56 pages • 1-hour read
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Bailey tells Nekesa about the Breckenridge trip and her feelings for Charlie. Nekesa says that she hasn’t told Theo about Bailey and Charlie, but Theo knew that something would happen between them. Bailey is annoyed that Theo isn’t minding his own business but doesn’t say this aloud.
They meet up with Dana, who has begun dating Eli. She mentions that Charlie’s mother is out of town, so he’s having people over, and she asks if Bailey is going. Though Charlie told her his plan, she hasn’t decided if she’ll go yet. Later that day, Charlie texts Bailey his address and insists that she come that night.
When Bailey returns from school that afternoon, her mother is home alone and invites her to go out for pizza, just them, like old times. Bailey excitedly agrees. At lunch, Emily informs Bailey that her father has sold his house and is moving to an apartment in the city. Bailey is surprised to hear this, and when her mother asks when she last talked to him, Bailey admits that it’s been a few months. Emily is instantly worried when Bailey explains that she’s been waiting for him to call since she’s always the one to initiate.
Their conversation is interrupted by Scott’s arrival, and Bailey is frustrated that he is interrupting a vulnerable moment between them. Things only worsen when he proposes to Emily. Emily accepts the proposal, and Bailey congratulates them, even though she’s sick to her stomach. She leaves, mentioning that she’s got plans with Charlie.
Charlie and his friends are prepping the house for the upcoming party when he receives a text from Bailey, asking him to pick her up at a nearby Walgreens. She mentions that Scott showed up and proposed to her mother while they were having dinner.
Without hesitation, Charlie informs his friends that the party is cancelled. He drops everything to go pick up Bailey. His friends are frustrated and assume that this is about Becca because “she texts, and [he] jump[s]” (340).
Charlie picks up Bailey, who has been crying. He texts Emily to inform her that Bailey will be staying the night so that she doesn’t worry. He takes Bailey to his apartment, where they make a blanket fort in front of the TV. He subjects her to a marathon of his favorite terrible movies while they eat ice cream and junk food.
Though Bailey attempts to forget about the proposal and her father’s move, panic about the change in her life threatens to overwhelm her. When she checks her phone, she finds texts from her mother checking in and offering to be there whenever Bailey is ready to talk. She even finds a text from her father, who has spoken to her mother and also offers to talk.
Rather than responding to either, Bailey begins to cry. Charlie says that he’s there for her, and he calls them friends for the first time. When Bailey teases that he’s got friend feelings for her, Charlie admits to feeling more. They kiss, but Charlie ends it before they go too far. Though he doesn’t want to stop, he states that he doesn’t want to take advantage of her in an emotional state.
When Bailey wakes the next morning, the apartment is empty. She finds a note from Charlie telling her to let herself out. Offended at being left alone in his apartment, she jokingly texts him about it but gets no response. Bailey asks Nekesa to pick her up after explaining the situation.
Nekesa drops Bailey off at home, where Emily talks to her about the engagement. Bailey admits that she doesn’t want to move in with Scott and his daughter, whom she’s never met. Emily insists that while change is hard, she wouldn’t agree to this if she didn’t think it would be good for them. Bailey agrees to give it a chance.
She attempts to call Charlie but gets his voicemail for the first time. She informs him via text that she and her mother will be moving in with Scott, but when he never replies, she realizes that Charlie is avoiding her. Bailey becomes upset that he’s not even there for her as a friend and feels like a fool for falling for his “nice guy” act.
After a weekend of no contact with Charlie, Bailey prepares herself to return to work at Planet Funn. She gets confirmation about his avoidance of her when she finds Theo working Charlie’s shift. She confronts Charlie via text about avoiding her and asks to talk, but he responds by asking her to just move on.
Scott shows Bailey around his place. He promises that she can have the entire basement to herself when they move in in a month. Nekesa calls, crying, and asks Bailey to come over because she and Aaron have just broken up. When Bailey arrives, Nekesa informs her that Theo kissed her after their shift the other night. She admits that she didn’t stop him for a few seconds, curious if what she felt for him was more than friendship. Though the kiss confirmed that she considers Theo only a friend, when she confessed to Aaron, he was so upset that he broke up with her. Nekesa wishes that she could go back before the lines between her and Theo became blurred. Bailey feels guilty for not stepping in when she felt the urge to.
