Summary

• Rory and Jess share a passionate romance but don't end up together, leaving fans hopeful for a future reunion.
• Jess's arrival in Stars Hollow disrupts Rory's relationship with Dean, leading to a complex love triangle.
• From their flirtation in season 2 to their mature friendship in the Netflix revival, Jess and Rory's bond remains strong.

Rory and Jess are a favorite couple on Gilmore Girls, and it's fun to watch the two bookworms realize they have more in common than they originally thought. When the moody Jess moves to Stars Hollow in Gilmore Girls season 2, he incurs the wrath of the town, but Rory can tell he's a sweet person underneath his anger and rebellious teenage energy. By the time they see each other again in the Netflix revival A Year In The Life, Jess is older, wiser, and ready to help Rory out during a tough time.

The Rory and Jess romance is full of passion, but the two don't end up together. From the episode when Rory and Jess start dating to when they break up, there's a lot to look back on for the on-again-off-again couple. Although several years have passed since A Year In The Life, some Gilmore Girls viewers are still hopeful that in the future, Jess and Rory could start dating again. The characters still share the same bond and chemistry, and it's interesting to think about the ups and downs in Jess and Rory's relationship throughout Gilmore Girls.

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Season 1

Rory Is Dating Dean And Has No Idea She Will Fall For Jess

Gilmore Girls fans debate Dean and Jess as Rory's love interests, so it can be tough to choose who is the best partner for the character. In season 1, Rory enters her first relationship and enjoys being with Dean. She has no idea that she will meet Luke's nephew Jess in the next season, and she doesn't know how much her life will change when this bad boy begins living in Stars Hollow. For now, Rory is happy (besides her brief breakup with Dean).

Rory and Dean aren't perfect, however, as he seems to want her to be more like TV housewife Donna Reed, and she focuses more on school and future plans than he does. This sets the stage for her chemistry and attraction with Jess.

Season 2

The First Meeting And Their Flirtation Begins

Jess first appears in the Gilmore Girls episode "Nick & Nora/Sid & Nancy" and the townspeople believe that Luke has his work cut out for him with his rebellious nephew. Jess seems to be incredibly rude, but he's actually nice to Rory, and as soon as they meet, her peaceful life changes. Everything that Rory believed she knew about her relationship with Dean changes because she realizes that maybe something is missing in her life.

Jess and Rory then spend the rest of the season getting to know each other and flirting. They love the fact that they understand each other and can talk about books. Rory doesn't have this kind of relationship with anyone else, but, of course, Rory is still dating Dean, which makes things complicated and awkward. The more Rory gets to know Jess and increases her focus on school, the less time she has for Dean.

The characters also experience some major drama when they get into a car accident and Lorelai is angry at Luke. While there's a wedge between Lorelai and her friend, it only means that Rory and Jess grow closer since by then, Rory knows him better and doesn't blame him for what happened. Jess and Rory even kiss at the end of season 2, setting the stage for their romance, though Rory doesn't leave Dean behind.

• Season 2, Episode 5 "Nick & Nora/Sid & Nancy": Rory meets Jess for the first time and realizes she's attracted to someone other than Dean
• Season 2, Episode 10 "The Bracebridge Dinner": Rory and Jess end up on a carriage ride together
• Season 2, Episode 13 "A-Tisket, A-Taket": Dean and Jess get into a bidding war over Rory's picnic basket at a charity auction

• Season 2, Episode 16 "There's The Rub": Rory and Dean argue when he finds out Jess drops by when Lorelai is gone
• Season 2, Episode 19 "Teach Me Tonight": Rory tutors Jess, but Jess takes the opportunity to make it a date, and they end up in a car accident
• Season 2, Episode 21 "Lorelai's Graduation Day": Rory and Jess spend the day together in Manhattan
• Season 2, Episode 22 "I Can't Get Started": Rory and Jess kiss at Sookie's wedding, and she starts to doubt her relationship with Dean

Season 3

Jess And Rory Officially Start Dating (And Rory And Jess Break Up)

Rory takes an internship in Washington between Gilmore Girls seasons 2 and 3, and it's revealed that she didn't speak to Jess the entire time she was gone and is still dating Dean when she returns. The Rory and Jess romance is on pause during this time, as Jess decides he isn't going to wait around for Rory to make up her mind and starts dating Shane. This short period of time in their relationship speaks to not only their feelings for one another but how much the two grow over the course of the series.

Fans love Rory and Dean's Gilmore Girls episodes, but once season 3 rolls around, Rory can't hide her romantic feelings for Jess. No matter how hard Rory tries to tell people (and herself) that she and Jess are just friends, it's clear that there are deeper feelings between the two of them. For the first few episodes of the season, Jess is the conflict in the middle of Rory and Dean's relationship as a result. Dean dumps her very loudly and publicly at the town dance marathon, and Rory and Jess can officially be together.

Following the start of their relationship, much of the awkwardness is a result of Lorelai not liking them together. She even offers up some criticism of their chemistry the first time she sees Rory and Jess kiss, which makes Rory so self-conscious that she actually seeks Jess out to give him a more passionate kiss later. It's clear that Lorelai prefers Rory to date Dean at this stage, but that's only because she won't take the time to get to know Jess the way Rory initially does.

It seems like as soon as they're actually dating, they can't get along quite as well. Once the anticipation of being in a relationship is gone, the pressure to maintain one is on. With Rory finishing up her time at Chilton and headed for Yale, it's clear to Jess that he might not have a place in that world, creating even more tension between them. Rory graduates and gets a phone call. She knows Jess is calling her, but he has no idea what to say, and he takes off. They never officially split or have closure.

