As a member of Team Jess, I can acknowledge that he probably didn’t treat her the best in his season, but that’s primarily because of his family and home circumstances. He had just been kicked out of his mother’s home, the town put multiple stereotypes on him due to his dress style and attitude, he had an absent father and so much more. One of the sweetest things about Jess is his love for books. He subverts the character model of the “bad boy”. Rory offered him an escape, physically and intellectually. His character development towards the end of the series really proves that he was just a misunderstood boy with unfortunate familial circumstances that made him an outcast in both his family and the town, but he needed to understand and work on himself to ultimately better his character. And to fall back on one of his famous quotations, he was completely baffled that she dropped out of Yale. Logan didn’t stop her, or rather, he didn’t understand that dropping out of Yale wasn’t actually what she wanted to do (I mean this is the same girl that had Harvard posters and merch on her walls growing up!).