The Upside of Falling is about two teenagers who have actively avoided romantic relationships until their final year of high school. Brett believes having a girlfriend will only distract him from football and his life after high school, while Becca has allowed her parents’ divorce to give her a more cynical worldview about dating. Becca believes that love is “destructive” and “dangerous,” and instead of experiencing it for herself, she believes that “books [are] enough of an experience for [her]” (6) without any of the risk. However, as the novel progresses, Light uses Becca's journey to show that falling in love might come with risks, but the experience can be beautiful, enriching, and fulfilling to a person’s life.

After seeing her parents’ marriage fall apart, Becca swore off real-world love. However, she still wants to experience love, so rather than partaking in it herself, she dives into the world of romance novels. Becca explains that there are two types of love: real and fictional. She says that “the real kind [is] what [she] thought [her] parents had, pre-divorce,” and ever since her parents’ divorce, “the fictional kind [is] what [she has] preferred” (9). Becca believes that if she were to fall in love for real, she would wind up with a broken heart full of regrets.