For legal reasons, writer and director Roger Kumble had to ask all of the actresses auditioning for Cecile how old they were, because of a sex scene between the character and Sebastian in the movie. "So we were bringing in all of these people", he recalled to Cosmopolitan, "and they were all good, but I remember Selma (Blair) came in and I said, 'How old are you?' And she goes (in Cecile's bratty voice) 'How old are you?' And she was so obnoxious, and I couldn't get it out of my head."
Columbia Pictures wanted Katie Holmes to play Annette Hargrove, but writer and director Roger Kumble didn't think she had enough strength of character for the role. Ryan Phillippe was already signed on as Sebastian Valmont when Kumble asked about his girlfriend, Reese Witherspoon. "So, basically, we took Reese out to dinner to get her drunk, and we ended up getting drunk," Kumble revealed in 2014. "And I literally got down on my knees and begged her: 'Please, it'll be fifteen days, you'll be great.'" Witherspoon agreed.
The movie was originally called "Cruel Inventions," but test audiences thought that made it sound like a science fiction film, so the name changed before it was released.
An avid collector of antique books, Sarah Michelle Gellar owns an early edition of Pierre Choderlos de Laclos' "Les Liaisons Dangereuses".
During the movie, Ryan Phillippe and Reese Witherspoon were dating. The couple got married three months after the movie's release and had two children together, but ended up divorcing in 2008.