The Vicious Kind
Tags: bleak, romantic, comedy, entertaining, flashback

Plot synopsis:
The film opens with Caleb Sinclaire sitting in a diner, forlorn and smoking a cigarette. He begins to cry, but composes himself when his younger brother, Peter approaches the table. Peter is an idealistic college student on Thanksgiving break and Caleb is begrudgingly giving him a ride home. At school, Peter has found a new girlfriend, Emma Gainsborough, and Caleb immediately grills him for details. Emma and Peter met each other while Emma was on campus meeting some fraternity boys; while Peter says she’s a good girl and nothing happened, Caleb immediately perceives her as a whore. On the way to get Emma, Caleb reveals that he hasn't slept in a week.
Caleb is immediately antagonistic to Emma. Caleb drops them off at his father, Donald’s house, revealing to Emma that he and Donald do not get along and this will be the last time he will see them this weekend. Donald comes off as well-meaning, if somewhat flirtatious.
Caleb meanwhile, has been trying to sleep, but keeps seeing images of his last girlfriend, Hannah, who behaves and looks strikingly similar to Emma. Hannah has continuously called Caleb, so he drops off pictures of himself having sex with a prostitute named Samantha at her doorstep, ringing the bell and fleeing.
Caleb, arrives at work and belittles fellow worker JT. Later, Emma and Peter go bowling and Caleb secretly watches them. In the bowling alley lobby, Caleb bumps into Emma. They have an awkward conversation and she asks him for cigarettes, revealing she secretly smokes. Caleb obliges; Emma asking him to promise not to tell Peter, and Caleb asking not to reveal he was there to Peter or Donald.
Later Caleb runs into Emma. He ends up viciously physically and verbally attacking her, and threatens her not to hurt Peter, who is a good kid (and a virgin). Moments later, he breaks down, begging her forgiveness. Confused and outraged, Emma punches him, bloodying his nose and dropping him to the pavement. Caleb sits on the ground crying and apologizing.
That night, Emma sneaks out for a cigarette and meets Caleb trying to sneak around the yard with a camera. Emma wants an explanation about what happened earlier. Caleb goes into his belief on what he heard about her at school, his girlfriend Hannah who cheated on him, and his lack of sleep, which has further muddled his actions and behavior. Caleb eventually leaves, feeling better after these confessions.
The next morning, Donald and Emma go jogging together. Emma asks about Peter’s mother, and Donald reveals that she died when Caleb and Peter were young. Donald also says that his wife cheated on him prior to being diagnosed with cancer and that no one came to visit her in the hospital the last four months of her life. At work, Caleb reveals he managed to fall asleep for a few minutes the night before.
At a cheap restaurant, Caleb, Peter and Emma are together. Caleb and Emma get a few moments alone, and Caleb assures her that he doesn’t have feelings for her. Caleb ends up forcibly kissing her. Emma says nothing about it to Peter. Caleb privately warns Peter to watch Emma carefully, because she's been eyeing him. Peter says he’s in love with her and wants to give her his virginity, and Caleb laughs at the idea. Caleb apologizes for his ideas that she was a whore.
While Peter and Emma prepare to have intercourse, Peter reveals that what Donald told her is true, except that Caleb was the only one to see their mother before she died, and Caleb and Donald haven’t spoken to each other since. Caleb goes to see Samantha, and asks her if it’s normal to be in love with a perceived image of someone, even if that’s not who they really are (likening Emma to Hannah). Caleb asks Samantha if she was abused as a child, and Samantha is offended. Caleb loses his temper, then comes back and gives her a better tip, implying that his perception and treatment of women is evolving.
Caleb tries apologizing to Emma for kissing her and says he’ll try not to bother her anymore. Emma reveals she has accidentally locked herself out of the house, and Caleb manages to get them both inside through a window. Emma falls on top of Caleb, and they seem like they might be about to kiss. But she rebukes him and asks him never to see her again. Caleb leaves, and Emma returns to the place they embraced to masturbate.
At a bar, JT asks Caleb if he’s had sex with Emma yet, and he says no, but he wants to. He spots some men sexually harassing a woman and ends up fighting them, marking another change in him.
Peter tries to have sex with Emma but ejaculates prematurely. Caleb drives over to see Emma, and this time, she doesn’t rebuke him when he kisses her, and eventually, they end up having passionate sex in Caleb's old room.
Emma asks why Caleb was the only one to see his mother before she died. He reveals he was hurt by her cheating, and shut her out of his life. However, he eventually discovered that Donald had been the one cheating until his wife finally left, never thinking that he would refuse to let her see her sons. Caleb never told Peter because he was only 12. Emma tells Caleb she was a virgin. Caleb leaves and reminds Emma that Peter is in love with her. On his way out, he runs into his father who deduces what happened and says he’ll tell Peter. Caleb calls him a coward for erasing him out of his life; in the last 8 years, Donald never attempted to re-enter his life. They both hide quickly as Peter goes to Emma’s room, and Caleb dictates to Donald that he won’t tell Peter what he did, otherwise he’ll tell him Donald’s secrets and he’ll lose both his sons. Peter and Emma sleep together, and he loses his virginity to her.
The next morning, Donald drives them to the train station back to school. Donald confesses that he’s made mistakes to Peter, and that sometimes, people know what they are doing is wrong but they do it anyway, because the right thing is painful. On the train, Peter tells Emma he loves her, but it causes Emma to cry. The two of them alone again, Caleb rings Donald’s doorbell and Donald invites him in, their relationship beginning to mend at last.