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Ever since EP009 and Giselle, the writers did not really allow Ash to have visual infatuation or a true crush on a girl. Doing this kept has the show as a whole about Pokemon and not the humans, and side characters like Brock can get away with romance because they're not connected to the main protagonist. In fact Takeshi Shudo, the head writer for the first 5 years, confirmed this reasoning himself:
>___ has no romantic feelings for Satoshi. If ___'s romantic feelings for Satoshi were to become one of the themes of "Pokemon," the entire structure of the "Pokemon" series would be destroyed.
>Even if a childish love affair with Satoshi were to develop in ___, if it were depicted, "Pokemon" would have another built-in theme, and the basic theme would not only be complicated but also diluted.
The writers set this up early on and Ash's denseness/nonromanticness wasn't just invented by the DP writers to downplay Pearlshipping. This goes as far back as the Original Series and continued into the Advance era (anyone remember Anabel's "Guess you can’t sense feelings yet..."??).
With Ash's denseness and romantic limitation as the premise, one might think the writers clearly don't want any "ship" to happen. However, we've seen characters in-universe as well as the writers themselves bringing up the topics of "Ash becoming boyfriend/girlfriend" and "becoming a couple in future" in a way that is more serious and less of a gag (see the Lyra question and the Serena kiss Yajima interview). We've also seen certain visual and even lyrical (High Touch) touches that go beyond Ash loving everyone equally in the long-run. It's clear that based off what the writers actually decided to do, the writers actually adore the shipping/bond aspect when it comes to Ash's companions and want to seriously build something up for a ship, rather than merely insert romance as a one-time gag or joke (e.g. Ash x Lana in SM). And out of the Ash ships, the "seriously build up/setup something" inclination of the writers most notably and seriously favors Pearlshipping, especially after JN.
In short these are two premises/assumptions to keep in mind:
- Ash is dense, will not canonically like anyone romantically in OS-JN (If they bring Ash back, who know what will happen lol)
- The writers do in fact have an interest in seriously building up a "shipping foundation" for Ash for the long-run (Shown by my prior reasoning of in-universe characters+writer interviews)
When you have these two ideas combined as the starting point, Pearlshipping becomes less about the 'siblings/besties' energy that some think they have, and more about what the writers are trying to setup (and not tear down) with the limits they have.
Ash's denseness makes any subtext, off-screen lore, and framing much more meaningful - something Pearlshipping has a lot of
People think that visual and on-screen declarations and indicators are all that matter for a ship. If the writers were allowed to give Ash romantic feelings then visual and on-screen declarations would definitely be what matter most - there would be way more on-screen hints for all the ships. But that's not the case. Remember that we established Ash must stay dense but the writers are invested in building a "shipping" foundation. This means the writers would have to be a lot more hidden and subtle and pour in more effort/hints (while keeping it subtle) where there's less public eyes and scrutiny, and that's exactly how we saw it play out.
There are plenty of examples but High Touch is the most significant example of this - it features Ash singling out Dawn by saying his other companions aren't as easily understood, even Pikachu isn't enough sometimes, and Dawn's smile specifically being with him no matter how many regions he goes to. This shows Dawn is not a generic friend but a special one - one that has received statements, sentiments, and placements only an actual romantic girlfriend would receive. This is exclusive to Dawn because it was only ever done with Dawn, not letting others get the same treatment points to exclusivity. In other words, this is framing from the writers on who's the best choice for Ash's girlfriend, without actually needing to give Ash a canon crush. High Touch is so significant that the staff even decided to quote the song in 2023 as a final nod before Ash left the series for good. (while barely giving nods to other Ash ships)
All Ash ships are considered one-sided canon at best
Even the most popular Ash ships can only have Ash reciprocating as headcanon, Pearlshipping included. From both an enjoyment and canon standpoint, Pearlshipping does not falter as much here because its power is from their special tier of friendship/partnership and life integration (and also both of them being dense/clueless together at times!), whereas other Ash ships get their power from the crush-coded visual and spoken moments and confirmations that can become more of a dead-end due to Ash's denseness. It's hard to pull a significant lead over Pearlshipping no matter how canon the crush, thanks to Ash's denseness.
The JN writers brought up Ash's denseness using Dawn, and didn't bring it up for the other girls
Dialogue from Chloe and Dawn's official conversation about the topic did more than just bring up Ash's denseness by itself. The writers had Dawn saying Ash's denseness as connected to Buneary's crush on Pikachu and 'Pokemon and trainers start resembling each other'. Dawn worries Pikachu is dense, but the funny part about this is Pikachu isn't actually as dense as Ash - if you go back to DP137 both Pikachu and Dawn react to Ash's denseness in the same way! Pikachu and Dawn might be a little dense but definitely not as dense as Ash, as DP137 showed. This supports the idea that Pikachu being dense wasn't a serious claim - it was more about the writers finding an excuse to connect Pikachu x Buneary to Ash x Dawn.
One could claim this is an anti-feat (let's not get into other ships anti-feats but I digress) that "proves" they're never meant to be romantic, after all Ash's denseness isn't brought up with the other girls with canon crushes. The logic could be "denseness was never brought up with ___, therefore _____ is romantically coded for Ash and Dawn is not."
However, in JN94 the writers brought up Ash being dense on-screen with the Heracross and Pinsir love story. This highlights that Ash's denseness wasn't a one-time moment to downplay Pearlshipping since they're willing to bring up Ash's denseness at other points in JN. I would say the most important reason is that the easiest thing to do is not bring up Ash's denseness at all - this was a deliberate choice. The writers chose and wanted to bring it up the very moment Dawn entered the picture. Keep in mind Dawn continued to get Pearlshipping moments in JN after that denseness conversation - Ash never rejects Dawn outright, so Ash being dense not a "no" but a "not yet" from the perspective of the writers' framing.
Conclusion
With Ash being dense, the question is less about 'who Ash likes the most' or 'who likes Ash the most' in-universe. The question becomes 'who did the writers most likely setup being together down the line, if they had to choose one girl for Ash'.
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"Clueless" image from Inse: https://x.com/Inse_on_x/status/2071219343698891244