In a parking lot in Los Angeles, teenage filmmaker Eric [Matt O'Leary] tries to document the wannabe lifestyle of Allison Lang [Anne Hathaway] and her boyfriend Toby [Channing Tatum] and their circle of white, upper-class teens living in the Pacific Palisades. A tense brawl erupts between Toby's crew and a rival gang, and both sides scatter just before the police arrive. Later that night, Toby's gang heads to a party at Eric's house, where the complexities of Allison's relationship with Toby and the dynamics with her friends Emily [Bijou Phillips] and Sam [Joseph Gordon-Levitt] become more loaded. At the party's end, Allison performs oral sex on her boyfriend.
The next day, Allison meets with her father, Stuart [Michael Biehn], at work, and the awkward, strained exchange reveals a virtually non-existent relationship with her parents. Afterwards, she and her friends drive downtown into East Los Angeles, intent on buying marijuana, where they encounter Mexican drug dealer Hector [Freddy Rodríguez] and his crew. Toby tries to press Hector for more, but Hector pulls a gun and humiliates him in front of everyone; Allison manages to talk Hector into letting Toby go.
That night, Allison and her girlfriends return to the drug deal site and are invited to Hector's party at his house. Hector then points out a motel where his crew routinely parties, hinting at what lies ahead. The next day, Eric continues filming at Allison's home, and Allison turns his interview of her into a strange, mind-bending game that blurs the lines between reality and performance.
Later that evening, Allison meets Hector again in a store, where he gives a guided tour of his neighborhood. A forceful drug bust arrives, and Allison is arrested along with others, but she is released after a dispute with her parents and Toby. The experience only deepens her fascination with the inner-city lifestyle. The night after her release, Allison and Emily decide to head downtown again to hang with Hector's crew.
They reconnect with Hector and his gang at a motel, where a night of partying leads to a chilling initiation: to join the gang, they roll a dice, and the number rolled determines how many gang members they must have sex with. Allison rolls a one and Emily rolls a three. Hector pairs off with Allison, but she withdraws and is thrown out when she tries to get Emily to leave with her. Emily eagerly participates with Hector, while another gang member guards the door. Emily cries out as the others join, and Hector yells at the girls before they are left to deal with the aftermath.
The next day, Allison returns to the motel to confront Hector, who insists he did nothing wrong and that he simply did what they asked. A woman arrives at the door, and Hector mocks Allison for thinking he has real feelings, branding her a poseur who only knows how to play games and nothing about gang life.
Meanwhile, Emily is shown at a police station accusing Hector and his crew of gang rape. Allison is questioned but claims she knows nothing about it. Hector is arrested, and members of his crew vow to find and silence both Allison and Emily, though they end up getting lost in Bel-Air. Toby and his gang are shown posing with guns, threatening revenge against Hector's crew, while Eric shows Allison the footage. She phones Toby to try to talk sense, but the plan backfires and she realizes the danger of what’s unfolding.
Allison informs Emily of Toby’s intended actions and tells Emily's parents about the motel events. Emily's distress nearly pushes her toward suicide, but she and Allison eventually reconcile. Toby and his gang crash Hector's motel, but their violent confrontation falters when the pleas of a baby among the Latina women foreground the human cost, and Toby, overwhelmed, cannot bring himself to shoot and storms out.
As the two gangs drive home, they pass each other and exchange wary looks before the screen fades to black. A few seconds later, the sounds of tires screeching, shouting, and a gunshot echo the looming violence.
The film ends with a third showing of Allison's segment in Eric's footage, this time framed by a sense of enduring ambiguity about the life she chased and the consequences it wrought.
> "bored"