Betting on You

Betting on You (2023) is a young adult contemporary romance by Lynn Painter that follows Bailey and Charlie, two teens who bond over healing from their parents’ divorces. Charlie, who believes that all relationships are doomed to fail, realizes the error in his beliefs as he falls in love with Bailey. This coming-of-age novel explores themes including The Costs of Early Maturity, Overcoming Resistance to Change, and Becoming Unjaded About Love.

This guide refers to the e-book edition, published by Simon & Schuster in 2023.

Content Warning: The source material and guide feature depictions of mental illness and cursing.

Plot Summary

Shortly after their parents’ divorces, teenagers Bailey and Charlie meet on a flight from their fathers’ homes in Fairbanks, Alaska, to Omaha, Nebraska, where their mothers reside. Their first meeting is the opposite of a traditional meet-cute: Bailey refuses to allow Charlie to cut the line, and Charlie is annoyed by her rule-follower attitude and high-maintenance habits. During the long flight home, Charlie tells Bailey his beliefs on love: All relationships are meant to fail, so he doesn’t find them worth the effort, especially if they’re long distance (which explains why he intends to ghost his girlfriend back in Fairbanks); he also believes that there is no such thing as platonic friendship between a girl and a boy, as one person, likely the boy, will want more at some point. Bailey vehemently disagrees with his theories, which she believes are ridiculous.

A few years later, Bailey and Charlie meet for a second time at the movies. Bailey and her boyfriend, Zack, are in the lobby when they witness Charlie enacting a “promposal” for his girlfriend, Becca. Later, when Bailey buys popcorn for her date, Charlie recognizes and approaches her. Bailey is surprised to learn that Charlie is less cynical about love after dating Becca for over a year. Despite this, they find each other just as annoying as the first time they met.

One year later, in the present day, Bailey visits a coffee shop with her friend Nekesa shortly after her breakup with Zack. Bailey is devastated when Zack arrives with his new girlfriend, Kelsie, whom he takes for coffee dates, just as did with Bailey.

Nekesa and Bailey begin training at Planet Funnn—a massive hotel with entertainment features—where they will be working for the foreseeable future. Bailey is surprised to discover that Charlie has also been hired to work there. Meanwhile, Nekesa reconnects with an old friend, Theo, another employee, and they exchange flirtatious banter despite Nekesa’s happy relationship with her boyfriend, Aaron.

Charlie still believes that boys and girls cannot be platonic friends, and though Bailey is not inclined to bet on her best friend, he goads her into betting: Charlie believes that Nekesa will have a fling with Theo, while Bailey believes that she will remain loyal to Aaron. Charlie gives Bailey his number to keep in contact about the bet.

When Bailey returns home, she finds her mother’s new boyfriend, Scott, on their living room couch. He scolds her for missing curfew, and though he seems nice, Bailey is not happy about how comfortable he’s becoming in her life and with parenting her. Her status quo is further threatened when she finds him still in her home the next morning, clearly having spent the night. When she tells Nekesa, Charlie, and Theo about it at work later on, they encourage her to make Scott miserable to strain his relationship with her mother, Emily, slowing its progression before it’s too late.

Bailey invites Charlie home with her when she realizes that Scott will be there for dinner, hoping that Charlie’s fearlessness in speaking his mind to his mother’s boyfriend will rub off on her. Charlie succeeds in irritating Scott and causing a disagreement between him and Emily—who briefly scolds Scott for his treatment of Charlie—but they quickly bounce back from the interference. In the following weeks, Bailey continues to invite Charlie over to bother Scott.

Meanwhile, Charlie oversteps their usual boundaries to invite Bailey to a party that his friend is hosting. He wants Bailey to attend to distract him from his ex-girlfriend, who will be in attendance. Bailey agrees, though pretending to be romantically interested in him temporarily blurs the boundaries of their usual relationship, leaving them both confused. As Charlie and Bailey face a shifting dynamic, so do Nekesa and Theo—they become closer during their time at Planet Funnn, making Bailey uneasy and Charlie smug.

Scott books a trip to Breckenridge, Colorado, that he believes will be a great bonding opportunity for him, Emily, and Bailey. Though Bailey is caught off guard and not thrilled to attend, she begrudgingly agrees when Nekesa is invited to come along. However, when Nekesa gets grounded for missing curfew, she suggests that Bailey bring Charlie without her mother’s consent. Though it is out of character for Bailey to pull something like this, she is desperate not to be stuck alone with Emily and Scott for a weekend. She not only agrees to bring Charlie but also agrees to fake date him to further annoy Scott and her mother.

Leading up to the trip, Theo confronts Charlie about a bet they made, which Charlie completely forgot about since he hadn’t intended to make it in the first place. Charlie bet Theo that he could get Bailey to date him after Theo joked that she was too uptight to give any guy a chance. Charlie is anxious about the truth getting back to Bailey, but he keeps the unintentional bet quiet.

While Emily and Scott are not thrilled at having Charlie join them without prior notice, he is accepted. While pretending to fake date over the weekend, which justifiably bothers Emily and Scott, boundaries between Bailey and Charlie become more blurred. They inwardly recognize feelings for each other, and Bailey is open to acting on them if given confirmation that Charlie feels the same. However, Charlie is intent on keeping his emotional distance from her, despite multiple slip-ups in which they make verbal confessions, flirt, or kiss.

After getting too close during their weekend together, Bailey—who has decided that Charlie does not like her as much as she likes him—suggests that they go on a double date. She sets Charlie up with her friend Dana, while he sets her up with his friend Eli. Unfortunately, things do not go as planned, and Dana and Eli end up liking each other. Feeling glum at being ditched, Charlie and Bailey decide to attend the fall formal together since there is no one they feel particularly attached to. Meanwhile, Theo makes a move on Nekesa, which leads to an unwanted breakup with Aaron, leaving her devastated.

Bailey becomes excited when her mother invites her out to pizza, which they used to do often with just the two of them. They have their first vulnerable one-on-one in a while, but their outing is interrupted by Scott’s arrival. He ruins Bailey’s time with her mother by proposing, and Emily accepts.

Bailey becomes distraught and flees the venue, calling Charlie to pick her up. Charlie takes her to his home, where he comforts her with a movie and ice cream. They become close, and he kisses her after confessing his feelings for her. Charlie later considers this a moment of weakness. Bailey falls asleep at his house, but Charlie leaves his apartment before she wakes the next morning, leaving a note to let herself out. He then avoids her for weeks, effectively ruining the friendship that he sought to preserve by avoiding romantic entanglement.

While trying to fix their friendship at Dana and Eli’s shared birthday party, Charlie accidentally lets slip about his bet with Bailey concerning Nekesa and Theo. This temporarily ruins Nekesa and Bailey’s friendship. Theo gets revenge by revealing his bet with Charlie, further ruining Charlie’s chances of reconciling with Bailey. Though Charlie attempts to make contact with Bailey afterward, claiming that he misses her, she does not respond.

Bailey and Emily officially move in with Scott. Eventually, Bailey makes up with Nekesa, and they attend the formal together. At the formal, Nekesa and Aaron reconcile, and Bailey feels like a third wheel. When she leaves the dance, Charlie approaches. He tells her that he loves her, and they reconcile and begin dating. A few months later, Bailey and Charlie attend Emily’s wedding to Scott. Though Bailey hasn’t completely come to terms with her new reality, she’s open to adjusting.