>>23198366I think, realistically speaking, Dawn is the one who fits him best. They'd have the most harmonious relationship because they're the ones who most understand the way each other work. Misty, in retrospect, was more of a big sister to him than anything, and her crush on the bratty boy she was constantly bullying and trying to change isn't really sustainable for a long term relationship, compounded when you consider that he's not the same kid he was almost two decades ago.
May and Ash had the most platonic teacher/student relationship of them all, and I think they see each other as siblings more than anything else. Besides, May has Drew.
Unpopular opinion, but I think he and Iris could actually work for a time, but at the end of the day they'd get on each other's nerves too much and they'd realize they're better off as friends. I really love his and Iris's friendship.
As for Serena... Ash just doesn't seem to care about her, and she's so spineless when it comes to him I don't see them working either. She dreams of him being a perfect husband like the one in her fantasies and Ash Ketchum is never going to be that guy. Even if he does get married I think he's always going to want to travel and meet new people, and I don't see any of the girls being okay with that except for Dawn, who has her own ambitions and simultaneously doesn't try to change him because they operate on the same wavelength.
