The film's male protagonist. A lover of literature, at 24 he's just obtained his Masters in Education and started teaching Dramatics & Literature at his old high school. Recently became engaged to his high school sweetheart, Allison. A compassionate, funny guy who finds himself becoming close to his student, Margot, despite all the challenges and conflicts that come along with that- simply because she needs a friend.
The film's female protagonist. A sweet girl, much more mature than her beginning age of 16 and more mature than most of the people around her. Very talented and smart with a huge passion for writing, but also very pessimistic and sad because of her difficult home life. Finds something special in her friendship with her teacher, Mr. Levitt. Feels something more for him. He brings out her love for writing and also, simply, listens.
Cole's fiancée and girlfriend since high school. Allison tries to be very self-assured but is essentially very lost and needy. When things begin failing with Cole, she clings to the relationship, because it really is all she knows- she's in her mid twenties and has been with the same guy since she was a teenager, and starts to see that fall apart.
Cole's best friend from college, a goofy math teacher who helps get him the teaching job at the high school. A bit of a womanizer who also envies what he sees as Cole's stable home life. Tries to see the lighter side of things, but can be serious when the time calls for it.
A class clown high schooler who hates Mr. Levitt's class, partially because he doesn't like literature, and partly because his eventual girlfriend Margot seems to have a thing for him. Can be charming, but gets to be more obnoxious.
Margot's best (high school) friend. A gossipy but well-meaning teenage girl. Loud and outgoing but also has a soft spot for Margot, especially after seeing her parents go through serious problems.