The film actually opens with I Yurim (Bak Haeil), a teacher at a middle school or high school, making an overtly sexual remark to Choe Hong (Kang Hye-jung) while sitting on a bench in front of the school. This slice is clearly taken out of time with the rest of the film, which proceeds linearly from there. Hong is a new student teacher assigned to Yurim and Yurim, although he has a girlfriend of six years and Hong has a fiance, propositions her for sex and continues to badger her in an attempt to get physically intimate. Hong, clearly reserved, takes a quiet passive approach to dealing with his advances and things get more entangled there, as we learn more about why Hong is a 27-year old student teacher.
Okay, first of all, Yurim is a slimebag and the film doesn't really hold back in how much of a slimebag he is. What he does to Choe in his single-minded pursuit of sex will be pretty close to unforgivable for most, especially in the first half of the film. He's dishonest, manipulative, coercive and abusive, but the film doesn't stop there and surprisingly humanizes him as the film progresses. This is somewhat problematic because the film (and Hong) almost seems to forgive his misdeeds, even though it doesn't let him be a karma houdini outright. The film is likewise complicated with Hong and Yurim's strange relationship as the power dynamic fluctuate as the two become more emotionally entangled. It's this factor that makes the story much more complex, and consequently, more interesting. It's that Yurim can't be painted as purely a villain, nor Hong as merely a victim that keeps the story interesting as well as watching the drama that erupts from their emotional development.
The film has a lot of handheld shots, which seemed to be in vogue during the mid-2000s in Korean filmmaking. It works in some scenes due to the uncertainty and underlying tension within them, but sometimes I felt like it was just a purely aesthetic decision that didn't add to storytelling in many other scenes. The production values are solid, as is typical for a mainstream-geared post-Korean New Wave film and writer-director Han Jaerim does a good job of keeping an eye on the storytelling, minus the handheld abuse mentioned above. However, with a film with characters as complex as Rules of Dating, a lot rests on the shoulders of the actors and Bak and Kang breathe a lot of life into their characters. Bak plays the slimebag Yurim excellently, convincingly showing his self-serving manipulation that he himself believes in, but yet maintains just enough of his humanity in the performance that it doesn't slip into farcical territory. Kang, on the other hand, has to play mouse for much of the film, which admittedly isn't too hard, but once her character starts opening up, she really captures her thawing well.
I end up with mixed feelings about this film, because of Yurim's sexually harassing character and how Hong eventually somewhat accepts him (not a good message, folks!). At the same time, I appreciate how the film paints neither character with broad strokes and honestly develops the characters and their strange relationship. Backed by strong performances, I can say that Rules of Dating is a genuinely interesting film, even if the story might be conveying a problematic message. As such, it might be an interesting film for some to check out, but I don't think it's for everyone. 6/10.