Attention to detail

Ok, that's not exactly true, he is pretty dense in DP still, but is interesting to notice that he seems to notice when Dawn is not feeling well and he seems very empathetic of her struggles.

Moments such as in DP061 {Team Shocker}, where Dawn loses in the appeal round for the second time (while using Ash's ambipom nonetheless) and tries to put a happy façade about it and we see Ash be specially pained by her attempt at keeping positive.

Or in DP062 {Tanks For The Memories!}, when Dawn is having difficulty in finding motivation to train and Ash sees her crying, he notices, looking at her sadly and when she lies about being hungry and he offers for them to go eat Ice cream. While this scene showcases some denseness in him, is interesting how sadly he looks at her initially. He knew something was wrong to the point of asking jer about it and that's interesting considering how something like this would've slipped his attention completely in other situations.

How in DP075 {Our Cup Runneth Over!}, after Dawn talks about wanting to meet Wallace, Ash is the one to offer that they go search for him (despite the man not even wanting to be found lol). And when they do find Wallace, Ash is the one to tell him about Dawn's struggles, her wish to participate in the Wallace cup and even offers to have a contest battle with her so Wallace can give her tips on it.

This one is specially interesting cause Ash does have a tendency of spilling his friends true feelings when they're hiding it (like the instance with Angie in DP098 and with Serena in XY053), but he never really went nearly as far as he did for Dawn. Even to the point of taking on her suggestion and participating in a contest because she needed the extra support. Gosh, he went the extra mile and perfected Ice Aqua Jet during the Wallace Cup! A move she came up with but never managed to control. And he used it, during a time where she was the most insecure with her own abilites as a coordinator. Ash, in his own way, did the most he could for Dawn and that's very showing of how much he cares for her.

Even during their goodbye in DP0191 {Memories are Made of Bliss}, despite him and Brock being all the way in a parting ship, Ash notices Dawn's sadness, calls her and says her catchphrase right back at her. Something simple but that gets her to break into a smile.

Seeing Ash be this reactive to Dawn's feelings is interesting as he didnt seem to notice when other of his friends were in pain, such as when Misty didn't want to leave him to go back to her gym; How he didn't seem to notice how much Serena's first showcase loss hurt her; or Goh's inner struggle about parting ways with Ash.

Ash puts a lot of effort in understanding Dawn and how to cheer her up.

In fact, Ash seems to even learn how to best cheer her up. After the incident in DP062, where he offered to go for Ice cream with her and that seemed to make her lighten up, he did the same in DP161 {Yes in Dee Dee, It's Dawn}, offering a cup of warm milk after she passed out due to panic of seeing Minun and Plusle (althought he says that was Brock's suggestion, is still funny to me he is the one that offers it to her). And then seasons later he offers her croquetes in JN089 {The Gates of Warp}, when she was crying and feeling defeated over the fact someone had stolen Piplup.

Is a consistent little trait of his to cheer her with food (something he himself love) and I think it's anice showcase of how much he cares for her.

That's when I worry the most

We get him freaking out over her natural ability to find trouble in DP046 {A Maze-Ing Race} to the point of running aimlessly looking for her (and then even losing Pikachu in the way).

In DP060 {Journey To The Unown}, we get him and Kenny (who notoriously has a crush on Dawn) running to Dawn's aid without thinking when she is falling. All the while Brock has the capacity of keeping a cool head enough to call his pokemon to help with that instead.

When Piloswine runs to attack Dawn in DP106 {A Breed Stampede!}, Ash is the one to notice it is not stopping and takes Dawn out of the way.

In Movie11 {Giratina and the Sky Warrior} we get plenty of instances where Ash would just jump into danger to protect Dawn, with him jumping without a second a thought after her when she is sucked in the first reverse world portals. Later when they enter the reverse world for the second time, Ash stops Dawn from falling down a ravine by catching her and holding her whole body, while with Brock he stops him from falling by grabbing his hands.

Even during her contests, Ash always seem very invested on her battles, sometimes even getting out of his seat when things don't go her way or to cheer for her (such as in DP162).

Train with me

Ash loves training with his pokemon, that's something that became a staple for the character around Hoenn and stuck since. But one fact is interesting: Ash rarely trains with his friends. The only 2 instances in which Ash would constantly train with a companion was when he and Iris trained their baby mons (Scraggy and Axew). And. Dawn.

