Becca is a 17-year-old high school senior and one of the two main protagonists in The Upside of Falling. She is the only child of a single mother, and her parents divorced when she was 12 years old. Becca’s last name is a play on the word “heart”: a nod to her obsession with romance novels and her complicated relationship with love and romance. Although Becca can be stubborn and a self-proclaimed “pessimistic downer” (10), she is a loyal friend, and according to Brett, there is a “kindness” and “intelligence” about her, “like she [understands] more than she let[s] on” (78).

Becca is an avid reader, and her interests are mostly book-related. When she thinks about her life after high school, she states that “the only thing [she] really like[s] [is] reading” (85). Becca is especially passionate about romance novels; even though she refers to them as “unrealistic crap” (3), she can’t get enough of them. Becca is often characterized as always having her nose in a book, and her bedroom is full of her favorite love stories. In the real world, Becca scoffs at the idea of love, but deep down, she is a romantic soul who longs to feel all the thrill of falling in love without the risks. She uses the fantastical world of fiction to daydream about the beautiful aspects of love while avoiding all the risks of opening her heart to another person. By living vicariously through the characters in her books, Becca can keep her heart under lock and key and pretend that “all the problems in [her] life don’t exist anymore” (101).

Becca was deeply impacted by her parents’ divorce. She watched as her mother and father’s seemingly happy marriage ended without explanation, and her father walked out of her life with no warning. After this, Becca states that she has spent the last five years “locking everyone out” because she “knew [she] couldn’t handle another person walking out on [her]” (199-200). Becca has kept to herself at school and shown no interest in dating someone in real life. For Becca, rejection has taken many forms: Her father rejected her to have a “fresh start” with a new family, and her former best friend ditched her in pursuit of popularity. Becca is terrified of falling in love and forming an attachment to someone who might leave her as her dad and best friend did, but when she kisses Brett for the first time, it “dredg[es] up all these feelings [she] never wanted to feel” (175). Becca begins to question her decision to keep her heart under lock and key. Becca realizes that the pain of her past doesn’t have to define her future, and she chooses to let her guard down and love fearlessly.

Brett is a 17-year-old high school senior and one of the two main protagonists in The Upside of Falling. Like Becca, Brett is the only child in his family, but unlike Becca, his parents are still married. Brett’s parents were high school sweethearts, and when Brett’s mom learned she was pregnant during her senior year, Brett’s dad gave up a football scholarship to stay in Crestmont and raise his son. Brett is a charming, charismatic leader at his school, and when Becca introduces Brett at the novel’s beginning, she compares his presence to “sun pour[ing] in through a window, slow and captivating” (3). Brett is handsome and likable and wants to make his parents proud, especially his father.

Becca portrays Brett as someone with an almost mythical existence in Crestmont. Brett is the embodiment of “unwavering perfection” (3). He is popular, athletic, and stable; by all measures, he seems to have a picture-perfect life. Becca thinks that Brett is “the one person who could blur the lines between reality and fiction” (3), and when she describes his golden-brown hair and bright blue eyes, she says that he “could have walked out of the pages of a book and materialized in front of [her]” (3-4). Brett exudes confidence and kindness that attracts other people, and he is willing to go out of his way to help a friend in need. Becca claims that half of the school is in love with Brett Wells, but despite this, he has never dated anyone. Brett has actively avoided “high school drama,” and although he has had crushes throughout high school, they “never turned into anything more” (18). Brett is too focused on making his parents proud, playing football, and preparing for life after high school, and he wants to wait for the kind of love his parents have.

Despite his picture-perfect life, Brett wants to leave Crestmont and believes football is his ticket out of his small town. Brett also devotes himself to football because he wants his father to “witness [Brett] living out [his father’s] dream like [his father] intended” (70). Brett idolizes his father, and when Brett learns that his dad has been having an affair during his “business trips,” Brett’s entire worldview comes crashing down. For years, Brett has tried to live up to his father’s expectations and be the perfect son. He held his father in the highest regard and thought his parents’ marriage was perfect. When Brett learns that his father isn’t the man he thought he was, he questions his own path in life, and he realizes that he wants to pursue his own passions outside of his father’s obsession with football., Brett is disillusioned and has to find his purpose and value outside his father’s shadow. Brett wrestles with his anger and loneliness, and in the end, he decides not to allow his anger toward his father to poison the things he loves.

Jenny is another high school senior and Becca’s former best friend. At the novel's beginning, Jenny’s character is almost antagonistic toward Becca. Becca explains that she and Jenny used to be best friends during their freshman year of high school “when [they] were both inexperienced fourteen-year-old girls” (7). When Jenny decided to run with the popular crowd at the beginning of their sophomore year, her friendship with Becca fell by the wayside, and the girls had spent the last two years virtually ignoring each other. While Becca buried herself in the world of books, Jenny “joined the cheerleading squad and racked up a trail of heartbreaks” (7-8). Jenny adopted a judgmental attitude toward Becca and her lack of experience with dating and boys. Just as Brett enters into his fake-dating relationship with Becca to appease his father, Becca hopes that her fake relationship with Brett will stop Jenny’s criticism.

However, Jenny is hurt to learn that Becca didn’t tell her about her relationship with Brett. Becca explains that Jenny “always mocked [Becca] for being single” and “made [her] feel horrible about it” (113), so Becca didn’t want to share the “news” with Jenny. For the first time, Jenny realizes how much her actions have hurt Becca, and she decides to “repent for [her] sins” (193) and repair her friendship with Becca. For the remainder of the novel, Jenny shares flyers for Becca’s mom’s bakery at school, drives Becca home after the fallout at the hotel’s grand opening, and goes to comfort Becca at the bridge. Jenny realizes that she hasn’t been a good friend to Becca for the last few years, and although she knows that she and Becca probably won’t be best friends again, Jenny hopes they can at least be civil with one another. After all, Jenny once thought that popularity was all that mattered, but she realized that her friendship with Becca was special and worth fighting for.