8. The Rules of Attraction (2002)
The Rules of Attraction is the film that took James Van Der Beek out of the creek and into a drug-fuelled college love triangle. The film was completely panned when it was released and, granted, is not the best piece of filmmaking but that doesnt stop it from being anti-love. The characters are a bunch of superficial, self-centred, nihilistic liars who love themselves far more than they could ever love anybody else.
Why is it anti-love? In The Rules of Attraction love triangle the heart-broken is also the heart-breaker, the only thing stopping it from becoming a huge cycle of emotional destruction is that the love is shallow and meaningless.
Most anti-love moment? There are times when the person you are in love with doesnt feel the same way, and then there are times when the person you are in love with is completely oblivious to your existence even after you kill yourself for them.