>>56627753The way I imagine it the very second the final episode ended Ho-oh's curse of eternal youth wore off and all of the characters ages eventually ticked over to reflect something that would make actual fucking sense because 1000 episodes and 20 or so movies of adventure happening with no calendar time passed is goddamn retarded. Then Ash, in his late teens pulled out his Rotom phone or whatever they use now and called Serena to ask her out. She said yes and he immediately flew to Kalos or wherever she is now and from there they date/fuck like rabbits. They adventure through their early 20s and maybe explore regions, leagues, contests with friends together, but eventually settle down in Kanto to be closer to family, friends, and all the Pokemon still with Oak. Ash starts a gym or other such battle facility teaching younger trainers and Serena manages a contest hall out of the same building also teaching contests. They're both kind of wise mentory after all their experience. Once his son is old enough to go on a journey he does so in region unknown to avoid getting stuck in his father's shadow at home. Ash's son could be a rival to a new protagonist later on, but I don't want a Boruto. Also Pikachu never leaves his side. I don't know long Pikachus live but I'm gonna be generous and say he's still golden into Ash's 80s.
Probably include other characters in this timeline too it's not like they become hermits Ash and Serena keep in touch with their friends, help profs w/research, etc. If you're a fag you can replace Serena with another girl, but Serena is the canon girl and rightly so.