Comedy starring Matthew Broderick as Cooper, a Chicago-based journalist suffering from post-concussion memory loss who takes leaves from his job and returns to his rural Missouri hometown. There he runs into his recently-divorced high school sweetheart, Charlotte (Virginia Madsen), and, at his mother's request, attempts to persuade his Alzheimer's-impaired Uncle Rollie (Alan Alda) to move into a nursing home.

Would-be ballerina Sara (Julia Stiles) is forced to abandon her dancing plans when she leaves her smalltown home and moves to live with her estranged father in the dangerous South Side of Chicago. As a white girl in a predominantly black neighbourhood, Sara finds it a struggle to settle in, but when she meets black fellow-dancer Derek (Sean Patrick Thomas), she begins to feel much happier. The two set out together to realise their dreams, but as their relationship develops it brings forth major opposition from both their friends and their families, putting their future as a couple in jeopardy.