Caroline sleeps around and causes at least two guys to have emotional breakdowns over her callous attitude towards them. She's also suffering depression and having a hard time adapting to a new town.
Barry is reeling from a breakup that he can only handle by writing a novel where he's a troubled hero. While he does do some dubious things like sleep with a student and threaten to kill another out of jealousy, there's no doubt he needs serious help.
He Really Can Act: After Kat Dennings gained a reputation for playing quirky comedic characters, she proved here that she can also do dramatic roles.
One of Thurston's friends takes some homemade drugs during chemistry class. He's then perplexed by the teacher's increasing sense of panic as she looks straight at him. And that's when we find out that he's having an out-of-body experience while his body lies convulsing on the floor.
Barry's Sanity Slippage, causing him to make death threats and very nearly attempting suicide.
The car accident in the film's climax. The serial killer is found impaled on a massive wooden pike.
Unintentionally Unsympathetic: Thurston is supposed to be the better alternative to Barry, but he's only ever shown to be little more than a drug addict who falls head over heels for the first girl who'll sleep with him.
