There are many people that ship Ash with somebody. We like to pair him up with whoever we think he has the best relationship with. However we all know he'll never canonically get a girlfriend. But it's nice to fantasise.
So why do I think Ash should end up with Misty?
I know I did this in My Opinion Of Pokémon Ships, but this is gonna be better and longer. With some actual arguments. So, hope you enjoy!
Let's start by looking into their characters a bit more. And then I mean, their characters in the older generations. Because no matter what you tell me, I can't accept the Ash from Black & White and after.
Ash is mainly a goofball with big dreams. He's not especially smart or interested in the world, what he really wants is to show people who he is. The only time we saw Ash's past self was when he and Gary had fished this pokéball out of the river. Aside from that, we only know the Ash during his travels. At first he couldn't really get along with Pikachu. And the same thing happened with Misty.
Somewhere along the way he got wiser, however that was only used during battles. His friendships started to get stronger and he got more and more people he deeply cared for. The first person he encountered was Misty, later Officer Jenny, Nurse Joy, Brock and countless others. He traveled with different groups, and slowly matured a little bit. (The main thing people hate about B&W is that that tiny bit of character development that Ash got was just gone.)
Then there's Misty. She's the fourth sister of the Waterflower's. Her three older sisters run the Cerulean City Gym. Her sisters weren't exactly the nicest or most responsible people around Misty, and we've never heard of any parents. What we do know is that Misty was deeply unhappy when in Cerulean City. She went out on a journey on her bike, in the hope to become stronger and show her sisters she was good too. Unfortunately, some idiot stole and destroyed her bike. She followed him around in the hope he would get her a new bike. Later however she had become extremely good friends with the boy (none other than Ash Ketchum). He helped her become strong as much as she helped him. They parted later and Misty became the Cerulean City Gym Leader.
Ash and Misty's relationship was, in my opinion, one of the best written relationships in the entire show. Misty was not some goody-goody girl, which is already a lot better from later characters in the show. Ash was not even relatively good at Pokémon Battles before meeting Misty. Their personalities clashed, and if Ash hadn't destroyed Misty's bike, it's very unlikely she would have followed him around.
They fought a lot. Misty tried to help Ash to understand the world, but she mostly just ended up with the conclusion Ash could never mature. At first Ash wanted Misty to leave him alone, but he gradually started to grow closer to the girl to the point where he even showed jealousy when someone was flirting with her.
Misty, too, had her times when she was jealous of the attention some girls gave Ash. This change of heart is pretty much the reason I think they like each other. Is there anything else to know?
Yes. Yes, there is.
"But Ash already loves Serena."
Where did you get that information? As far as I know only Serena has showed to like Ash. You can ship it all you want, but Ash never showed any romantic interest in her. Sorry.
"What about the high fives with Dawn?"
High fives are something you do among friends all the time. It's not romantic, really. As I see it, neither Dawn nor Ash really like each other that way. However Dawn did get to think about it a bit.
"There are strong hints toward Ash and May being a future couple."
They never showed to like each other, the hints came from other's. Not from Ash and May themselves. Plus, we've got some pretty strong hints towards Drew and May, too.
"Ash and Iris practically went on a date."
Nice to know that a day out with a friend is already considered a date.
This
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Is the closest we'll ever get to seeing Ash showing interest in a companion.
That is, for now. Maybe someday we'll see some chemistry between a new character and Ash. Or maybe there's even a little bit of chemistry between Serena and Ash, who knows.
