Reece McHenry (Sam Shepard) and Carol Fritzsimmons (Diane Keaton) share a friendship that few will ever experience.  Their experience commences in 1966, when Reece takes a break from land development to open a used clothing store.  Shortly afterward, Carol consults him about a job as a seamstress.  He hires her immediately.

Later that year, fate again intercedes, creating a surprise meeting in a vacation town, enabling them to interact as friends, not just colleagues.  As coincidence would have it, they stay at the same hotel, unaware that Reece's son Tom (Robert Patrick) and Carol's daughter Katherine (Diane Lane) have already discovered each other.  Tom experiences his first kiss and determines that he will marry Katherine someday.  Unfortunately, Katherine leaves home, taking pubescent Tom's heart with her.

As Reece and Carol's relationship flowers, they run into an insurmountable obstacle.  As a young man, Reece exchanged vows with his wife and stayed with her through a tragic accident that sent her into a coma from which she will never wake.  Despite her hopeless condition, Reece will not break his promise and annul the marriage.

After a decade, Reece and Carol are inseparable. They share a life custom-made for each other.  Reece abandoned his high profile enterprises to focus on the more intimate world of the clothing store.  Every day he and Carol work sideby-side.  During this time, Katherine returns home, encountering Tom, without knowing his identity.  Their first-glance attraction ignites a passionate affair, an affair that seems natural considering who their parents are.

Katherine enters Tom's social sphere, making Tom realize that the playboy lifestyle he used to share with his a rainy day friend Eddie (Tate Donovan) is no longer fulfilling.  Everything seems beautiful until a,tragic illness strikes Carol's sister.  Family duty forces her to relocate in Canada, tearing her from Reece.  Desperately hoping to stay near Reece, she faces the toil of losing him as she leaves for Canada alone.  Katherine follows suite and leaves town in search of illusive pipe dreams.  Once again she takes Tom's heart with her.

 After Carol's funeral, Tom returns home to Reece.  Realizing that his son is missing his last chance to have a family and spend his life with Katherine, Reece drags Tom out of the house and catches up with Katherine.  Unwilling to see his son face the same fate he has experienced, Reece forces Tom to express his feelings to her.