18 Reasons Why Jess Mariano Was Rory’s Worst Boyfriend on Gilmore Girls

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His smile could easily make a girl melt in a matter of seconds. He was passionate about books, he enjoyed intellectual conversations and he loved clever literary references. He was also witty and adventurous, and he had that bad boy charm that no one could resist. Jess Mariano was essentially every book nerd's dream guy (and arguably one of the best characters on Gilmore Girls). He and Rory also seemed to fit together like hand in glove. But even with their cutest moments and Jess's better qualities, we can't deny the fact that he was actually a huge jerk.

He did so many selfish and unforgivable things, but what's more frustrating is the fact that he often got away with his behavior because of his charm. During their relationship, Rory had to put up with so much of his crap, and in the few times that she called him out, he never really owned up to his mistakes. He either shrugged it off or somehow turned the blame on her. This isn't to say that her other boyfriends were a lot better than he was (Rory had the worst luck with guys, unfortunately). But if we had to pick the most inconsiderate, manipulative, and borderline abusive boyfriend of the group, then it would totally be Jess. Here's why: