Popular and rebellious teenager Landon Carter (Shane West) is threatened with expulsion from school after he and his friends leave evidence of underage drinking on the school grounds and seriously injure another student as the result of a prank gone wrong. The head of the school gives Landon the choice of being expelled or atoning for his actions by tutoring fellow students and participating in the school play. During these functions, Landon notices Jamie Sullivan (Mandy Moore), a girl he has known since kindergarten and who has attended many of the same classes as him, and who is also the local minister's daughter. Since he's one of the in-crowd, he has seldom paid any attention to Jamie, who wears modest dresses all the time and owns only one sweater. Jamie is labeled an outsider and a geek. She makes no attempt to wear make-up or otherwise improve her looks or attract attention to herself.