There are three distinct storylines going on in Cruel Intentions. One of them connects the other two. In it, step-siblings Kathryn (Sarah Michelle Gellar) and Sebastian (Ryan Phillippe), make a bet. They, being incredibly popular, wealthy and manipulative, decide to see if Sebastian will be able to get a virgin named Annette (Reese Witherspoon) into bed. She’s staying at their summer house for the summer, giving him a month or two to attempt it. If Sebastian is successful, he gets to spend a night with his step-sister, seemingly the only woman in the world he can’t have. If she wins, and he fails at his seduction, she gets his car.

That’s the overarching storyline that holds the rest of Cruel Intentions together. Each of these two characters has a separate story as well. Sebastian’s is obvious: He has to try to get Annette to fall in love with him, which she claims is the only way she’ll lose her virginity. Kathryn, on the other hand, becomes a tutor to the naïve Cecile (Selma Blair), someone who is willing and ready to experience more of the world.

Oh, and did I mention that these characters are all in high school? Their outfits and the fact that, at the time of filming, they were all in their early-mid twenties makes them seem a lot older, not to mention that the three out of the four are all made to act more mature than your average high schooler. If the film didn’t let us know that they were in a prep school, I would have guessed they were all in college. The only “young” character is Cecile, who is supposed to be just entering high school, despite her actor being several years older than the rest of her co-stars.

Despite the two leads getting their own story, Kathryn’s falls into the background and is eventually ignored completely without even really finishing. Granted, there’s not a lot that you can do with it after you reach a certain part, but some amount of closure with it would have been nice. The focus is on Sebastian and Annette, or Sebastian and Kathryn, and while a few other characters come and go, the only real interest that Cruel Intentions generates comes from one of these two storylines.

The first one is enjoyable because it features character growth on the part of Sebastian, while also presenting us with two actors who have a lot of chemistry (considering they were dating and eventually became engaged while the film was in production, this isn’t surprising). The other plotline is interesting because it’s more or less a battle of wills between Kathryn and Sebastian. Their banter, while never really going anywhere, is fun to listen to, and they seem like two peas in a pod. They’re both manipulative and downright nasty people, but engaging because of this.

The film is an adaptation of the French novel Les Liaisons dangereuses. Considering that the novel was written in the 18th century, it’s fairly obvious that it did not take place in New York in the 1990s, like our film. The setting has been changed, which is an interesting development. It perhaps allows for more freedom in the story, while also making it more appealing and commercially available. I like the decision, especially considering there’s a fine film that was released in 1988 that already set this story in the period it was designed for.

It’s all really cliché, and you’ll probably figure out the majority of the story way too early for it to make much of an impact. The ending is the only surprise, although only one element of it will come as a shock. The rest is pretty standard affair, which remains enjoyable only because of the characters. Not the actors, as they’re mostly wooden (in the case of Gellar, Phillippe and Witherspoon) or way too over-the-top (Blair and pretty much everyone else), but the characters themselves who are interesting.

Despite the interest, watching Cruel Intentions isn’t always easy. Take, for instance, the opening scene, which shows Sebastian both taking advantage of his therapist, while also taking advantage of his therapist’s daughter. He’s ruined the daughter’s life, and when we learn about this, the film plays it for laughs. He has done genuine damage to someone’s life, and yet the cheesy music begins to play, and we learn that we’re supposed to be rooting for this guy. Almost all of the sexual predators’ scenes come off this way. It’s all light-hearted fun for them, which is somewhat off-putting. Interesting, sure, but it’s not always easy to watch them so easily manipulate people simply for the sake of destroying them.

I’m not sure if I really enjoyed Cruel Intentions, but it’s a film that’s worth watching if only for its characters, which were well-written and intriguing. Seeing them manipulate their victims might not be endearing, but it’s engaging. The story is full of cliché, and the actors aren’t exactly all that good, but I still can’t say that I had a bad time while watching it. This is a film that takes an 18th-century novel and transplants its setting to New York in the 1990s. I was always interested in what would happen next, and I have to give it a slight recommendation because of that.