Rory and Jess might be the most controversial relationship in Gilmore Girls - some fans love Jess's intelligence and bad boy ways, and others think that he was just flat-out terrible for Rory and should have been ditched on the double. He remains controversial right through to the Year In The Life revival, where he reappears and makes fans wonder if he's still in love with Rory, and with good reason.
At the end of the day, Rory and Jess were incredibly important to each other, and they always will be - and that's something that any fan of the couple can get behind. From his time as a reluctant and angry teen to a successful author, Rory and Jess will always be there for each other, and fans of the couple will love these episodes.
Updated May 7, 2020, by Rose Moore: Fans are still hoping that a second season of Gilmore Girls: A Year In The Life could be forthcoming - and while there are no official plans, there are some hints that a sequel is on the way. If it does, a huge hope for Rory and Jess fans is that there will be more between the two as adults, as they were only given a few scenes in the revival, and those scenes suggested that Jess still has some feelings for his high school sweetheart. In the meantime, though, there are some great episodes for fans of the couple to rewatch.
15 The Bracebridge Dinner (S2 Ep10)
This isn't the first time that Rory meets Jess, but it's the time that really points toward what is waiting for them... and for her and Dean. In this episode, Lorelai has a huge dinner planned, which is canceled because of a snowstorm. She ends up inviting the townspeople to the event instead (seeing as everything is already arranged), and when the dinner ends in a sleigh ride, Rory ends up sharing a carriage with Jess. It's romantic enough there, but Jess pushes Rory to really think about her relationship with Dean - and everyone knows what is coming.
14 A Tisket, A Tasket (S2, Ep 13)
Stars Hollow has all kinds of ridiculous and adorable traditions, and this episode focuses on one of them - the picnic basket auction. Here, Jess decides to outbid Dean for Rory's basket, although tradition would dictate that Rory's beau take the honor. It stokes the resentment between Jess and Dean, for one thing, but it also creates space for Rory and Jess to spend some time together, and realize just how much they have in common.
13 There's The Rub (S2, Ep16)
Jess proves his literary chops in this episode, where Rory tells Dean that she wants to spend time alone, only for him to catch her with Jess and Paris. Of course, she originally did want to spend that time by herself, and she didn't invite either Paris or Jess over, they just kind of (individually) showed up. But it's a great one for Jess fans, as it shows that he has the ability to connect with Rory and Paris on an intellectual level - something that Dean fails to do.
12 Teach Me Tonight (S2, Ep19)
Despite Jess's intelligence, he struggles with schoolwork (out of boredom and a lack of motivation, largely). Luke, however, thinks that he needs tutoring, and this is where Rory comes in. Of course, their 'tutoring' really just gives them more time together, a deeper connection, and pushes Rory to realize how much she cares.
This is especially clear in 'Teach Me Tonight', when they go for a drive together, and Rory wants to keep driving rather than going back to study. Of course, every fan knows how badly that goes, when they end up in an accident.
11 Lorelai's Graduation Day (S2, Ep21)
Some of the best episodes for Rory and Jess are some of the worst for Rory and Lorelai - and this is definitely one of the worst for that, as Rory misses her mother's graduation because she's playing hooky with Jess in NYC. Of course, as much as this was a terrible-daughter moment, it was a seriously romantic day for Jess and Rory, as they wander Manhattan and flirt all day.
10 I Can't Get Started (S2, Ep22)
This is one of the big ones for Rory/Jess fans - as after a whole lot of build up, the two finally kiss! Of course, it's not quite as romantic as it should be, given that the kiss comes at Sookie's wedding, which Rory is attending with Dean. However, when Jess asks to come back to Stars Hollow, and then this happens, everyone knows that Rory and Dean are on their last legs.
9 Eight O Clock At The Oasis (S3, Ep5)
Dean and Rory are still together at this point, but it's obvious that they are on the way out, and that Rory and Jess are going to be the next cute couple of Stars Hollow. The episodes in between their kiss at Sookie's wedding and them actually getting together are packed with great moments of chemistry, but this is a particularly noteworthy one. Rory gets caught dealing with a broken sprinkler, and Jess ends up coming by to fix it... but, as they stand together soaking wet, Rory tells him that Dean is on the way to help her himself. Showing remarkable consideration for their relationship, Jess turns the sprinkler back on, and walks away... leaving Rory (and fans) gazing after him.
