When our heroes barely miss the boat that will take them to Lily Of The Valley Island and the Sinnoh League, they begin stumbling upon several old friends. First they encounter Kenny, then Gym Leader Jasmine of Olivine City, and even Flint of the Elite Four!
Everyone wants to catch up after a long time apart, and with so many top-tier Trainers in one place, a few Pokémon battles are bound to break out! First, Jasmine challenges Flint, seizing her opportunity to take on one of the Elite Four. Flint calls on his Infernape to defeat Jasmine’s Steelix, and afterward explains his battle strategy to Ash, who’s been watching intently with his own Infernape.
Then Kenny speaks up—he plans to challenge Ash to a battle, and if he wins, he wants Dawn to go on a journey with him! Dawn is taken aback by this surprising offer, and when the group takes a break for dinner, she turns to Jasmine for some girl talk about what she should do next. Meanwhile, Brock offers Kenny some advice on affairs of the heart.
The next morning, it’s battle time: Kenny’s Empoleon vs. Ash’s Buizel. As the two Water-type Pokémon clash, Ash keeps Flint’s defensive battle strategy in mind...but soon discovers that it might not be the best strategy for him, as Kenny and his Empoleon emerge victorious!
In the meantime, Dawn makes up her mind about Kenny’s offer. She decides to continue with Ash to the Sinnoh League in order to cheer him on, and leaves a letter for Kenny explaining everything.
Our heroes finally catch the ferry to Lily Of The Valley Island, bidding a fond farewell to Jasmine and Flint. Dawn calls her own goodbye to Kenny from across the water...and Kenny loudly assures her that they will meet again!
On their way to Lily of the Valley Island, the site of the Sinnoh League, Ash, Dawn, and Brock are seen waiting for their ship to come. While waiting they run into Kenny, who has set his goal to the next Grand Festival, was having a special training session with Olivine City's Gym Leader, Jasmine. Kenny tells Dawn how great she was in the Sinnoh Grand Festival and was impressed that she made it all the way to the final round before losing to Zoey. After hearing that, Dawn starts to stress about not making her future goal yet. At that moment, Kenny tells Dawn that if he beats Ash in battle, she has to travel with him.
Suddenly, Team Rocket shows up and takes Kenny's Floatzel until Flint's Infernape saves Floatzel with a powerful Overheat. Jasmine then introduces herself and challenges Flint to a battle. Flint sends out his Infernape and Jasmine sends out Steelix. Dawn scans Steelix with her Pokédex and comments on the type advantage Infernape has, but Ash comments on how Steelix is also Jasmine's strongest Pokémon. Ash then decides to send out his Infernape so that it could watch Flint's Infernape battle and take notes. After a tough battle and because of a type advantage, Flint's Infernape defeats Jasmine's Steelix with a powerful Flare Blitz.
After the battle, Kenny (carrying on with his plan) challenges Ash to a battle, and Ash happily accepts, so the battle is then scheduled to go on for tomorrow. Afterwards, Flint tells Ash about a past battle when his Infernape was still a Monferno and of the time he won the Sinnoh League. Flint also tells Ash that he is training for his upcoming match with Cynthia, and how he was unsure if he was either ready or not. Later on, Ash sees Kenny training his Empoleon, encouraging Ash to train Buizel, but Buizel's SonicBoom is deflected of a tree and then Empoleon deflects it back at Buizel. Because the two Water types are so eager to battle each other, Kenny makes the request for the battle to be Buizel vs. Empoleon, and Ash happily accepts the offer. The next day, the battle Ash against Kenny starts.
Ash sends out Buizel and Kenny sends out Empoleon, much to Dawn's surprise. During the battle Ash uses Flint's battling style and remarks that he wanted to polish Buizel's defense. The battle ends with Buizel losing after taking a direct hit with Drill Peck. After, Flint decides to go ahead and battle Cynthia, the gang and Jasmine wish him luck and promise to root for him. At the lighthouse where they were meant to meet, Kenny waits for Dawn but instead finds a letter with a Piplup figurine. In the letter, Dawn states that she wants to cheer for Ash at the Lily of the Valley Conference before deciding her future plans, but knows that she'll continue her campaign to become a Top Coordinator, and as long as they share the same goal she knows she and Kenny will meet again. The boat the gang are travelling on passes, and Dawn waves goodbye to Kenny as the two friends promise to meet again. Behind the ship, Team Rocket follow determined to seize their dreams to capturing Pikachu.
The episode ends with the gang travelling to Lily of the Valley Island, Jasmine returning to Olivine Gym, Flint preparing to challenge Cynthia, and Kenny setting off on his new journey.