Top 10 Unforgettable Jess & Rory Moments
These two are super cute and we love them together! For this list, we're looking at our favorite moments from Jess and Rory's relationship in both the original series and 2016 Netflix revival. We've included the sprinklers moment when Jess comes to Rory's rescue. Another favorite moment is Rory & Jess' Car Ride! That's when Rory lets loose and lets herself enjoy hanging out with him. From that she realises that they share many things in common and might actually be compatible. We also love the time Rory visits Jess in NYC. Though nothing overtly romantic happened while they were together, the final moments as Rory boards the bus are indicative of something more to come!
#10: The Sprinklers “Eight O’Clock at the Oasis”
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At the beginning of season three, Rory and Jess seemingly hated each other, but fans knew that it was all the unresolved romantic tension between them manifesting in outwardly aggressive behavior. When Lorelai signs up to help a neighbor out when he’s out of town, Rory unsurprisingly ends up picking up the slack for her. This includes following a strict lawn watering schedule. The sprinklers malfunction however, and Jess comes to Rory’s rescue. While up until this point he’d done everything in his power to anger Dean, in this moment, Jess lets Dean play the hero despite having already saved the day himself. It’s a move that’s classy, caring, and oh so charming.
#9: Catching Up “Fall”
When fans heard that “Gilmore Girls” was getting a revival, they were thrilled. And of course, they quickly began to ask which of Rory’s exes would be making an appearance. Even though Jess doesn’t have a ton of screen time in the revival, every scene he’s in really counts. Seeing the two of them catch up over drinks at Rory’s office was heartwarming, and the fact that he pushed Rory in the direction of writing her own book brings their storyline full circle from the original series. The longing look Jess gave Rory in the revival’s final scenes left viewers clamoring for more, and with the sneaking suspicion that their story is far from over.
#8: Rory Visits Jess In NYC “Lorelai’s Graduation Day”
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At the end of the show’s second season, the youngest Gilmore girl makes the very un-Rory-like decision to secretly travel to New York to visit Jess. She ends up stuck on a bus on her way home and misses her mom’s graduation from business school. Though the decision came with serious repercussions, it did give Rory/Jess shippers the sign they wanted that Rory really did have feelings for Jess. Though nothing overtly romantic happened while they were together, the final moments as Rory boards the bus are indicative of something more to come.
#7: Rory & Jess' Car Ride “Teach Me Tonight” While we all know that this outing doesn’t exactly end well, seeing Rory and Jess spend time getting to know each other is sweet nonetheless. Rory is trying to tutor Jess so he can do better in school and of course he is not cooperative. She tries everything she can to make him focus but it isn’t working so she finally gives in and says they can go get ice cream. When Rory lets loose and lets herself enjoy hanging out with him, she realises that they share many things in common and might actually be compatible.
#6: "Dean Was Right" “They Shoot Gilmores, Don’t They?”
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In this fan favorite episode, Stars Hollow is hosting a dance marathon and Rory and Lorelai are competing together. Jess is attending with his new girlfriend and won’t stop taunting Rory and Dean throughout the event. Eventually Dean reaches a breaking point and not only breaks up with Rory in front of the whole crowd, but goes so far as accusing her of wanting to be with Jess. When Rory goes off to have a moment alone, Jess follows and she utters these fate-sealing words. Though it’s a sad moment, it’s also the beginning of a real relationship for these two.
#5: Jess Says I Love You "Nag Hammadi Is Where They Found the Gnostic Gospels"
It had been half a season since Jess left town without a word, so when he shows up in Stars Hollow again, things are predictably tense between him and Rory. He manages to evade her over and over again until they finally have a confrontation in the street. Rory is understandably still bitter about how he ended their relationship and asks him what he could possibly have to say to her. When he responds with “I love you”, viewers were just as shocked as she was. Jess certainly pulls his weight in making Stars Hollow interesting.
#4: "You Looked It Up" "Happy Birthday, Baby"
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For the first few seasons of the show, Rory is defined by her aspiration to go to Harvard. When she’s finally accepted to Harvard, Yale and Princeton however, she realizes she has an important decision to make. After much deliberation, she picks Yale and when she’s talking to Jess about it, he reveals that he had already searched to see how long it would take to get there. This may seem insignificant, but considering his flighty attitude, the fact that he was doing that kind of forward thinking is notable and revealing.
#3: Jess Wrote a Book "Let Me Hear Your Balalaikas Ringing Out"
Fans were forced to go two whole seasons without seeing Jess but this season six episode fully made up for it. Jess is in Hartford so he and Rory make plans to meet up because he wants to share something with her. When he shows up at the Gilmore residence, he hands Rory a book- one that he has written. Rory’s unabashed pride in him is adorable, and fans loved seeing them on good terms after the tumultuous relationship they had had. The real kicker is when Jess tells Rory he never could have done it without her. Cue our hearts breaking.
#2: "This Isn't You!" "Let Me Hear Your Balalaikas Ringing Out"
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We wouldn’t typically take two moments from the same episode and put them side by side on our list but this one totally merits it. After their evening takes an unpleasant turn once Logan joins them, Jess decides to confront Rory about the recent life decisions she has made. We had all been watching Rory’s spiral into a life that clearly wasn’t for her, but it took this wake up call from Jess for her to actually do something about it. We could not have handled one more episode of Rory and Lorelai feuding so this could not have come at a better time. Before we unveil our top pick here are a few honorable mentions. The Bracebridge Dinner "The Bracebridge Dinner" Jess' Food Care Package "There's the Rub" … Jess Bought Rory's Basket "A-Tisket, A-Tasket"
#1: Their First Kiss
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Our top pick may be a controversial one but we’re sticking to it. In the finale of season two, Jess returns from New York and makes an appearance at Sookie’s wedding. Rory may still be with Dean, but that doesn’t stop her from doing something totally impulsive and kissing Jess like she means it. This moment had been a long time coming so fans were overjoyed when it finally happened, despite the fact that Rory was technically cheating. Of course, they got another chance at a proper first kiss the following season when they actually started dating, and that one was thankfully guilt-free.