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 (2002) is listed, which also starred Maggie Gyllenhaal.
Don Roos wrote the role of Frank for Tom Arnold but the film's producers wanted a bigger-named actor to play the role. Jeff Bridges, Michael Douglas, and Alec Baldwin were offered the part but they all turned it down.