NOTE: This spoiler was sent in by Marcus
The film begins in New York, 1994. Luke Shapiro (Josh Peck) sits in the office of Dr. Jeffrey Squires (Ben Kingsley). Luke doesn’t know what to talk about, and says that he’s going to make something up. He says that he’s having problems getting laid. Squires asks him if he ever had sex before, and Luke says that he almost did with a drunk girl in a park, but the cops broke them up before they could. Luke asks Squires how much weed he needs, and gives him the amount he asked for (which entitles him to another 48 minutes of therapy). Squires says that tomorrow’s going to be a big day for Luke, and he sees that there’s no joy in his face. Squires then pulls out his bong and starts to smoke the weed. Luke asks him if he feels like a fuck-up for buying weed from the same guy that sells to his daughter Stephanie. Squires corrects him by saying that Stephanie is his step-daughter. Luke leaves his office.
During the opening credits, Luke rides his bicycle through New York and says via voice-over that he’s a drug dealer. Squires thinks that it’s a cry for help, and Luke is starting to think that he’s right. While riding the subway, Luke says that he gets to travel all over New York to sell weed and he likes his impure thoughts about all the girls around him. He even fantasizes about girls dancing all around him while he listens to his headphones. Luke goes home and walks past his parents arguing about something, locking himself in his room and giving his parents the middle finger behind closed doors. He plays Nintendo and hangs out by himself. Tomorrow comes, and it’s his high school graduation. Luke says that after he graduates, he’ll go to his safety school, grow up, and die like everyone else. Squires shows up along with his wife Kristin (Famke Janssen), and introduces himself to Luke’s parents. His step-daughter Stephanie (Olivia Thirlby) also walks up, and Luke is instantly attracted to her. The Squires family takes pictures but keep on messing up their poses. Later on, Luke is called to a party and Justin (Aaron Yoo) answers the door. They go to the bathroom and Luke says that he didn’t know he was having a party. Justin says that it’s the graduation party, and Luke obviously wasn’t invited. Justin also asks for Luke to spot him some money because he only has four dollars. Luke gives him a bag of weed worth thirty bucks and tells him to keep his four dollars. Justin says that it’s going to last him until he goes to Amsterdam with some friends. He leaves Luke alone in the bathroom. Stephanie shortly walks in the bathroom and asks Luke if he wants some Ritalin. She also asks him what he’s up to during the summer. Luke says that he’s going to stay and make money, and Stephanie says that she’s going to be an intern for one of Squires’ patients. Luke says that it’s only going to be them out of their class that stays, but Stephanie tells him that they won’t hang out. Luke sits on a rooftop alone and watches the party below. Justin laughs at him, and Stephanie sees him, but turns her attention back to the guy she’s dancing with. Luke stays on the roof the rest of the night and smokes his weed.
June Luke watches TV in bed and sees that it’s going to be a hot summer. He walks out of his room and sees his parents fighting again. It becomes clear that his father has lost much of their money and they are going to be evicted, even though his father tries to deny it. Luke gives his mother a wad of his own cash and leaves to go work. Luke goes to see Percy (Method Man), his supplier of weed. They listen to Notorious B.I.G.’s new song on Percy’s sound system and Percy asks Luke what’s wrong. He says that he’s going to need more weed to sell than usual. Percy gives him enough to fit in his backpack and tells him to be careful, because Giuliani is cracking down on drugs. Percy also gives him a mix tape to listen to before he leaves. While at home, Luke listens to the mix tape to drown out his parents fighting again. Luke splits up his weed into baggies and places it in his ice cart. Luke goes all around New York and sells his weed to various people, using his ice cart as his cover. Luke goes back to Squires and asks him if he can prescribe medicine. Squires asks him why he wants medicine, and Luke says that he’s depressed and doesn’t sleep well. Squires asks him if this has anything to do with Kurt Cobain’s death. Luke no longer wants to talk, and Squires tells him that men do the things they need to do to become the men they want to be, which includes asking for help. Luke vents about his parents fighting like kids, and says that his life sucks. Squires tells him that he would give anything to be his age again, and tells him to make the most of his youth. He refuses to give Luke pills, and tells him to talk with a friend. Luke says that he doesn’t have any friends, and so Squires tells him that he can talk to him.
