Kenny, Dawn's childhood friend and rival from Twinleaf Town in Sinnoh, attended the same nursery school. An incident where Dawn was shocked by Plusle and Minun, leaving her hair standing on end, inspired Kenny to jokingly nickname her "Dee-Dee" or "Diamond Dandruff." This nickname persisted into their journeys, initially used for teasing and sharing embarrassing stories, but later became more affectionate as their friendship matured. Kenny began his Pokémon journey before Dawn, choosing Piplup as his starter from Professor Rowan. His Piplup evolved fully into Empoleon, contrasting with Dawn's Piplup which refused evolution, reflecting Kenny's distinct approach as a Pokémon Coordinator. His team included Alakazam for early Contest appeals, Breloom (which assisted Ash's Turtwig in learning Energy Ball), Machoke, and Floatzel. He typically wore a green T-shirt over a darker green undershirt, khaki pants, and a Pokétch, switching to an elaborate teal-and-gold outfit for Contests. As a Coordinator, Kenny earned five Sinnoh Contest Ribbons to qualify for the Grand Festival. His journey featured early losses to Zoey and later defeats by Dawn in Floaroma Town and Jessie in Solaceon Town. He secured victories in other Contests, defeating Dawn's Ambipom in the Sandalstraw Town finals using strategic combinations like Machoke's strength displays and Prinplup's Drill Peck. At the Sinnoh Grand Festival, a misdirected Hydro Cannon during his Floatzel and Empoleon appeal disrupted their routine, resulting in early elimination. Kenny frequently crossed paths with Dawn, Ash, and Brock during their travels. He assisted Ash with Turtwig's Energy Ball training and collaborated against Team Rocket threats. His interactions with Dawn evolved beyond teasing; he expressed concern during her losing streaks and encouraged her persistence in Contests. Unspoken feelings surfaced when he challenged Ash to a battle, vowing to ask Dawn to travel with him if he won. After defeating Ash, he extended the invitation, but Dawn declined to support Ash in the Lily of the Valley Conference. Following the Grand Festival, Kenny trained in Sunyshore City with Gym Leader Jasmine to refine his Contest techniques. He ultimately departed Sinnoh alone after Dawn reaffirmed their shared dream would reunite them.