In order to prepare for their roles, the leads were all put through a finishing school two weeks prior to filming. However, in contrast to the film's depiction, Wellesley College was never a finishing school. It was a private women's liberal arts college which emphasized social activism.
Krysten Ritter and Lily Rabe, now both well-known actresses, appear in numerous scenes as extras - playing students in the art history class.
Prior to the film's premiere, the producers held a special presentation of the film for Wellesley alumnae who had graduated in 1954. However, this publicity stunt back-fired when the graduates ridiculed the film as historically inaccurate. Among the many complaints voiced by the graduates: No one wore pearls, earrings or girdles to classes. Instead, students wore jeans and sweatshirts. No instructor ever encouraged them to marry or to be submissive. In fact, students were renowned for knitting in class and having food-fights in the corridors.
Part of the film was shot at Columbia University from which both Julia Stiles and Maggie Gyllenhaal graduated.
The war story that Bill Dunbar tells during his Italian class is borrowed from the World War I novel "All Quiet On The Western Front" by Erich Maria Remarque.