Love is in the air when Principal Skinner and Mrs. Krabappel are finally getting married. They each have their bachelor party, with Mrs. Krabappel having hers at the Simpson house with Duffman and a topless Chief Wiggum as strippers, and Principal Skinner having his at Moe's with Homer. However, at his party, Skinner admits that he has doubts about marrying Mrs. Krabappel. When the wedding is held at Springfield Elementary's gymnasium, Edna learns that Skinner does not want to marry her, and runs away from the ceremony as Skinner tries to catch up with her while Nelson plays a prank on her. The wedding is called off.

After it is called off, Homer and Marge try to get Skinner and Krabappel to be engaged again, but it is halted by Homer and Marge's own marriage problems. Mrs. Krabappel returns a wedding gift to the Comic Book Guy, and she finds him to be an interesting man. Homer gets Skinner to serenade Krabappel using a band made up of Bart, Milhouse, and Martin, but that fails when he learns that the Comic Book Guy and Krabappel are in love. The family visits the Bi-Mon-Sci-Fi-Con to confront Comic Book Guy, who proposes to marry Krabappel after the family sees Futurama creator Matt Groening. Skinner, dressed up as Catwoman (who he thought was Catman) battles the Comic Book Guy. Krabappel interrupts their fight to declare that she will not marry either man. When she tells the Comic Book Guy how they had fun but are very different, he accepts her decision, though Skinner is still upset. Later, at the Simpson house, Homer asks Marge to remarry him, which is done in the style of a mock Klingon wedding, and she accepts.