Ash and his friends walk around Kasado City and notice that everything is shaped and decorated in the Silver Wing motif. A street salesman approaches the group with 100% pure Silver Rock Isle pins. A woman comes by and takes one, but she breaks it, proving that the guy's a con artist, so the vendor runs off. Ash wonders how that woman would know that the pin was a fake. She reveals that she has a pin as well; when she tries to bend it, it doesn't break. She takes them into her gift shop, introducing herself as Ariene. Ash presses her for more information about the Silver Wing, and Ariene considers a friend who might know something more.
They arrive at a house, with Ariene shouting the name, "Jenaro." After he offers no reply, she opens up the door, Ash being a little hesitant about coming in. They look around to see if there are any clues. They find one when Ash trips on something. Ariene opens up the windows to let in some light and they find a Sandslash with a burning fever lying there. They also find Jenaro, unconscious. Ariene puts Jenaro into bed as Brock treats Sandslash's symptoms. Ariene is annoyed with her good friend for working on his Silver Rock sculptures instead of looking after himself. She officially introduces Jenaro to the group before getting him some replenishing food to eat. Meanwhile, Team Rocket are approached by the Silver Wing conman from earlier, and after hearing that his stock will bring them luck, they quickly raid his pockets and make off with everything.
Ariene and Jenaro continue to trade insults, but Misty is quick to pick out that they actually like each other. Ariene decides to leave for home and Jenaro, aware of Ash’s interest in the Silver Wing, invites the group to stay over for the night. Later on, Jenaro tells the group a story from his four times great-grandfather that a storm sunk a sailing ship. Though the crew and their Pokemon were rescued after a mysterious Pokémon appeared, and then a Silver Wing floated down to them. Since that point, many people have looked up to the Silver Wing as a symbol of luck. Ash pleads for more information, and Jenaro reveals that the shipwreck is supposedly near Ogi Isle, so the group decides that Ogi Isle will be their next destination.
Overnight, Pikachu notices that Jenaro isn't in his bed; Ash wakes up and notices it as well. Jenaro is outside, working on a Silver Wing pin, just about ready to give it some final touches. The gang goes outside to see what Jenaro is doing. He explains that tomorrow is Ariene's birthday, and he really wants to surprise her and propose to her, as he loved her. Making a replacement pin was the only thing he could do. Just one problem: he's a little shy, afraid of what to say when he gives her the gift. Ash and Misty offer some encouragement, while Brock tries to ignore this revelation.
The next day at the town, Jenaro dons a white tuxedo and has flowers and a small box as his gift at the ready. He's a little embarrassed, and still afraid of what to say. Misty tries to get him to go to Ariene and get it over with, except something's up. All the Silver Wing jewelry seems to be getting sucked up. Everyone looks up and sees that it's Team Rocket with a giant vacuum. The trio are feeling lucky with the Silver Wings on their side, and proudly wear some of their loot as they perform their motto. They show off their catch and turn the vacuum onto a higher setting. Jenaro tries to run towards them but he trips, and his gift box falls out of his pocket and gets sucked into the vacuum. After that Team Rocket floats away with their loot, with Ash running right after them. Team Rocket floats away faster than Ash can run, so he sends out Noctowl to puncture the balloon. When Team Rocket crash lands, the gang make it there. It looks like Team Rocket won't go without a fight. Jessie sends out Arbok and James sends out Weezing. Ash uses Pikachu to make short work of the two Pokémon, but Weezing spews a Smokescreen, blinding Pikachu. Arbok attacks with Poison Sting, hitting Pikachu. Then both attack, giving Pikachu no chance to retaliate. Then Ariene and Jenaro get there, Jenaro's Sandslash uses Sandstorm to send the attacks back at Team Rocket's Pokémon. Ariene tells Sandslash to use Swift, but Jenaro gives her an odd look saying that he was going to tell Sandslash to use that attack. Sandslash does so anyway, knocking them back to the balloon. Pikachu blasts them off with a Thunder, and the attack also reveals that their Silver Wing jewelry are all fakes.
Afterwards, Jenaro gets back his present, but he is still unsure and afraid. He tries to say something, and Sandslash pokes him; but just as he is about to pop the question, Ariene asks him the same. Jenaro pushes the gift into her hands, and fumbles through his proposal. Ariene ends up stealing his line, and Jenaro goes on to formally ask Ariene to marry him. Ariene is quick to answer “yes”, and the pair laugh afterwards, but are relieved to have finally revealed their feelings to each other. They argue for a few seconds, but they realize they both love each other. Misty and her friends wish Jenaro and Ariene all the best before leaving for Ogi Isle.
The group later reach the inlet caves and they pass through the underwater tunnel system. On the other side, they find themselves on a cliff. They take a breather, enjoying a soft wind that comes by when they notice a Pikachu in some grass. The Pikachu turns around, and the group recognizes it as Sparky.