>>36718985Ash and Misty have similar personalities so as a whole their friendship is a lot more stable. Yes, they butt heads and argue, but they respect one another immensely. Having similar childhoods (neglected by parents, always left "behind" by the other kids around them) and dreams makes them very compatible with one another. I always saw Misty as the female Ash (even when the anime tried to force May to be that Ash, especially when AG ended; despite that, May's personality and priorities were significantly different from Ash's and Misty's). Ash and Misty both have something to prove to the people who put them down and to the world. They want to be the best and pursue strength for the sake of that. At the same time, they care immensely for Pokemon and put themselves in danger constantly to save them. Ash saving Sycamore's Garchomp and Pikachu. Misty risking her life to stop the Tentacruel from attacking.
Serena is different. She tries to conform to Ash. Her personality is very submissive, friendly, and warm, but if she has to fight, she exudes an inner strength and resilience. In some respects, she is like Delia. So a relationship like this could work; people usually go for partners that are like their parents. Still, I don't think Ash would be particularly happy with this arrangement. Ash never really expressed any significant care or love for his mom outside of what she can do for him. Ash takes Delia for granted; the same can be said about Serena. Also, Serena being very submissive to Ash and rarely taking the initiative. A relationship is supposed to be 50-50, not 0-100. Ash will likely see Serena as just another mom, and not as an equal like Misty.
The writers forced the Ash/Serena ship down our throats because they ran out of ideas to develop female protagonists. Still, Serena's obsession with pleasing Ash, and Ash's complete ineptitude when it comes to intimate matters such as love and romance, will cause rifts in the relationship.
Misty wins.