for the trip, her machinations as a matchmaker are evident. She not only orchestrates the plan but also ensures Bailey’s emotional well-being, knowing she would panic without support.
Theo: Though off-page, his role in the group chat and his encouragement of the fake-dating idea suggest he is invested in both Nekesa and the plan’s success.

Themes, Symbols, or Motifs

Fake Relationships as Rebellion: The fake-dating scheme is a direct act of defiance against Scott’s control. It symbolizes Bailey’s resistance to allowing Scott to dictate her happiness and her willingness to disrupt his authority.
The Comfort of Banter: The long phone conversation between Bailey and Charlie highlights their easy, teasing dynamic. Their ability to laugh about his beard or her “clumsy” legs shows a friendship that can withstand awkward topics and vulnerability.
Fear of Crossing Lines: Both characters express anxiety about the fake dating—Bailey worries it will alter their friendship, while Charlie initially calls the idea “bonkers.” This tension sets up the central conflict for their trip: can they maintain the boundary of “just friends” while pretending to be romantic?
Absent Parents: Charlie’s offhand remark about his mother being happier when he’s gone echoes Bailey’s own fears about being replaced by Scott. This parallel deepens their connection and underscores a shared loneliness.

Why This Chapter Matters

Chapter Twenty-Four is the turning point that launches the main plot of the Breckenridge weekend. It moves the story from everyday workplace and friendship dynamics into a high-stakes, intimate trip where Bailey and Charlie must share close quarters and perform as a couple. The chapter solidifies their alliance against Scott and introduces romantic tension that has been simmering beneath the surface. It also reveals crucial character details—Charlie’s home situation and Bailey’s hidden attraction—that will inform their actions in the following chapters.

Study Questions and Answers

1. Why does Bailey finally agree to the fake-dating plan despite her initial horror?
Bailey agrees because she feels she has no other option. She cannot bear to spend the weekend alone with Scott and her mother, and the thought of having Charlie there makes the trip bearable. Additionally, reading the group chat shows her that Charlie is willing to help, and his confidence that they cannot be sent back bolsters her own courage.

2. How does the phone call between Bailey and Charlie reveal that they are more than just coworkers?
Their conversation is filled with personal teasing, shared memories, and confessions about first impressions. Charlie admits he once thought Bailey was “hot” at the movies, and Bailey confesses she found him “cute and jacked” before remembering she “hated” him. They also discuss family dynamics—Charlie’s feeling that his mother doesn’t want him around—which shows a level of vulnerability they do not share with others.

3. What role does Nekesa play in this chapter, even though she is grounded?
Nekesa acts as the primary instigator of the plot. She comes up with the fake-dating idea, coordinates with Theo and Charlie in a group chat, and then presents the plan to Bailey as a fait accompli. Her sneakiness is motivated by love, as she wants Bailey to have a good weekend. She also deflects Bailey’s concerns about her relationship with Theo, hinting at a developing subplot.