Maggie Gyllenhaal was not the first choice to play Jude. Gwyneth Paltrow was originally slated to play the part, but dropped out and was replaced by Jennifer Garner. After Garner left the project, Gyllenhaal was awarded the role.
During the scene (1:21) when Charley and Gil are looking for something to watch on TV, the movie Secretary is listed, which also starred Maggie Gyllenhaal.