Chapter 23: Kidstreet – 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
Jolene meets Cliff for a scheduled training session on workplace communication. Cliff has donuts and a prepared PowerPoint. During the presentation, Jolene notices a yellow legal pad on his desk with the header “Employees to support.” Her name appears next to the words isolation, colleagues, and help her feel safe. Cliff quickly hides the pad. Jolene then spots a photo on the windowsill: a young Cliff on the 1990s game show Kidstreet. They bond over the show’s trivia and Cliff’s chosen prize (a Nerf gun). Jolene deflects questions about her high school years, lying about where she attended. Cliff says the present-day Jolene is “pretty great,” which briefly lifts her mood. After the session, Jolene returns to her desk and sees an email from Cliff to their boss Gregory requesting a meeting about employee management. She panics, replaying every word she said in the meeting, and decides to bug the boardroom where the meeting will take place by leaving her phone inside.
Key Events
- Jolene tries to lighten the mood by mocking Cliff’s PowerPoint, then challenges him to add showmanship.
- Cliff’s legal pad reveals his concern for Jolene’s workplace well-being, listing terms like “isolation” and “help her feel safe.”
- Jolene discovers a framed photo of Cliff as a child on the game show Kidstreet.
- They share an enthusiastic conversation about the show; Cliff chose a Nerf gun over moon boots.
- Jolene lies about her high school location to avoid any connection to Ellie’s death.
- Cliff softens and tells Jolene she is “pretty great” now.
- Jolene later reads an email from Cliff to Gregory asking for a meeting to discuss employee management.
- She decides to eavesdrop by leaving her phone in the boardroom.
Character Development
Jolene
Jolene’s paranoia deepens in this chapter. The note on Cliff’s legal pad—help her feel safe—both touches her and frightens her. She craves safety but cannot fully trust anyone, especially after her secret slips (the high-school evasion). Her decision to bug the boardroom shows she is willing to cross ethical lines to protect herself, even after a warm bonding moment with Cliff.
Cliff
Cliff reveals his caring, methodical nature. He takes notes on employees’ struggles and tries to help Jolene feel safe. His childhood appearance on Kidstreet humanizes him, showing a meticulous, thoughtful kid. Yet his email to Gregory undercuts the trust Jolene had started to place in him—whether intentionally or not.
Gregory (mentioned)
Gregory appears only via email, but his presence looms as the authority figure Jolene fears will learn her secrets.
Themes, Symbols, or Motifs
Trust and Suspicion
The central conflict of the chapter is the fragility of trust. Jolene alternately believes Cliff is kind and suspects he is reporting her. The maroon folder—identical to her own—symbolizes their shared role in HR, but also the potential for betrayal.
Childhood and Vulnerability
The Kidstreet photo reveals a younger, vulnerable Cliff. The game show represents a safe space where he could be himself. Jolene’s own childhood was marked by trauma (Ellie’s death), and she deliberately hides that past. The contrast shows how both characters use memory to cope.
Surveillance and Secrets
Jolene’s plan to eavesdrop mirrors her earlier hacking of coworkers’ messages. She feels compelled to gather information to regain control, even though it risks her integrity.
Why This Chapter Matters
Chapter 23 marks a turning point in Jolene’s trust arc. She has a genuine connection with Cliff, yet she cannot sustain it because of her deep-seated fear of exposure. The email from Cliff to Gregory forces her to act on her paranoia. This decision sets up a major conflict: will Jolene’s surveillance be discovered? And is Cliff actually a threat, or is she misreading his intentions? The chapter also deepens Cliff’s backstory, making him more sympathetic and complex.
Study Questions and Answers
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Why does Jolene lie about her high school?
Jolene lies because she fears Cliff will search for her school and find news articles about Ellie’s death, revealing her secret. She deflects to protect the story she has worked to hide. -
What does Cliff’s note “help her feel safe” reveal about his character?
It shows that Cliff has been thoughtfully observing Jolene and wants to support her. The note suggests he sees her struggles with isolation and is trying to create a comfortable environment. -
How does the Kidstreet photo change Jolene’s perception of Cliff?
The photo makes Cliff seem more human and relatable. Jolene sees him as a nerdy, earnest kid, which breaks down some of her professional distance. It is the strongest emotional bond they form, but it also makes the later email sting more deeply.