Kenny likes to tease Dawn. He often calls her by her nickname, '''Dee Dee''' (Japanese: '''ピカリ''' ''Pikari''). It was revealed in ''[[DP161|Yes in Dee Dee, It's Dawn!]]'' that he came up with the name to make fun of her when they were younger. In [[Four Roads Diverged in a Pokémon Port!]] right before the [[Sinnoh League]] and after the Grand Festival Kenny showed to have developed a crush on Dawn. He challenges Ash to a battle and and asks if he wins,would Dawn go on a journey with him. Kenny manages to beat Ash and says he would be waiting at the lighthouse
is Dawn decided to go with him. At the lighthouse Dawn leaves him note saying for now her plans were to cheer Ash on in the Sinnoh League,but she continue trying to be a [[Top Coordinator]]. Although as long as they share that dream they would certainly meet again.