As a childhood friend of Dawn, Kenny likes to tease her. He often calls her by her nickname, Dee Dee (Japanese: ピカリPikari), which he made up when he was younger to make fun of her. He also likes to share stories of their kindergarten days to embarrass Dawn. Despite this, he still cares about her, as show in Team Shocker! when he became concerned after seeing her getting depressed for not making it to the Contest Battles of the Solaceon Contest.
Despite being friends with Dawn for a long time, he said in Getting the Pre-Contest Titters! that she had never noticed he was also interested in Pokémon Contests when they were younger. In Settling a Not-So-Old Score!, he stated that he was glad to have become a Pokémon Coordinator because that way he and Dawn would see each other often in Contests.
In Four Roads Diverged in a Pokémon Port!, Kenny was shown to have developed a crush on Dawn. He challenged Ash to a Pokémon battle and stated that if he won, he would like Dawn to go on a journey with him. Though Kenny managed to defeat Ash, Dawn sent a message to him saying that her plans were to cheer Ash on in the Lily of the Valley Conference and assuring him that as long as they have the same dream, they would certainly meet again.
- Kenny has a blue Pokétch, the one given to male players in Pokémon Diamond and Pearl.
- Kenny is the only one of Dawn's rivals that didn't progress to the second round of the Sinnoh Grand Festival.