In the film, the characters played by Julia Roberts and Susan Sarandon are often at odds with each other. In reality, the two are close friends, and chose this project specifically to work on together.
The film was dedicated "In loving memory of Irene Columbus", director Chris Columbus's mother, who in the year before the movie was released had died of cancer, a similar circumstance to one of the main characters in the movie.
The restaurant called "The '76 House", featured in two dinner scenes, one with Jackie and Luke and one with Jackie and Isabel, is a National Historical Site in Tappan, Rockland County, New York. Major John Andre, a British officer who assisted turncoat Benedict Arnold, was held there while awaiting trial by then General George Washington. At the time, it was a tavern and inn, but located across from the town meeting hall and church where the trial was held; another National Historic Site.
Director Chris Columbus previously directed Home Alone (1990) and Home Alone 2: Lost in New York (1992) starring Macaulay Culkin. Jenna Malone, who plays Anna, and Culkin would both go on to star in the indie comedy Saved (2008) with Susan Sarandon's real-life daughter Eva Amurri Martino.
Jenna Malone (Anna) and Liam Aiken (Ben) would go on to star in movies with actress Emily Browning. Malone-Browning in Sucker Punch and Aiken-Browning as brother and sister in Lemony Snicket's A Series of Unfortunate Events (2004)