When Dreamland by Sarah Dessen opens, it is Caitlin O’Koren’s sixteenth birthday and her eighteen-year-old-sister, Cassandra (Cass), has just run away from home. Caitlin’s mother, Margaret, automatically assumes that Cass has run off to be with her boyfriend, Adam. Adam works in New York on the Lamont Whipper Show breaking up fights between guests on the show. Caitlin’s father works as Dean of Students at a university. He automatically begins calling the authorities and the numbers of Cass’ friends in order to find his missing daughter. Caitlin, meanwhile, finds the present her sister left for her, a dream journal titled “Dreamland,” with a message that reads “I’ll see you there.”
In the aftermath of this loss, Caitlin slowly adjusts to life without her older sister nearby. She and Cass have always been close. The closest thing to a fight between them was a childhood incident in which Cass hit Caitlin in the head with a shovel, which left a scar. Although the scar is barely noticeable, Caitlin knows that her sister always sees it. In fact, she often reaches out to touch that scar.
However, in some ways, they differ. Cass had been accepted to Yale for her impressive academic performance and her prowess on the soccer field. Caitlin, in contrast, has second-place medals and certificates on her shelves. Now, Rina, Caitlin’s best friend, encourages Caitlin to join the cheerleading squad. Thinking that it is something that Cass would never have done, Caitlin allows herself to be talked into trying out. Rina’s looks are enough to earn her a spot on the squad, but Caitlin’s acceptance comes from her gymnastic talent. When she comes home, her mother is thrilled to see that Cass has joined a team, and she even posts the cheerleading schedule on the fridge. Caitlin notices that this is exactly what her mother used to do with Cass and her sports schedules. It is as though her effort to become someone other than her sister has transformed her into Cass in their mother’s eyes.
Still, cheerleading does seem to have gained Caitlin entrance to a new social circle. She now goes to parties that are full of her school’s most popular students. Before long, Rina has entered into a relationship with the quarterback, and she is organizing a relationship for Caitlin as well. However, when Mike, a member of the football team, offers Caitlin his jacket, she instead leaves the party with Rogerson Biscoe. Rogerson has dreadlocks, a mysterious look on his face, and a sleek BMW. When he drives her home that night, they make out in the car, an experience that she describes as going “under.”
When she next sees Rogerson, he is doing community service and they agree to go out again. Their first date is unusual compared to the dates that Rina has with her boyfriend. Caitlin and Rogerson drive off, and he takes her into a stranger’s house to sell pot to the quarterback of a rival football team. He then talks Caitlin into smoking pot before he takes her home to meet his parents. Rogerson’s mother is a successful real estate agent, and she is quickly drinking wine when she meets Caitlin. Rogerson’s father ignores Caitlin and yells at his son for being late before he punches Rogerson in the temple and leaves Caitlin to tend to his wounds. After that, Rogerson and Caitlin become a couple.
Their relationship seems to be going well. Caitlin eventually introduces Rogerson to her parents and her parents’ best friends, Boo and Stewart. Rogerson impresses them with his knowledge of trivia. Caitlin soon realizes that Rogerson knows everything: his grades are impressive, and his counselors report that he is “driven but misguided.” Over time, Caitlin seems to be getting to know Rogerson better, slowly figuring out how his mind works. She also gets to know some of Rogerson’s clients better,...
(The entire section is 1582 words.)