Betting on You

“‘Everybody knows that if the shit goes down, we’re dead.’ His voice was deep and rumbly as he murmured, ‘They go through these motions to give passengers a false sense of hope, but the reality is that if the plane crashes, our bodies are going to be splattered for miles.’”

Painter introduces readers to Charlie’s cynicism early on, depicting his bleak outlook on life through his diction, which includes dark humor and sarcastic comments. A clear picture of Charlie is portrayed through his dialogue in these early chapters. This vivid portrayal also heightens the contrast between his character and Bailey’s, which also highlights the opposite ways in which they will navigate handling their parents’ divorces.

“He gave his head a slow shake, as if I were the world’s biggest fool. ‘Oh my God, you are precious. You’re like a sweet baby child who believes everything her mommy tells her.’”

In contrast to the jadedness that Charlie is showcasing, he teases Bailey for her naivety. Her parents have gotten divorced more recently than his have, so in his opinion, she is still childlike in her navigation of this new post-divorce territory and thus not yet jaded about life and love. This juxtaposition highlights the theme of Becoming Unjaded About Love by setting up Bailey to contrast Charlie’s cynicism.

“Seeing Mr. Nothing left me…unsettled. Maybe it was his tie-in to the shitty time in my life when my parents fell out of love, we moved to a strange place, and my dad stopped caring about me. I still couldn’t listen to the Taylor Swift album that’d been popular at the time, because it made me cry. Every. Single. Time. Hell, the day of that flight, just before I’d slid into line behind Mr. Nothing, I’d cried my eyes out in the airport bathroom. No wonder the sight of him was accompanied by a general sense of dread.”

Rather than being upset by Charlie himself, Bailey associates him with the exact moment her life was upended—her parents’ divorce, the move, and the emotional withdrawal of her father. The intensity of this emotional imprint is reinforced by sensory triggers like music and setting, which continue to evoke visceral responses long after the events. Seeing Charlie again brings those unresolved feelings to the surface, highlighting how deeply Bailey’s past still affects her present.

“I couldn’t explain it, but our fleeting moment of commiseration had felt good. It was nice to have a partner in suffering.”

This quote captures the early emotional bond forming between Charlie and Bailey, rooted in their shared experiences with parental divorce. Their mutual understanding provides a rare moment of comfort during a time of personal upheaval. The idea of having a “partner in suffering” highlights their loneliness post-divorce and the need to feel seen, especially in pain.

“We’re like soldiers, comparing scars and stories of our shitty battles. People who haven’t been there don’t understand, but we do.”

This quote illustrates a deep bond forged between Charlie and Bailey through shared trauma. The metaphor calling the two teens soldiers emphasizes the emotional toll of their parents’ divorces and how it sets them apart from their peers. Their connection stems from mutual understanding and a sense of being permanently changed by their experiences.

“But inside, I was raging. This man was speaking to me about my mother? Scott was talking about her like she was his primary concern, like it was his job to make sure she was happy?”

This moment captures Bailey’s visceral resistance to the idea of Scott stepping into a parental role. She hates that his words symbolize the shifting dynamic in her family and the implied replacement of her father. Bailey’s reaction reflects her deep discomfort with change and the loss of control that comes with it. Her internal rage reveals how fiercely she guards the remnants of her old family life, even as her mother moves forward.

“The real reason you don’t want to make the bet is because Nekesa is your friend and you know you should have faith in her. But deep down, you also know the truth about love. You try to deny it, like a little kid convincing themselves that they didn’t see their parents putting Santa labels on the presents under the tree, but it’s there, deep in your psyche.”

This passage exposes Charlie’s deeply ingrained cynicism about love, portraying it as something he intellectually wants to believe in but emotionally can’t trust. The Santa metaphor underscores how his jaded worldview stems from childhood disillusionment—particularly witnessing the collapse of his parents’ relationship. By likening belief in love to belief in magic, the quote suggests that Charlie sees romance as something naive or delusional.

“I knew—I fucking knew—that relationships and love were sinking ships of bullshit, but for some reason, that knowledge went out the goddamn window every time I engaged with Becca.”

