The scene in Sideshow Bob's Last Gleaming (1995) where Milhouse is in a jet pretending to fire missiles at his parents is where the writers got the idea to have his parents' marriage be in trouble.
The writers originally wanted Sheryl Crow to sing the song "Can I Borrow a Feeling" over the end credits, but Crow declined the offer and the concept ended up being dropped from the story line.
For the second half of the episode, Luann was redesigned to look more youthful and was given a new outfit.
The writers wanted to do an episode that involved a couple getting divorced. They had wanted to break the sitcom convention that characters who look like they will divorce get back together and have two characters remain divorced even after the episode. The Van Houtens were chosen because the writers felt that they were the most developed couple next to Marge and Homer and the Lovejoys.
This is the first episode in which Kearney is shown to have a son and mentions previously being married. This goes on to be a recurring gag.