Gilmore Girls: Rory And Dean's Relationship Timeline, Season By Season

The pilot of Gilmore Girls reveals Rory Gilmore (Alexis Bledel) as a sweet teenage girl who dreams of getting into Harvard, but it also marks the start of Rory and Dean’s relationship timeline. She’s leaving her small-town high school behind when she meets new kid Dean Forester (Jared Padalecki). Suddenly, she wonders if she should go to the prestigious private school Chilton after all, which starts a big fight between her and her cool mom, Lorelai (Lauren Graham).

The foundation of Gilmore Girls is the relationship between Rory and Lorelai, but the romantic entanglements in the series play a big part in Rory’s coming of age and Lorelai’s allowing her daughter to spread her wings. Gilmore Girls deals with teenage life well and part of that includes Rory and Dean’s relationship. From their meeting to the early days of their romance, along with their two break-ups and reunions later on in their lives, this love story is an important part of the show.

Season 1: Rory And Dean’s Meet-Cute

A Sweet Romance And First Break-Up

Rory and Dean’s relationship timeline begins in the very first episode of the series, unlike Rory’s connections to other characters in Gilmore Girls. Rory and Dean meet each other in the Gilmore Girls pilot and they have a truly adorable scene. Rory makes a joke about Rosemary’s Baby and is shocked and thrilled when Dean understands it. Pop culture references are a big part of the show for both Rory and Lorelai, so it’s hard for them to bond with others who don’t get their references.

After kissing at Doose’s Market, which is awkward but cute, and Lorelai inviting Dean over for a movie night, Rory and Dean enter an official relationship. He’s a sweet partner, making her a bracelet and always making time for her, and things seem to be going well, though their relationship isn’t without a few TV stumbling blocks. When Rory learns that Dean likes the idea of a TV version of a 1950s housewife taking care of him, she decides to pretend to be one for the evening to teach him a lesson about gender stereotypes.

The two survive that stumbling block just fine. They also survive their entire relationship being put under a microscope in their small town. When Dean accompanies Rory to a dance at Chilton, the two end up leaving early after he gets into an argument with another student. They read for a while in the local dance studio, falling asleep, and spending the entire night out, only to be discovered by a bunch of gossiping adults the next morning.

Because Rory is so beloved by so many people in the small town of Star’s Hollow, everyone always seems to have an opinion about her relationships in the show, even her first with Dean. While it’s sweet that so many care about her, it’s also a look at how gossip can get out of hand.

In fact, their relationship seems to be going well until he says he loves her on their three-month anniversary, and she can’t say it back. While that’s a common stumbling block in tv relationships, it briefly ends Rory and Dean’s. Suddenly Rory is single and learning to wallow from her mom, who swears that junk food and pop culture will help her grieve the loss of Dean. Rory does briefly try to find comfort in Chilton student Tristan (Chad Michael Murray), but the series makes it clear that despite their chemistry, Rory and Tristan aren’t right for one another.

Rory and Dean’s relationship timeline makes for a mostly typical first love on television, especially in the first season as all of Rory’s firsts are experienced with Dean. He’s her first kiss, her first boyfriend, her first heartbreak, and the first person she tells she loves. All in just one season.

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Season 2: Jess Comes To Stars Hollow

Jess Makes Waves In Rory And Dean’s Seemingly Perfect Love Story

In season 2 of Gilmore Girls, there are some problems in Dean and Rory’s relationship, as he thinks she cares too much about Chilton and getting into Harvard. He complains about not getting enough time with her, which creates even more stress in her life. This is actually the crux of the problems for the couple throughout the Rory and Dean relationship timeline in the series. As much as the two care about one another, they are always moving in different directions, and that’s made especially clear in season 2.

Rory thinks their relationship is flawless until Jess (Milo Ventimiglia) moves to town, and she starts to like him, too. Jess creates major waves for Dean and Rory, flirting with Rory every chance he gets. Fans can tell that this won’t end well for Dean, and it seems like nothing can stop Jess and Rory’s feelings for each other. While fans love Dean initially because Rory loves Dean, it’s pretty clear that Jess and Rory might actually be a better match from their early meetings.

Even though Jess is hostile to everyone he meets, he’s not to Rory, showing who he is underneath all the other drama he’s dealing with, and that’s what initially puts Dean on edge about him. Dean might be painted as insecure for much of season 2, but his fears about Jess being able to win Rory over are well-founded. Jess and Rory read the same books, share a lot of the same interests, and as Rory moves forward academically at Chilton, she moves farther away from Dean throughout season 2.