This quote reveals the internal conflict between Charlie’s rational disillusionment and his emotional vulnerability. Despite his insistence that love is doomed, his continued attraction to Becca shows he’s not as detached as he claims to be. His use of harsh language reflects frustration—not just at relationships but also at himself for still wanting connection despite believing that it will fail.

“I’d been serious about trying to help her, mostly because Bailey seemed so wide-eyed and trusting that she was going to be shattered when reality reared its ugly head. I knew we weren’t going to be able to stop it, because life, but at least if we fought, she wouldn’t feel helpless. I fucking hated feeling helpless. Because helplessness was a little like waterboarding (I said a little). Someone else has all the control while you feel like you can’t breathe and like it’s never going to stop.”

This quote exposes Charlie’s protective instincts and the emotional trauma that drives them. His desire to help Bailey isn’t just about supporting her—it’s about shielding her from the same powerlessness he’s felt in his own life. His intense reaction to helplessness and the allusion to waterboarding reveal the depth of his trauma. By trying to equip Bailey to fight back against disappointment, Charlie is also attempting to reclaim a sense of agency for himself.

“How was I supposed to jump in front of the Mom-Scott train when it was chugging along so well? I desperately wanted her to be grinning and happy, I really did, but I just didn’t want some guy to be the one responsible. I didn’t want him to be responsible. Not because I was like some third grader screaming You’re not my dad to every man my mother dated; I was good with her having a social life. She’s my favorite person in the universe and deserves every good thing. But on the other hand, like, dammit if I wasn’t a twelfth grader who knew exactly how quickly things changed.”

This passage captures Bailey’s complex emotional response to her mother’s new relationship and the deep-rooted fears it stirs, highlighting her struggle in Overcoming Resistance to Change. Her resistance isn’t rooted in immaturity or possessiveness but in the emotional fallout of her father’s abrupt abandonment. She supports her mother’s happiness in theory, but she fears that giving another man a role in their lives will come at her own expense—just as it did when her father prioritized a new relationship over her.

“I hated confrontation, but I hated this stranger butting into our business even more. He knew nothing about me, and the fact that he dared to butt in felt so intrusive, it was almost suffocating. Somehow it felt like an insult to my dad, too, which didn’t make sense but added to the painful burning sensation in the center of my chest.”

This quote reveals Bailey’s deep discomfort with the intrusion of a new parental figure. The suffocating sensation reflects how powerless she feels in these changes, and her irrational sense of betrayal underscores how fear can manifest as misplaced anger. The sensory imagery of the passage, with words like “suffocating” and “burning,” highlights the depth of her discomfort.

“Scott posed a threat to the comfort in my life. Not comfort as in something that pampers, like nice sheets or soft slippers, but comfort as in the part of your life that provides healing. The part of your life that you can relax and take some kind of comfort from when the rest of the world is on fire. The part of your life that you can burrow into. Our life—the one we’d carved out post-dad and pre-Scott—was the comfort. Which made Scott the anti-comfort. The potential agent of change in a place that desperately wanted to remain unchanged.”

This passage articulates Bailey’s emotional resistance to change through her perception of Scott as a threat to her comfort. Her home life with her mother has become a space of hard-earned stability and healing. Scott’s arrival endangers that sanctuary, and he is a disruption to the fragile equilibrium that she and her mother have built. Her reaction isn’t just about disliking a new partner—it’s about defending the only part of her world that still feels safe, familiar, and wholly hers.

“I went into my room and closed my door, feeling like garbage. For yelling at my mom, for disappointing them about the trip, and mostly for the inescapable fact that things were definitely progressing with Scott and pretty soon his presence in our life would be constant. I could feel it now. I blinked back tears—stupid, immature tears—and wondered when life would stop changing up on me.”

Bailey is faced with emotional exhaustion as she confronts the inevitability of change. Her guilt over lashing out is compounded by the creeping realization that Scott’s presence is becoming permanent, no matter how much she resists. Her tears, which she dismisses as immature, actually reflect a mature response, but her difficulty with them illustrates The Costs of Early Maturity. She is reacting reasonably for a child her age in this situation but views her reactions as childish, thus dismissing them.

