The movie is loosely based around a true story. In 1959, Steven Clark Rockefeller, son of New York Governor Nelson Rockefeller, married Anne-Marie Rasmussen, a maid who had worked at his family's Manhattan hotel.
The pink gown that Jennifer Lopez wears to the fund-raising dinner is a vintage gown from the 1950s. This was stated by Jennifer to a contestant auditioning on American Idol: The Search for a Superstar (2002), season fourteen. The contestant told J. Lo she was a big fan of her and the movie, and tried to find a duplicate of that same gown for her prom, but was unable to find one.
John Hughes was originally set to direct from his own screenplay, titled "The Chambermaid", with Hilary Swank as the lead. In January 2001, the Dallas Morning News reported that Hughes would produce only, with a start date of March 2001. Al Cohn of the Illinois Film Office was hired as location manager for the shoot. By July, Variety was reporting that Hughes and Swank were out, and Jennifer Lopez was in negotiations for the lead. Wayne Wang was hired as director in October 2001, with a new screenplay by Kevin Wade, which updated the story from the 1920s. Sandra Bullock had expressed interest in the lead at one point, and Julia Roberts passed on the script early on.
The last movie co-produced by Hughes Entertainment, the production company John Hughes founded in 1987.