>>19094134Objectively and honestly, I think Misty/May/Dawn all "deserve" to win Ash.
I think Misty should win though. Pokeshipping had blatantly obvious romantic undertones and it's objectively the most mutual pairing on the show. Ash/Misty had the most entertaining verbal/physical chemistry, instances of jealousy from both, was the subplot of an arc, and was teased on several occasions by characters on the show.
Anyway, if I had to pick the next character after Misty, it would have to be Dawn because her and Ash have this platonic friendship that I guess could become romantic too. Although it just seemed both of them friendzoned each other in DP.