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Milhouse is frequently the butt of a variety of jokes, such as being beaten up by Nelson for delivering a love note from Lisa (which Nelson thought was from Milhouse himself), having the door slammed in his face while playing pin the tail on the donkey, having his possible budding homosexuality given away by his school counselor to Homer and ...
Meanwhile, Lisa fears that Zia is spending too much of her time going into the "Ultranet", a digital world that people enter with their consciousness by plugging themselves into a laptop. Milhouse suggests to Lisa that she spend time with Zia in order for them to have a better connection, so Lisa decides to take Zia to her parents' house, too.
After Milhouse is taken to the hospital, Lisa confesses to Nelson that she wrote the note and soon she spends more time with him, inviting him to her house and even visiting Nelson's own. At Marge's suggestion, Lisa decides to turn Nelson from a troublemaker into a sweet, well-behaved young man like how Marge had done with Homer. Lisa compels ...
In this episode, Lisa discovers that her ancestors from Florida helped a black slave named Virgil escape to freedom, but Milhouse has a piece of family history that shows Lisa's ancestors giving Virgil up in an act of cowardice. The episode was written by Ian Maxtone-Graham and Billy Kimball and directed by Raymond S. Persi.
Lisa becomes engaged to, and later almost marries, Hugh Parkfield in "Lisa's Wedding" and the episode "Holidays of Future Passed" suggests that Lisa will go on to marry Milhouse Van Houten. However, " Holidays of Future Passed " also show Lisa being in both a monogamous , and later polyamorous , lesbian relationships.
Lisa is graduating two years early and has a scholarship to Yale University, while dating a muscular Milhouse and Bart dates a skateboarder named Jenda. He also shows them a picture of Lisa at age 12 (2009) after she was saved by Milhouse from a fire, which she later learns that he started.
In a parody of Chronicle, Bart, Lisa and Milhouse are walking through a forest. Bart scares Lisa with dead owls, and she hits Milhouse's nose with the camera, making him lose his balance and fall into a giant hole. Bart and Lisa decide to jump into the hole to rescue him, making all the three stuck inside of it with nuclear waste from the power ...
Milhouse and Bart loosen every bolt and screw in Springfield Elementary, leading to mass chaos when the building and its contents fall apart. Milhouse is apprehended by Principal Skinner, and suspended from school for a week to be subsequently grounded. Bart, whose involvement with the prank was not discovered, promises to visit Milhouse every day.