It's undeniable (and I don't just say this as a biased fan who is still mourning the fact that these two did not end up together): Gilmore Girls ' Rory and Jess were one of TV's greatest romances, right from their book borrowing beginnings. What can I say? They had us from Howl. Though they ultimately were not endgame when the series ended in 2007, the couple went from young love to dysfunctional relationship to near-reconciliation in record time over the course of the four seasons Jess took part in — and every moment of their relationship was a flawless moment on television. As two characters who bonded so thoroughly over books, music, life, and everything in between, they should have found their way back to each other before the series came to a close — they were too perfect not to.
Think about it. Jess' final two appearances in Season 6 certainly suggested he had grown into a man who could love Rory the way she deserved to be loved — and at the end of the series, Rory was ready to embark on an adventure that Jess would have gladly supported her through.
Ultimately, Rory didn't choose any love — and though that was a great ending for the new post-grad, her story with Jess was always so open-ended that, if Rory had ended up with him, it would have made total sense. Here's why:
1. Jess Brought Out Rory's Rebellious Side
Every teenager needs a little bit of rebellion in their life — without it, how else will they grow? Jess was constantly pushing Rory to take chances. Whether it was through small things like ditching studying for ice cream or bigger things like proposing they run away together, Jess pushed Rory beyond her comfort zone. If she had never been with Jess, would she have ever been brave enough to skip school to spend a day in New York City? Jess helped Rory see the world in a way no one else ever could.
2. Rory Gave Jess Stability
On the flipside, Jess never felt like he had a reason to stick around any one place for too long — but Rory was the first person who gave him a reason to stay. He still ran, but throughout everything, Rory was his constant. Without her, he may have never formed such a close bond with Luke, or even reconnected with his mom. Rory taught Jess what it meant to have a home.
3. They Spoke the Same Language
What more can anyone ask for in this world than to find someone who gets you? Jess and Rory were both book lovers, music lovers, and culture lovers. They both had complicated families with largely absentee fathers who disappointed them. They understood each other, but they weren't so alike that they couldn't engage in debates. They were the kind of couple who could have talked to each other for a lifetime without running out of things to say.
4. They Saved Each Other
After Jess writes his book, he makes a point to find Rory and tell her he was able to accomplish what he did because she was in his life. Rory pushed Jess to see his full potential, and Jess pushed Rory right back. When he found out she had dropped out of college, he gave her a much-needed reminder of just how awesome she was. If he had not, who knows what it would have taken to make Rory wake up.
5. Jess Was Rory's Luke
Lorelai was always supposed to end up with Luke. He was her person — her lobster. In life, we don't always get a singular person, but TV characters generally do. Jess was Rory's Luke. He was the long haul, forever guy. He was the slightly grumpy yen to her perky yang. Jess was even Luke's nephew. The universe — and by universe, I mean the genius writers — knew they were destined.
6. They Never Really Said Goodbye
It's true: They never truly say their goodbyes. Every time he comes back and every time Rory goes to visit him, it is the wrong time for one of them to start up a relationship again. It's crazy painful, but it is comforting to know that since Luke and Lorelai are assumed to have ended up with each other at the end of the show, Rory and Jess will probably never truly leave each other's lives.
7. The Book Love
The couple that shares books together is supposed to stay together.
8. They Made Each Other Happy
Jess and Rory went through a lot of angst, but when it was just the two of them talking, teasing each other, and simply being together? They were so happy. There's no way those two weren't supposed to get a lifetime of that.
9. They Knew Each Other Better Than Anyone Else Did
How many times did they tell each other — and everyone else — that they knew each other the best? So many times. They said it in good moments (when Rory proclaimed Jess' book to be like nothing else but him) and in bad (when he begged her to run away from Yale with him). The good, the bad — they saw it all, they acknowledged it all, and they still loved each other anyway.
10. Because Jess Never Would Have Proposed at Her Graduation Party
While it's understandable that Logan loved Rory, it doesn't change the fact that she was standing on the precipice of the beginning of her adult life when he proposed marriage. Jess never would have made such a colossal mistake. Since Jess was the guy who pushed Rory to take back control of her life, I feel confident in saying he would have understood how important freedom was to her in that moment — and he never would have made his proposal a public affair.
11. Because It Is What It Is
The last time we ever see Jess and Rory together, he tells her, "It is what is, me and you." And what it should have been was a forever that involved adventures, books, late night conversations, and so, so much happiness. Call me a dreamer if you must, but I still haven't given up on these two.
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