We start off by seeing George (Freddie Highmore) drawing in his textbooks and not turning in homework. He also has a smart remark about being too distracted by death or that school is far less important than other things in life for the teacher when asked to turn in an assignment. He gets a few laughs from the high school class, but is sent to the principal’s office to finish his assignment.
He stops outside the school grounds for a smoke first and then the principal (Blair Underwood) calls him on it when he gets there from the smell, reminding him that he will have his off-campus privileges revoked if he’s caught smoking anywhere. You can tell George has been in the unfinished homework situation previously and he and the principal have some witty banter about getting it completed. George ends up convincing the principal he’ll change his ways, (which seems to be a common way he wriggles out of trouble). When George gets home, his mom (Rita Wilson) says the school put him on academic probation, and he said to not worry about it. She seems a bit distracted by other worries, but he convinces her the same way as the principal, that it will all turn out fine. Later, in art class, George just doodles on his canvas in pencil instead of painting like the teacher requests.
George goes up to the school roof one day and sees Sally (Emma Roberts) smoking off in the corner. He is just getting some fresh air when a teacher comes up and asks who is smoking. George quickly pulls out a cigarette and pretends it was him, so Sally wouldn’t get in trouble. She silently thanks him as she slips back inside. George’s English teacher (Alicia Silverstone) asks him a question in class when he’s not paying attention and thinks she’s going to catch him. While he wasn’t listening to her in class, he is able to stun her with his answer about Hardy’s novel, and she tells him that he has the topic for his term paper. George goes back to scribbling in his book, and Sally turns to look at him.
Sally meets up with George after school and thanks him for helping her out on the roof and asking why he did it. He says he is more experienced at getting in trouble and would be able to talk his way out of it easier. Sally seems interested and starts talking to him about her life. She has him come inside her apartment, and she, George, and Sally’s mother all talk over beers. We get the sense that Sally’s mom is constantly having flings and is an irresponsible parent. George goes home, and we meet his step-dad. Their apartment is full of candles and George gets upset that the electricity is off, pretending it’s because he can’t do his homework now. His mom says it was silly and she just forgot to pay the electrical bill, and passes it off.
George sits with Sally and her friends Zoe and Will (both rich, but mildly accepting of George), and they get to know each other a little better, with Sally asking why George is so antisocial and never does his homework. Will admires George’s drawings and asks him to draw a poster for a party his brother is throwing at a club.
Sally and George skip class and go out into New York City. George leads her to all the places he goes to when he skips class and they see George’s stepfather nowhere near his office. They follow him, and he goes to a cheap coffee shop and does some work. George is caught coming back to school and is asked by the principal (in place of getting a suspension) to escort one of the visiting career day people around soon. He reluctantly agrees when he finds he can’t talk his way out of it. Turns out it’s an artist, Dustin, who is not incredibly established, but had recently graduated from the school and George in inspired by his demeanor and thoughts about life. He brings Sally with him to visit Dustin’s studio, and Dustin is attracted to Sally. He pulls George aside to ask if they’re together. When George says no, Dustin almost decides to make a move, but senses George actually likes Sally. He tells George that he should like her and to go after her. When they are leaving the studio, Sally asks if Dustin had asked about her. She sensed the attraction from Dustin when he asked how old she was. George says no.
George is invited by Sally to Zoe’s for New Year’s Eve and shows up underdressed. He holds his own against an ex of Sally’s when he insults George and Sally laughs. They all head to the club for Will’s brother’s party, showing George the poster with his artwork. George says it’s not his thing, but Sally convinces him to stay and dance with her and promises to not lose him. He is slow to get into it. Sally’s ex starts pushing in and dancing and Sally dances with him instead. George walks away and is offered repeated shots by Will and Zoe. They offer to find him a girl, but he turns them down. Zoe says she knows who he is waiting for, but George denies liking Sally, who continues to dance with her ex. George gets drunk and pukes outside the club, falling asleep in the alley. Sally finds him there, apologizing that she broke her promise about not losing him. She takes him back to her place, tucks him in on a cot in her bedroom, and changes into pajamas in front of him as he falls asleep. He wakes up and watches her sleep for awhile in the bed above him and then wakes up again to her smiling at him. Sally’s mom gives him a Bloody Mary for a hangover cure, and he leaves. Her mom then warns Sally not to play around with the good ones as it’s not fair. Sally says they’re just friends.