Ever since the aforementioned episode, where Dawn came up with a dodging roll technique and Ash asked her to teach it to him, training pretty much became their thing.

It's something that would be sprinkled to pad episodes and in some instances we would have whole episodes focused on it. It even extended to tag battles, which is something the two would often do together, and that would be used to showcase their closeness and understanding of one another, as battling with another person needs both trainers and pokemon to be in sync to make their combinations work and get a win.

For you, I would

I already mentioned that, but both times Ash participated in contests in DP, it was because Dawn suggested him to.

In DP025 {Oh Do You Know The Poffin Plan} we get the first time ever where Ash tries anything related to cooking. And this only happens after Dawn explains about poffin, how to make them and asks him and Brock to participate in the cooking class with her. He would only ever try to cook again in the privacy of Kukui's home along Pikachu.

In DP086 {Arriving in Style!}, Ash participates in Hearthome Collection, a pokemon fashion show along with Dawn. Again, after her (and Paris) suggest that he does it.

Even in later seasons, such as in BW0087 {Expedition to Onix Island}, Dawn suggests that instead of training te whole gang goes visit an island and have some fun and while he tries to disagree at first he ends up accepting the idea in the end.

And the biggest example of them all: Ash only ever traded pokemon with Dawn.

Ash always had issues trading pokemon, with him undoing the first trade he did it with Butterfree and with him looking peeved by the simple idea when Goh suggested it. Is a running gag how much Ash hates the idea of trading pokemon.

And yet. As long it was with Dawn, he did even that.

Patience

Or how in DP016 {A Gruff Act To Follow!}, when Dawn offers for Ash to use her water pokemon aggainst a rock gym leader and he rejects her in a way mellower way than in the past.

When they fight back in DP029 {The Champ Twins}, it doesnt last long, with them making up later in the episode and having their first tag battle win ever.

Tell me more

Like, in DP039 {Steamboat Willies}, when the 3 humans are out doing some shopping, Ash turns to Dawn and wonders about some pokemon medicine and if it would be good for pokemon. Sure that's just him making small talk but I still find it funny as hell how he would ask her about something like that instead of, I don't know, the soon to be pokemon doctor right next to them?

This happens some other times, such as in the opening sequence of Movie13 {Zoroark: Master of Illusions}, where they're all watching Baccer and Ash turns to Dawn to talk about how cool the game was. While completely ignoring Brock who is sitting on his other side.

In DP082 {Cream of the Croagunk Crop} Ash, densest boy #1, asks Dawn to go dance with him in the Croagunk festival. She rejects him (which. Hilarious. some other people in the anime would die to be in her place and she just rejects him, queen of not giving a fuck). And that scene is extra interesting to me cause the whole atmosphere is very similar to the time Misty asked Ash to a dance in EP020, which in itself had a lot of romantic undertones.

Even when interacting with childhood friends of Dawn, Ash always seemed interested in knowing more about her. With him seemingly having fun learning about Dawn's embarassing stories from Kenny and even commenting on it on occasion. Not to mention how he would always try and ask about the D.D. nickname when he met someone that knew its origins.

But what about..?

With Giselle, it was pulled for jokes. That was done in a time where the staff didn't have a proper grasp of any of the characters (not to mention the constant use of 90s anime tropes, which is what this one is more than anything). So we can assume that one is not as relevant for the character. But two things are worth mentioning: Giselle is a very feminine girl and also a very good battler. Two things you could also say about Dawn.

Now, with Misty.

Back in episode 020 {The Ghost of Maiden's Peak}, when Misty invites Ash to a dance at the festival, he even as much as blushes seeing her dressed up in a kimono. Is interesting that this is one of the only times he blushes ever and the only time he blushes at Misty. Maybe because she was dressed in a more feminine way?

Ash had shown romantic interest in Misty in other situations, such as the times he acted jealous of her in Orange Islands. Such as in episode 103 (Misty Meets Her Match), where he seems jealous of Rudy's constant flirting with Misty.

However, later in Johto, those moments would simply disappear.

And at most, we could consider how he acts in JN058 {A Rollicking Roll… // Eyes on the Goal!}, willingly holding hands with Goh and not feeling ashamed of it (while Goh is having some gay panic about it) a hint of him having some attraction towards the boy.

For any other character, Ash has not shown any interest whatsoever.

Final thoughts