• Season 3, Episode 1 "Those Lazy-Hazy-Crazy Days": Rory spends her summer not speaking to Jess to avoid conflict
• Season 3, Episode 5 "Eight O'Clock At The Oasis": Jess helps Rory with malfunctioning sprinklers, but pretends he didn't to avoid making waves with Dean
• Season 3, Episode 6 "Take The Deviled Eggs...": Rory throws deviled eggs at Jess' car instead of admitting her feelings
• Season 3, Episode 7 "They Shoot Gilmores, Don't They?": Dean breaks up with Rory in front of everyone
• Season 3, Episode 8 "Let The Games Begin": Rory and Jess officially start dating
• Season 3, Episode 9 "A Deep-Fried Korean Thanksgiving": Lorelai criticizes Jess and Rory's kiss
• Season 3, Episode 10 "That'll Do, Pig": Rory and Dean decide to try and be friends, Jess accuses Dean of trying to get Rory back
• Season 3, Episode 14 "Swan Song": Jess comes to Friday night dinner for the first time
• Season 3, Episode 15 "Face-Off": Rory thinks Jess can't make plans, but he surprises her with concert tickets
• Season 3, Episode 18 "Happy Birthday Baby": Rory and Jess make plans for the future
• Season 3, Episode 19 "Keg! Max!": Jess is flunking school and acting out, and Rory refuses to sleep with Jess
• Season 3, Episode 22 "Those Are Strings, Pinocchio": Jess tries to call Rory about leaving Stars Hollow, but can't bring himself to talk to her, so she tells him off

Season 4

Rory Has Totally Moved On

Season 4 sees Rory enrolled at Yale and learning how to be an independent person away from her mom and Stars Hollow. Instead of pining for Jess or wishing that their romance had ended more happily, Rory really seems to forget all about Jess. She's distracted by sleeping with Dean at the end of the season and losing her virginity to him, which creates conflict as he's married to Lindsay.

Jess does return briefly to Rory's life during the season, and those episodes only prove that the two still have chemistry despite them ending their relationship on a sour note in Gilmore Girls season 3. They still care about one another, which is why Jess' future appearance in the series works so well. Not only does Jess tell Rory he loves her in season 4, but he also offers for her to come with him to New York. Both times, Rory and Jess still end up going their separate ways.

• Season 4, Episode 13 "Nag Hammadi is Where They Found the Gnostic Gospels": When Jess and Rory meet up again, he tells her he loves her, but they don't get back together.
• Season 4, Episode 21 "Last Week Fights, This Week Tights": Jess asks Rory to come to New York with him, but she turns him down

Season 5

Rory Doesn't Talk To Jess And Begins Dating Logan

Season 5 of Gilmore Girls sees Rory moving on even further by starting her first real relationship following Jess. Rory doesn't seem to talk to Jess anymore, and he isn't mentioned here. She begins dating Logan, and he is more similar to Jess than Dean, as he has a conceited attitude, but he comes from a wealthier background. Logan is a poor influence on Rory in some instances and viewers are unsure that he's the right person for her. He and Jess share a willingness to stir things up, and Rory grows immensely because of her relationships with them.

Season 6

Published Author Jess Has Two Reunions With Rory

Rory and Jess have two reunions in season 6 of Gilmore Girls and in both of them, it's clear that Jess is doing much better than his ex. Season 6 is a season of growing pains for Rory. In the episode "Let Me Hear Your Balalaikas Ringing Out," Jess learns that Rory has left Yale, is dating Logan, and doing community service. Jess knows this is the opposite of where she should be at this point, and he's worried for her.

In "The Real Paul Anka," Rory goes to see Jess at the publishing house he works at in Philadelphia. This is a big moment for the former couple as they share a kiss, but Rory wants Logan to be jealous since they're having relationship problems, and Jess realizes he's being used. It's not Rory's best moment with Jess.

• Season 6, Episode 8 "Let Me Hear Your Balalaikas Ringing Out": Jess visits and Rory finds out he's written a book
• Season 6, Episode 18 "The Real Paul Anka": Rory kisses Jess to make Logan jealous

Season 7

Rory's Still All About Logan (But Remembers Jess' Words)

In some ways, Logan is a great boyfriend for Rory, and it makes sense that by the time season 7 begins, they are still in a relationship. But even though Rory might not be in touch with Jess in this season, his words in season 6 had an impact on her. She goes back to Yale and is determined to graduate on time and make something of herself. She thinks about grad school, internships, and job applications, and wonders how she'll become a journalist. Thankfully, Paris is totally obsessed with future plans and inspires and motivates Rory even more.

A Year In The Life

Rory & Jess Are Just Pals And Giving Life/Work Advice

A Year In The Life has some flaws, including when Rory and Logan have an affair. It's safe to say that many fans hoped Rory would get back together with Jess. Dean is married and has a family, and Logan is engaged, so why not pick Jess if the series wants to revisit a past relationship of Rory's?

In these four revival episodes, Jess and Rory are just friends, and Jess is once again in the position to give Rory some great life and work advice when he returns in the episode "Summer." He suggests writing a book inspired by her life and childhood, which is a brilliant idea considering her fun upbringing with Lorelai. While fans wanted to see them kiss or confess their love for each other, it's still satisfying to see them in a good and peaceful place after knowing each other for so long.

• A Year In The Life "Summer": Jess gives Rory some friendly advice

It's clear that Jess and Rory end on a good note in the revival. Of course, Jess makes a point of telling Luke that he's completely over Rory, which does seem like a case of him protesting too much. If Gilmore Girls is ever revisited in another sequel or revival series, it's likely there will be more of Jess and Rory's relationship to be explored.