56 pages • 1-hour read
Betting on You
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Chapters 11-20Chapter Summaries & Analyses
Content Warning: This section of the guide includes discussion of mental illness and cursing.
Chapter 11 Summary: “Bailey”
Bailey goes into the kitchen for breakfast the next morning in only a T-shirt and is surprised and uncomfortable when Scott enters. He leaves to shower after the brief, awkward encounter, and Emily suggests that she get dressed before leaving her room when people are over.
Scott staying the night unmoors Bailey, who realizes that the relationship is progressing faster than she thought. She is also upset that her morning routine will be disrupted by him being around. When she tells Nekesa about it later, Nekesa looks Scott up on social media. Photos on his feed reveal that his daughter is Kristy Hall, a rude, popular girl from school who hates Bailey.
Chapter 12 Summary: “Charlie”
Just before Charlie’s shift at Planet Funnn, he receives a text from his ex-girlfriend Becca, asking if she can call him. Charlie calls her, feeling like a fool for still being at her beck and call. She asks if he’s told anyone that they still talk sometimes. Charlie is annoyed that this is why she asked to talk. He claims that he hasn’t before hastily hanging up.
Chapter 13 Summary: “Bailey”
During their first break at work, Bailey talks with Charlie, Nekesa, and Theo about the Scott situation. Charlie suggests that she make Scott’s life so miserable that he never wants to return to their apartment. When the conversation shifts, and Nekesa begins teasing Theo for liking wrestling, Charlie gives Bailey a smug look, which makes Bailey shake her head. She has faith in Nekesa’s ability to remain faithful to Aaron and maintain a platonic friendship with Theo.
As her workday is ending, Bailey receives a text from her mother saying that she and Scott will order pizza for dinner. Charlie says again that Bailey should make Scott’s life miserable in any way possible, but Bailey isn’t keen on doing so. She knows that it would make her mother unhappy. Bailey doesn’t dislike Scott; she just dislikes how he threatens the status quo that she and her mother have established since the divorce.
Charlie suggests a less confrontational way of sabotaging their plans: He invites her to ditch them and hang out with him. They grab pizza, and Bailey begs Charlie to come home with her. She thinks that she’ll be braver with him there and more able to speak her mind. When she says that it would be a nice, friendly thing for him to do, Charlie says that they’re only coworkers, but he agrees to stay long enough to make trouble for Scott.
Chapter 14 Summary: “Charlie”
Chapter 15 Summary: “Bailey”
Bailey and Charlie return to her apartment, where she introduces him to her mother. Charlie purposefully calls Scott Bailey’s father, which makes everyone uncomfortable. When Scott calls himself a friend of Emily’s, Charlie gives him a strange look, which annoys Scott. Bailey pulls Charlie into the kitchen, where she laughs about how he’s already gotten under Scott’s skin.
Charlie leaves, and Emily asks about him. When Bailey states that he’s only a friend, Scott announces his relief, saying that Charlie seems “great for a friend, not so great for a boyfriend” (113). Bailey is annoyed that Scott is weighing in on her own dating life, but she keeps her anger bottled up. She thinks of her father, who has recently begun seeing a woman named Alyssa and is now too busy to call or text Bailey. She worries that her mother will act the same way if she and Scott get too serious.
Bailey returns to her room and texts with Charlie. He tells her about how he’s still hung up on Becca, who dumped him. Bailey relates—she hasn’t had closure from her relationship with Zack, which has made it difficult for her to get over him.
Chapter 16 Summary: “Bailey”
During the next few weeks at work, Bailey and Charlie become closer, but he still insists on calling them coworkers, not friends. While they work Tuesday and Thursday, Nekesa and Theo work Monday and Wednesday. The only time they all get to work together is the weekends.
To pass the time, Charlie makes everything into a game, from guessing what vending machine snacks customers will buy to counting the number of times Nekesa and Theo touch each other’s arms during a shift. Charlie often goes to Bailey’s house after work because she’s realized that Scott goes quiet when he’s around. If Charlie arrives before Scott, Scott won’t show up at all.
One night, Bailey receives a text from Charlie. He invites her to a friend’s party and explains that Becca will be there, and he doesn’t want to seem pathetic. Having Bailey there as a date will help him relax and have fun without looking sad. Bailey begrudgingly agrees, though it crosses the boundaries of their usual arrangement.
Chapter 17 Summary: “Charlie”
Just before Charlie leaves for his friend’s party, his mother asks him if he’s had his TUMS and tried the exercises that Dr. Bitz gave him. Charlie says yes, but he hates that she’s reminded him about his anxiety, which gives him acid reflux. While he has invited Bailey to show Becca that he’s moved on, Charlie is also intrigued to genuinely get to know Bailey, so he’s looking forward to the party.
Chapter 18 Summary: “Bailey”
When Charlie comes to pick Bailey up for the party, she is impressed by how good he looks and smells. On the way, she asks about his ex and his friends. When she asks if they’d like her, she is disappointed when he makes a joke instead of assuaging her insecurities.
