Don Johnston (Bill Murray), a former Don Juan having made a small fortune in the computer industry, wants to live in quiet retirement. He is content to lounge around watching old movies and listening to classical music. His current girlfriend, Sherry (Julie Delpy), is ending their relationship and moving out of his house when a letter in a pink envelope arrives. After she walks out, Don reads the letter; it purports to be from an unnamed former girlfriend, informing him that he has a son who is nearly 19 years old, and who may be looking for him. Initially, Don doesn’t intend to do anything about it, but his busybody neighbor Winston (Jeffrey Wright), who is a mystery novel enthusiast, urges Don to investigate. Winston researches the current locations of the five women most likely to have written the letter and gives Don the information along with maps and flight reservations, and urges him to visit them. Don finally agrees and Winston tells Don that he will drive him to the airport the next morning.
Later, Don stops at a florist to buy flowers from a friendly and attractive young woman named Sun Green (Pell James) who bandages his cut. Don leaves the flowers at the grave of the fifth woman, Michelle Pepe, who Don originally thought might be the mother before finding out she had died five years prior. Finally, Don returns home where he meets a young man in the street (Mark Webber) whom he suspects may be his son. He buys him a meal, but when he remarks that the young man believes that Don is his father, the young man becomes agitated and flees. As Don attempts to chase the man, he notices a Volkswagen Beetle drive past. A young man in the passenger seat (played by Homer Murray, the real-life son of Bill Murray) is listening to the music which Don himself listens to as Don is left standing in the middle of a crossroads.
It was filmed in Rockland County and Westchester County, New York, as well as in New York City and the townships of Mahwah and Wayne, New Jersey. In agreeing to do this film, Bill Murray set the conditions that it would only take six weeks and that he was never more than 60 miles from his home in Rockland County, New York.
Later, Don stops at a florist to buy flowers from a friendly and attractive young woman named Sun Green (Pell James) who bandages his cut. Don leaves the flowers at the grave of the fifth woman, Michelle Pepe, who Don originally thought might be the mother before finding out she had died five years prior. Finally, Don returns home where he meets a young man in the street (Mark Webber) whom he suspects may be his son. He buys him a meal, but when he remarks that the young man believes that Don is his father, the young man becomes agitated and flees. As Don attempts to chase the man, he notices a Volkswagen Beetle drive past. A young man in the passenger seat (played by Homer Murray, the real-life son of Bill Murray) is listening to the music which Don himself listens to as Don is left standing in the middle of a crossroads.
It was filmed in Rockland County and Westchester County, New York, as well as in New York City and the townships of Mahwah and Wayne, New Jersey. In agreeing to do this film, Bill Murray set the conditions that it would only take six weeks and that he was never more than 60 miles from his home in Rockland County, New York.