I'm the same age as Rory and hated Jess from the beginning, so I don't think it has to do with my current age. He was rude and disrespectful to everyone except Rory and even then, that was only until they got together. I liked him well enough in season 6(?) when Rory tried to use him to cheat on Logan and enjoyed him in the revival, but wouldn't buy them as a couple now. It's been too long and, ironically enough, I think Jess has outgrown her and is now too good for Rory.
For what it's worth, same goes for the Dean we saw in the revival. Rory is pretty much the same person she was towards the end of season 7. Dean and Jess both appeared to act like men in their thirties. Let her be with Logan who will always be 21.