At a party, sitting at the dining room table, Jeffrey asserts that James is a poser, he's wrong if he thinks he's cool, and that he's a piece of shit. James sits across from Jeffrey, nodding his head. Jeffrey loses his virginity to a freshman in his best friend's parents' bed a couple weeks later, at another party, and the following week, on the phone with his best friend silent on the line, breaks up with her. After they hang up, his best friend laughs. He says that Jeffrey is so crazy. A different friend acquires two pairs of boxing gloves shortly thereafter. For weeks, a large group of his friends spend a lot of time after school using the boxing gloves. Jeffrey goes twice, both times avoiding boxing, and then begins to go straight home after school, letting his voicemail answer his friends' calls. Inevitably he finds himself in a situation where both his friends and the two pairs of boxing gloves are present, and on this occasion Jeffrey is pressured into a match with a taller friend and never lands a solid punch. Just after the match ends, his friend turns away. Jeffrey punches him on the back of his head. Jeffrey's friends make fun of him for this for at least the next month.

Jeffrey's parents begin thinking about divorce and do so by Thanksgiving Day, the process culminating in an episode when Jeffrey sits alone in the downstairs living room, clenching the armrests of the green leather recliner, sweating and short of breath, listening to his mother upstairs behind his parents' closed bedroom door go what he will later describe to himself as "insane." His father doesn't seem to say anything. By Christmas, Jeffrey has moved into the basement of the house and begun using a separate entrance, and the day after Christmas break is over, he and his friend smoke marijuana behind the school parking lot. James unexpectedly shows up with Robert, who Jeffrey heard via classmates once brought a sawed-off shotgun to a church parking lot where a group of kids were supposed to fight and threatened to kill everyone. James pushes Jeffrey around for a few minutes and forces Jeffrey to say that he is a little bitch. Robert interjects calmly something about notes passed around in class that reference Jeffrey constantly talking shit on James. Jeffrey keeps swallowing involuntarily.

In February Jeffrey convinces both of his parents to let him switch to a public school that's closer to his house. He doesn't make any friends. He discovers the rave scene and tries ecstasy, and a year later his mother finds around 30 hits of LSD in his car and sends him to live with his father. His father grounds him for a month; Jeffrey can't move his bowels for a week. He gets sick. During the worst of it, he's overcome with sweating and fever, and lies in bed with the space heater turned on high, thinking that, in order to move his limbs, he must first activate in his body a number of strings, levers and pulleys that he can't stop himself from constantly visualizing. Jeffrey drives to a friend's house shortly after he's ungrounded. His friend isn't there but his door's unlocked, so he decides to wait inside. His friend pulls into the driveway with James in the passenger seat. Jeffrey runs out the back door and through the neighboring back yard. A half hour later he tells his friend on AOL Instant Messenger that he had been inside his house but had seen James in the passenger seat and so had run away. His friend replies that Jeffrey is a pussy and that he's laughing, and that James and another kid are there, and that they are all laughing.

Jeffrey begins to occasionally wear pajamas to school. This behavior progresses to wearing pajamas and eating LSD at school almost every day. In the middle of that year, his junior year, he wins the school art competition with a black and white photograph of a cactus that he colored with colored pencils while high on LSD. At the next parent-teacher conference, the photography teacher tells Jeffrey's mother that Jeffrey has a gift and his mother beams. Jeffrey is sitting beside her. A week later, he walks into a party, this one hosted by friends from his former high school, the one he had left after the incident with James and Robert, and he sees James standing at the top of the stairs. Jeffrey avoids him. James later approaches and says not to worry. He will not beat Jeffrey up, he says. Then he says that he's sorry and that it must suck to have to wear diapers whenever he's around. He grins and laughs. Jeffrey watches him.

Jeffrey takes college classes between his junior and senior year of high school so he can graduate at the end of the first quarter of his senior year. Shortly after senior year begins, the media reports on live television that two airplanes have been flown into the World Trade Towers in New York City. All students are let out of school early. On Jeffrey's last day of high school, no one has any idea that it is his last day of high school.

