Summary

• Rory and Jess's relationship is controversial, but Jess's intelligence and bad-boy ways intrigue Rory.
• A second season of Gilmore Girls: A Year In The Life may be in the works, hinting at more Rory and Jess storylines.
• Jess and Rory share important moments throughout the series, showing their connection and potential as a couple.

Rory (Alexis Bledel) and Jess (Milo Ventimiglia) might be one of the most controversial relationships in Gilmore Girls, but fans of the pairing will find the best Rory and Jess episodes aren't all about them as a couple. Some fans love Jess's intelligence and bad-boy ways, and others think that he is flat-out terrible for Rory. 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.

The possibility exists 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 Gilmore Girls sequel is on the way. If it does happen, there could be more story to come between Rory and Jess, as they were only given a few scenes in the revival, and those scenes suggest that Jess still has some feelings for his high school sweetheart. Rory and Jess were incredibly important to each other during their formative years, and they always will be.

20 "Nick & Nora/Sid & Nancy"

Season 2, Episode 5

This episode is only a must-watch for Rory and Jess fans because it’s Jess’ first appearance in Gilmore Girls. He’s not a huge player in the storyline yet, and the audience doesn’t know him very well beyond his bad boy vibes that emerge from his first interactions with Rory and Luke. That being said, the chemistry between Rory and Jess is immediate.

The two of them meeting isn’t as sweet as Rory first meeting Dean in the pilot episode of the show, but Jess’ presence in the show means the literary references start to rival the general pop cultural references from this point on. It’s also very noticeable that Jess and Rory are immediately intrigued by one another. Jess is surly to everyone he meets in Stars Hollow except for Rory. Rory is ready to banter with him without knowing his backstory.

This is the episode that makes the audience wonder if Rory might be better suited to someone other than Dean.

19 The Ins And Outs of Inns

Season 2, Episode 8

...helps to solidify that they are the love triangle of the show for the foreseeable future.

Just three episodes after Jess makes his Gilmore Girls debut, this episode is meant to establish Jess as a troublemaker even more than his surly introduction. All it really does is establish him as a prankster. Case in point: he makes a chalk outline of a supposed body in front of Doose’s. Rory thinks it’s funny and Jess never its he’s the one who did it.

This episode drives home the point that Jess is still being sarcastic and annoying toward everyone in town, including Luke, except for Rory. And Rory, to her credit, calls Jess out on his treatment of Luke. Even though she seems to understand that he’s mad at the world, she points out how badly he’s treating the one person trying to help him, and it does get through to Jess. He even fixes Luke’s toaster, though, like the chalk outline, he won’t it that he’s the one to fix it.

This is also the first episode in which Jess and Dean meet. Jess doesn’t even know that Rory has a boyfriend up to this point, and that reveal helps to solidify that they are the love triangle of the show for the foreseeable future.

18 The Bracebridge Dinner

Season 2, Episode 10

"The Bracebridge Dinner" isn't the first time that Rory meets Jess, but it's the first time that points toward what is waiting for them - as well as what's waiting for Rory and Dean (Jared Padalecki). In this episode, Lorelai (Lauren Graham) has a huge dinner planned for an event at the inn, 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.

While carriage rides are often reserved for romantic moments, the ride isn't really about romance. The sequence features Jess pushing Rory to really think about her relationship with Dean. It's when Rory first begins to doubt that she and Dean aren't meant to be, even if she's not ready to it it to herself, and even if the audience can see it coming.

17 A Tisket, A Tasket

Season 2, Episode 13

When fans talk about Jess and Rory episodes of Gilmore Girls, "A Tisket, A Tasket," always gets mentioned. It brings the rivalry between Jess and Dean out in the open. 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.

Jess' action stokes resentment between Jess and Dean. While Dean has already been suspicious of Jess before this in the series, he outright cannot stand Jess after this. Dean becomes openly hostile toward Jess, which only eggs Jess on in his interest in Rory. The episode also creates space for Rory and Jess to spend some time together, and realize just how much they have in common. While Rory is outwardly resistant to Jess' attention, it's clear that she is fascinated by him and appreciates how much of the same interests in art and literature they have.

