Telly, Leo Fitzpatrick, a scrawny 16-year-old, and a virgin 12-year-old girl lie on a bed as they share a moment of intimacy. After their encounter, he talks with his best friend, Casper, Justin Pierce, about what just happened, and it becomes clear that Telly has started to seek out sexual experiences with virgins. They head to a local store where Casper shoplifts a 40 oz bottle of malt liquor, and on the way out, he also grabs two peaches from a Korean fruit vendor. In search of drugs, food, and a place to hang out, they make their way to their friend Paul’s apartment, though they don’t really like him. Seated there, they watch skaters on the TV and Casper quietly indulges in a whippet, while the group boasts about their sexual exploits, their casual attitude toward unprotected sex, and their lack of concern for venereal disease.
Across the city, a group of girls talk about sex, offering a contrasting voice to the boys’ bravado. Two of the girls, Ruby, Chloë Sevigny and Jennie, mention that they were recently tested for STDs: Ruby tests negative despite numerous encounters, while Jennie tests positive for HIV. Jennie confides that her infection came from a single sexual experience with Telly and she desperately tries to locate him to prevent further spread. In the meantime, Telly and Casper steal money from Telly’s mother as they continue to drift through the night.
After purchasing marijuana from a Rastafarian drug dealer, the pair gathers with a few friends and together they taunt a gay couple passing by. While Casper rides a skateboard, he carelessly bumps into a man who becomes violent; the man is knocked unconscious when Casper’s friend Harold strikes him with another skateboard, and the beating continues until the final blow renders him unconscious. Jennie is later seen in a cab, and the taxi driver offers her advice about finding happiness.
Telly and several skaters then pick up a 13-year-old girl named Darcy, Adriane Brown—the virginal younger sister of an acquaintance—whom Telly wants to have sex with, though Darcy resists at first. The group sneaks into a pool to swim with a few more friends, while Harold showboats his genitals for the others. Later, they head to an unsupervised party at the house of their friend Steven.
Jennie meets Misha, a girl who dislikes Casper and notes Telly’s possible whereabouts at The Shelter. When Jennie arrives at the club, she runs into a boy named Fidget; they go into a backroom and witness someone making out with three girls at the same time, and Fidget pushes a pill into her mouth. Jennie learns that Telly is at Steven’s house. On the way there, she drifts in and out of consciousness due to the effects of the pill, a roofie.
Inside Steven’s house, Telly is in his parents’ room trying to persuade Darcy to have sex with him; Darcy eventually agrees. Jennie arrives too late and discovers Telly having sex with Darcy, failing to intervene as Telly exposes Darcy to HIV. Jennie cries and collapses among the partygoers after the roofie takes effect.
The next morning, a drunken Casper rapes an inebriated Jennie, unknowingly exposing himself to HIV. A montage then shows homeless people and drug users across New York City, and a voiceover by Telly proclaims that sex is the only worthwhile thing in his life. The film closes on a stunned Casper, naked, asking, “Jesus Christ, what happened?”
