Confession: I probably dislike Jess more than any adult person should dislike a fictional character. I feel like at this point it's just purely to spite the rational part that is like "c'mon, it's been YEARS." No, shut up rational part. I'm a good person. Just let me have this, okay? LOL. Tangent. Anyway, it's hard as a non-Jess fan and a Lorelai fan that she has these moments where I have no choice but to defend Jess. (Car gate is the other one.) I think it was two-fold. One, Lorelai did genuinely want to help Luke out and two, she was used to teenagers being more amenable with her (Rory, Dean, Lane, hell, she even had moments where she managed to calm Paris down.) but like, read the room, woman!
If I was 17, had been pretty much for all intents and purposes kicked out of my house, sent to live with my uncle in a town of crazies (I mean this in an endearing way....sort of. Most of the time, I did find them funny, but other moments, like yeah, Lorelai, how awful of you to not try harder to get like 40 extra college graduation tickets so the whole town can attend!), the very last thing on earth I'd want is some lady telling me how great it is, give it a chance, etc.
Even with the best of intentions, there's just times you don't need to be spreading your wisdom like that. It was misguided and patronizing. That being said, the sleeping with Luke comment did hit way closer to home. It's telling that that is the comment that set her off.