13 Rory & Jess Moments In 'Gilmore Girls' That Will Forever Toy With Our Heartstrings

We all know it was always supposed to be Luke and Lorelai, together forever, in Gilmore Girls, but when it came down to Rory's love interests, it was consistently a debate among the fandom. You may have friends who believed that Rory was supposed to end up with her first love, Dean, or her college bae, Logan. And yes, they were both great matches for Rory at different stages of her life, but in my opinion, it was Jess who was the one. Your friends can disagree with you all they want, but it's hard to argue with all of these Rory and Jess moments in Gilmore Girls that just prove these two were #MFEO.

Much stood in their way (and yes, I get it, Jess was kind of a jerk at times), but that's only because he was a misunderstood bad boy. Jess and Rory's love story was kind of tragic, because we were all rooting for these two but they just couldn't get it right. I mean, Jess was a perfect match for Rory, because they could talk about books and music together, and have you seen how much of a hunk Milo Ventimiglia is?! Who wouldn't be madly in love with him?

It's too bad Jess and Rory's time together was all too short, and watching these 13 Jess and Rory moments will play with your heartstrings. You never know, though. Just like it took Luke and Lorelai years to finally get it right, maybe one day Jess and Rory could do the same. We're keeping our fingers crossed.

When Jess Brought Rory Food
BTH on YouTube

We all know Jess totally lied about Luke sending over food for Rory when she was home alone. It was simply his excuse to come over and hang out with the girl he was hardcore crushing on. Jess was always so smooth, and let's be honest — we'd fall for any guy who surprised us with that much delicious food, too.

When Jess Bid On Rory's Basket
Jade Bates on YouTube

Poor Dean lost out on Rory's basket, and she ended up going on a picnic with Jess instead (yassss). His excuse was that he wanted to see Dean get upset, but we always knew he had a crush on Rory and wanted to take her out. And, Rory, you could have acted upset as much as you wanted to, but we low-key knew you wanted to be there with this hunk, too.

When Rory Helped Tutor Jess
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Jess and Rory's flirty study session turned into an adorable date where they ended up grabbing ice cream. When Jess asked Rory if they should get back to studying or turn right to keep driving around, Rory told him to turn right. She was just as much in love with this guy as we were with this moment.

When Rory Skipped School To Visit Jess In NYC
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Rory loved school, so the fact that she ditched it to go see Jess in NYC on impulse just proved to us how much she cared about this guy. Ugh, just be together forever you two!

When They Had Their First Kiss At Sookie's Wedding
Jade Bates on YouTube

When Jess came back to Stars Hollow, he immediately found Rory to tell her. She kissed him, and we all immediately died from happiness. Unfortunately, Rory told him to not say anything and ran away, but this was our first bright light into the Rory and Jess relationship saga.

When Rory Tearfully Confessed That She Likes Jess
Jade Bates on YouTube

Finally, these two got together at last. We spent most of the season watching the Rory, Dean, and Jess love triangle just hoping for Rory and Jess to finally come together. It all happened the night of the dance marathon when Dean broke up with Rory because he saw what we all saw since day one... which was that Rory and Jess were meant to be together.

When Jess Left Town
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No, Jess, don't leave us. This is probably the most heartbreaking Jess and Rory moment in the entire series because this was when we realized they were done. We're so mad at Jess for leaving without saying goodbye, but he was young and dumb. That definitely doesn't mean they shouldn't be together now that they're older and more mature, right?

When Jess Told Rory That He Loves Her
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Jess told Rory, "I love you," and then left... again. Why did you keep doing this to us, Jess? You know our little hearts just could not take it. Even after all of the time apart, Jess still loved Rory. This gave all of us loyal Rory and Jess shippers hope that one day the timing would be right and these two crazy kids would finally get back together.

When Jess Revealed To Rory That He Wrote A Book
Tischdecke on YouTube

Jess wrote his first book and had to tell Rory about it, because he couldn't have done it without her. See, when you're in a relationship you should strive to make each other better, right? Rory made Jess better by inspiring him to go after his dreams. She was always his best cheerleader.

When Jess Told Rory She Should Go Back To Yale
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We were all mad at Rory when she dropped out of Yale. Nothing was going to make her get back on track... that is, except Jess. He's the one who finally convinced her to go back to school. He knew the real Rory and what was best for her. And that, my friends, is true love.

When Rory Traveled To Philadelphia To See Jess
Tischdecke on YouTube

They were both guilty of playing with each other's emotions, and they were the most guilty of playing with our own. Rory traveled to Philadelphia to see Jess when she was fighting with Logan. Rory, why would you ever try to hurt Jess like that? Not cool. His response, though, showed us that he matured, and he truly cared about her.

When Jess Helped Rory With Her Rut
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Jess was always the one to help Rory when she was at her worst. He was right about her going back to Yale, and later on in Gilmore Girls: A Year In The Life, he told Rory she should write a book. Come on, Rory, realize that Jess was the best thing to happen to you.

When Jess Was Definitely Not Over Rory
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In Gilmore Girls: A Year In The Life, Luke asked Jess what was going on between Rory and him. He said it was just a work thing and it's over between them, but when we saw him looking back at Rory we knew in our hearts he was full of it. It's not over between the two of them, and it never will be over for all of us.