The entire movie was shot backwards for two key reasons: so that the character's relationships could grow over time (or appear in the film to fall apart towards the end), and because of the severe physical changes that the actors had gone through since graduating from high school. Of all the actors, Nicholas Zebrun went through the greatest physical change: growing a goatee and gaining nearly 30 pounds. Throughout the entire shoot, Zebrun lost and gained weight continually and had to grow three different goatees after continually shaving them off.
Filming began on October 17, 2003 and finished over five years later on March 8, 2009. Intense scheduling conflicts and casting irregularities caused several delays in the shooting process. One benefit to this was that it gave Nicholas Zebrun enough time to rework scenes in his original script he was not happy with.
Nicholas Zebrun wrote the part of Jennifer specifically with Chelsea Collins in mind. When he first offered it to her their Sophomore year in high school, she turned it down, citing scheduling conflicts. Part of the reason the film never got made during Zebrun's high school tenure was because of his reluctance to re-cast the role, feeling that Collins was perfect for it.
Although the school is never mentioned by name in the film, in the original script it was referred to as Addie Ross High School. Addie Ross is the name of a character from one of Nicholas Zebrun's favorite films: A Letter to Three Wives (1949). Despite this, several shots of the school and letter jackets are often shown with initials SHS, or Southwest High School - where the bulk of the movie was shot.
Three high schools and two college campuses where edited together to form the High School. Southwest High School (Nicholas Zebrun and David Sowden's alma mater; used for most of the interiors), Arlington Heights High School (most of the exteriors and occasional interiors) and Trimble Tech High School (selected exteriors) where all used together. Both Texas Christian University (TCU) and Tarrant County Community College (TCC) South Campus where used for selected interior and exterior shots during their summer school program when high school shooting was deemed impossible. The school was intended to be a labyrinth of halls, parking lots and classrooms. Thus shots and locations were purposely designed not to match up, so as to give a sense of disorientation and confusion - recreating the blur of classrooms and buildings that formed several of the crew members' high school years.
Nicholas Zebrun: [The Hulen Corporation] The driver's ed instructor holds up a manual sponsored by the Hulen Corporation, a company used in most of Nicholas Zebrun's productions.
Nicholas Zebrun: [long take] Inside the car with Greg and Melissa late at night, the entire shot lasts two minutes.