9 Bad Boys You Can’t Help Falling for on TV (PHOTOS)
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Jess was insufferable. He knew Rory had a boyfriend and pursued her anyway, like it was a game. Once he had her, he barely paid attention to her and treated her like crap. His sexual assault of her in 3x19, where she had to tell him "No" THREE TIMES before he got off of her was appalling. That alone makes Jess her worst boyfriend, even if he did eventually grow up off-screen (too little too late). I don't know why Dean gets so much hate, when Jess was worse. Dean was possessive and controlling, but he never sexually assaulted Rory. Sexual assault is much worse than an affair. On his worst day, Dean's still better than Jess for that alone.
Then, Jess tried to FORCE her to go back to Yale by YELLING at her about her life choices, because he was jealous she'd moved on. He had no right to show up and criticize her life choices, let alone act like he knew her better than anyone, when they hadn't dated in years. The year before, he'd begged her to drop out of Yale himself and run away with him. lol Hypocrital much?
Rory was always going to go back to Yale, but Lorelai and Jess wanted to FORCE her to do it instead of letting her come to that decision on her own. At least Lorelai had a valid reason to, as her mother. Jess didn't. He came off controlling, which is often a criticism Jess fans use against Dean. I'm glad he grew up, but I'm also glad Rory drew a line in the sand with him in 3x22 and never went back to him. He treated her horribly. She deserved better.