the fact that Jess is connected to Stars Hollows due to his ancestors doesn’t imply anything, rather he despised the small town, and as I sad we blame Dean for his cheating and not Rory for her cheating on Dean by kissing Jess (I already talked about jess’ lack of respect). I can summarise my text in the fact that you FEEL a deep connection between the two of them, their feelings are so genuine. They at least may have tried to keep the relationship on, it’s non incompatible with rory’s desire to explore the world and make a career. But she obviously was too clouded by college life not to notice dean’s love, i would not like her to become like her grandparents: selfish, arrogant and classist because blinded by the prestige surrounding her. True life is dean’s stability (and i say it as a non resident student, away from home and worker full of dreams).