>>55365843Pretty cliche and standard personally. I think part of the appeal of Jessie (beyond her appearance) is her being an antagonist with Ash and evil ladies are hot. A story that would end up pairing them beyond a one night stand would require her to stay villainous to that degree, and yet give her a reason to keep that twerp around as a possible love interest in her head.
Then meeting before is a good idea, so maybe we can steal an element of Serena indirectly by having them meet in the past, although not as childhood friends. Some age shit may need to be modified because a forever 10 Ash just doesn't make sense to me, but I could see him indirectly influencing Jessie into looking at Team Rocket if the past has anything to say.
Like if both of them got into a spat over some weird romance rumor despite them hating each other's guts, and yet Ash still chose to defend her when said rumors ended up turning to blows. He himself would denounce truth and love and stand up for doing what he thinks is right instead, like dumbass Shirou's quote: "Just because you're correct, doesn't mean that you're right."
She may misinterpret those words, but still take them to heart as the first string that tied them together. Ash may or may not remember this encounter, but Jessie certainly does, and I think it would at least try to set something up to happen in the future when he first starts his journey.