Soon Jeffrey moves into a house with a couple he knows from the rave scene. One day at this house with them he snorts ketamine and inhales nitrous oxide using a large pink balloon while concurrently smoking marijuana, exhaling the marijuana smoke into the nitrous oxide-filled balloon and then rapidly inhaling and exhaling until both the marijuana smoke and nitrous oxide are gone, causing his vision to malfunction and him to perceive the living room he's sitting in as a compact disc sounds when it skips—a number of frames rapidly replacing each other, so fast that it becomes less and less of a comprehensive sequence and eventually something like a vibrating, silver fractal. The following morning he finds out that the girl he lives with has moved out during the middle of the night.

Jeffrey moves back into his mother's house and gets a job as a security guard. He is hospitalized three times: once for a skateboarding accident, once for a snowboarding accident, and another for an affliction called "epiditimytis" that is so embarrassing to him that he can easily recall its name after he moves back from Portland, where he had moved with a friend after eight months of being a security guard, worked at Wendy's, and attended his freshman year of college. The summer before his college sophomore year, Jeffrey drives to Arizona to visit a friend. On the last night of his stay, Jeffrey blacks out from alcohol consumption. A few months later, at a house party, Jeffrey finds out about that night. He finds out that he followed a student and his girlfriend for an inappropriate amount of time accusing them of stealing his hat until the student slapped him. Jeffrey had apparently punched him in the face, and the man and his girlfriend had run away. Coincidentally it is at this same house party that Jeffrey sees James again, this time walking through the front door and directly at him, telling Jeffrey that he had wanted to talk to him, and that he's sorry, and that he's been an asshole, and that he wouldn't have known what to do if he was in Jeffrey's situation. Jeffrey says that it's okay. He acquires a girlfriend, moves into a big house with cheap rent and some people with whom he went to high school, grows marijuana in the attic, dresses up in a suit, and hosts a cocktail party. James and a large blond man show up. In the kitchen, the large blond man turns to Jeffrey and tells him twice that he's a little girl. Jeffrey's girlfriend says that Jeffrey is her friend and that she wants the large blond man to be nice to Jeffrey. Jeffrey says that he isn't a little girl. James is staring at him, forming a wide, toothy grin in slow-motion.

Jeffrey is accepted into a study abroad program in the south of Holland and breaks up with his girlfriend on the way to the airport. He flies to Amsterdam and on his second night there after smoking marijuana and taking both sleeping and anti-anxiety pills faints in the bathroom of his hostel. He comes to and spends around five minutes trying to find the light switch. He calls his ex-girlfriend on the third night, takes a train south on the fourth night, and over the course of that year, blacks out probably over 20 times from alcohol consumption, smokes marijuana on a daily basis, and spends many weekends dancing to techno, high on MDMA, speed, marijuana, alcohol, or a combination of these at all night squat parties that last until noon to 2PM the next day. He sleeps with a number of foreign women, concluding with a German with whom he becomes romantically involved, and after moving back to the States, he graduates with a degree in psychology and acquires a job at a reality television show in Portland. The German moves to the states to be with him and he and breaks up with her after three months. In a gesture of emotional support, his father, who's in Portland on vacation, offers to take Jeffrey out for a night of drinking with his friends. Jeffrey obliges. After initial introductions are made that night, the first thing one of his father's friends—an overweight, bearded man in a Hawaiian shirt—does is point at a bartender and say to Jeffrey, "See that bitch over there? I fucked her on the stairwell of The Hilton last night." Jeffrey averts his eyes, nods his head and says "Nice."

