Things Only Adults Notice In Cruel Intentions

Dark teen dramas were all the rage in the late '90s. Films like Fear (1996), The Craft (1996), Wild Things (1998), and Jawbreaker (1999) proved that high school era narratives can be intense and dangerous while still capturing the nuances of adolescence. Cruel Intentions (1999) fit right into that mold of movies that subverted the bubbly teen movie genre and took its characters into twisted new territory.

The film centers on a pair of wealthy step-siblings named Sebastian Valmont (Ryan Phillippe) and Kathryn Merteuil (Sarah Michelle Gellar), who decide to play terrible games with people's lives, including innocent young women like Cecile Caldwell (Selma Blair) and Annette Hargrove (Reese Witherspoon). Sebastian and Kathryn aren't afraid to use sex, drugs, and sinister scheming to get their way, no matter who gets hurt in the process. 

While the movie was popular and certainly made its mark at the time of release, it hasn't exactly aged well. Those who try to revisit Cruel Intentions in adulthood might find that there are a lot of unintentionally confusing and unsettling moments scattered throughout the film. Here are some of the things you'll only notice about Cruel Intentions as an adult.

A hack therapist

When we first meet Sebastian, he is finishing up a session with his therapist, Dr. Greenbaum (Swoosie Kurtz), and it is pretty clear she is not very good at her job. She is constantly checking the clock, tuning him out, and even shilling her book to him, and what's worse is that she gets a little too personal for the typical patient-psychiatrist relationship. It's bad enough when she hugs him, but she then proceeds to tell him highly personal details about her own life, including her daughter's name and where she is planning to attend college. 

None of this is news to Sebastian, of course, but the fact that she so eagerly pierces the veil of professionalism — and even forgets to tell him that their sessions are about to end — means she must not have paid much attention to the ethics portion of her training. Anyone who's been to a therapy session or even just seen one on TV knows this is not how a shrink is supposed to behave.

A botched manifesto

When Sebastian sets his sights on Annette Hargrove as his next target of seduction, it's because she's written an op-ed in an issue of Seventeen magazine about why she plans to wait to have sex until marriage, and he sees her as a real challenge. 

Interestingly, the cover shown is from the real February 1997 issue featuring Jennifer Love Hewitt, and that choice may be an intentional Easter egg, since that was the same year Ryan Phillippe and Sarah Michelle Gellar starred with Hewitt in I Know What You Did Last Summer. Furthermore, if you press pause on the film when they show Annette's article, there are only a few lines that are actual writing, and the bulk of the piece is nonsensical typesmash. 

So, all of those lines that Sebastian so disdainfully reads off from Annette's piece are completely fabricated and don't even appear on the page. Considering the props team took the care to make an elaborate graphic to showcase her commitment to marrying before making love, the failure to actually finish the article — to include, at the very least, the words that are being attributed to it — is rather hilarious in retrospect.

A cheap shot

The LGBTQ community is not the only group that is bound to have a problem with what they see and hear in Cruel Intentions; the film also casually tosses in an unnecessary line that is bound to distress disabled people as well. 

In a scene in which Kathryn and Sebastian are discussing the progress of their plan to sully the reputation of Cecile Caldwell, whose only crime is to accidentally attract the interest of Kathryn's ex-boyfriend Court Reynolds (Charlie O'Connell), she airs her dissatisfaction with Ronald Clifford (Sean Patrick Thomas)'s speed of courtship of the character. "Unfortunately our Don Juan is moving with the speed of a Special Olympic hurdler," she says nonchalantly about the situation. 

Even assuming the remark is meant to underscore the brazen thoughtlessness of Kathryn, it is still pretty jarring to hear her use such provocative turns of phrase without consequence like this. Her complete disrespect for marginalized groups is not truly paramount to the overarching narrative, since her actions speak loudly enough on their own, so the offensive line could have easily been removed without detracting from the story.

A casual racist

Cruel Intentions can also rightly be criticized for its lack of cast diversity, as both the central cast and most of the supporting players are white. The one exception is the character Ronald, who, despite being a pre-Juilliard student who lives at the posh locale of 45th Street and Park Avenue, is made to suffer the ignorance of Mrs. Caldwell (Christine Baranski). 

