19 Thoughts I Had Watching ‘Cruel Intentions’ for the First Time

Selma Blair, Reese Witherspoon, Sarah Michelle Gellar, and Ryan Phillippe in Cruel Intentions
Everett Collection

[Warning: The following contains MAJOR spoilers for Cruel Intentions.]

I’ll admit it: I am a romance writer, but I’ve never seen Cruel Intentions. Blame it on me being Gen Z. The movie came out in 1999. I wasn’t even born yet.

But everything changes today.

This viewing is monumental for multiple reasons, but most importantly, it marks the first of Swooon‘s new First Time series, in which our staff catches up on our individual romance blind spots. Cruel Intentions for me, Heated Rivalry, You’ve Got Mail, Barbie as the Princess and the Pauper, and more beloved love stories for others.

When I sat down to watch Cruel Intentions, I have to say, I had no idea what I was in for. I knew a little bit about the recent Prime Video series starring Sarah Catherine Hook, but I have to say, the masterpiece led by Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon, and Selma Blair was not on my radar.

Below, you can find my full, unabridged thoughts from my introduction to Cruel Intentions. But first, I’d like to share the Swooon-notes version of my opinion.

Here’s my summary: A man quits therapy and destroys the lives of numerous people in order to sleep with his stepsister. He promptly dies. For that reason, my key takeaway from Cruel Intentions is that men need therapy to avoid destructive behavior and untimely death. Sebastian Valmont, I’m looking right at you.

Cruel Intentions, Streaming, Amazon Prime

Cruel Intentions movie opening
Prime Video

1. First impression: I’m dizzy. Why does this begin with minutes of spinning graveyard? (Note: I should have picked up on this foreshadowing, but I was simply too dizzy for critical thinking.)

Swoosie Kurtz as Dr. Greenbaum in Cruel Intentions
Prime Video

2. Is it just me, or are therapists not supposed to touch their clients? Dr. Greenbaum (Swoosie Kurtz), I would not recommend your practice.

Selma Blair as Cecile in Cruel Intentions
Prime Video

3. Who is this diva?! A) I love the koala shirt and desperately need one. B) Please don’t tell me this entire movie won’t be these siblings picking on Cecile. She’s so precious, and they’re so… odd.

Sarah Michelle Gellar as Kathryn in Cruel Intentions
Prime Video

4. Speaking of costumes I want in my closet, when I saw Kathryn’s accessory, I thought, “Wow, Kathryn has a freakishly large cross.” Little did I know, a baby spoon was inside for easy access to cocaine. Here I was thinking this was something I could go pick up at Hot Topic, and BAM, drug paraphernalia. Still, maybe I could use the tiny spoon for tiny soup or something. I’m open to suggestions.

Sarah Michelle Gellar and Ryan Phillippe as Kathryn and Sebastian in Cruel Intentions
Prime Video

5. WAIT, WHAT?! Is that not your stepsister? Stop grabbing her boob! Don’t put anything anywhere that’s your stepsister! Dearest Dr. Greenbaum, my earlier qualm was a speculation. Now I know that you are clearly not a very good therapist because your client is about to make out with his STEPSISTER!

Reese Witherspoon and Ryan Phillippe as Annette and Sebastian in Cruel Intentions
Prime Video

6. Honestly, this would be a pretty cute meet-cute if he weren’t staring at Annette’s butt the whole time. And he didn’t just try to kiss his stepsister. And he wasn’t trying to swindle Annette into sleeping with him. And he wasn’t just doing it to sleep with his stepsister. You know what, I take it back. From zero angles is this a cute meet-cute.

Selma Blair and Sean Patrick Thomas as Cecile and Ronald in Cruel Intentions
Prime Video

7. String instrument playing should never — and I mean never — be this sensual.

Sarah Michelle Gellar and Hiep Thi Le as Kathryn and Mai-Lee in Cruel Intentions
Prime Video

8. New favorite character unlocked! Mai-Lee (Hiep Thi Le) is soooooo over Kathryn’s BS. (Note: Mai-Lee was never seen again.)

Ryan Phillippe as Sebastian in Cruel Intentions
Prime Video

9. If someone looked at me the way Sebastian looks at Annette in that indoor swimming pool, I would simply doggie paddle away. There is no shot of playing mermaids with the holder of that creepy gaze.

Eric Mabius as Greg in Cruel Intentions
Prime Video

10. Thou shalt not give thineself thine own nickname. And if you do, why would you ever make it the Gregster? Why, Greg, why? Least favorite character alert. Gregosaurus Rex was right there.

Reese Witherspoon and Ryan Phillippe as Annette and Sebastian in Cruel Intentions
Prime Video

11. I think I just got the ick. Is it possible to get the ick from Reese Witherspoon, Ms. Elle Woods herself? Honestly, I’m frightened.

Selma Blair as Cecile in Cruel Intentions
Prime Video

12. They can’t make me hate you, Cecile. You are too precious for this school, this movie, and this life. This song is about to go multiplatinum in my house.

Reese Witherspoon and Ryan Phillippe as Annette and Sebastian in Cruel Intentions
Prime Video

13. Wait, are Annette and Sebastian going to pound town in Penn Station? The NJ Transit I know and love would not stand for this! (Note: JK, that’s totally not Penn Station. We’re in the clear, commuters.)

Ryan Phillippe as Sebastian in Cruel Intentions
Prime Video

14. I’m going to ignore the weird seduction happening in this scene and focus on the scenery. Why does she have a framed photo of herself? Why don’t I have a framed photo of myself? Why does her mirror have a smaller mirror friend?

Sarah Michelle Gellar as Kathryn in Cruel Intentions
Prime Video

15. I’ve gotta be real, I don’t think Sebastian loved Annette. I DO think Sebastian felt a feeling for the first time. But those two things are not the same.

Reese Witherspoon as Annette in Cruel Intentions
Prime Video

16. If someone gave me their detailed sex journal saying how he tricked me into sleeping with him, I would simply not forgive him.

Reese Witherspoon and Ryan Phillippe as Annette and Sebastian in Cruel Intentions
Prime Video

17. DID HE JUST GET HIT BY A CAR?! I swear, if she takes him back because he got hit by a car, I’m gonna lose it. He’s barely even bruised. ‘Tis but a teeny weeny scratch!

Cruel Intentions Funeral
Prime Video

18. WAIT, SEBASTIAN DIED?! He was so uninjured. Like, barely scratched at all. You mean to tell me this is his funeral? This is not where I expected this story to go.

Selma Blair and Sarah Michelle Gellar as Cecile and Kathryn in Cruel Intentions
Prime Video

19. Was this the original Burn Book? I’m sensing some parallels. Except, this book contains detailed sexual encounters with almost everyone at the school, and yet everyone seems cool with it besides the lone burnee, Kathryn. Kathryn, in times like these, we must turn to your friend from another life, Scooby Doo, say, “Rut-Roh, Raggy,” and move on.