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Can anyone here imagine Jess living in Stars Hollow with Rory and not his baby? Jess always resented Stars Hollow and its residents, including his supposed love's own family. Jess is way too manipulative and selfish and angry for me to ever want Rory to be with him.
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I'm sorry if this is the wrong place to post. However, I really like some of the last posts (huntzmore's long post, but also others: fox24, Talula78) and I would like to sparkle a little bit of a debate. Feel free to delite this post though, because I don't hate Jess.
I don't see Jess as Rory romantic partner, but as a very close family member, who will support her and "protect" her and her child from Huntzberger family (if she won't be with Logan and especially if Logan will be married).
Jess would be a "cool uncle" to her child.
I could see him picking fights with Logan's family, opposing their methods of upbringing a child etc.
I agree, that Jess would not live in SH, but in revival Rory doesn't want to live there either. So, they might live in the same place (Brooklyn for example) and be very close friends.
IMO ultimately Rory would side with the Huntzbergers, although that would hurt Lorelai and Luke too (I could see a huge ideological/political conflict between the families).
Yes, Jess thinks that he knows Rory. But he actually only knows Lorelai's and Luke's world and he thinks, that Rory is similar to them. But we don't know, who Rory trully is, because she hasn't decided yet. She is still "lost" and still searching for herself.