"Some people live their whole life, and never fall in love. I lived my life. I fell in love."
Not unlike "Pretty in Pink" (1986), this film is a melodrama entwined with issues relating to class. A girl must choose between a boy from her town whom she already knows, and one from a very different social situation, with all the difficulties of family and the question of long-term commitment which go along with this.
A guy (Chris Klein) who goes to a upper-class school, decides to hang out at a working-class diner. He flirts with the waitress (Leelee Sobieski), which angers her boyfriend (Josh Hartnett). The two boys insult each other, and a conflicts erupts which escalates until it culminates in a destructive encounter. This results in a court order which orders both boys to repair the damage that they made, which requires the rich kid from Boston to live for awhile in a rural Massachusetts town.
At first he stays aloof from everyone else, but gradually a relationship develops between himself and the girl he met in the diner. This creates alot of emotional stress and confusion for those involved. The girl must try to work out whether she likes the new guy better than her old boyfriend, and whether or not she should still honor her usual social obligations/outings with him. Also, she is forced to examine the issue of whether or not he is only having a brief fling before returning to his old life, (like others of his class had done in the past), or whether a serious relationship was possible.
At the end, the movie raises more questions than it answers. The ultimate resolution of the basic conflict is, in an emotional sense, left unresolved, due to tragic circumstances which end the game for all those involved.
However, the movie does show in a realistic way interpersonal relations in a variety of different situations. The result is a work of art which is thoughtful, if melancholy. It is not the best or the superlative of excellence, but it will serve as a welcome relief to all those who do not have the temperament to endure the movies about violent crime which are produced in such great numbers.