Things Re-Watching 'Cruel Intentions' Taught Me

ICYMI, on Thursday night, something incredible happened: The ladies of Cruel Intentions — that is, Sarah Michelle Gellar, Reese Witherspoon, and Selma Blair — met up for a girls' night that was years in the making. Sixteen years to be exact. Apparently, the gals reunited to attend a performance of the musical parody of the film they all starred in back in 1999. Understandably, seeing those three women together made me want to re-watch Cruel Intentions for the first time as an adult — considering the film pretty much defined an entire generation, I was curious to see how I'd react to it now, so long after the movie was originally released.

But, like with any movie (or book or song) that seemed so significant when you were young, experiencing it as an adult is something completely different — and that's exactly what happened with Cruel Intentions. From my perspective now, as an adult, the film was cringeworthy at times, kind of still hot at others, a little too obvious in some places, and incredibly empowering in others. In other words, it was a lot.

I also realized there are a lot of things many viewers probably didn't notice in the film when they were younger — like, for instance, the following:

1. It Is SO Obvious That Sebastian Is Going To Die From The Beginning

The film starts out with an abstract pan across a cemetery, guys. A CEMETERY. Then, as the camera widens out, it catches Sebastian, speeding down the highway toward the New York skyline in his Jaguar roadster. There is so much foreshadowing in that first minute, it's almost painful — or, maybe genius. Either way, the answer was in front of us all along.

2. Did This Movie Just Create Revenge Porn?

Sure, acts of revenge have always been around in various antiquated ways, but the Internet made it easier for terrible people everywhere to impart revenge on people who rejected them by posting private, often sexual pictures and/or videos of them online. It's a terrible, awful, heinous thing — and I'm pretty sure Sebastian was one of the first to have done it in this film, when he posts personal photos of his psychologist's daughter online. Sort of makes the fact that we're supposed to like this guy by the end of the movie even more ridiculous.

3. The Half-Up Hairdo Was Never Anyone's Friend

No. I love you, Reese Witherspoon, but no.

4. It Got Pretty Problematic

The number of times the characters use the word "gay" as an insult in casual conversation is disturbing. Also, the side plot of Greg, the star athlete, being blackmailed into giving up information about Annette in exchange for keeping his homosexuality a secret is pretty problematic — and the way that Sebastian entraps him during a rendezvous with Blaine is horrible to watch.

5. Kathryn's Speech About Double Standards Is RIGHT. ON.

It's one of the few moments where I actually rooted for Kathryn: In a brilliant monologue directed at Sebastian, she calls B.S. on the fact that Sebastian is excused for his sexual transgressions, while she is considered promiscuous because of them. Even though the movie had its problems, this speech was absolutely on point.

6. The Symbolism Is Over-The-Top.

Really? A bowl of cherries are sitting next to the bed after Cecile loses her virginity? OK.

7. The Entire Plot Is Contingent Upon Convincing Girls Who Don't Want To Have Sex To Have Sex.

While Annette decided to change her values in the end because she loves Sebastian, the fact that this entire film is one long string of sexual assaults, coercions, and exploitations is really problematic. Not cool, 1999. Not cool.

Images: Columbia Pictures (8)