Years later and both Ash and Misty are feeling pain of their decisions, but not necessarily on account of each other; they haven’t been in contact for years since the calling off of their engagement, Misty married Gary (ugh) without inviting Ash to the wedding, but did invite his Mother. Ash married Lana, and didn’t invite Misty to the wedding. Now here’s where the details may change, Lana and Ash, Gary and Misty, both conceive children together, now I can’t quite decide on how I want this to go but my initial thought was this: Ash and Lana start having fights, they divorce, Lana a month later ends up in a severe boating accident, and doesn’t make, her dying wish was for Ash to take care of their only daughter (she has slight traces of Ash’s spikiness, but is for the most part looking like Lana, except she has more natural blue eyes as opposed to Lana’s slightly freaky blank expression).
After news of Lana’s passing, their daughter - I’m thinking of calling her Lisa - ends up with Ash. Ash moves from Alola and somehow ends up in Kalos where he becomes reacquainted with Serena, they marry but that too isn’t going too well (I plan to hop right into the Ash/Serena problem, and Ash says through dialogue what he’s been through following his and Misty’s break up) and are fighting, much to the chagrin of their own son.
Subsequently Misty too is on her second husband, Rudy, and that isn’t going well either. Gary and her didn’t work out and Misty had custody of their son - whom I’m thinking of naming as Jordan. But under Rudy, she and him did conceive, but their daughter was unfortunately loss in an accident, and Rudy hasn’t been the same since.