As Luke leaves his office, Stephanie runs into him with Squires’ dog named Jesus Christ. Luke says that he was just there to sell weed to Squires, and Stephanie says that he tells her everything about his patients, which makes Luke uneasy. She talks about a patient he has that is a chronic masturbator. Jesus pisses on Luke’s cart, and Stephanie asks if the cart is his. He says that it’s a cover, and shows her that the inside is full of weed. She asks him how it works, and he says that she can come with him while he deals. Stephanie drops off Jesus with Squires and walks around with Luke. They go to the park, where Union (Mary-Kate Olsen) is dancing around after eating some mushrooms. A guy bangs on some bongos and Union explains that they met while at a concert. Union tells Luke that he looks like Jason Priestly with his hair. Luke sells her some weed and then they go on to his next client. Elanor (Jane Adams) sees Luke and Stephanie through her peephole and asks him if she’s a cop. He tells her everything’s cool, and she lets them inside. Elanor apologizes for the cop thing, since she’s paranoid about Giuliani. She called Luke over because she’s having a guy coming over tomorrow, and they have nothing to talk about unless they’re stoned. Elanor asks Luke why men are so different, and it becomes clear that he doesn’t know anything about her. Elanor mistakes Luke and Stephanie for a couple, and when they say they’re not, she tells him that they should try it since they have good chemistry together. Luke sells her weed and then they quickly leave. Luke walks Stephanie home and she tells him to call him. He thinks she wants weed, but she says that they should hang out since they’re the only ones in the city and it gets lonely. Later on, Luke looks through his yearbook and sees a page dedicated to Stephanie. There’s a picture of her in a bikini while on a beach, and he fantasizes about having sex with her on the beach. Luke masturbates, but is interrupted by his father, who tells him to turn off the air conditioner.
July Squires stands on the balcony of his apartment and overlooks the city. He goes inside and tells Kristin that it’s such a beautiful evening that they should go out. She tells him no, and so he takes some prescription pills he has in his cabinet. Luke wakes up sweating due to the heat, even though his feet are in his mini-refrigerator. We next see Luke going back to Squires, who tells him that he needs to get laid. He asks him if there’s anyone he’s interested in, and Luke says that there’s one girl. Squires asks if Stephanie knows her, but Luke doesn’t tell him that she’s the girl he’s interested in. Squires says that he needs to befriend the girl he likes, earn her trust, and then stick his tongue down her throat when he’s most unthreatening. Squires says that all men need sex, and he says that he can get Luke a prostitute if he’d like. Luke says that he was close to respecting him before he said that. Nonetheless, Squires tells Luke to call up the girl he’s interested in and get laid. Luke leaves and Squires lights up his bong again.
Later on, Luke calls Stephanie at home. Squires, who is throwing water balloons at the people walking on the sidewalk below, rushes over and answers the phone. Luke tries to disguise his voice, but Squires recognizes him. Squires tells him that he knows he’s calling for his sex quest, and he invites him out to a bar. They go to a bar and there are no women there at all. The place is pretty barren, and Squires buys Luke alcohol at the bar. Luke says that he listens to rap and hip-hop, and Squires tries to get him into classic rock. Squires says that he hates his wife, and Luke says that he hates his parents. They both agree that they both need to get laid. In walks Union and some of her friends. Squires quickly takes off his wedding ring, but Luke tells him to stay away from her. Squires doesn’t listen and chats up Union while her date vomits nearby. They all sit down at a table, where Squires and Union are having a good time, but Luke is stuck sitting next to Union’s passed-out date. They roll up a blunt and light it up. Luke goes to the bathroom, and when he comes back he sees that Squires and Union are gone. He finds them making out in a phone booth, and the bartender kicks all of them out.
