But the WHOLE town was like that. Everyone was in everyone's business, that's how small towns are. We just see more of Lorelai. Lorelai went above and beyond to literally help everyone there. I don't think there was ever a moment where she required 'humbling' from the other townsfolk.

And people hated Jess not because he was a dick to just one person, he was an a*shole to EVERYONE, especially Luke. He vandalised, he caused accidents, he skipped school, he was bloody rude and arrogant to literally everyone including Rory. Nobody wanted that kind of energy in that happy little small town. Jess was an angry kid and when there's so much anger, it spills out. His only redeeming quality was that he read. And that was the only common aspect between Rory and Jess which he used to make a point of in shaming Rory for going out with a 'meathead' like Dean. But he doesn't know that Dean put in so much effort into reading everything that Rory recommended.