56 pages • 1-hour read
Betting on You
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Character Analysis
Bailey
Bailey is the teen protagonist of the novel. She is introduced to the narrative as having glasses, braces, and unruly, frizzy hair, but after a few years, she loses the braces and tames her hair into a sleek, shoulder-length bob. Practical and bookish, Bailey is used to being in control of her feelings, her routines, and nearly every aspect of her life.
Bailey is defined by her need for stability and her resistance to change. Her reluctance to accept her mother’s new relationship is due to her fear of disrupting the status quo. Much of Bailey’s growth involves learning to let go of control, trust the people who show up for her, and believe that love—romantic or familial—can endure upheaval, developing the theme of Overcoming Resistance to Change. She’s also fiercely loyal and deeply compassionate, often putting others’ comfort ahead of her own. Though Charlie and Nekesa see her personality as uptight and believe her compulsion to people-please to be a potential flaw that others take advantage of, Bailey has a secret strength. While Charlie becomes jaded and hateful following his parents’ divorce, Bailey remains positive and open to possibility.
When the novel begins, Bailey is still recovering from the emotional fallout of her parents’ divorce and struggling with the slow collapse of her once-close relationship with her father. She lives with her mother, whom she’s incredibly close to—even more so now following the divorce—and deeply fears losing that bond as her mother’s relationship with a new man, Scott, becomes serious. While she isn’t thrilled about the addition of Scott to her life, nor is she happy to slowly lose contact with her father, Bailey remains open to the idea of her parents finding another partner to be happy with. She makes an effort to recognize that her negative reactions are caused by her resistance to change, not because she dislikes her new stepparents. However, this acceptance and openness aren’t easy for her, highlighting The Costs of Early Maturity.
Bailey meets Charlie at the airport, where their witty dynamic begins. She’s immediately annoyed by his cocky, easygoing nature, and she assumes that he’s just another charming slacker who doesn’t take anything seriously. When she later discovers that they’ll be working together at Planet Funnn, she’s less than thrilled—but over time, their coworkers-to-rivals-to-friends-to-something-more arc becomes the novel’s emotional core.
While Bailey is independent and self-aware, she is also naive when it comes to her own emotions. She spends much of the novel denying her attraction to Charlie, even after it becomes obvious to everyone around her. Her romantic journey is complicated by past heartbreak with her ex Zack, whom she is also emotionally naive over. Though he doesn’t respect her as much as she deserves—having moved on so easily from her after a minor fight they had—she is still hung up on him.
Throughout the novel, Bailey’s internal conflict revolves around her resistance to change—whether it’s accepting a new stepfather, moving into a new home, facing the fact that her father has become emotionally distant, or allowing herself to fall in love. Her character arc is about embracing uncertainty and understanding that change doesn’t always have to be negative or scary. In the end, Bailey is no longer just a rule-following teen afraid of disruption. She’s someone who allows herself to feel deeply and let go of the rigid expectations she once clung to for safety.
Charlie
Charlie is a witty, sarcastic, and emotionally guarded high school senior who becomes both Bailey’s coworker and her eventual love interest in Betting on You. At first glance, Charlie appears to be the typical charming flirt—he’s laidback and confident and never seems to take anything seriously. However, beneath the teasing and bravado lies a deeply sensitive person navigating the aftershocks of his parents’ divorce and a newfound jadedness about relationships.
Charlie initially meets Bailey at the airport, where their banter-filled first interaction sets the tone for their evolving dynamic. He quickly becomes intrigued by Bailey’s no-nonsense, hyper-competent demeanor, dubbing her an “uptight rule-follower” even as he enjoys getting under her skin. What begins as light antagonism transforms into a genuine connection as the two grow closer.
Though Charlie presents himself as someone who doesn’t care deeply about anything, his actions betray just how much he does. He cancels plans with his friends to pick Bailey up when she’s upset, creates blanket forts and movie nights to comfort her, and quietly monitors her moods even when they’re not on speaking terms. Charlie’s avoidance of romantic labels is less about disinterest and more about fear. He believes that once friendships cross into romance, they’re doomed to fall apart. His reluctance to define his connection with Bailey—repeatedly referring to them as “coworkers” long after it’s clear that they’re more—comes from a desire to preserve what they have, even if it means stifling his real feelings. That same fear causes him to pull away just as their relationship begins to deepen, mistakenly thinking that protecting her means distancing himself.
