A rustic Oregon town is the backdrop for this tale of men and women touched by love’s inescapable spell. From Bradley, the hopeless romantic who looks for love in all the wrong places; to Harry, a local professor with the wisdom and experience to guide those close to him; to young, beautiful Chloe, who defies fate in romancing the troubled Oscar.
The movie deals with love and its various incarnations, set within a community of friends in Portland, Oregon. Harry Stevenson provides narration about how love can affect one's life.Bradley Smith (Greg Kinnear) runs a small cafe in Portland. He has been married to his wife Kathryn (Selma Blair) for six years. However, their marriage becomes strained. Soon enough Kathryn begins a lesbian relationship with a woman, named Jenny (Stana Katic), whom she meets playing softball, and leaves Bradley.Meanwhile, Oscar Gamlen (Toby Hemingway) is a young man working at Bradley's cafe who soon meets and falls in love with a girl named Chloe (Alexa Davalos). However, Oscar is revealed to be living with his alcoholic and abusive father, Bat (Fred Ward). When Chloe visits a fortune-teller, she is told that Oscar will die. Chloe, though upset at first, straightens her resolve about her love for Oscar and their future together. Coming home, she urges Oscar to get married to her immediately.Bradley's divorce from Kathryn greatly, but he soon finds love again in Diana Croce (Radha Mitchell), who also has a past with a married man named David Watson (Billy Burke).Diana is a successful realtor and has been carrying on an affair with the married David. Though she asks him numerous times to leave his wife of 11 years, Karen, he cannot bring himself to do it. Their relationship becomes even more volatile when Diana begins dating Bradley and falls in love with him. David insists he loves Diana, but is unable to leave his wife.Also, Harry (Morgan Freeman) and his wife Esther (Jane Alexander) are an interacial couple who have been married a long time. Harry is a regular patron at Bradley's cafe and often provides the younger generation with advice on love. However, it is revealed that Harry and Esther are masking their own grief after the death of their adult son, Aaron some years ago.Diana marries Bradley and ends her affair with David. However, their love is later rekindled when Karen discovers her husband was cheating, leaving him. Free at last, David and Diana have an emotional confrontation in the park that ends with a kiss that Bradley sees, fueling their divorce.Now twice divorced, Bradley suffers a mini-breakdown and stabs himself in the hand. As he is getting stitched up in the hospital he falls for his doctor, Margit (Erika Marozsán).At Chloe and Oscar's wedding, she reveals to Harry that she is pregnant, and plans to have another baby right after due to Harry's advice of having "two."Everybody gathers for an afternoon in the park. While playing football, Oscar collapses; despite an attempt to get him to a hospital, congested traffic interferes, and he dies of a heart defect. Bat attempts to avenge his son's death by harming Chloe but Harry scares him off, and then asks Chloe if he and his wife Esther can 'adopt' her as their own.In the film's conclusion Diana and David are shown as a public and functionally happy couple.Bradley asks Margit for her hand in marriage and she accepts.Harry reveals the nature of his son's death to Chloe, whom he and Esther grow very close to. Harry has also been struggling with the decision of going back to work as a professor at a university.In the film's conclusion, after Oscar's death, Harry and Esther offer to adopt a now widowed and pregnant Chloe, who tearfully accepts their offer.