Milhouse is known for trying to put his moves on Lisa, and never really getting far, as she puts, she's been turning him down for the prom since kintergarten. He finally managed to win her heart when he pulled him out of a housefire, at the age of 12 in GABF12 - Future Drama. Lisa later found that he started that fire. But she still goes out with him anyway.

Lisa appears to be at or have been at Band Camp when Milhouse told her about starting the fire. She is wearing a red "Band Camp" labelled sweatshirt and as a point of note, she is wearing braces which here are perfectly visible, despite the fact that in 9F15 - The Last Exit to Springfield they were shown to be invisible at the end of the episode.

Sometime in the next eight years, Lisa had been skipped ahead two grades and was in the same grade as Bart, for which Marge is proud of. Lisa is still dating Milhouse, so much so that he takes her to the prom and is taller than he is. Lisa advises Bart to take a job and eventually he rescues Mr. Burns, who gives him the Yale Schollarship that was intended to go to Lisa. Bart, after finding out how bad Lisa's life will be with Milhouse, he stops the two from making out and he gives her the schollarship.

Throughout the episode, Lisa is shown wearing various outfits. The first is her prom dress, which is coloured orange, with straps over her shoulders, and orange high-healed shoes, she is also wearing her normal white pearl necklece and has pink lipstick on. Later, she is seen at the kitchen table wearing a dress somewhat similar to her normal one at eight, but again with straps. Later she's wearing a white dressing gown in the kitchen, at the graduation, she's wearing a black graduation gown and mortarboard and lastly, she has an orange jacket, a light orange shirt with a blue colar and blue trousers.

In 2010, Lisa is 23, and enrolled into an Eastern University, shown in 2F15 - Lisa's Wedding. We don't know what courses she was taking, but she seems to take it seriously. (more so than I do in my own university courses! :P). While there she keeps bumping into an annoying British man, Hugh Parkfield. But after a small reading compitition between the two, they fall in love and find that they both have a lot in common. On a vacation to England, Hugh proposes to Lisa, who accepts. However, Hugh, on the wedding day admits to Lisa that he can't stand Homer or Bart, as a result, Lisa breaks up with him.

At first, Lisa doesn't wear her pearls, but she has a pink sweater, with blue jeans and white boots. On her wedding day, she adds her pearls back as "Something Old", along with her white wedding dress, and an antique broach from Hugh's mother.