Sebastian says "God, we sound like a canceled television series" and that's exactly what happened.
This film was originally a TV series based on Cruel Intentions (1999) titled "Manchester Prep" with three hour-long episodes filmed: the pilot (#1.1), Pretty in Plaid (#1.2), and Disfunction Junction (#1.3). They were scheduled to premiere on the Fox network in September 1999, but the show was canceled before any of the episodes aired. According to Tane McClure, Fox execs felt the series was too much because it was dealing with teens having sex and this was to be a prime-time show. Also, the scene where Cherie has an orgasm on the horse in Episode #1.3 reportedly outraged Fox chairman Rupert Murdoch. Producers quickly regrouped and decided to turn it into a movie. New explicit scenes, nudity, and dialogue were added to footage from the completed episodes. The plot was reworked to serve as a prequel to Cruel Intentions rather than a retelling or sequel.
Sean Patrick Thomas returned from the first film portraying a different role but his scenes were left out of the final cut.
In order to change the storyline from its original structure, several characters got their names changed with the help of dubbing techniques. For instance, Danielle Sherman was originally named Annette Hargrove and Cherie Claymon was originally named Cecile Caldwell.
On the DVD, there are 'Talent Files' for each of the four main actors (Robin Dunne, Amy Adams, Sarah Thompson, and Keri Lynn Pratt). Keri Lynn Pratt played 'Cherie Claymon', but in her file, it lists her character as 'Cecile Caldwell'. Cecile Caldwell doesn't appear in this film. She is played by Selma Blair in the original Cruel Intentions (1999), which takes place years after this film. However, Cecile and Cherie both have a few things in common: they are both daughters of socialites; ditzy; virgins when they start at Manchester; and both lose their virginity while attending there.