>>53729264None of this is easy to predict because after teens mature into adulthood, their social personas change a lot. People change a lot in their teenage years so any pairing prediction is just blind guessing really, realistically, none of your ships will be canon and all the characters will end up with different random people.
If we do assume pairing, even like that, then it would be....
>>Ash/SerenaVery unlikely. The only time we saw Ash explicitly romantic was with Giselle so that gives us a clue in what Ash values in women - assertiveness and perception, so Latias/Anabel/Miette/Giselle are way more likely to fall into Ash's social orbit when he grows up to start flirting and stuff, Ash is masculine enough to invoke interest in all of the aforementioned girls. Unless Serena chads up with an exreme behaviour change, I can't see her being able to have a pull on Ash.
>>May/DrewGiven that both May and Drew are conscious on the whole romance thing, thi is the one where it's most likely. I can see May eventually outgrowing Drew psychologically in their teens so by that point it would be a question of whether Drew would be able to catch up to May in character growth.
>>Dawn/KennyThis is just zero probability. Dawn is basically confirmed lesbian and I don't see Kenny ever cultivating any sort of appeal to win her over. Kenny would be a good fit for Misty their aggressive personalities would balance out well.
>>Cilan/GurbundyBurgundy is too beta for a person with refined tastes like Cilan. I'd imagine he'd rather try going for an open girl like Skylar since he would feel more comfortable being the sophisticated one in a relationship, Cilan would feel too overwhelmed by a girl with sophisticatedness close to his own
>>Goh/Koharu...Maybe? I can't imagine Goh being invested in romance but if he was he'd probably feel too awkward projecting his sexual desires onto a childhood friend while Koharu would be too indifferent to bother trying to appeal to him sexually.