I saw this really good comment/character analysis on this video last night
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Jess loved Rory a long time before he told her and even before he knew and I think it scared him because he has a dad who doesn't care about him and a mom who doesn't want him and an uncle who doesn't know how to show affection and I know he acts like a punk sometimes but good Lord this boy has never had anyone care about him before and when Rory starts to care about him you can see how it just completely blows him away every time he looks at her and I'm so mad at him for screwing it up with them but also I get it because he doesn't know how to communicate or be vulnerable but I'm convinced he would actually do anything for her continues rambling about this for eight years
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This is a really good analysis of Jess and the main reason why he fell for Rory. It wasn't just the common interests or her beauty - it was her kindness and caring for him. However, after this kiss, Rory screwed up. Instead of facing her feelings and breaking it off with Dean to be with Jess, she left Stars Hollow and spent the whole summer in Washington. She didn't say goodbye to Jess, she didn't call him, she didn't write anything. How was he supposed to feel? Abandoned. Just like he was feeling all his life - abandoned by his father, by his mom.
That's why he has an attitude when she comes back after the summer.
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https://www.youtube.com/watch?v=O58M...ptroVdp4AaABAg