Gilmore Girls: Rory And Jess' Relationship Timeline, Season By Season

The Rory and Jess timeline in Gilmore Girls was fun to watch as the two bookworms realized they had more in common than they originally thought. When the moody Jess moves to Stars Hollow in Gilmore Girls season 2, he incurs the town’s wrath, but Rory can tell he’s a sweet person underneath his anger and rebellious teenage energy. While their romance didn’t last, 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 during a tough time.

The romance between Rory and Jess is full of passion, but the two don’t end up together. From when Rory and Jess start dating to when they break up, there are great episodes to look back on for the on-again, off-again couple. Although several years had passed since A Year In The Life, Gilmore Girls kept teasing hope that Jess and Rory could get back together. 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.

Season 1

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

There has always been a debate about who should have been together on Gilmore Girls — Dean and Rory or Jess and Rory. It’s a tough choice since Dean was Rory’s first boyfriend on the show. They start dating in season 1 and have a sweet courtship that is the embodiment of young love. Rory 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.

However, in season 1, Rory seems very happy in her relationship other than her brief breakup with Dean. Rory and Dean’s romance isn’t perfect, however. 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 conflict with Dean offers contrasting moments compared to her chemistry with and attraction to Jess when he arrives in season 2.

Season 2

Rory & Jess’ First Meeting And Beginning Of Their Flirtation

Jess first appears in Gilmore Girls season 2, episode 5, “Nick & Nora/Sid & Nancy.” Based on first impressions, the townspeople believe Luke has his work cut out for him with his rebellious nephew. Jess seems incredibly rude, but he’s actually nice to Rory, and as soon as they meet, her peaceful life changes. Everything Rory believed she knew about her relationship with Dean changes because she realizes something is missing. Jess and Rory then spend the rest of the season getting to know each other and flirting.

They love that they understand each other and can talk about books. Rory doesn’t have this kind of relationship with anyone else, even though she is still dating Dean, complicating things. The more Rory gets to know Jess and increases her focus on school, the less time she has for Dean. This leads to Dean and Jess battling for her affection, such as in “A-Tisket, A-Taket,” where they have a bidding war for her picnic basket at a charity auction.

The characters also experience major drama when they get into a car accident, and Lorelai becomes angry with Luke. While there’s a wedge between Lorelai and her friend, it only means that Rory and Jess grow closer. Rory knows him better and doesn’t blame him for what happened. Jess and Rory kiss in the season 2 finale, “I Can’t Get Started”, setting the stage for their romance, though Rory doesn’t break up with Dean yet.

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Season 3

Jess And Rory Officially Start Dating (And Break Up At The End Of The Season)

Still dating Dean, Rory takes an internship in Washington between Gilmore Girls seasons 2 and 3, and doesn’t speak to Jess the entire time she’s gone to avoid conflict. Jess decides he won’t wait for Rory to decide and starts dating Shane (Jessica “Sugar” Kiper), leaving him and Rory at odds.

While there are many great Rory and Dean Gilmore Girls episodes, once season 3 rolls around, Rory can’t hide her romantic feelings for Jess. No matter how hard she tries to convince herself that she and Jess are just friends, it’s clear that they have deeper feelings. Jess is the conflict between Rory and Dean’s relationship for the first few episodes of the season. In season 3, episode 7 “They Shoot Gilmores, Don’t They?”, Dean’s had enough and finally breaks up with Rory at the town dance marathon, meaning Rory and Jess can officially be together.

Following the start of their relationship in episode 8, “Let The Games Begin,” things remain awkward because Lorelai does not like them together. She even criticizes their chemistry the first time she sees Rory and Jess kiss in “A Deep-Fried Korean Thanksgiving”, making Rory so self-conscious that she 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 because she won’t take the time to get to know Jess the way Rory initially does.

However, as soon as they’re dating, they don’t get along as well as before. Once the anticipation of being in a relationship is gone, the pressure to maintain it 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 takes off. They never officially split or have closure.

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 their romance had ended more happily, Rory seems to forget all about him. She’s distracted by having sex for the first time when she sleeps with Dean at the end of the season, which creates conflict as he’s married to Lindsay (Arielle Kebbel).

