George, portrayed by Freddie Highmore, is a pessimistic high school senior endowed with a remarkable talent for art. He often grapples with the daunting awareness of his mortality, which leads him to abandon his schoolwork—deeming it all pointless. Consequently, he finds himself on academic probation. The following day, while on the school roof, he encounters Sally, played by Emma Roberts, who is smoking. When a teacher approaches, George instinctively pulls out a cigarette to take the blame. Grateful for his sacrifice, Sally seeks him out to express her appreciation; although George is initially hesitant to engage, he gradually warms to her charming personality.
During Career Day, George meets a vibrant young artist named Dustin who ignites inspiration in him with his perspectives on life. Inviting Sally along, George joins Dustin, but it soon becomes clear that Dustin has an interest in Sally. As the New Year approaches, Sally extends an invitation to a party. At this gathering, she dances with her ex-boyfriend while a drunken George embarrassingly ends up outside, eventually falling asleep in an alley. Finding him there, Sally offers her apologies.
As Valentine's Day rolls around, George and Sally go out for dinner, and she surprises him by asking if he wants to sleep with her. Stunned, George remains silent, prompting Sally to backtrack, saying that perhaps they shouldn’t as he is her only true friend. This conversation leaves George in a daze, and he subsequently withdraws from Sally, ignoring her attempts to reach out, while she starts to spend time with Dustin.
The consequences of George's negligence catch up with him when he is summoned to the principal’s office for not completing his English term paper. Faced with the ultimatum of expulsion or fulfilling a year’s worth of missed assignments, George clashes with his stepfather over a deception regarding his schoolwork. He seeks refuge at Sally's place, where they share a kiss, but she abruptly pulls away, revealing she is with Dustin. Hurt and angered, George storms out.
The next morning, George finds solace in the park with his mother, who divulges that his stepfather has been dishonest about work and that they are heading for divorce. This revelation prompts George to reassess his relationship with Sally. At school, he gathers his missing assignments to tackle. One significant art project challenges him to create a piece that is honest and true. As he diligently finishes the assignments and prepares for final exams, Sally’s romance with Dustin continues to flourish.
In a twist of fate, George and Sally meet at a bar, where she announces her plans to backpack through Europe with Dustin, opting out of the graduation ceremony. Heart open, George confesses his love, and they share a passionate kiss in her apartment. Sally reciprocates his feelings and promises they will find their way to one another someday. With renewed determination, George submits all of his work, impressing his art teacher with his heartfelt project.
On graduation day, George’s name is announced, and his mother beams with pride. Returning to the art classroom, George gazes at his completed project—an artwork capturing Sally’s radiant smile. Just as the film concludes, Sally appears, having decided against her trip with Dustin, and they share a tender moment as they admire the painting together.