When Nekesa asks about Charlie, Bailey admits that they still haven’t spoken. They receive a text from Dana, inviting them to her and Eli’s shared birthday dinner at Applebee’s. However, when Nekesa and Bailey show up, they find both Theo and Charlie in attendance. Bailey decides to stay when it’s clear that Nekesa needs the distraction, but when Charlie attempts to chat with Bailey like nothing is wrong, she ignores him. He resorts to karaoke to get her attention, which enrages her enough to walk out of the restaurant.
Charlie follows her out, but she tells him to leave her alone. When he says that he knew their friendship would be ruined when something deeper happened, Bailey retorts that they’re only ruined because he pushed her away afterward. When Bailey says that his “ideas [about guy-girl friendship] are bullshit” (380), Charlie reminds her that he won their bet about Nekesa and Theo.
Nekesa, who followed them out of the restaurant, overhears this and interjects to ask about the bet. She is hurt to learn about the bet that Charlie and Bailey made about her and asks Dana for a ride home. When Theo, who followed Nekesa out, amusedly states that Charlie likes to bet, he reveals that Charlie also made a bet with him about getting Bailey to fall for him. Charlie attempts to explain what really happened, but Bailey says that their friendship is over and walks off.
The next few weeks are miserable for Bailey. She and her mother move out of their apartment and into Scott’s. Nekesa doesn’t reach out or answer Bailey’s texts. Though Charlie texts often to tell Bailey that he misses her and sends her photos of Puffball—which Bailey asked her mother to return to him—she is still too upset with him to answer. The only upside is that Bailey’s father has been in contact more after her conversation with her mother.
Eventually, Nekesa forgives Bailey, and they become friends again. Nekesa reveals that Charlie talked with her. He took full responsibility for baiting Bailey into the bet and said that Bailey only agreed in order to prove him wrong about her friend. Nekesa tells Bailey that Charlie and Theo fought recently. Bailey worries about Charlie’s anxiety and misses him but remains steadfast in her decision to leave things be.
Nekesa and Bailey hang out and watch a movie after work. Charlie texts Bailey, saying that he still wants to take her to the fall formal so that he can fix things between them. Nekesa texts him back on Bailey’s behalf, telling him to leave her alone—she will be going to the formal with Nekesa.
Charlie is hollowed out by the text he receives from Nekesa. He worries that he has irreparably ruined his friendship with Bailey, and it is worse than he ever imagined. While he intentionally blew Bailey off to stop romantic emotions, his aim was to revert to their prior friendship. He hadn’t meant to hurt her.
Becca interrupts his wallowing, texting him to tell her about the movie she just watched. Charlie feels nothing, not even jealousy or excitement, about Becca’s text. When she asks what he’s doing, Charlie admits to feeling devastated over ruining things with Bailey. Becca responds that she knew that Charlie liked Bailey. She offers to listen while Charlie talks through things. Charlie wonders why she’d do that, and Becca says that they’re friends.
Charlie is baffled and wonders if he and Becca are really friends. Charlie realizes that he should recognize that he’s been wrong about boys and girls being friends. He also recognizes that the only person he wants to talk to about his feelings is Bailey.
Bailey and Emily move into Scott’s house the day before the fall formal. When Bailey and Scott run into each other in the kitchen, they’re cordial, but Bailey notices that Scott is upset that she hasn’t fully warmed up to him yet. He acknowledges her feelings and assures her that his daughter, Lucy, is dealing with the same feelings. He assures Bailey that he loves Emily and wanted to ease her into the change. He admits that he went through the same thing when his own parents divorced. While this doesn’t automatically change things, it does make Bailey feel more at ease.
Nekesa and Bailey go out for a fancy dinner before the fall formal. Nekesa’s ex-boyfriend Aaron happens to be at the same restaurant with his friends. When he sees Nekesa, he approaches and apologizes for how he treated her during their breakup. He admits that he still has feelings for her, and they reconcile. He joins them for their ride to the formal, and while Bailey is happy for them, she begins to feel like a third wheel.
At the dance, Nekesa and Aaron dance together, leaving Bailey alone on the sidelines. Zack approaches her, and while he seems interested in her and tells her that he misses her, Bailey feels nothing romantic toward him anymore. Dana tells her that Zack and Kelsie have broken up, but Bailey isn’t interested. Bailey learns from Eli that Charlie cancelled his party the night she called him and needed a ride home. She’s still upset with Charlie, but hearing that he canceled his plans to help her eases these feelings.
