When Ash and his friends pass a village that's holding an informal Pokémon Contest where the prize is a year's supply of fruit, Dawn is eager to enter. Ash is just eager to get his hat back once Aipom grabs it and runs off, as usual, but Aipom runs too far and ends up stranded on a perilous spire of rock. Team Rocket wants to enter the Pokémon Contest too, and Jessie sees her chance when she finds and rescues Aipom. As thanks for the rescue, she persuades Ash to let her borrow Aipom for the Contest, and even Aipom seems eager to make the switch!
Once the Contest training begins, Ash is nervous about how easily Jessie and Aipom are working together. During the first round of the Contest, Aipom and Jessie make a fantastic team, and Ash starts to panic—what if Aipom doesn't want to come back? Meanwhile, Dawn's Pachirisu has a case of stage fright, but it manages to come through with a good show. Jessie and Dawn will now face each other in the final round.
Dawn's Pachirisu is brave, but it's unexperienced compared to Jessie and Aipom. Aipom wins the Contest with ease, although Team Rocket is so used to thievery that they steal the prize pile of fruit anyway. To Ash's horror, Aipom chases after them and joins their gang. Luckily, Aipom only wants some of the fruit, and when Team Rocket tries to steal Pikachu too, Aipom uses Swift to send them flying before returning to its real Trainer, Ash!
As Ash trains for his next Gym battle, Pikachu practices a Volt Tackle. Noticing Ash's attention towards Pikachu, Aipom takes Ash's hat and jumps up to a tree branch, irritating Ash. Meanwhile, Dawn finds out about an informal Pokémon Contest not sanctioned by the Pokémon Activities Committee and wants to join with Pachirisu in order to get experience. Dawn and Brock see Ash chasing after Aipom and follow. Meanwhile, Jessie finds out about the contest, as well as the prize of a year's supply of fresh fruit. She asks for James's Carnivine, but he refuses. She then decides to find another Pokémon to use.
They hear Aipom crying and rush to find Aipom, spotting the Pokémon atop a precipice, trying to balance on a flat rock. They don't realize that she is Ash's Aipom and when Jessie sees Aipom cry she decides to save Aipom. She uses a log to form a bridge to the isolated rock. She walks across the log, seemingly calm and balanced. She gets close and grabs Aipom, but ends up jumping onto the rock Aipom was trying to get off. Ash's hat comes lose and flies with the wind back to Ash. Ash retrieves it but hears Aipom cry, prompting them to rush to the location. Jessie holds Aipom, trying to balance on the rock. Ash and his friends arrive and notice the situation as Jessie and Aipom lose their balance, sliding down the cliff similar to snowboarding. The two fly in the air and land on the grass, Aipom landing safely but Jessie crashing face-first. Aipom hugs up to Jessie as Ash and his friends approach. Team Rocket finds out Aipom is Ash's and Ash reluctantly thanks Jessie for saving Aipom. Jessie decides to use the situation to her advantage, wanting to use Aipom in the contest. Ash believes Aipom doesn't want to, but Aipom actually does, which Meowth seconds. Ash decides to let it happen, though reluctantly.
In the village, several stands are set up as Brock notices all of them, despite the contest not being official. Dawn signs up successfully as they notice Ash spying on Jessie training with Aipom. Aipom shows off Focus Punch and Double Team to catch the food falling out of the tree and forming a pile in front of Jessie. Brock believes that Aipom won't show all of its moves to Jessie, but Aipom shows off Swift as well. Ash gets nervous at that she will win the contest, which also affects Dawn.
The event starts, with the local Nurse Joy and the village chief serving as judges, revealing the prize of a year's worth of fruit. Dawn takes the stage first with Pachirisu. Dawn calls for Sweet Kiss, but Pachirisu suffers from stage fright since it is Pachirisu's first. Dawn reassures her Pokémon and calls for the move again, this time Pachirisu performing, catching the crowd's attention. She calls for Spark, creating flower shapes with the attack. She finishes with Discharge, but it unfortunately attacks everyone in the audience. Afterward, Ash and Brock congratulate Dawn for her performance even though she is less confident. Other Coordinators perform, most of them with lackluster results. Jessie performs last in the Appeals Round with Aipom. Aipom uses Swift and follows with Focus Punch to smash the Swift into dust, gaining a powerful appeal. Ash watches with awe as Aipom uses Double Team to dance and uses a combined Swift to create a cyclone. Aipom hugs Jessie and Ash is shocked, believing that Aipom might leave Ash. He has an image of Aipom leaving him, which result in him acting it out in reality.
After the round ends, Dawn and Jessie make it to the second round. Brock notices that Ash is angry with Aipom for doing so well. The Battle Stage starts with Aipom against Pachirisu. Pachirisu uses Spark, but Aipom uses Double Team to dodge, following with a special combination of forming a circle with the Double Team clones and flying around like a Frisbee, which causes Dawn to lose points. Jessie gets cocky at doing so well, but Dawn mentions that Ash trained Aipom well, which is the only reason she is winning. Pachirisu tries to use Discharge, but Aipom's Swift attack counters it, creating a fireworks appeal and dropping Dawn's points more. Aipom attacks with Focus Punch, knocking out Pachirisu and netting Jessie the win.
James shows up in the Meowth Balloon and Jessie climbs in as they recite their motto. They grab the fruit with a net and leave, thinking they stole it, but they actually won it. Aipom watches the balloon leave and jumps off Ash's shoulder and goes after the balloon. Jessie notices and thinks that Aipom wants to go with her. As Aipom jumps onto the net, Ash believes that his nightmare came true and he looks down, wanting to cry. However, Pikachu points up as they notice that Aipom only wanted the fruit, eating several of the bananas and tossing the peels. Ash and his friends run after the balloon, but Ash trips on a banana peel. Meowth tries to grab Aipom with a mecha arm, but Ash calls for Focus Punch to break it. Aipom jumps off and Ash tries to catch Aipom, but slips on a banana. Still, he catches Aipom and both are happy. Team Rocket launches another mecha arm, but Aipom's Swift destroys the balloon and sends Team Rocket flying.
Ash scolds Aipom for being wild, but Brock gets Ash to let it go since Aipom wants to be with Ash, the Pokémon jumping on his shoulder. Dawn also notices that Aipom has a love for Pokémon Contests, but Ash believes that Aipom likes Gyms more and Aipom takes his hat again and runs around, Ash pursuing.