Lisa befriends Harper Jambowski, a new kid at school who happens to be super-rich. Then, Homer befriends Harper's dad and is able to enjoy the perks of Lisa having a rich friend, as well. But Lisa decides that Harper is a bully and moves to end the friendship, which prompts Homer to try and smooth things over so he can continue to enjoy the good life. 
Homer is watching TV when he sees an advertising for a self-lifting chair. He gets interested in buying it, but it costs $1,100, So he goes to Moe's to get some ideas to raise money. Lenny and Carl give him the idea for crowdfunding. He records a failed video for a website, which commoves almost everyone in Springfield, so he gets enough money to buy a chair in almost no time.
Meanwhile at Springfield Elementary's club sign-up day, Lisa is trying to get signatures for The Magic Club, when she first meet Harper, who appears interested in joining the club because it was the only one that doesn't creep her out. Lisa shows interest in her new friend, discovering that she's also a pretty talented magician.
When the Springfieldians realized that their money was spent on such a useless thing, they formed a mob and went to the Simpsons' House to burn the chair down. At night, Homer gets angry about the chair, complaining that he never gets the finest things in life. That's when Lisa asks him to take her to an Australian boy band concert with Harper, as her father has bought the seats. Feeling unconfident, he takes Lisa to the show.
At the sports arena, Homer is surprised when he's given platinum with stripes VIP wristbands. That's when he first meets Harper's dad. They discover that they also have a lot of things in common, and that Harper's father is extremely rich. On their way back home, Lisa complains about how Harper didn't let her say a word at the show, so Homer tries to convince Lisa to keep her as her best friend. That's when Harper invites them to see a David Copperfield presentation.
At the show, once again, Harper didn't let Lisa participate while their fathers were enjoying the good time together. So Lisa gets even more upset with Harper while Homer enjoys his great friendship with Harper's father, who invites the family to spend a week at their private island, But they can't go as the kids have school. That's when Skinner calls the Simpsons, saying that school next week has been cancelled.
Later, Harper gives Lisa a gift: a new bicycle, but Lisa doesn't accept it for the emotional values of her old bike. This makes Harper mad, and soon it evolves into a discussion and they decide to end their friendship. As they wouldn't go anywhere, the family gets angry at Lisa, but Homer realized that he and Harper's father were still friends, so they could go to the island.
At the island, The family's fun is ruined when Harper and Lisa fight once again, so Homer has to make a hard decision: continue being friends with Harper's father or go home so Lisa can be more happy. He decides to leave the island and go home, saying that Harper is "kinda spoiled" and that she doesn't deserve Lisa.