Luke and Squires walk around the city. Squires tells Luke not to try to get a quick fix in life, and not to become like him. They light up a joint while Luke tags a wall with a sharpie. Squires decides to tag the wall also, only he writes out his full name. While they laugh about it, they are seen by two cops. Squires pumps up his shoes and tries to make a run for it, but he slowly runs right into the cops. They are arrested and sent to jail, which is overbooked. Squires talks to a man who stabbed his wife in the vagina, and they both are shortly bailed out by Stephanie. She says that she won’t tell her mother what happened if Squires drives her car back home and if Luke goes out with her. Squires tells Luke not to touch his daughter, but Stephanie and Luke both correct him by saying she’s his step-daughter. While walking around, Stephanie asks Luke what’s the deal with him and her step-father. He says that they’re just friends and hang out together. Squires goes back home and tells Kristin that he was stuck in jail, but she doesn’t care because she’s currently working out.
Luke and Stephanie sit by a lake and chill. She asks him why they didn’t hang out in high school, and Luke truthfully says that he was a loser. He gets them some beer from his ice cart and they also smoke a joint. She likes the song he’s listening to on his boom box, and tells him to make her a mix tape. Luke rushes in and tries to kiss her, but she stops him. She has him try again, and they continue to kiss each other. Luke gives her a goodnight kiss before dropping her off at home, and he dances on the sidewalk outside (with each step lighting up the ground). Luke goes home giddy, uses some eye drops, and greets his mother in the kitchen. He says that he’s in love. Meanwhile, Stephanie eats and smokes on her couch while watching TV. Squires comes in and asks her if she likes Luke. She says maybe, and Squires tries to turn her off by calling him a drug dealer. It doesn’t work, and so he sits down and watches TV with her. Later on, Luke goes back to Squires and he bluntly tells Luke to stop seeing Stephanie. He warns him that she’s just bored and she’ll break his heart. Luke calls Squires a hypocrite and calls him a weird old idiot for hanging out with him. Squires cuts their session short, and Luke gives him a mix tape before leaving (along with some weed). At night, Squires listens to his mix tape. He dumps all his prescription pills and flushes them down the toilet. Luke continues to sell drugs and Squires continues to see other patients, but is clearly bored with all of them.
Squires sits in bed and plays a guitar. Kristin asks him why he’s home early, and he says that his last patient killed himself the previous day. He asks her if she loves him anymore. Since their marriage is straining, Squires says that they should go have a second honeymoon. Kristin points out that they didn’t even have a first one, but agrees to go. Stephanie tells Luke that her parents are going out for the weekend, and invites him to spend the weekend with her at their home at Fire Island. They take a boat to the island and Luke wraps his sweatshirt around Stephanie’s shoulders. They drink some whiskey and Luke plays a mix tape he made for her. At night, they sit on the beach drunk. Luke tells her that he doesn’t know what to do in this situation, and asks her what will happen when everyone comes back to the city. She says that it doesn’t matter, and Luke follows her into the water. Stephanie tells him that he only sees the wackness (negative things) in life while she looks at the dopeness (positive things). They go back inside and they start to have sex. Luke is nervous and asks for a condom, but she says that she’s using birth control. After riding him for a little bit, she notices that he’s not hard.
Stephanie makes coffee for them so that they can sober up. Luke confesses that he’s never had sex before. Stephanie tells him that it’s okay and she can teach him. She asks him if he’s sober yet, and then says that it’s time for their first lesson. Luke chugs down the coffee and they go back in the bedroom. Luke gets on top of Stephanie, but shortly after entering her he ejaculates. Luke cries, and Stephanie holds him. Meanwhile, Squires and Kristin have stayed up all night drinking and smoking. They reminisce about doing coke in the past and having great sex. Shortly afterwards, they have sex while watching a porno movie. Luke sits on the beach and while he watches Stephanie swim, he practices telling her that he loves her. Later on, Luke showers and Stephanie joins him. They wind up having sex standing up in the shower. After they are finished, Luke tells Stephanie that he loves her. She gets uncomfortable and walks off. They go back to the city but are distant from one another, as are Squires and Kristin. Luke and Stephanie awkwardly say goodbye at the subway station and Stephanie says that she’ll call him that week. Squires and Kristin both decide to get a divorce. Kristin asks Stephanie how her weekend was, and she says that it was uneventful. Luke goes home and is immediately beeped by a client.
