okay so the more dipper reincarnates, the more people seem to figure out their deal. in the sense that they know that 'once every X years the evil demon chooses a human companion' or whatever. they may never know the nitty-gritty specifics of it, but it doesn't seem to be too much of a stretch to assume people might notice he chooses a very specific kind of guy every time. they might see Dipper's birthmark as a sort of 'mark of Cipher', for example.
many, MANY incarnations down the line
Dipper is born with his mark, and at this point it's more or less common knowledge what this mark means, and his parents, being loving parents but also sorta overprotective freaks, fly off the rail trying to trick fate and hide him, so he never has to live up to his demon-wrangler glory.
from there, i see two possibilities - either Dipper's contrarian, naturally curious and drawn-to-weirdness nature kicks in and he escapes-
or, more interestingly in my opinion, he just grows up like that. always on the run from the abstract pending doom, stowed away in remote places and hidden bunkers.
i like to think he grows up very resourceful in a doomsday prepper kind of way. very feral. ready to fight this all-powerful entity that his parents always warn him about, that will try to rip him away from his family.
how would Bill deal with this kind of Dipper? that has been raised with this very specific agenda against him and their contract, that he's coincidentally unaware of?
idk i think he'll be very annoyed lol
Well, assuming that we're talking the second Dipper - one where his natural curiosity didn't lead him to leave and his stubbornness didn't cause him to rebel -
I actually think Bill would have a relatively easy time breaking him out of that mentality!
That kind of situation implies a bit of Stockholm Syndrome or Indocrination going on if he hasn't been even a little interested in poking at this Dangerous Evil Entity. Normally he'd at least want to sneak out and get a glimpse of the guy!
So once they meet, all Bill needs to do is find one little crack in that foundation of justification, shove his crowbar of annoyingness and temptation in there, and wiggle it around a bit! From there Dipper's clever brain will do the work, and the rest of that house of cards will crumble like a pile of dice. Jackpot.
Besides, Dipper may not know it, but he is in love with the guy. Bill's got a leg up on him right down on the soul level.
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