Using the internet, Jeffrey acquires a job teaching English at a school in Seoul, buys his plane ticket, and calls the school two days before his scheduled flight and tells them that his father has died; that actually he won't be able to come to Seoul. After moving out of his apartment and into a shared housing situation, he goes home the following Christmas to visit his mother and has sex with a girl he's known mostly over the internet. He has nobody in Portland. The day after Christmas, he walks into a coffee shop with an old friend and immediately sees James sitting to the right of the doorway, and his friend is friends with James, so they all sit together. While Jeffrey's friend buys a cup of coffee, Jeffrey and James chat about their current housing situations and the cultural differences between Europe and the United States and about James' job installing flooring. Jeffrey's friend comes back with a coffee and the three of them do a crossword together. Jeffrey and his friend leave after saying bye.

Upon his return to Portland in January, Jeffrey finds in his mailbox an envelope containing a professional, black and white photograph of a woman piggybacking his father, both of them grinning, and in a large cursive font printed underneath, the word "ENGAGED!" Three months later, after the woman in the photograph bears a child named Vincent, she, Jeffrey and Vincent's father, and Vincent relocate to Kansas City. The woman in the photograph works at a number of law firms, supports Vincent's father as he makes his way through an MBA program, and has an affair with a coworker who once impressed Vincent, then 5 years of age, with his soccer skills at a company party to which the woman in the photograph had taken him. She buys Vincent a bird. A year later, while roughhousing with a friend, the bird viciously attacks the friend in an attempt to protect Vincent. The episode culminates in his friend in a fetal position on the floor, screaming and crying as the bird pecks and scratches him in an intense aerial assault. Vincent and the bird develop a very close relationship; the bird trusting only Vincent and sometimes Vincent trusting only the bird. The bird soon flies away. It is the first month of fifth grade. This month, he and his friends expose their pubic hair to each other one day; the first friend says he has a forest, the second says he has a meadow, and Vincent says he has grass. His face appears increasingly nervous as the day goes on, but to his credit, Vincent is socially average, and does enjoy hosting the occasional sleepover. During dinner at one of the sleepovers—his friend, his father and the woman in the photograph at the table—he spills water on a slice of white bread, immediately soaking it and turning it into a translucent, paste-like substance. His father stares at him and says "Eat it." As he eats it he gags a number of times. Everyone watches.

At the beginning of sixth grade, Vincent suddenly notices that he isn't as obviously more talented than the rest of his Little League baseball team as he used to be. His confidence begins to diminish after a number of episodes on the baseball field, and he finally breaks down after he pitches his first home run. As the batter runs the bases, Vincent begins to cry. His father jogs to the pitching mound, takes him off the field, drives them home at a frightening speed, and says when they walk through the door of their home that sometimes he hates Vincent. Vincent has three violent experiences: the first after jumping into a pool and accidentally landing on his friend's older brother, the older brother responding by punching him in the face and Vincent responding by acting like he didn't notice that he was punched in the face; the second after throwing a rock from the end of a soccer field at a classmate standing at the other end of the soccer field, the rock hitting him on the forehead, knocking him out and causing severe bleeding and his school to call 911; the third after picking up a large clump of dirt, yelling "Curveball," throwing it, from almost 20 feet away, directly into an older classmate's open mouth, and the older classmate chasing Vincent down, pinning him, and laughing while crumbling handfuls of dirt onto Vincent's face while Vincent screams.

Vincent attends seventh grade in Denver, Colorado after being moved again by his father (reasons obscure) and discovers, at a more detailed level than ever before, sex. In a game where he and his new classmates describe it only through gesticulation, Vincent jumps into a large playground tire, then jumps up and down rapidly. A lot of classmates laugh.

Vincent acquires his first girlfriend in the summer before his eighth grade year. In a movie theater she tells his two friends that she really wants him to finger her. She doesn't understand why he hasn't yet, and Vincent's friends take him out of the theater and urge him to finger her. Vincent doesn't, but later lies to her that his father beats him on a regular basis. The lie is partly a consequence of his friend's stories of being beaten by his dad on a regular basis. Vincent lies again in his freshman year of high school, this time to his entire social circle, that his family tree consists mainly of Native Americans from the Iroquois tribe, and throughout that year, continues to lie about a broad range of subjects. Everyone begins to joke about Vincent in secret, and then the joking is open and communal, and Vincent develops a compulsive urge to avoid social interaction.