“I opened the fridge and grabbed a bottle of mocha Frappuccino, unable to believe I’d just heard Charlie call my mom Emily. When exactly had they become best friends? It was a little adorable, but it made me uneasy. I didn’t want my clueless mother to form a bond with my fake boyfriend. That couldn’t end well, right?”

Bailey’s discomfort here reflects her fear of blurred boundaries and emotional entanglements in an already fragile situation. Charlie casually calling her mother by her first name triggers Bailey’s worries about the lines between real and pretend becoming too muddled. What began as a fake relationship now threatens to invite real emotional consequences, especially as it begins to involve people beyond just the two of them. Her unease reveals a deeper fear of losing control and watching yet another dynamic in her life shift unexpectedly.

“But. Was it strange that at that moment, I wanted his words to be true? This whole thing was just a game, and the real Charlie Sampson was a huge pain in the ass, but in that mountain moment, under the gorgeous moonlight, I wanted fake Charlie to be real and to mean what he’d just said.”

This quote captures Bailey’s growing emotional confusion as her pretend relationship with Charlie begins to feel real. Though she intellectually knows that it’s all a game, her heart starts to blur the lines between performance and sincerity. The description of the setting mirrors the dreamy, almost surreal nature of the moment.

“I’d known that men and women couldn’t be friends. It was something I considered to be a universal truth. But somehow, with Bailey, lines got crossed. […] Somewhere between Omaha and Colorado I’d fallen truly, madly, fucking ridiculously hard for Bailey Mitchell. She was all I could think about, all the time, and sometimes it felt like I’d do anything—anything—just to make sure she was happy. […] Every single person tried to convince me that true love and happily ever afters were a possibility. But it was simply not true. Yes, there was the obvious baggage in my life to which a therapist could attribute my beliefs: my parents fell out of love, every person I’d ever dated had fallen out of love, my grandparents had all split up—even my aunts and uncles had RIP’d their marriages. Anyone related to me wasn’t a part of the HEA crowd. You could argue with me all day about the merits of true love, but in my opinion, it wasn’t worth the risk. It always came to an end. And then there was nothing.”

This quote exposes the full depth of Charlie’s emotional conflict and the cynicism he’s internalized about love. His sweeping generalization—that love always ends—reveals a worldview shaped by repeated disappointments. Despite his growing love for Bailey, which he admits with raw honesty, Charlie is still imprisoned by the belief that love is doomed, making his feelings for her both intoxicating and terrifying. His resistance to embracing the possibility of happiness reflects a fear not of love itself but of its inevitable loss—a fear so strong that it nearly keeps him from the one person who might prove him wrong.

“I felt crushed. It was silly, because the world wasn’t ending and no one was dying; people’s parents got remarried all the time. But I was devastated. It probably meant that I was an immature child, but every time I thought about the fact that my mother was getting married, a heavy weight settled on my chest. It was suffocating, this panic that I had about the life changes I could no longer avoid. […] It felt like the world was crumbling and changing under my feet, and there was nothing I could do to slow it down. I wasn’t a child; I knew I’d adjust to leaving the old behind. But dammit, I wasn’t ready to let go of it. Of us. Of life as I knew it. Very soon—it might’ve happened tonight, actually—the roles would shift. It would no longer be her and me, with the rest of the world as something we navigated. It would be her and him, and I would be part of what they navigated together, as partners.”

This passage lays bare the raw emotional turmoil that Bailey feels in the face of her mother’s impending marriage. Her devastation isn’t about the remarriage itself but about the symbolic loss of the “us” she shared with her mother, which became stronger in the aftermath of her parents’ divorce. This strengthened bond became her foundation and what she’s built her entirely new life on top of. As that foundation threatens to crumble, Bailey becomes unsure about all aspects of her life that she built around it.

“I closed my eyes, but every time I did, the worries about my life and how it was about to change wouldn’t stop. Now that they are engaged, will they want to move in together immediately? How long until they get married? Will they go on a honeymoon and leave me to stay home alone with a new stepsibling who’s a stranger? Will I have to meet Scott’s parents? Will they want to be my grandparents? I opened my eyes, but then I just stared at the TV-illuminated wall—and kept thinking. Because no matter how much I wanted to just think things like Everything will be fine and hope for the best, the reality was that everything I’d worried about was now happening.”

