Pearlshipping has quite the history of parallel pairs. In Movie 10, we had Tonio and Alice, and in Galactic Battles we had Lyra and Khoury. The parallelism between the pairs and positioning of them has been executed in a way that basically assumes that they are pairs. And in the this analysis, I will look into a third couple that parallels Ash and Dawn: Iris and Cilan. While Best Wishes disappointed many fans, there were also connections that definitely made Dawn's cameo worthwhile and memorable. To me, this parallel is one of those.
The first similarity involves Ash and Cilan’s ‘feelings’ for Dawn and Iris respectively. While both events are because of the girls’ teasing, they definitely make a great parallel for the guys.
As you may know, Iris has always called Ash a kid. In the episode Expedition to Onix Island, Iris calls Ash kid again. Ash is usually affected and tells Iris to knock it off. But for some reason, he doesn’t react to Iris’s initial remark this time. However, when Dawn makes the teasing comment, “I sure hope he doesn’t go overboard”, Ash’s head snaps hard! He turns to face her and is very disappointed; Ash obviously seeks Dawn’s approval much more than Iris’s. Ash's seeking of Dawn approval can lead to the inference of Ash's feelings for her.
In parallel to Ash’s occurrence, Cilan does exactly the same thing but with Iris instead in the episode Mystery of the Missing Cubchoo. After Cilan ‘fails’ his detective work while still happy, Dawn makes the remark “Well I’ll never hire you”. Cilan doesn’t move and remains unshaken. However, when Iris makes the comment, “But when it comes to pains, you rule!” Cilan becomes extremely disappointed, even more than Ash. There is even more proof that Cilan specifically cares about Iris from the exact words that he uses. “A pain she says, a pain.” Cilan is sad directly because of Iris’s comment because he repeats pain, the term Iris uses. Furthermore, Cilan says she, so he is definitely emphasizing Iris. Just as Ash seeks Dawn’s approval, Cilan seeks Iris’s approval.
This next similarity also involves Cilan and Ash for Iris and Dawn. This scene takes place in the episode Expedition to Onix Island. On Onix Island, Ash and Cilan get separated from Dawn and Iris. Now this is no ordinary one minute separation. The girls and the boys are basically separated for most of the episode! Anyways, when they finally get back together, Ash and Cilan are the first ones to immediately feel relieved by seeing their ‘girl’ again. You can guess who I’m talking about here. Upon seeing them, Cilan says “Iris!” and Ash says “It’s Dawn!” What else can I say? Ash is obviously happy to see Dawn and Cilan is obviously happy to see Iris. This shows that it’s them specifically they care about! To top it off, Ash and Cilan did this at the same time; there is definitely parallelism between the boys’ hints here.
Now if you watch what the girls say, it’s different. Iris says, “It’s Cilan and Ash” and Dawn hugs Piplup. But I don’t think this means Dawn doesn’t like Ash. Besides, Ash would have done the same thing with Pikachu. I think the hints from Ash’s side matter most since most of rival pairings are a change of female with Ash. Any girl can like Ash. But Ash’s feelings for a girl really mean something else.
It’s even better when the writers notice two couples together, which I think they did in Dawn’s cameo. And when you can watch both Ash and Cilan showing particular concern and relief for their specific girl at the same time, that's great.
Ash Encourages Cilan and Dawn Encourages Iris
In the episode Battling Authority Once Again, Dawn and Cilan lose their respective battles in the Pokémon World Tournament Junior Cup. Despite this, it’s actually as if Iris and Cilan both lost; Dragonite didn’t follow Iris after all and Iris becomes sad again. Fortunately, there’s always Ash and Dawn to encourage them, and they do it in a parallel way.
Cilan’s Crustle lost bad to Trip’s Serperior, and Cilan feels beat. He tells Ash he got “pureed” since he makes culinary referneces after all. But remember, Ash is very encouraging. Ash first tells Cilan that he battled great out there. He then goes into how strong Serperior was, and this is to show that Cilan did the best he could against the powerful Pokémon. The most important part is how Cilan is after this. Cilan says “always upbeat” about Ash’s encouraging words. Ash has definitely encouraged Cilan here.
One might point out how Cilan encourages Ash afterwards, but the point is that it's Ash who is the encouraging and upbeat one. Ash Encourages Cilan Ash Encourages Cilan <-(click to watch video clip link)
Now I just said how Ash was the encouraging and upbeat one of the guys' side. In the same way, Dawn is the encouraging and upbeat one of the girls' side.
Here’s where it gets interesting. Just as Ash encouraged Cilan, Dawn encouraged Iris when Iris was saddened about Dragonite not listening. Dawn talks about how she had a hard time with Mamoswine’s obedience just like with Dragonite. Ash talks about Serperior and Dawn talks about Mamoswine. Both Ash and Dawn talked about the Pokémon Cilan and Iris “lost” to.
