The Book is based around social outcast Jenna Hamilton who, after receiving a "carefrontation" letter, has a legitimate accident, though it appears as if she tried to commit suicide. By making changes and embracing her misfortune, she becomes well-known to her peers through her Diary on Wattpad. After losing her virginity to the popular Matty McKibben, Jenna continues a secret relationship with him due to his embarrassment of her. Jenna later then begins to develop a relationship with Matty's best friend, Jake Rosati. Jenna ends her relationship with Matty to be with Jake, and both eventually agree to not tell Jake about it. Jake falls in love with Jenna oblivious to her lingering feelings toward Matty and his best friend's feeling towards his girlfriend. Towards the end of the second season resident mean girl and Jenna's nemesis, Sadie, exposes the relationship to Jake who then breaks up with Jenna. Matty goes to Jenna's house to comfort her and they end up kissing. Jake, realizing he had made a mistake breaking up with Jenna, also goes to her house and witnesses the kiss. What then follows is a public fist fight between Matty and Jake later at school and their eventual make up and a decision to force Jenna to choose between them.