People Watching Chapter 17: Vulnerability and the To-Do List
⚠️ 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
Milo attends a family dinner at Nik and Sef’s house with Prue. Prue holds newborn Harper while Sef recounts the birth story. Milo cannot stop staring at Prue, who is wearing a short pleated skirt and a sleeveless sweater vest that leaves him distracted and aroused. After dinner, Nik catches them kissing in the kitchen. They leave and drive back to Prue’s studio at Welch’s. Inside, Prue shows Milo her “No-Longer-a-Prude To-Do List,” a handwritten list of seven sexual acts she wants to experience. She explains that the list helps her manage her perfectionism and anxiety about trying new things. Prue also admits the list serves as an emotional boundary to protect herself from developing feelings, since Milo has made clear he only wants casual. Milo promises open communication during intimacy. They become physically intimate, with Milo performing oral sex on Prue. The chapter ends with Prue asking Milo to take off all his clothes.
Key Events
- Milo’s family gathers for dinner; Prue meets Harper, Nik and Sef’s newborn daughter.
- Milo is openly aroused by Prue’s outfit—a short pleated skirt and sweater vest—and struggles to focus.
- Nik catches Milo and Prue kissing in the kitchen and teases them.
- Milo and Prue return to her studio apartment at Welch’s.
- Prue presents her “No-Longer-a-Prude To-Do List” with seven sexual items.
- Prue admits she created the list to combat perfectionism and to create emotional distance.
- Milo promises they will communicate openly during sex and tells her bad sex comes only from communication problems.
- The two begin making out, foreplay escalates, and Milo removes Prue’s tights and panties.
- Milo goes down on Prue after she verbally asks him to take off his clothes.
- Prue explicitly tells Milo she wants him completely naked.
Character Development
Milo shows a softer side beneath his confident exterior. When Prue mentions the list protects her from developing feelings, he responds, “No one ever has” fallen in love with him, hinting at deep-seated insecurity about his own lovability. He prioritizes Prue’s comfort and consent, repeatedly checking in and promising to stop if asked. His actions reveal that he is more emotionally invested than he admits.
Prue takes control of her sexual exploration for the first time. The to-do list represents her practical, structured approach to managing anxiety. She confesses she likes being good at everything on the first try and worries about failing. By showing Milo the list, she demonstrates trust and vulnerability. Her decision to use the list as an emotional boundary shows self-protection but also hints at the impossibility of keeping things purely physical.
Nadia and Nik appear briefly but reinforce Milo’s family dynamics: Nik is protective and teasing, while Nadia’s past gift of the “Drive Safe, Somebody Loves You” bumper sticker carries emotional weight for Milo.
Themes, Symbols, and Motifs
Vulnerability. Both characters lower their defenses. Prue shares her list and her fear of failure; Milo reveals his belief that he is undeserving of love. The cozy, fairy-lit loft bedroom creates an intimate space where honesty emerges.
Communication. Milo explicitly states that they will tell each other what feels good, what does not, and how to adjust. This theme of open verbal communication is central to the chapter. He emphasizes that bad sex is always a communication issue, not a skill issue.
Casual versus emotional connection. Both characters try to frame their relationship as practical and temporary. Prue uses the list to prevent emotional entanglement, but the depth of their conversation and physical intimacy contradicts the casual framework they claim to want.
Lists and control. Prue’s to-do list becomes a symbol of her need for structure and mastery. She uses it to transform anxiety into action, turning potential shame into accomplishment. It also acts as a shield against vulnerability.
Consent and agency. Milo repeatedly asks for permission: “May I?”, “Can I take these off?”, “Do you want me to?”. This emphasis on enthusiastic, verbal consent reflects the novel’s broader treatment of sexual ethics.
Why This Chapter Matters
Chapter 17 is a turning point for Milo and Prue’s relationship. It establishes the explicit “rules” for their physical encounters while simultaneously complicating those rules with genuine emotional intimacy. Prue’s to-do list becomes a recurring device that will structure their future sexual experiences. The chapter also deepens Milo’s characterization, revealing his fear of being unloved beneath his confident, casual persona. The scene in the loft solidifies the physical and emotional chemistry between the two characters and sets up the central tension of the novel: whether a relationship built on a “no feelings” agreement can survive genuine connection.
Study Questions
1. Why does Prue create her “No-Longer-a-Prude To-Do List,” and what does it reveal about her personality?
Prue makes the list because she likes being good at everything on the first try and becomes frustrated when she is not. The list gives her checkable tasks that make her feel accomplished even if she performs poorly. It reveals her perfectionism, her anxiety about new experiences, and her need for structure and control. The list also acts as an emotional boundary meant to prevent her from catching feelings for Milo.
2. How does Milo’s response to the list demonstrate his approach to intimacy?
Milo immediately reassures Prue that she cannot be “terrible at sex” and that bad experiences come from communication failures, not personal inadequacy. He promises they will talk openly about what feels good and what does not. This shows that Milo prioritizes mutual pleasure, consent, and emotional safety over his own gratification. It also reveals a more thoughtful and caring side than his casual persona suggests.
3. What tension exists between the characters’ stated desire to keep things casual and their behavior in this chapter?
Both Milo and Prue explicitly agree their relationship is casual and practical. Prue even uses the list to “protect” herself from developing feelings. However, their behavior contradicts this agreement. Milo reveals a vulnerable fear that no one has ever loved him. Prue shares her deepest insecurities. Their physical intimacy is intense and emotionally charged. These moments suggest that feelings are already developing despite the boundaries they try to maintain.