After telling Iris that Dragonite and Iris will become friends eventually, Dawn ends her signature “No need to worry”. As with Cilan, the most important part is how Iris feels after her encouragement. Iris says “I feel like everything is going to be just fine now”. Iris feels “just fine” because of Dawn just as Cilan is feels encouraged by Ash that he did great. See the parallel? Ash and Dawn supported both Cilan and Iris after their ‘losses’. (Iris still feels like she lost because of Dragonite.)
Dawn Encourages Iris Dawn Encourages Iris<-(click to watch video clip link)
The point is not that Dawn likes Iris just as Ash likes Cilan. Rather, Cilan and Iris were the ones that needed support and Ash and Dawn were doing the supporting. And as we know, Ash and Dawn have been supportive like this to each other in the past. After all, supportiveness is in Ash and Dawn’s character!
Ash Reacts to Dawn and Cilan Reacts to Iris Part 2
These next hints are a continuation of Ash and Cilan both reacting to Dawn and Iris respectively. This time, however, these scenes involve Ash and Cilan reacting because of something warming their female said. While these two events are not as similar, these two moments prove the overall point and parallel that Ash reacts to Dawn just as Cilan reacts to Iris.
In the episode And Then There Were Three, Ash suffers a loss against Trip and his Serperior in the finals. Cilan tells Ash the same thing he told him after Cilan lost to Serperior: Serperior was just too strong. However, after Cilan tells Ash this, he doesn’t feel any better and he doesn’t even react to Cilan’s comment. Right after, Dawn then makes her encouraging remark to cheer Ash up. And boy does Dawn’s words have an effect on Ash. Dawn tells Ash “But Pignite sure showed everyone its courage and strength”. During the episode, the camera then focuses on Pikachu, Piplup, Axew, and Meloetta trying to making Ash feel better, but the Pokémon are NOT the reason Ash feels better. Ash responds with the word “Right!”; this is a direct reaction to Dawn’s comment. Ash continues with “We’re going to get stronger and stronger, and then we’re going to beat Serperior. It is noted that Ash actually does beat Serperior in the Unova League after Ash makes that statement thanks to Dawn’s words. Furthermore, Iris says “Dawn’s right”, which further highlights the fact that it was Dawn’s words that made Ash feel better. Out of everyone in the room, it was only Dawn that Ash reacted to and it was Dawn specifically that made Ash feel better. Dawn ends with “That’s the Ash I know!” Dawn is obviously concerned about Ash’s well being.
As you may recall, Iris called Cilan a pain in the episode Mystery of the Missing Cubchoo, deeply affecting Cilan. If you don’t take Cilan’s feelings for Iris seriously, then consider how long Cilan is moping in the corner for after Iris’s remark. He is basically in deep sorrow for the next 2 minutes 40 seconds, which is the length of the entire battle between Larvitar and Cubchoo. And why? It’s not because of Dawn or Ash, but solely because of Iris. Cilan wanted Iris’s approval without a doubt, and he became sad when Iris disapproved him for being a pain.
After the battle, Ash, Dawn, and Iris tell Chris that going on a journey is how to learn how to battle and make new friends. Of course, Iris makes the comment “You also meet people who can be a pain”. But immediately after, she says, “But that’s what makes it fun, right Cilan?” This shows that Iris still enjoys how fun Cilan is despite his drawbacks. In the same episode, Iris also tells Dawn that Cilan is a great cook and really dependable in the same episode; this reveals more of the traits Iris likes about Cilan.
As soon as Iris says “Right Cilan?”, Cilan immediately perks up from his sadness. He literally explodes from sadness to being overjoyed as Iris redeemed him and gave him the approval he wanted. The same person that made Cilan sad also made Cilan happy. Simply put, Cilan deeply cares about Iris. Iris made Cilan feel better just as Dawn made Ash feel better.
It is also notable that while Iris is talking about pains with her eyes turned away, Dawn is simply just happily smiling and staring at Ash. Notice how Dawn didn’t move her attention as Iris was talking about ‘pains’. Also, consider the fact that Dawn may have thought Ash was a ‘pain’ when he did ‘childish’ actions. Because Dawn did not say anything about Ash being a pain even after the teasing she has done, this could mean that Dawn feels the same way. Just as Iris cares for Cilan regardless of his faults, Dawn also cares deeply for Ash no matter what his flaws may be.
(And remember what Ash said about Dawn's smile? "Your smile is always there!")
In conclusion, Ash and Cilan both reacted to Dawn and Iris respectively. These two moments were Ash and Cilan reacting in a positive sense this time.