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11. Jess was willing to let Rory go so that she could grow as a person.
Jess never wanted anything but the best for Rory. Ironically, he ended up being the best influence on her of anyone she dated.

After all, he didn't get married and then proceed to carry on an extramarital affair with her (*cough* Dean *cough*). And he most certainly was not present during that awkward moment when she stole a yacht and dropped out of college. Oh, Logan.

In fact, Jess was willing to let Rory go so that she could grow as a person. So that they both could, really. It's my belief that he waited for her, though –– and still is. Until the Gilmore Girls revival, that is.