This quote captures Bailey’s spiraling anxiety as her fears about change shift from hypothetical to real. Her inability to sleep—trapped between closing her eyes and opening them to the same dread—reflects the all-consuming nature of her thoughts. Each question she poses isn’t just about logistics but about her literal belonging: where she fits in this new version of family and whether she’ll be left behind in the process.

“Part of me thought I was ridiculous for being pissed, because Charlie hadn’t technically made any promises. But the angry part of me disagreed, because dammit, he had made promises. We might not have labeled what we were, but when he’d kissed away my tears, that was a promise. When he’d held me while I cried, that was a promise. Maybe not a promise to be my boyfriend, but a promise to be something to me. He knew that he’d become my something, and it felt so fucking personal that he was fine with just leaving me alone when he knew I needed him. If he were to text me about something happening with his mom and her boyfriend, I’d respond—even this very second—because aside from everything else, I cared about his feelings. He obviously didn’t feel the same.”

Bailey’s anger in this moment is rooted in the emotional betrayal that comes when someone you’ve let in pulls away. The passage reflects how profoundly meaningful Charlie’s gestures were to her, even without a label, and her repetition of the word “promise” reflects how seriously she took them. The fact that he could abandon her during a moment of great need brings her immense pain, making his silence feel like rejection on a deeply personal level.

“Speaking of the cat, my mother delivered Puffball to Charlie’s house like we were people divorcing and exchanging custody of our ward. Puffball was a fucking custody kid, for the love of God, and that full-circle unhappy ending was too depressing for words.”

This line uses dark humor to convey Bailey’s emotional devastation as she processes yet another loss—this time symbolized by the shared custody of the cat, Puffball. The imagery of Puffball becoming a “custody kid” mirrors Bailey’s own unresolved feelings about being passed between divorced parents, making the moment sting with bitter irony that actually resembles the dark cynicism of Charlie. This passage suggests that she might be turning just as jaded as Charlie has become.

“I was in the doorway when he said, ‘My parents got divorced when I was fourteen, Bailey.’ That made me stop and look back. ‘My mom started seeing a guy a year after they split up, and we moved into his house a few months later,’ he said, staring into space as if watching a memory being played back. His face was relaxed, like the story didn’t hurt him anymore. ‘I can still remember the way I felt in his house. Like everything was wrong and smelled weird and like I was forced to live with strangers in a house that didn’t feel like home.’”

This moment is pivotal in bridging the emotional gap between Scott and Bailey. By sharing his own experience with parental divorce and remarriage, Scott shifts from being a perceived intruder to someone who genuinely understands the emotional disorientation that Bailey is grappling with. His vivid sensory memory evidences how deeply such transitions imprint on a child. In revealing his past, Scott offers Bailey a relatable glimpse of himself that challenges her assumptions about him.

“I’ve never had a good relationship—ever. They all go to shit in a big way. So when I started falling for you, I forced myself to ignore it, to deny it, because I couldn’t stand the thought of losing you from my life if we got together and then split up.”

Charlie’s confession lays bare the root of his emotional avoidance: a deep fear of loss shaped by a lifetime of failed relationships. By admitting that he forced himself to deny his feelings, Charlie reveals the internal battle between his heart’s desire and his trauma-conditioned logic. This moment marks a turning point where vulnerability becomes his path forward, as he begins to accept that love, while risky, might be worth the fall, traveling further along his character arc of becoming unjaded about love.

“So basically, Charlie had been doing his best—all day—to make sure I was distracted and okay as my mom got remarried. Surprisingly, I was. I still wasn’t thrilled about the change, and I hadn’t completely adjusted to living at Scott’s house, but it wasn’t as terrible as I’d imagined. My stepsister, Lucy, was actually very sweet. And she didn’t get along with her mean cousin Kristy at all.”

This passage reflects Bailey’s quiet evolution in accepting the changes she once resisted so fiercely. Charlie’s efforts to distract and support her during the wedding illustrate how love can anchor someone through emotional upheaval. Though Bailey doesn’t claim to be fully comfortable with her new reality, her acknowledgment that it’s “not as terrible” signals growth—she’s beginning to let go of fear and make space for new dynamics.