Emily Collins: The main character of the novels. The stories focus on her journey through high school--the obstacles she encounters and overcomes, and her rapid growth and transition from naivety to maturity. She's always been shy and rejected by the popular crowd, but she's very bright (the only honor student in her group) and has a group of close friends who are also fellow outcasts. Emily has many personal issues remaining from a tumultous childhood--in high school, she turns the tables to reject the popular crowd herself. She tries throughout the series to fight the teachers' and administrators' favoritism of the popular kids.

Betsy Kennedy: Emily's best friend and confidante. Emily is more of a sidekick to Betsy than Betsy is to Emily. She is quite the opposite of traditional Emily, dressing in gothic clothes, listening to heavy-metal music, and attracting numerous boys--otherwise, she is fairly average. She tends to be the leader of her outcast group.

Curtis Johnson: Emily's friend and Betsy's boyfriend (for a short time). Curtis enjoys tinkering with anything mechanical, particularly cars. He has a pleasant, fun-loving, easygoing personality and is always the life of the party.

Nick McStandish: Emily's friend whom she meets for the first time the summer before high school. He remains Emily's love interest throughout the series, though at times he is put on her back burner. Nick is outgoing and attracts younger girls like a magnet, but often uses his popularity as a cover for personal issues. He floats in between Emily's group and the marching band crowd.

Melissa Sullivan: Emily and Betsy's friend. Even after overcoming a learning disability, Melissa still struggles in school, but her happy-go-lucky personality and perseverance pull her through. A minor car accident during her senior year leaves her a little "crazy." She is known to be two-faced at times, but remains a loyal member of the group.

Hannah Kramer: Emily and Betsy's friend. Hannah dislikes school and struggles to pass her classes; she finally drops out after her junior year. She spends much of her time taking care of her younger brothers. Although generally pleasant, she often blows petty arguments out of proportion and becomes anxious over trivial matters.

Darian Callaway: Emily's somewhat popular football-player crush during Freshman and Sophomore Years (he is present throughout the series, but not as prominently in the last two novels). Emily falls for his good looks and, during Sophomore Year, gathers the courage to write him a letter stating her feelings; he nabs her for sexual harassment and gets her a three-day suspension out of school. After that, Emily feels quite hateful towards him. Because Emily ends up having at least one class per year with Darian (they are in the same advanced science program), some of the story focuses on her trying to forgive and forget him.