August Luke flicks the middle finger at everyone on the street and walks to a pay phone. He calls Stephanie but gets her answer machine. He’s upset that she hasn’t called him back, and asks her if she didn’t call him back because he told her he loves her. At first, he says that he didn’t mean it, but then he says that he really meant it. He gets angry and tells her to fuck off. Luke goes to see Squires and tells him that he was right about Stephanie. Squires tells him to forget about it. Luke asks Squires for help, and tells him that he has some extra weed he needs to unload this month. Squires pushes Luke’s ice cart and accompanies him on his deals. Luke gives pointers on how to sell weed and Squires is eager to learn. Luke even sells weed to his old math teacher. Luke is happy to make a lot of money, and says that the money is for college. Luke brings Squires with him to see Percy, and his guards don’t trust him. After smoking weed and talking about Percy’s mother, Squires and Percy become friendly. Luke brings Squires with him to see Elanor, and he’s instantly attracted to her. She again says that she needs weed so that she can talk with the guy she’s seeing, and Squires compliments her. Elanor gives Luke a rock CD and Squires loves her taste in music. Luke calls Stephanie again and says that it’s a shame she’s ignoring him, since he’s leaving for school in a couple of weeks. He tells her that he misses her and hangs up.
Kristin leaves Squires, and Stephanie will stay with him in the meantime. Stephanie listens to Luke’s last message, and then the phone rings. She answers, thinking its Luke, but it’s Justin. He’s back from his trip and invites her out to a club that night. Luke goes home to see that his family is getting evicted (all of their belongings are being packed up). Luke says that he has twenty-six thousand dollars for them to use, but his father tells him that it’s not even close to the amount they need. He tells Luke to go upstairs and pack up his room. Depressed, Squires tags his name on all his possessions with a sharpie and Stephanie helps him. Luke stays in a one-room motel with his parents. He rides his bike and goes to see Stephanie. He says that even though the summer is almost over, they can make this work and have a long-distance relationship. It turns out that Stephanie slept with Justin the previous night, which clearly hurts Luke. He asks her where Squires is, and she tells him that he’s at Fire Island. Luke takes off without giving her a chance to speak. Squires has been on a drug binge at Fire Island and has written a note on Jesus Christ “Please take care of me. My owner killed himself”. Squires is surprised to see Luke show up at the beach house, and he gets him to partake in his drug binge.
After getting incredibly messed up, they sit on the beach and watch a woman walk by. Luke says that he wants a vagina, and Squires says that he should’ve known that Kristin wasn’t right for him once he found out she didn’t like dogs. Squires mentions that he tried to kill himself twice that day the first time he tried to overdose on pills, but he has a high tolerance and the second time he tried to hang himself but did it wrong. Squires tells Luke that he’s glad he came to see him off and walks off in the ocean to drown himself. Luke follows him into the water and tells him that he can’t give up and he’s his best friend. Luke desperately tries to bring Squires back, but soon loses him. After a while, Luke is successful in bringing Squires back to the beach (along with his hat). They sit on the beach again and Squires tells Luke that what he said was really cheesy. They laugh about it, and then go back to the city to fill out Squires’ prescriptions. Luke tells him not to try to kill himself again, and says that his family is going to move in with his grandparents in New Jersey. Squires says that he’s sorry about what happened with Stephanie, and wishes Luke good luck in school (while also telling him to try to have sex with a black girl). Squires cries as they say their final goodbye’s together. As Luke leaves, Stephanie tries to talk with him. He tells her don’t talk and just stand at the door until he leaves, because he’s never had his heart broken before. Luke walks outside, listens to a mix tape Squires made for him, and almost gets hit by a water balloon thrown by Squires.
Luke and his family have dinner at his grandparent’s house. They ask him what he wants to be when he grows up. Luke says that he wants to become a shrink, because everyone around him is crazy. Squires sits by himself on a bench and takes his prescription medicine. While overlooking the city, he gets paged by Elanor. She says that Luke gave her Squires’ phone number, and they make plans to meet that night. The film ends with Luke standing at a train station by himself and flicking his cigarette at the ground.