So how likely do you think it is that Rory ends up with Jess by the end of the GG revival?! I'm trying to temper my expectations :)
I’m tentatively hopeful but don’t want to be too overexcited!
I think ASP really liked Jess. She went to a lot of trouble to show how he grew up and made a great life for himself. Jess also constantly came back into Rory’s life, and was the only one who could get her back to Yale. Unlike Dean, who was used to show how he and Rory could not work beyond the age of sixteen, Jess and Rory always had unfinished business and a deep connection. In The Real Paul Anka, the only reason Rory stops kissing Jess is that she’s still in love with Logan (or thinks she is) and not because she is unattracted to him. I think there’s something very poignant in how Rory always had faith in Jess to do better, and he gave her the push to go back to school.
Jess and Rory to me are the kind of people where it doesn’t matter how much time has passed. They will always have a bond, the kind of easy fall into conversation and friendship. To quote ASP - ‘ Jess and Rory have other things in common other than the make-out, other than the sex. You know, the sex is there, which is nice and enjoyable for all those who want to enjoy it, but they have the books and the music and the reading and the literature and the intellectual standpoint, and you can’t ignore the fact that there is a meeting of the minds there.’
I think Rory and Jess became more compatible as they got older. When they dated, they were too young and had too many issues (Jess with his parents, Rory later with Yale) and they both had to grow up and learn to communicate. So while Dean was the prototype of ‘perfect first boyfriend’ (which I don’t see, but anyway) and Logan fitted the stage of Rory’s college years, where she wanted to explore more of the world of privilege, they didn’t work out longterm. Jess was always written as being more than the stereotypical bad boy you date in your teens, just as Rory was more than a bookish, slightly naive girl. I think they both saw more depth in each other than those around them.
Jess and Rory seem to be the couple who had to grow up separately before they were right for each other and, when they did, they were incredibly well-suited. While I find it a little hard to believe that their paths haven’t crossed in ten years, or that they haven’t become close in that time, I’m willing to accept whatever reason ASP supplies. I may be wrong entirely. If Jess does appear, it could be that he and Rory merely make peace with each other. Their last conversation was terribly unfinished. I don’t want to believe that he and Rory will definitely get back together, but I do think, either way, ASP saw the strength in Jess and Rory’s bond, and that it was much more than a teenage relationship.