How do siblings deal with each other in their targets? This is the question tackled in this movie. Blue-collared Mickey drives a New York taxicab since the breakup with his promiscuous ex-fiancée Heather two years ago. His younger, white-collared brother, Francis, cannot let Mickey forget the tragedy of the "hairy ass": (Mickey's image of his apartment floor of the guy having sex with Heather after walking in on them). Finding relief in driving his cab, Mickey meets an art student named Hope whom he marries after knowing her for only 24 hours. Mickey also meets his old lover Heather, and learns more about life itself as taxi fares in the course of a summer. Francis, a young Wall Street corporate raider, unhappy in his marriage to Renee and led by his infidelity, continues his shots at Mickey throughout the film, only to find himself a plot device that lends humor and lessons about marriage and brotherhood when he meets and starts an dangerous affair with Heather...

After his wife Maggie passes away, Sam Baldwin and his adolescent son Jonah relocate from Chicago to Seattle to escape the grief associated with Maggie's death. Eighteen months later, Sam is still grieving and can't sleep. Although Jonah misses his mother, he wants his father to get a new wife despite Sam having not even contemplated dating again. On Christmas Eve, Sam, on Jonah's initiative, ends up pouring his heart out on a national radio talk show about his magical and perfect marriage to Maggie, and how much he still misses her. Among the many women who hears Sam's story and falls in love with him solely because of it is Annie Reed, a Baltimore based newspaper writer. Annie's infatuation with Sam's story and by association Sam himself is despite being already engaged. But Annie's relationship with her straight-laced fiancé Walter is unlike her dream love life in the movie (1957). She even writes to Sam proposing they meet atop the Empire State ...