Detective Cassie Mayweather (Bullock) suspects more at work than an unplanned act of violence when a young woman is found strangled to death in a ditch. Her gut instincts get her in trouble with her supervisors, but they lead her correctly to privileged, smug high school student Richard Haywood (Gosling)... and from there to brooding Straw Nihilist Justin Pendleton (Pitt). The connection between the two boys is more than imagined, and as their mind games played with the police and with each other grow still more complicated, Cassie attempts to find some way to put an end to their plans.
This film provides examples of:
- In Medias Res: The film opens with a scene from about its middle.
- It Works Better with Bullets: Richie uses this trope during an attempted suicide pact with Justin. It fails majestically.
- No Sense of Personal Space: Richard doesn't really care about personal space around Justin. He invades it on a daily basis and makes a point out of hugging him any chance he gets. Not that Justin seems to mind all that much.
- Outlaw Couple: Face it, this film is built on Ho Yay.
- Prisoner's Dilemma: The detectives try to pull a classic Prisoner's Dilemma in the interrogation scene, but the trust between the prisoners and the arrival of the lawyers prevents the defection.
- That One Case: It haunts Cassie's career and clouds her judgement, since her current suspect reminds her of the perp. That case being her own attempted murder at the hands of an abusive husband.
- Very Loosely Based on a True Story: Very, very vaguely inspired by the Leopold and Loeb case.
- You Taste Delicious: Richie licks Cassie's face during their last scene together.