Disclaimer, I love the Gilmore Girls.
I've been watching a lot of Gilmore Girls recently, and I've come to the conclusion that often Lorelai isn't a very nice person. Much is made in the show about Lorelai having escaped her upper class upbringing, but frequently she actually behaves like an entitled rich kid. For instance--
She treats Luke appallingly, especially before they are in a relationship. She expects him to drop everything every time she needs his help, regardless of what he has going on in his life, and she never seems to repay the favour.
She's frequently rude and condescending to people she views as less intelligent, witty and pop culture literate than she is.
She's massively PFB about Rory and expects, almost demands, that everyone else sees her as being as special and amazing as she does.
She's a classic example of someone who thinks the rules apply to other people but not to her. She uses her phone in Luke's despite it being a phone free zone, she drinks and drives (when visiting her parents she always has alcohol then drives back to Stars Hollow), in one episode where she's dating Digger/Jason they sneak into the staff room of a supermarket at night and muck about with the time cards, most likely causing some poor minimum wage employee grief in the morning.
There's probably more but I can't think of any right now.
(I'm still hugely excited about the Netflix reboot though)