Bart gets expelled from school and transfers to a Catholic school, where a hip priest named Father Sean tries to convert Bart and Homer to Catholicism, which worries Marge when she believes that Catholics do not go to the same heaven as Protestants and discovers that Catholic women do not use birth control.
Flanders rents a room to two college girls who, without his knowledge, use the spare room to broadcast live softcore pornographic web videos of themselves. Upset that no one in town told him this (and that Homer was the one who told everyone), Ned moves to the seemingly perfect town of Humbleton, Pennsylvania, while a brash coach moves into Flanders' house and begins harassing Homer the same way Homer harassed Ned.
Homer sees a movie about the end of the world and fears the same thing will happen in real life after seeing a chain of random occurrences (celebrities ["stars"] falling from the sky, raining blood, a man in a realistic devil costume) and doing a complicated math equation that predicts the end will come on May 18th, but when the end does not come, Homer discovers a flaw in the equation and ends up in Heaven where he meets God and learns that God is planning The Rapture.
The Simpsons' roof springs a leak when the perfect storm hits Springfield. And when Marge asks what type of father can't keep a roof over his family's head, Homer tries to fix things up, but falls through the roof. Sick of being unwanted, Homer befriends a man who works as a roofer. However, no one else can see him and Homer's insistence that the roofer does exist prompts everyone to think he has gone crazy.
Through Professor Frink's future machine, Bart and Lisa see their lives in the year 2013, where Bart steals Lisa's chances at going to an Ivy League school in order to impress a skater girl named Jenda while Homer (now separated from Marge and living in an underwater apartment) fights Krusty the Clown after Marge begins dating him.
Selma has a severe hot flash while giving Mr. Burns his driving test. Dr. Hibbert explains that Selma is experiencing the onset of menopause. Selma, decides she wants a baby rather than grow old alone. Adoption is suggested, but the Springfield orphanage is empty. Lisa suggests adopting a baby girl from China - but when the Chinese government only allows married couples to adopt, Selma writes down Homer's name as her husband.
Marge gets her kitchen remodeled and the dishes she makes inside it get rave reviews. The suggestion of Ned Flanders leads her to enter a cooking contest. However, Marge realizes the competition is harder than it seems. Meanwhile, Bart finds Homer's vintage Playdude magazines and decides to adopt the lifestyle he sees within the articles.