Rory Gilmore and Jess Mariano 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, he incurs the wrath of the town, but Rory can tell he's a sweet person underneath his anger and all of that rebellious teenage energy.
Fans enjoy watching Rory and Jess realize how much they like each other, and 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 love story between these fan-favorite characters is definitely dramatic. From the episode when Rory and Jess start dating to when they break up, there's a lot to look back on when it comes to this popular pair.
Updated on December 2nd, 2021 by Aya Tsintziras: Although several years have passed since the four episodes of A Year In The Life, some Gilmore Girls fans are still hopeful that in the future, Jess and Rory could start dating again. The characters still seem to share the same bond and chemistry that they once did, and it's interesting to think about the ups and downs in Jess and Rory's relationship throughout every season of Gilmore Girls.
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 this character. In the first season of Gilmore Girls, 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 Donna Reed and she focuses more on school and future plans than he does. This is fascinating and sets the stage for her chemistry and attraction with Jess.
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 super rude, but he's actually nice to Rory, and as soon as they meet, her peaceful life changes.
After this episode, Jess and Rory 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. Of course, Rory is still dating Dean, so that makes things complicated and awkward. The characters also experience some major drama when they get into a car accident and Lorelai is angry at Luke. Jess and Rory kiss at the end of season 2, setting up their romance.
Fans love Rory and Dean's Gilmore Girls episodes but once season 3 rolls around, Rory can't hide her romantic feelings for Jess. Dean dumps her very loudly and publicly at the town dance marathon, and Rory and Jess can officially be together. Jess and Rory start dating in the season 3 episode "Let The Games Begin."
Once Jess and Rory start their relationship, they do have some hard times, such as Jess skipping school and upsetting Rory. It seems like as soon as they're actually dating, they can't get along quite as well, and 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. At the end of season 3, 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 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, she really seems to forget all about him. 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.
Season 5 of Gilmore Girls sees Rory moving on even more by starting her first real relationship after 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's got a bit of a conceited attitude, but he definitely comes from a wealthier background. Logan is a poor influence on Rory in some instances and many viewers are unsure that he's the right person for Rory, although many think that he has a lot of positive things going for him.
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.
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.
In some ways, Logan is a great boyfriend for Rory, and it makes sense that by the time season 7 begins, the two are still in a relationship.
But even though Rory might not be in touch with Jess in this season, it does seem like 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 the journalist she wanted to become. Thankfully, Paris is totally obsessed with future plans and inspires and motivates Rory even more.
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 she would get back together with Jess. Dean is married and has a family, and Logan is engaged, so why not pick Jess?
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. 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.
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