Roswell has a lot on her mind. She becomes adept at expressing it in her journal, as her life becomes increasingly difficult, during a tumultuous semester.
When we meet Roswell, she is a sophomore in a private high school on Maui – a seemingly fortunate situation, but Roswell is not happy. She experiences her fellow students as being cliquish and far more moneyed than she is. She hates the small condo that she and her mother were forced to move into, when her father left his family, for a young “bimbo,” as Roswell refers to her. Roswell is also contemptuous of her mother, whom she considers a victim, addicted to “useless and pathetic” self-help programs.
At the beginning of her story, Roswell has two burning ambitions; one, to keep up her grades so that her father will continue to pay her tuition and two, to win the love and attention of Sean, a very attractive and charismatic fellow student. It takes Sean, the son of a wealthy travelling windsurfer, businessman and playboy, a while to notice Roswell as little more than a useful study partner. Supermodel-styled Elena, also from the wealthy, international set, effectively attracts his attention.
Roswell dedicates her efforts to becoming Elena’s rival for Sean’s attention. She hopes that if she can get a car, stylish, sexy clothes and just the right attitude, she can attract Sean. So, Roswell adds two part-time jobs to her already demanding schedule of schoolwork and basketball. It’s a lonely, frustrating endeavor, especially since Jade, her “best bud,” has found a new college boyfriend and is no longer available to her.
Along comes Michael, a seventeen year old, good-looking senior at the school. As Roswell pursues Sean, Michael always seems to be around to rescue her from loneliness and despair. Roswell accepts Michael’s friendship, reluctantly, because his “annoying niceness” and strong Christian beliefs turn her off. However, Michael finds one of Roswell’s jobs for her at his parents’ imported furniture store, resulting in their seeing each other a lot at work. Michael seems unfazed by Roswell’s prickliness and encourages her to believe in herself and God’s love, manifest in her life.
Roswell needs Michael’s friendship when things get even more difficult in her life. Sean’s absorption in Elena and his “rich boy” lifestyle cause her to despairingly give up on ever attracting him. At the same time, Jade is impregnated and dumped by her “jerk” boyfriend. Roswell turns her efforts and savings to helping Jade run away from her strict, old-fashioned Catholic parents and get an abortion. Their plan fails when Jade’s anger-crazed father finds her and virtually jails his daughter in their home. Michael is upset that he cannot persuade Roswell how wrong abortion is and their friendship becomes strained.
Roswell’s increasing loneliness leads her to close her heart further, still. She attempts to forge a new approach to life, based on material achievement and success, but it is not enough to shield her from the charms of Sean. After Elena is expelled and sent back to Brazil, Sean decides to pursue Roswell, attracted by her new aloofness. Tired of lonely struggle, Roswell succumbs to Sean’s invitations and finds herself way over her head in Sean’s life of casual sex and “recreational” drugs.
Roswell’s story intensifies when Jade disappears, leaving behind a suicide note. It is Michael, not Sean, who comes to Roswell and Jade’s rescue in the worst trouble they’ve ever been in.
In the end, Roswell reconsiders the beliefs she had formed, based on anger and pain. She begins to allow true friendships, hope for a good future and real love into her life.
