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On their way to Lily of the Valley Island, site of the [[Sinnoh League]], {{Ash}}, {{an|Dawn}}, and {{an|Brock}} are seen waiting for their ship to come. While waiting they run into {{si|Kenny}}, who has set his goal to the next [[Grand Festival]], was having a special {{pkmn|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, {{TRT}} shows up and takes Kenny's {{p|Floatzel}} until [[Flint's Infernape]] saves Floatzel with a powerful {{m|Overheat}}. [[Jasmine]] then introduces herself and challenges {{EF|Flint}} to a battle. Flint sends out his Infernape and Jasmine sends out {{p|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 {{AP|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 {{TP|Kenny|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 {{AP|Buizel}}'s defense. The battle ends with Buizel losing after taking a direct hit with {{m|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 {{DL|Grand Festival|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.
* {{p|Snorlax}} (unnamed Trainer's; flashback)
* [[Professor Oak's Big Pokémon Examination]]: {{p|Nidoran♀}} and {{p|Nidoran♂}}
* As of this episode, half of the Johto Gym Leaders have appeared in the {{series|Diamond & Pearl}}, though Jasmine is the only one who has appeared in person.
** Aside from her, only [[Clair]] has been seen in her Generation IV outfit, with [[Whitney]] and [[Morty]] appearing in their Generation II designs. Jasmine is also shown in her Generation II outfit in flashbacks in this episode.
* Music from ''[[M08|Lucario and the Mystery of Mew]]'' is used as background music in this episode.
<gallery perrow=5>
File:Flint Monferno.png|Monferno's discolored eyes
File:DP180 Error.png|Piplup's discolored beak
File:DP180 Error 2.png|Infernape's discolored shoulder pads
File:DP180.png|Empoleon's discolored chest
==In other languages==
|zh_cmn={{tt|小智對健悟!各自的起步!!|Ash vs. Kenny! Setting off for Respective Roads!!}}
|nl={{tt|Een Viersprong in een Pokémon Haven!|A Crossroad in a Pokémon Port!}}