At the party, Bailey meets Charlie’s friends Adam, Evan, and Eli. They seem to know who she is already, as if Charlie has talked to them about her before. She is invited play trivia and teams up with a girl named Clio. Charlie is considered a free agent in the game, and teams can pay a dollar for him to answer any question they’re stumped on. Bailey is impressed, as she hadn’t pegged him as a genius. Even though if a team gets a question wrong, they must perform a karaoke song, Bailey refuses to pay Charlie for an answer when she and Clio get stumped. They are forced to do karaoke when she is unable to provide the correct answer.
Chapter 19 Summary: “Charlie”
Chapter 20 Summary: “Bailey”
Charlie is enjoying Clio and Bailey’s performance when Becca and her new boyfriend, Kyle, enter the party, ruining his mood. Bailey’s mood is killed as well when she sees how much Becca still affects Charlie. When Becca and her boyfriend approach after the song, Bailey pretends to be into Charlie romantically. Charlie leans close to wipe an eyelash from Bailey’s cheek before putting his hand on her thigh, making her unsteady. As soon as Becca walks away, he pulls back and thanks Bailey for playing along.
Later, Charlie insists on driving a drunken Clio home. During the ride, Charlie mentions to Bailey that Eli wants to ask her out. Bailey doesn’t shut the possibility down, but she admits that she’s still hung up on her ex-boyfriend Zack. She explains that their relationship never got closure; they fought one night, and she expected to get back together the next day, but Zack started dating other people. When Charlie asks if she’d take Zack back, she says that she probably would, even though she knows it’s the wrong answer.
Chapters 11-20 Analysis
Painter begins to shape the emotional stakes of the story by blending the romantic tension between Charlie and Bailey with the threat of change presented by Emily’s deepening relationship with Scott. Beneath the comedic banter and parent-trap hijinks, Bailey’s escalating discomfort with Scott’s presence in her home highlights the novel’s growing theme of Overcoming Resistance to Change. In Chapter 11, what begins as a slightly comedic and awkward morning encounter in a T-shirt is actually a turning point for Bailey, who rants in her internal monologue,
What did his having a daughter my age have to do with the fact that I wasn’t wearing pants—or a bra—in front of him in our kitchen? […] Since I wasn’t related to this jackass of a man in any way, shape, or form, I was going to have to disagree with him and say that it wasn’t okay for me—at seventeen—to be nipping out and bare-legged in front of his fortysomething ass (86).
The situation prompts Bailey to realize that her mother’s relationship is moving forward—and that change is arriving without her consent. Her private world, previously shared between just her and her mother post-divorce, is now under threat of invasion. Bailey’s visceral reaction to Scott’s intrusion on her daily habits stems less from dislike of Scott and more from fear of losing the fragile stability she has rebuilt after the divorce. Charlie mirrors this resistance in his own family life through his resentment toward his mother’s boyfriend. Both protagonists—despite their vastly different coping strategies—are dealing with the emotional whiplash of their parents dating post-divorce and the subsequent, messy intrusion of new relationships.
This dynamic feeds directly into the theme of The Costs of Early Maturity, which plays a role in much of Bailey’s and Charlie’s character development. Their situations have prompted both to learn to internalize (Bailey) or deflect (Charlie) their feelings for the sake of surviving day to day. Bailey bottles up her frustrations to avoid rocking the boat, shown in Chapter 15 when Scott comments on her dating life, and she swallows the urge to scream that he’s not her father. Charlie, meanwhile, often hides emotional vulnerability behind sarcasm. Their late-night text conversations in these chapters become a space where they can safely show the pain they hide in daily life and practice the emotional honesty that neither of them can find elsewhere. However, Charlie’s jadedness about love persists, and even while he and Bailey develop a friendship—which real romantic feelings hide beneath—he still insists on labeling them only as coworkers and nothing more.
Painter also uses the bet between Charlie and Bailey as a narrative device that keeps returning the characters to the theme at the heart of the novel: Becoming Unjaded About Love. Charlie remains adamantly cynical, reading romantic interest in every act of male-female friendship and believing that infidelity is inevitable. Bailey, still hoping to defend the possibility of loyal, healthy love, challenges him at every turn—but the cracks in her idealism begin to show. The ease with which her ex-boyfriend Zack was able to move on to someone new so soon after their breakup and her father’s distraction because of a new relationship have chipped away at the fairy tale she clings to.
The party scene, in which Charlie and Bailey attend his friend’s party, pushes both characters into new emotional territory. Charlie invites Bailey to be his date despite repeatedly claiming that they are just coworkers. Bailey pushes the boundaries further by pretending to date him when Becca shows up. Bailey’s reluctant agreement to attend the party, her subtle insecurities about whether Charlie’s friends will like her, and her jealousy when Becca arrives all hint that her feelings for Charlie are transitioning from friendly to romantic. When Charlie brushes an eyelash from her cheek and puts a hand on her thigh in front of Becca, the supposedly performative moment feels charged with real tension. In these scenes, Painter skillfully blurs the line between what’s fake and what’s real in their relationship, creating tension that feeds into the growing conflict of the novel.
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