Charlie’s growth throughout the novel centers on Becoming Unjaded About Love. By the end, he begins to understand that emotional distance doesn’t prevent pain—it causes it. He confronts his fears of losing people, admits the damage caused by his bet with Theo, and chooses to fight for Bailey instead of running from his feelings.
Nekesa
Nekesa is Bailey’s best friend who provides emotional insight, positivity (in contrast to Charlie’s cynicism), and moral clarity throughout Betting on You. She is friendly, observant, and wise in a way that differs from Charlie. She offers gentle but pointed truths that Bailey might not want to hear, but needs to, particularly involving Charlie.
At the start of the novel, Nekesa is in a happy relationship with her boyfriend, Aaron. Though Bailey is positive that their relationship is stable and faithful, Nekesa’s growing flirtation with their coworker Theo challenges the “naive” notions that Charlie claims Bailey has about love. Nekesa’s interactions with Theo unwittingly become the focus of proving whether love is an idealistic fantasy, as Charlie believes, or something that is pure and attainable, as Bailey wants to believe. Nekesa’s flirtation with Theo, though seemingly harmless, becomes more complicated when Theo kisses her and she realizes too late that things have gone too far. She treats her heartbreak over Aaron’s reaction and their breakup, as well as her subsequent regret, with maturity and complexity.
By the end of the novel, Nekesa reconciles with Aaron and is more self-assured about her boundaries and emotional priorities, providing a positive role model of relationships for both Bailey and Charlie. Her willingness to forgive, her emotional intelligence, and her loyalty to the people she loves make her one of the most influential characters in the story.
Scott
Scott is Bailey’s mother’s boyfriend—and eventual fiancé—and serves as one of the central sources of tension in Betting on You. Though he is not a villain, Scott’s presence disrupts Bailey’s sense of stability, putting him in an antagonist role for much of the novel. His character embodies the discomfort of post-divorce family change: He represents everything that Bailey feels unready to accept, from new household dynamics to the shifting boundaries of her relationship with her mother.
Despite his role as apparent antagonist, Scott is, in many ways, an objectively decent person. He plans thoughtful gestures, like a weekend trip to Colorado, in an effort to bond with Bailey. He tries to be respectful of boundaries and gives Bailey space instead of pushing too hard for connection. However, his attempts at kindness often backfire—not because of ill intention but because Bailey isn’t emotionally ready to let him in. He becomes a target for Bailey’s internalized fears: fear that her mother will sideline her, fear that their tight-knit dynamic will be replaced, and fear that he will further strain her divorced family.
Scott’s biggest missteps stem from a lack of understanding. He often reads Bailey’s resistance as rebellion rather than hurt, which causes him to draw harsh comparisons—like likening Bailey to his niece Kristy, a girl known for her bad behavior following her own parents’ divorce. He speaks critically of Charlie based on surface impressions, failing to understand how important that friendship is to Bailey. These comments highlight how little he truly knows Bailey, even as he tries to position himself as a permanent fixture in her life.
However, Scott isn’t emotionally out of touch. He recognizes Bailey’s discomfort, and while he doesn’t always handle it perfectly, he makes an effort to bridge the gap. When Emily explains that Bailey isn’t like Kristy and defends her daughter’s character, Scott listens. Later in the story, he shows surprising vulnerability by revealing his own childhood experience with divorce—an admission that complicates his character and allows Bailey to see him as someone capable of relating to. This moment of emotional honesty softens Bailey’s resentment and begins a slow, tentative shift in their dynamic.
Scott’s relationship with Bailey is not easily resolved by the end of the novel, offering a realistic ending. Even by the end, Bailey admits that she still isn’t thrilled about the changes—but she’s adjusting. That nuance is critical to Scott’s role in the story. He’s not a perfect stepfather figure nor a villain to be overcome. He’s a real person who is sometimes misguided but ultimately trying. His presence forces Bailey to confront her resistance to change, her fear of being replaced, and her ability to accept love in new forms.
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