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I'm glad you said that because I feel the same way. I go back and rewatch the series and each time I grow more irritated by Jess and how he treated Rory. I don't get it and I suppose never will. Even in the revival where people claim Jess is this new and improved version but I don't really see it, other than his new vocation as a writer? That doesn't mean he's all of a sudden this new, happy "I'm a God to women" kinda guy. He's just a jerk with a career now.
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I was happy to see that Jess has a good relationship with Luke in the revival. But he and Rory don't seem to have much contact anymore and I thought it was kinda silly for them to show him still pining for her.
But yeah, as someone who watched the show a long time ago and then came back I was sure I missed some episodes that he did some really amazing stuff but ... nope
Maybe a lot of it was because they dated in real life and that relationship was a nice one so people projected it onto the characters? I don't know ...