After she discovers that Ronald and Cecile have a budding romantic relationship, she confronts him by saying, "I got you off the streets and this is how you repay me?" Once he corrects her about his status, she snipes back with, "Oh don't give me any of that racist crap! My husband and I gave money to Colin Powell." Unlike the LGBTQ slurs and unnecessary disability diss, the exchange actually serves to elucidate Mrs. Caldwell's biases in a way that is relevant to the plot, but even so, hearing her all-too-realistic racist remarks is still incredibly uncomfortable.

A confusing character witness

The backstory of Greg McConnell (Eric Mabius) is nebulous. We're told he attended Manchester Prep School in New York before going to college in Kansas on a football scholarship. Since Annette is from Kansas, he's suspected to be the secretive source of damaging intel that she has received about Sebastian before meeting him. But when that turns out not to be true, he's asked to go back to Annette and change the narrative with nice stories about Sebastian instead. 

In the course of that conversation, he suggests that they have been close for a long time — even going so far as to say he considers her "like a sister" — but their connection makes absolutely no sense for two reasons. Not only has he apparently just moved to the area, while Annette has been there her whole life, but he also has zero credibility as a character witness since he refers to himself as "the Gregster," casually jokes about sexual assault and has a reputation for bravado as a "football stud." In other words, the idea that he knows Annette well enough to shepherd her, let alone be taken seriously as a source, is completely flawed.

An outright assault

Perhaps the most pernicious point in Cruel Intentions comes when Kathryn and Sebastian scheme to sully Cecile's reputation at her new school by "speed[ing] up her sexual awakening." They decide that to encourage her relationship with Ronald, and steer her away from Court Reynolds, Sebastian should seduce her and introduce her to the practice of sex. 

As awful as the plot is, the execution is even more deplorable. Sebastian invites Cecile over under the guise of helping her draft a love letter to Ronald and proceeds to get her intoxicated with a Long Island Iced Tea (which she does not know is alcoholic). After that, he threatens to expose her for sneaking out to her mother unless she lets him give her "a kiss" and then proceeds to perform oral sex on her without permission. 

The next day, when she confides in Kathryn that she feels taken advantage of, Cecile is told she should be happy about what happened and seek out more sexual encounters with Sebastian. In other words, Cecile not only endures sexual assault, but she is also then coerced into returning to her attacker's arms, which makes the scenes totally triggering and outrageous.

A quickfire courtship

The progression of Annette and Sebastian's romantic relationship is dizzyingly fast, to the point that it is hard to believe they are able to develop the deep, meaningful bond that supposedly unfolds. In one scene, for example, she's shown clasping his hand as a first sign of interest after a day spent volunteering together; and by their next encounter, he starts scolding her for "turn[ing her] back on love," just like that. In other words, they go from barely friends to forever in no time at all. 

Not only is he still carrying on his other dalliances all the while, which means he's probably not as serious about her as he's letting on, but there's very little substance to their connection as a whole, so her sudden about face on the subject of premarital sex is rather suspect as well. Mature audiences might have a harder time believing that a young woman who stayed abstinent throughout a year-long relationship and wrote a national magazine article about that decision would change her mind so quickly, especially since it's confirmed in the film's dialogue that everything transpires over the course of just a few days.

A parting gift

Like much of the movie, Cruel Intentions' ending is also a head-scratcher. By the final scene, Sebastian has died from being run over by a car while saving Annette, who was accidentally pushed into traffic by Ronald during a streetside confrontation conveniently coordinated by Kathryn. As if that whole encounter isn't strange enough, what happens next is even more contrived. 

Kathryn speaks at Sebastian's memorial service, and her squeaky clean image is finally tarnished when Annette and Cecile distribute copies of Sebastian's journal, which contains all the dirty details of the siblings' scheming and her secret drug habit. Somehow, the students who get their hands on the thick manuscript manage to read it at lightning speed because they start casting aspersions at Kathryn almost instantly upon receipt of the journal. 

Meanwhile, Annette somehow cruises away in Sebastian's prized Jaguar, despite the fact that she probably has no claim to the car, and the memorial service hasn't even concluded yet. In other words, the film gives little weight to realism right up to the very end, and anyone with even a casual understanding of the way the world works would see right through it all.