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They may never have found ever-lasting romance on the show, but in my heart, I believe that they got together sometime in the future, and that now they're living happily ever after, writing books and being in love and acting like the fact that their relatives are also together is cute, not creepy. original seven years run are back, and they're better/worse than ever. Jess runs a successful book press (he even offers to lend Rory money! Below, the (aka my) official (aka totally subjective) ranking of Rory Gilmore's boyfriends, dates, crushes and more, from worst to best: Although Emily did not approve ("Rory, you're in Yale, not Amsterdam!"), Rory decided to be bold and ask a guy out herself. It's not like anyone thought an Emily-arranged blind date would go well, but no one, especially Rory, imagined it would be quite that bad.
There were too many issues — his family stuff, his school problems, his jealousy — and while they had their moments, Jess and Rory's teenage romance wasn't what either of them truly needed.
Yet mention one aspect of the series to a group of fans, and you're bound to get a dozen very different, very heated responses: the topic of Rory Gilmore's boyfriends.
Because while fans might agree on practically everything else about the series, the issue of which guy in Rory's life was her true soulmate still reigns large, eight years after the show went off the air.
Not the worst of Rory's boyfriends, but also not the best.
I'm the first to admit that Jess wasn't the best guy for Rory while they were dating.