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 Pokemon 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 Pokemon 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 to 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!