Look, I know it would have been much more appropriate (and maybe cooler) to do a rehashing of why Cruel Intentions is still amazing on its 15th anniversary (you know, last year), but I’m not really one for conventional things anyway. I mean, I do work at Playboy.

I was 16 when I first watched Cruel Intentions, so I was already over my first horrendous kiss and thought I know knew everything about relationships. Well after watching this movie sneakily at my friend’s house, I realized I didn’t know shit about sex, french kissing, oh and yeah, lesbian kissing. So in my book, every year is a good year to celebrate a movie that literally helped most millennials through puberty. And what better way to commemorate Cruel Intention’s birthday than with 16 of its hottest scenes…via GIFs. Because why not?

1.This pickup line

2.This other rather blunt pickup line

3. Kathryn is pretty much the definition of sex

4….And she invented resting bitch face

5. Cecil and her uh, faces

6. This advice

7. We’re not responsible. I swear.

8. The movie’s honesty…

9. The fact that Sebastian is pure evil and it’s amazing

10. Kathryn’s self worth is admirable

11. Eye roll’s galore

12. That time when anal was put on the table

13. They told only the best secrets

14. The blackmail was spot on

15. Sebastian and Kathryn invented ‘90s cool


Nicole Theodore is an editorial assistant at Playboy.com. She practiced kissing on her hand for an unmentionable amount of time. Follow her on Twitter.