Jess returns briefly to Rory’s life during the season, proving that the two still have chemistry despite 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 “Nag Hammadi is Where They Found the Gnostic Gospels,” but he also invites her to come with him to New York in “Last Week Fights, This Week Tights.” Both times, Rory and Jess still end up going their separate ways.

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 after her breakup with Jess. Rory doesn’t seem to talk to Jess anymore at all, and he isn’t even mentioned in the season. She begins dating Logan (Matt Czuchry). The thing about Logan is that he is a lot more similar to Jess than he is to Dean.

Logan has an arrogant attitude, and he comes from a wealthier background. In many instances, Logan is a poor influence on Rory, and it seems that he is not the right person for her. However, he remains with her through the rest of the series, and it seems that she buys into the relationship even though her dreams begin to either change or die. Logan and Jess share a willingness to stir things up, and because of this, Rory grows immensely because of her relationships with each of them.

Season 6

Published Author Jess Has Two Reunions With Rory

In Gilmore Girls season 6, Rory and Jess have two reunions, and in both of them, it’s clear that Jess is doing much better than his ex. The penultimate season is one of growing pains for Rory. In episode 8, “Let Me Hear Your Balalaikas Ringing Out,” Jess learns that Rory has left Yale, is dating Logan, and is doing community service. Jess knows this is the opposite of where she should be at this point in her life, and he’s worried for her.

In “The Real Paul Anka,” Rory visits Jess at the publishing house where he works in Philadelphia. This moment is a big one for the former couple as they share a kiss. However, Rory wants to make Logan jealous since they are having relationship issues. They stop when Jess realizes Rory is using him. It’s not Rory’s best moment with Jess, but at least they leave each other on friendly terms when they realize she still loves Logan.

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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 they are still in a relationship by the time season 7 begins. But even though Rory might not be in touch with Jess during this season, his words in season 6 impacted her. He showed concern since she seemed to be drifting away from her dreams and losing touch with what she wanted her life to be.

Rory returns 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 (Liza Weil) is obsessed with future plans and inspires and motivates Rory even more. Rory ends up turning down Logan’s marriage proposal because she wants to focus on her career. If anything, this season shows how much Jess meant to Rory, even if just as a concerned friend, and it was a great look at how he proved everyone who considered him a bad influence wrong.

A Year In The Life

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

A Year In The Life has some flaws, including Rory and Logan having an affair despite his engagement and her dating Paul. 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 Jess seemed like an excellent option for the series. However, Rory remains in the controversial affair with Logan, and Jess is just a friend.

In these four revival episodes, Jess and Rory remain 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 brilliant considering her fun upbringing with Lorelai. While a romantic reunion might have been nice, seeing them in a good and peaceful place after knowing each other for so long is still satisfying.

Jess and Rory end on a good note in the revival. Of course, Jess tells Luke that he’s completely over Rory, which seem slike a case of him protesting too much, especially after that look of longing he gives her, the last shot of Jess in the revival. If Gilmore Girls ever returns in another sequel or revival series, there will likely be more of Jess and Rory’s relationship explored, and they could somehow still find a future together.

Gilmore Girls

In the fictional town of Star’s Hollow, single mother Lorelai Gilmore raises her high-achieving teenage daughter Rory. Mother and daughter rely on each other throughout their own life changes, romantic entanglements, and friendships.

Cast

Lauren Graham , Scott Patterson , Sean Gunn , Keiko Agena , Matt Czuchry , Alexis Bledel , Yanic Truesdale , Kelly Bishop , Melissa McCarthy , Edward Herrmann , Liza Weil , Jared Padalecki , Milo Ventimiglia

Release Date

October 5, 2000

Seasons

7

Gilmore Girls: A Year in the Life

Acting as a follow-up to the original series, Gilmore Girls, A Year In The Life is a comedy-drama series. Having completed her stint on the Obama campaign trail, Rory now finds herself as a freelance journalist with an inconsistent life. Meanwhile, Lorelei finds herself lost in life before her upcoming marriage to Luke. This four-part mini-series follows the titular mother-daughter duo as they continue to navigate their mother-daughter relationship in Star’s Hollow.

Cast

Lauren Graham , Alexis Bledel , Scott Patterson , Aris Alvarado , Sean Gunn , Frank Gallegos , Keiko Agena , Matt Czuchry , Yanic Truesdale , Kelly Bishop

Release Date

November 25, 2016

Seasons

1