16 Lost And Found

Season 2, Episode 15

Though there are clearly some more-than-friendly feelings between Jess and Rory, neither of them are itting it at this point in the show, and Rory has decided to be the only friend he has in Stars Hollow. She even invites him to one of her movie nights with Lorelai. It’s actually reminiscent of Dean’s first movie night with the Gilmores, except, of course, that Lorelai doesn’t actually want Jess there.

Despite that, Lorelai makes an effort to be fair to Jess. And Jess, despite reminding Rory that he hates parents and small talk, makes an effort with Lorelai as well. They dine on cold egg rolls and chat to make Rory happy, which seems to be something of a theme in the early days of Jess’ appearances on the show. It’s all about making Rory smile long before Jess gets to be happy in a relationship with her.

15 There's The Rub

Season 2, Episode 16

Another season 2 episode that allows Jess and Rory to get to know one another better while Dean ends up feeling like he's on the outside looking in is "There's The Rub." Jess proves his literary skills in this episode, where Rory tells Dean that she wants to spend time alone, only for him to catch her with Jess and Paris (Liza Weil). She originally did want to spend that time by herself, and she didn't invite either Paris or Jess over, they just showed up to spend time with her, thinking she would be lonely without her mother.

It's a great one for Jess fans, as it shows that he can connect with Rory and Paris on an intellectual level - something that Dean fails to do. Paris even appreciates Jess' mind in the episode. She covers for his presence when she realizes there's tension between Jess and Dean. Paris' approval of Jess is a big sign that he won't be a ing fling for Rory as Paris notoriously finds other people tiring.

14 Teach Me Tonight

Season 2, Episode 19

Despite Jess's intelligence, he struggles with schoolwork (out of boredom and a lack of motivation). Luke (Scott Patterson), however, thinks that he needs tutoring, and this is where Rory comes in. Their "tutoring" session in "Teach Me Tonight" really gives them more time together, a deeper connection, and pushes Rory to realize how much she cares about him.

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. The episode might not end in a great moment as Jess and Rory end up in a car accident that sees Lorelai wanting him out of her daughter's life completely, but their chemistry in the episode only furthers the idea that they're meant to be in one another's life in some capacity.

13 Lorelai's Graduation Day

Season 2, Episode 21

Some of the best episodes for Rory and Jess are also some of the worst for Rory and Lorelai - and "Lorelai's Graduation Day" is a great example, as Rory misses her mother's graduation because she's playing hooky with Jess in NYC. It's hard to watch any time Rory and her mother argue or disappoint one another because they are so unbelievably close in the series that they are the most important relationship in Gilmore Girls.

As much as this episode provides a terrible-daughter moment, it makes for a seriously romantic day for Jess and Rory. The duo wanders around Manhattan and flirts all day. It's not an episode full of big moments for them, but it is an episode that demonstrates what a relationship between them would look like as Jess shows her his life outside of Stars Hollow.

12 I Can't Get Started

Season 2, Episode 22

"I Can't Get Started" is one of the biggest episodes for Rory and Jess fans. It's the episode that makes it clear Jess isn't going to pretend he doesn't have feelings for Rory and that it's going to be impossible for her to just push him away in favor of Dean. After a lot of build-up, the two finally kiss when Jess returns to Stars Hollow and asks Luke if he can move back in with him.

Of course, it's not quite as romantic as it should be, given that the kiss comes at Sookie's (Melissa McCarthy) wedding, which Rory is attending with Dean and Rory isn't ready to let Dean go. The kiss is meant to be a goodbye of sorts, but it ends up being a promise of what's to come. When Jess asks to come back to Gilmore Girls' Stars Hollow, and then this happens, everyone knows that Rory and Dean are on their last legs.

11 Eight O'Clock At The Oasis

Season 3, Episode 5

Dean and Rory are still together at this point in season 3, but it's more obvious than ever that they are on the way out, and that Rory and Jess are going to be the next couple of Stars Hollow. The episodes between their kiss at Sookie's wedding and their 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 pays a visit to fix it.

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 given that he's made his feelings for her clear, Jess turns the sprinkler back on and walks away, leaving Rory gazing after him. While Jess is more than willing to tell the entire town how he feels about Rory, he never truly sets out to make things difficult for her with Dean. When she repeatedly chooses Dean, he does walk away to prevent a fight, which paradoxically, reinforces how much he cares for her.