Over the course of the series, it becomes clear that Rory systematically avoids any relationship that has the potential to really last. She literally always picks the flighty bad boy over the stable nice guy, flips out when any boyfriend gets to serious and finally breaks up with Logan when he proposes to her. On the surface, this just seems like she has to maintain her 'independent woman' status. But consider, girls innately tend to see their mothers as models for what they should be and their fathers as models of the boys they should pursue. Rory plays this for all it's worth, basically being a miniature version of her mother. So what does she take from her father? It's pretty clear that Rory unconsciously absorbed the idea that the proper role for a romantic partner is to hang around for a while, and then leave. In her mind, a key attribute for a man is "not there anymore."
Jess's perpetual irritation towards Lorelai and her self-declared "wild and awesome" persona makes a little more sense by the time his mother Liz comes into town. Liz has been described by both Luke and Jess as extremely flaky and negligent in raising her son and a throwaway line at her wedding revealed she had been heavily involved with marijuana use in the past. In other words, Liz Danes is the completely opposite of Lorelai, so Jess sees Lorelai as a mere pretender and faking her "craziness" when his own mother had been wild and crazy, with the implication that he had a rough upbringing.
Not only that, bear in mind that Jess was basically rejected by his parents because they didn't want to raise him while Lorelai rejected her parents in a fit of teen rebellion. Her attempt to parlay this into relating with him comes off as condescendingly patronizing in hindsight. It would have further exacerbate his irritation at being shipped off to Stars Hollow against his will.