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As hints and evidence for ships are mostly speculation, this page may contain personal points of view.
PenguinShipping (Japanese: ケンヒカ KenHika) 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).
- 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.
- When Dawn doesn't make it through the appeal round, Kenny says, "Oh, c'mon!" indicating that he wants Dawn to be there with him in the Contest. Also, when saying goodbye to her, Kenny shouts that he won't let Dawn quit Contests no matter what; when walking away, he sees that Dawn isn't waving goodbye like the rest, and looks upset.
- Kenny tells Dawn that her Piplup began to evolve because of what a great Trainer she is. When Piplup runs away, Dawn runs over to Kenny and the rest of the group, and Kenny is the one to ask her what was wrong.
- Kenny wanted Dawn to travel back to Twinleaf Town with him so that they could start training for the next Grand Festival together. But Dawn's not sure about going with him because she wants to root for Ash in the Sinnoh League. Kenny then tells her that he would battle Ash and if he won, she would have to travel back home with him. He also says "I just had to tell you how I feel." Even though Kenny won, he lets Dawn go with Ash thinking that she would be happier that way.
- Kenny, after making his appeal, talks alone with Dawn about watching her at the Wallace Cup and how he's going to follow, win, and get ahead of Dawn. In response, she blushes, holding her heart, and says, "Please, you're embarrassing me!" Also while waiting for the results of the appeal rounds, Dawn is nervous and tells Ash about her worries about Kenny. She blushes while doing this.
- When Kenny told Dawn that he wanted to go on a journey with her, he said "I know this is a bit sudden, but I had to tell you how I feel!" He then ran off. Dawn seems to be conflicted about Kenny's offer to go back to Twinleaf Town with him or going to the Sinnoh League with Ash. When Dawn sees how upset Kenny is after agreeing to let her go with Ash, she becomes greatly saddened. Later she leaves a Piplup figurine as well as a note behind at the Vista Lighthouse wishing Kenny luck in the future. She then waves goodbye to Kenny while she's on the boat heading to Lily of the Valley Island as he stands at the lighthouse.
- At the end of the letter she left at the Vista Lighthouse it read, "P.S: One more thing, and I hope you don't mind, you looked kind of handsome when you beat Ash.
- 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.
- At the end of the episode, Dawn seemed concerned about Kenny leaving the Grand Festival so soon. Kenny then had said "Make sure that you don't lose to that girl with the Plusle and Minun, kay Dee-dee?". Dawn then replied by saying "it's Dawn", smiling then giggling. Kenny responds with "finally, a smile" then she laughs some more.
- Both have Pokémon of the Piplup evolution line.
- Both have known each other since they were young.
- Both are Coordinators.
- Both have owned a member of the Buizel evolution family.