Bailey stays at the dance for another hour before deciding to head home. As she’s leaving, she sees Charlie arguing with the security men at the entry. He has come to make up with Bailey. He tells her that he misses her and explains that he avoided his feelings because he didn’t want to lose her, which ended up happening anyway.
He also apologizes for the bet, explaining that it was all Theo and not something he wanted to be involved in. Charlie pulls Puffball from his jacket and states that he thought about giving the cat to Bailey to “prove that [he’d] be around because [he’d] want to see him every few days for […] forever” (413). Accepting his apology, Bailey kisses Charlie.
Charlie is giddy at giving in to his feelings for Bailey fully. He admits that he’d like to officially take her out and kiss her at all the places he’s fantasized about doing so. He also admits that he first thought about kissing her at the airport they day they met—at the baggage claim after their flight, where he watched her reapply her strawberry lip gloss.
Bailey and Charlie attend Emily and Scott’s wedding ceremony together. During the event, Bailey’s father texts her to check in, continuing to make more of an effort to stay in contact. Though Bailey is happy for Emily, she “still [i]sn’t thrilled about the change” and needs to adjust (419). However, she does get along with Scott’s daughter, Lucy.
Charlie and Bailey have been dating for a few months. Luckily, their friendship hasn’t changed because of it, which surprises them, as that is what they feared. At the wedding reception, which is held at Planet Funnn because of Bailey’s discount, Charlie and Bailey say that they love each other.
The final chapters of Betting on You bring the novel’s central tensions—romantic, familial, and thematic—to a satisfying resolution while still honoring the messy, imperfect process of growing up and healing from parental divorce. After spending much of the novel dancing around their feelings, Bailey and Charlie finally confront their false beliefs, fears, and resistance to change. Painter leans into classic rom-com elements in this section—miscommunications, the third-act breakup, and grand romantic gestures—to deliver a dramatic conflict and a wholesome reconciliation and resolution.
The turning point in the theme of Overcoming Resistance to Change comes during Bailey and Emily’s long-overdue lunch. Scott interrupts their vulnerable conversation with an ill-timed proposal that Emily excitedly accepts, and though Bailey has slowly been accepting the changes in her life and family, she isn’t ready for this massive change, and it sends her into an emotional tailspin. Her first real outburst occurs during this scene, when she flees the restaurant. The permanence of a marriage proposal is an official loss of control that Bailey cannot ignore, push down, or deflect—it is a wake-up call that her entire life is changing and that it’s not waiting patiently for her to accept it. The blanket fort that she builds with Charlie following the surprise proposal symbolizes her desire to return to the blissfulness of childhood. This temporarily makes her feel better, but the pressures of all the changes in her life overshadow this experience and make it hard to concentrate on anything else.
Painter maximizes the conflict of the novel by having the upheaval of Bailey’s home life coincide with the upheaval of her social and romantic life. By orchestrating a romantic moment between Charlie and Bailey the night of her mother’s engagement and then adding subsequent weeks where Charlie ghosts Bailey completely for fear of ruining their friendship, Painter eliminates all stability that Bailey has had in her life, even her best friend, Nekesa. She further heightens this climactic moment of the plot by stretching the fallout across multiple characters—even Nekesa and Theo—as the bets that Charlie made come to light.
The final chapters offer reconciliation, in line with the romance genre, but Bailey and Charlie’s reunion is realistically messy. While Charlie meant to make a grand gesture by showing up at the fall formal, Bailey isn’t necessarily happy to see him. They do reconcile at the formal after a confessional speech that he makes, but Painter subverts the “grand gesture” of a romance-novel reconciliation by keeping the conversation just between them. She also lightens even this climactic moment with the humor characteristic of her work through the detail of Puffball hidden in Charlie’s suit jacket.
Though Charlie’s speech hints that he is Becoming Unjaded About Love, the true proof of this is seen in the Epilogue, in which Bailey attends her mother’s wedding with Charlie after they’ve been dating for a few months. His willingness to tell her that he loves her without hesitation or fear for their future represents a huge change from his character at the beginning of the novel. The final chapter also suggests that change is still uncomfortable for Bailey, retaining the realistic portrayal of a changing family. She admits that she’s still not thrilled about Scott or her new home, but she’s adjusting, and her new, blended family dynamic feels less threatening now.



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