8 Let The Games Begin (S3, Ep8)
It's taken far too many episodes since that first kiss at Sookie's wedding, but Rory and Jess are now together - and they are absolutely adorable. Between dealing with Luke and Lorelai's reactions to their own first moments as a couple, this is a thoroughly heartwarming episode... even if it does have its moments of awkward teen love. Still, at this point, everything is exciting and new for the two of them, and it's a great episode to revisit that new love feeling.
7 Face Off (S3, Ep15)
This may not be a favorite, because most of the episode is spent with Jesse not treating Rory wonderfully, but it is an important one - and has a great ending. The focus of the episode is Rory and her inability to call Jess to make plans, but her fury with his casual 'maybe we'll do something' attitude that ends up with her home alone.
Throw in some Dean-with-a-new-girlfriend, and it seems like Rory and Jess are on the rocks... until he shows her how much he cares, and they get a sweet moment in the end.
6 Happy Birthday Baby (S3, Ep 18)
Having worked out their issues from Face Off, by this point in the series, Rory and Jess are happily, totally in love. Their relationship is often complicated, with as much time spent apart as together (far more time spent apart, in fact), but this is an episode that really shows how good they were. In it, Rory is making plans for university, and Jess is being 100% supportive. He is planning how they will stay in touch, thinking about visits, and showing her that he has every faith that they will stay together after she has gone to Yale. It's just a shame that this didn't actually happen.
5 Nag Hammadi is Where They Found the Gnostic Gospels (S4, Ep13)
Another slightly sad episode for Jess and Rory, as they've broken up at this point - but again, a big one. This is the episode where Jess, after all his time with Rory, and then his time apart from Rory (and his horrifying exit from Stars Hollow), finally tells her that he loves her. Sure, he then drives off, and this is after a day of running around avoid each other, but it's still a big moment.
4 Last Week Fights, This Week Tights (S4, Ep 21)
Rory and Jess may not actually get back together in the original series, but this is a moment that they could have done - and some might argue that they should have! Jess, after being away for quite some time, is back for his Mom's wedding - and he has started to grow up. This is also a great episode for Jess and Luke, as Jess acknowledges everything Luke did, and really thanks him for it. It also could have been a great one for Jess and Rory, as Jess heads to Yale and asks Rory to come back to New York with him. There's no way of knowing if they may have worked out had she taken him up on the offer, though, because she turns him down.
3 Let Me Hear Your Balalaikas Ringing Out (S6, Ep8)
This isn't the most romantic episode for Jess and Rory, but it's one that shows just how their relationship grows (and gives every reunion fan hope for the two of them!). At this point, Rory has dropped out of Yale and is living with her grandparents and not talking to her mother, so when Jess returns to see her, he is understandably surprised. And when she learns that he has written a book and generally got his life together, she starts to question her own choices. In many ways, it's Jess, and the moment that he calls her out on her current situation, that gets Rory to head back home and get back to what she really wants. What fan doesn't love Jess for that?
2 The Real Paul Anka (S6 Ep 18)
True Rory and Jess fans are still hoping for a second revival and a chance for these two crazy kids, but in the original series, this is the last big Rory and Jess moment - and it's a doozy. In 'The Real Paul Anka', Rory is still furious with Logan for sleeping around when they were broken up, and when he heads out with the Life and Death Brigade, she heads out to Jess's publishing house event. Unsurprisingly, they have all kinds of chemistry, and when Jess asks if everything is 'fixed' and she says it is, he kisses her! Which would be amazing, except of course, she is cheating on Logan, and gets upset and confesses everything. Poor Jess... but what a final kiss!
1 A Year In The Life: Summer
By the revival, it seems that Rory and Jess are almost completely out of each other's lives - Rory is dating someone else (who she routinely forgets about) and having an affair with Logan in London, but when Jess comes back to town in the summer, there's still chemistry between them. They also still make perfect sense together. Jess is now matured, and is still helping inspire Rory, as he is the one who plants the idea of writing a book in her head. At the end of the revival, Jess tells Luke that he's completely over Rory, of course, but the way he looks at her says otherwise.
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