Ash and his friends are walking through the countryside when they see a poster of a boy that looks a lot like James, a member of Team Rocket. A limousine pulls up and an old man asks Ash and his friends if they've seen the boy on the poster. Ash says they have and the man takes them in the limousine to a mansion. Team Rocket also sees the poster and Jessie and Meowth ask James if the boy in the picture is him. James says its not him and they follow Ash and his friends. James wanted to stay behind but Jessie and Meowth forced him to go against his will.
The man tells Ash and his friends that he is James' butler, Hopkins, and that James is a millionaire but ran away from home when he was a boy. Hopkins shows them the mansion where James used to live and he shows them James' pet Growlithe, Growlie's doghouse, which was smaller than James' big mansion. Team Rocket have also come to the mansion, but James isn't very happy to be there.
Hopkins takes Ash and his friends inside the mansion and explains that James' parents died this morning and James has to marry his fiancée within the next 24 hours or he won't inherit their fortune and the money will go to charity. Ash and his friends wonder how to find Team Rocket, when Team Rocket falls off the roof because Jessie and Meowth are beating up James because he doesn't want to get married. Ash tells Jessie and Meowth to stop and Brock says its James decision whether he gets married or not. James tries to run away, but Jessie pulls him back with a lasso.
James feigns amnesia because he doesn't want anyone to know about miserable his past life was, remembering things like flunking out of Pokémon Tech and Joining a bicycle gang. He did remember that a little boy and his Growlithe were trying to survive and the boy perished. Everyone but Misty got emotional with Misty yelling "JAMES IS STANDING RIGHT HERE!" Then Jessie and Meowth force James into going back again.
A little bit later, James is dressed in a blue suit and Jessie and Meowth are dressed in invisible costumes. James knocks on the front door and Hopkins is happy that James has returned home. He takes James up to the room where his dead parents are lying in their coffins. James hears laughter coming from the coffins and his parents pop out of them, alive! James knew that they would do something like this and he tries to escape but he gets captured. Ash and his friends realize that this was a trap to get James to come home and get married.
Upstairs, James is scared to meet his future wife, Jessibelle, who looks exactly like Jessie. Jessibelle takes James down to the basement, saying he needs to be taught a lesson for running away from home. James' Parents tell Jessie and Meowth that they can see right through their invisible costumes. Jessie uses a smoke bomb to escape but James was left behind.
Jessibelle then goes on a whipping rampage while James' Parents have tea. Jessibelle eventually catches James and sends out her Vileplume and has it use Stun Spore to keep James from escaping. Ash and co are also caught in the Stun Spore cloud. Jessibelle says she will teach James how to be a gentleman, even if it kills both of them.
Ash, his friends, Jessie, and Meowth are thrown out of the mansion. They hear a noise coming from the doghouse and Growlie leaps out of the doghouse and runs inside the mansion and rescues James.
James, Growlie, Ash and his friends, Jessie, and Meowth hide out in the doghouse. Jessie hates Jessibelle and James says Jessibelle is the reason he ran away from home. He says that since their engagement was announced, Jessibelle started following him everywhere, trying to change him, nothing he did was refined enough for her. James says that ever since he was a kid he hated how society had rules for absolutely everything, and if he married Jessibelle, it will be the biggest mistake of his life. He also says Growlie is the only friend he has at the mansion. Suddenly, Jessibelle and her Vileplume burst through the doghouse wall, sending Jessie and Meowth flying. Vileplume tries to use Stun Spore, but Growlie and Pikachu use Ember and Thundershock, making Jessibelle and Vileplume run away in fear.
Jessibelle knocks James' parents into a pond filled with Magikarp. James hides in the bushes and says good bye to Growlie and tells him to look after his parents. As James leaves, Growlie starts howling.
Meanwhile, Jessie and Meowth are sad because they think James got married. But then they see James coming, flying the Meowth Balloon and he brings Jessie and Meowth onto the balloon.
At the end of the episode, Ash and his friends are being chased by Jessibelle, who's demanding that they help her find James.
- James makes reference to the events that happened in "The School of Hard Knocks" and "The Bridge Bike Gang".
- "If you two... weren't such lousy parents.. you'd stop this mad woman!"
~James being chased by Jessibelle.