His father and the woman in the photograph separate in the middle of his freshman year of high school, and shortly thereafter, the woman in the photograph asks Vincent if he wants his father around anymore. Vincent says that he doesn't. The woman in the photograph divorces Vincent's father and explains to Vincent that, in Kansas City, she had slept with a coworker, and that she had confessed this to his father two months ago, and that he had quickly retorted by telling her that he had been having an affair with a local politician. The woman in the photograph cries as she recalls more detailed information while Vincent's face remains neutral. Later, among a new circle of friends, he exploits this information, further legitimizing his recently developed 'fucked-up' persona.

Vincent has sex for the first time in the guest bedroom of his house in his sophomore year of high school with an eighteen year-old telemarketer unaffiliated with his high school whom he met at a college party to which a group of seniors had taken him. During the latter part of this year, Vincent's father often shows up at Vincent's and the woman in the photograph's house uninvited, still having the garage door opener and keys. One day, his father arrives while Vincent is masturbating on the couch in the living room. Having no pants on or blanket to cover himself with, Vincent runs up the stairs as his father walks in and Vincent continues running until he gets into the upstairs bathroom. His father yells, "What are you doing?" Vincent yells "I'm sick." When his father shows up uninvited on another occasion—a day after Vincent had had an argument with the woman in the photograph that had ended with her sobbing and running out the front door—his father steps through the doorway, stares at Vincent, yells, and pushes him over, causing him to spill the glass of orange juice he's holding. Five minutes later, his father asks Vincent for a hug.

Vincent's father leaves the house after Vincent hugs him, drives to his newly acquired condo, drinks four 40 oz. bottles of Pabst, calls the woman in the photograph, and after she doesn't answer, leaves a voicemail saying that he wants to die. That night, he sits in front of his computer and discovers that the media's reporting that a global pandemic they're calling "Megaflu" is threatening international security and shutting down airports everywhere. He sighs, lies down on his couch, and closes his eyes. After five minutes, he runs to the bathroom and vomits into the toilet. Vincent's father returns to work the next day, and over the course of the next three months, lays off all of his employees due to diminishing investor confidence. He then lays himself off, sells his kit airplane and his Hummer, and liquidates the majority of the rest of his assets with the exception of his mini-yacht. He applies for unemployment and claims every week until his benefits run out, consuming, almost every night, four to seven alcoholic beverages. He manages to write a book called Putting the Pedal to the Metal: The Service/Quality System For High-Octane Corporate Performance, which is, via connections in the corporate world, quickly picked up by MacMillan of Canada. It receives initial positive reviews and generates average sales, but soon is accused of being, basically, a copy of a book that had been published twenty years previous—ironically, by MacMillan of Canada—called Firing On All Cylinders: The Service/Quality System For High-Powered Corporate Performance. His book never profits and is not reprinted.

Vincent's father spends the next seven years existing in relative obscurity, living off his retirement fund and social security checks, sometimes drinking alcohol all day and walking a block to the nearby bar at night, where he sits alone, often pretending as if he's talking on his cell phone or having a text message conversation with someone, glancing, sometimes, to his left and right, sometimes getting cut off by the bartender, until, after one night at the pub, he wakes up somehow already screaming in an antiseptic white and pale yellow room as a number of quickly moving nurses secure his wrists and ankles to a stretcher with metal restraints. He cannot see after this incident. Soon he is hit by a bus and killed. His funeral is the first instance that Jeffrey, the woman in the photograph, and Vincent are together located under one roof. As they say goodbye to each other after the funeral is over, they plan, grudgingly, on meeting for dinner next month, or sometime soon, whenever, whatever, all anticipating the event with a powerful sense of dread and feeling sick of themselves, sick of society, sick of the world, and wishing that people would just leave them alone.