Iris is the only girl where I could realistically see a relationship with Ash working out. Ash isn't going to change. He's gonna spend the rest of his life doing what's he's been doing since the first episode: Aimlessly wandering from place to place, camping the in woods, and never staying in one country for very long. Misty, May, Dawn, Serena, and Lana would all get fed up with his nomadic lifestyle after a couple years and want to return to society. Iris revels in living outdoors surrounded by Pokemon.