A few years before the events depicted in the 1999 film. It follows the lives of rich step siblings Sebastian Valmont and Kathryn Merteuil as they playfully manipulate the people surrounding them at their exclusive New York prep school.

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 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.

Sebastian:
[as they are kissing] You do realize you're my step sister.


Kathryn:
You know what they say about incest.


Sebastian:
Is there any line you won't cross?


Kathryn:
Only one... never in the butt.


Sebastian:
That's a good line.


Kathryn:
The Bradys never had it so good.

Boom mic visible: At the start of the film after Sebastian leaves the principal's office, as the principal says "Pansy" the reflection of a boom mike in the glass door above him is clearly visible.

Written by Greg Lattimer
Performed by Thin Lizard Dawn