Sally and George go out to dinner for Valentine’s Day where Sally says two singles need to stick together on the holiday. She eventually asks him to have sex with her after inquiring if he had ever done it before. Before he can answer because he’s so shocked, she says to forget it, and that they’re just friends, and it would be a bad idea. He’s quiet the rest of the dinner, and when they leave to go somewhere else, he says he’s going home. George won’t answer her calls or talk with her at all after that. George starts slipping again in class and tells his parents, when they ask why he’s not doing work, that he’s going through a thing right now.
George sees his step-dad around the city still not doing his work and finds an eviction notice on his old office. We see Sally inviting Dustin out for a drink and flirting with him. At first he resists, but then he kisses her and we see them together on dates or staying over at his studio in different scenes. George doesn’t do his term paper for English and he is brought to the principal’s office with his teachers waiting. The teachers say they won’t reward his bad behavior any longer, and since he has no respect for them and the school, they won’t waste any more time defending him. The principal says that he’s not going to graduate. The news hits George hard, and he starts to tear up as he realizes he’s run out of time to talk his way out of it. The principal says he has one chance: do every piece of undone homework, a year’s worth, or don’t graduate. If one assignment is left undone, he is expelled. He gets upset and says he might take the expulsion, but they ask him to take the weekend to think about it.
He leaves upset and comes home to his parents who have been told about his choice at school. He confronts his step-father about lying about work, and they get into a physical fight. After George slams him against the wall, hurting his shoulder, George takes off for Sally’s place. She answers the door and comes into the hallway. He tries to kiss her, but she breaks it off, showing him Dustin is inside. George runs away and Dustin catches up with him. He tries to explain his side, but George tells him how Dustin said he would back off and didn’t. George goes home and finds his mom crying outside. She says that his step-dad went out of business, asked her to get several mortgages and loans, and lied to her about trying to get back to work. She said they’re divorcing, and now she has to sell the apartment as she ruined her credit. George consoles her and starts to feel better himself, as well. He goes into school on Monday and gets each of his missing assignments to do. His one art project is to make a painting that is honest and real, and something he’s never told anyone. We see a montage of him doing his homework and taking final exams, his mom showing the apartment to interested buyers, and Sally with Dustin.
Sally sends a text to George saying she needs to talk with him. They meet in a bar where Sally says her mom is marrying a guy and moving to Texas and can’t pay for her college. She going to go backpacking with Dustin through Europe during the summer and is skipping the high school graduation ceremony. She said she still needs to be friends with him. George says that he’s always loved her and it wasn’t fair not to tell her that. He says they can be friends. They go back to her place, and she says that someday they’ll end up together. She just needs to go off with the backpacking thing, and he needs to go out with several girls to get it out of his system. He laughs, and they (presumably) have sex.
We see George handing in all of his assignments and the principal saying he’s going to check he has them all, and he’ll know if he graduates if he calls his name at the ceremony. George brings his artwork to his art teacher, who applauds and hugs George. We don’t see the picture yet.
At the ceremony, Zoe and Will are hurt that Sally didn’t say goodbye. George’s name is called, and his mom is proud of him. We see Sally at the airport with Dustin, reluctant to get on the plane. Dustin says the door is closing, and they need to get on, but Sally doesn’t move. George goes back to the art classroom and stares at the picture which we see if of Sally’s smiling face. Sally walks in, says the picture is okay, and they start kissing.
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