I guess I’ll start with one of the most bothersome things for me, personally. This being Rory and Lorelai’s attitudes toward men, most obviously portrayed in their mentality of complete entitlement that they should be allowed to treat anyone how they want because they’re just super special snowflakes and all of the men in their lives should be waiting on the sidelines desperate for an ounce of attention (and that is how the men act, because that’s how the show has written them). Today I’ll focus on Rory.
Rory becoming a homewrecker was the beginning of the end for me, as far as interest in the show and investment in the characters goes. It’s not that she made a mistake… sure, people make mistakes. But sleeping with a married person isn’t a “mistake”. It’s not something you just accidentally fall into, like an unseen pothole. There were plenty of opportunities for her to say “no, this is going too far”, even just recognizing her own desires before either of them actually did anything.