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This film was originally a TV series based on Cruel Intentions 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 the fall of 1999, but the show was canceled before any of the episodes aired. The scene where Cherie has orgasms on the horse in Episode #1.3 reportedly outraged Fox chairman Rupert Murdoch. New explicit scenes and dialogue were added to footage from the pilot and the first two episodes to make this film. The plot was reworked to serve as a prequel to Cruel Intentions rather then a re-telling.
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Sebastian says "God, we sound like a canceled television series" and that's exactly what happened.
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The trailer (that's included with the DVD release) features a lot of scenes that were originally recorded for the TV series and never show up in the movie.
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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, 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.
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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".
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After agreeing to take Danielle to a James Van Der Beek movie, Sebastian (Robin Dunne) mentions how he feels like a loser for "taking the school virgin to see Dawson." Robin Dunne guest-starred in 4 episodes of Dawson's Creek in Season 3.
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