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As hints and evidence for ships are mostly speculation, this page may contain personal points of view.
PenguinShipping is the belief of a romantic relationship between Dawn and Kenny. Kenny and Dawn are childhood friends, who are now Contest rivals. This Shipping is called PenguinShipping due to the fact that both of them have members of the Piplup evolution family. Even though not many hints exist due to Kenny's lack of appearances, it has been shown that he and Dawn know each other well. As a running gag in the series, Kenny calls Dawn Dee-Dee (Japanese: ピカリ Pikari). This shipping's main rival is TwinleafShipping due to the fact that both Kenny and Barry have known Dawn when they were young.
Most, if not all of this ship's hints come from Kenny's side.
- When Kenny sees Dawn in her contest dress, he is momentarily speechless. She starts flirting with Kenny and asks him if he thinks she's pretty. He blushes and quickly tries to change the subject.
- Kenny seems jealous of Ash and Dawn supposedly being together. He promises to Dawn after Jessie's appeal that he would make "that Seviper lady look bad."
- When Dawn is being lifted into the Solaceon Ruins due to the confused Unown, Kenny worriedly calls out her name. He does this again when Dawn falls, later in the episode. He is the only one who does this on both occasions. Towards the end of the episode, he wants to make sure Dawn did not find out how scared he was in the ruins. When Brock says, "Everyone has secrets hidden in their closet," Kenny gets embarrassed.