Season 3: An Intense Break-Up

Rory Moves On From Dean With Jess

In season 3, the bumps in the road that are caused by Rory’s connection with Jess are too much for Rory and Dean’s relationship. It’s not Rory, however, but Dean, who realizes that they can’t keep trying to fix things. In fact, for the first six episodes of the season, Dean is rarely around and Rory finds herself constantly in Jess’ orbit instead. Dean ends his relationship with Rory during the Stars Hollow dance marathon in the third season episode “They Shoot Gilmores, Don’t They?” and while it’s sad, it’s not a huge surprise.

Rory and Jess start dating immediately and by the next episode, they’re stealing kisses whenever they can, which must feel awkward for Dean since, of course, he still has to live in Stars Hollow. With Rory’s later relationships in the series, he isn’t there to witness her moving on. Rory, however, also has to witness Dean moving on as her relationship with Jess slowly fizzles out. It might seem like an end to the Rory and Dean timeline, but season 3 is still right in the middle of it.

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Season 4: Rory And Dean Reconnect

Rory Loses Her Virginity To Dean

Dean and Rory don’t actually spend a lot of time around one another during season 4 of Gilmore Girls. Rory is busy trying to find her footing in college and Dean is navigating married life. They both, however, have difficulties in their personal lives and are eventually drawn back to one another. Rory has sex for the first time with Dean in the season 4 episode “Raincoats and Recipes.” This changes their relationship, as after being exes for a while, they’re now in a strange place where they realize they still share an attraction and real feelings.

When Lorelai comes home, Rory shares that she lost her virginity to Dean, and Lorelai can’t understand why her daughter would make that choice because Dean is married to Lindsey (Arielle Kebbel). It’s one of the rare times when the mother and daughter duo don’t seem to see eye to eye, and it’s also obvious that Rory and Dean have a bond that has never really gone away. When it comes to the Rory and Dean timeline, season 4 might not feature a lot of interactions between the two, but it does begin their journey to a more adult relationship.

Season 5: Rory And Dean Briefly Get Back Together

Rory And Dean Also Finally Go Their Separate Ways

Rory and Dean officially get back together in season 5 of Gilmore Girls after Lorelai’s shock that Rory would sleep with someone who was married. This love story continues to be super rocky. When Lorelai suggests a double date with Luke and Dean, she and Rory struggle with how awkward it is, and Luke is upset because he doesn’t approve of Dean. After attending a Friday Night Dinner, Dean feels left out and like he can’t possibly be the right person for Rory now.

Season 5 finds the two of them falling back into old relationship patterns despite them no longer being teenagers. It’s hard for Rory to balance being a Yale student and spending time with him, which echoes their high school days when he said she spent too much time studying. Dean works two jobs as well, so he’s not available when Rory is. They break up again, and Rory starts seeing Logan (Matt Czuchry).

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Seasons 6 & 7: Officially Out Of Each Other’s Lives

While Dean Is No Longer In The Show, Rory Dates Logan

In seasons 6 and 7 of Gilmore Girls, Rory is all about Logan, and their relationship leads to some negative changes in Rory’s life. Rory and Dean seem to be out of each other’s lives for good. In season 6, Rory sees Jess a few times, but no one hears what Dean is up to, as his last appearance is in the fifth season.

At first, it must seem like things are simpler with Logan since he’s confident, fun-loving, and willing to commit to Rory, but of course, things get more complicated as Rory realizes Logan has some family problems that he tends to ignore. Logan’s father Mitchum is very judgmental and demanding, and he doesn’t support Rory and Logan’s romance. There are no major milestones for Rory and Dean’s relationship timeline in the final two seasons of Gilmore Girls though.

A Year In The Life: Bumping Into Each Other At Doose’s Market

Dean Makes A Brief Cameo In The Gilmore Girls Revival

Rory still loves Stars Hollow as much as ever in the revival A Year In The Life, and she even bumps into Dean at Doose’s Market, despite him having moved away with his new wife and children in the years in between the series and the revival. The meeting between the two exes provides closure for the characters about their relationship as much as it does the audience. It’s the final spot on the Rory and Dean relationship timeline.

Doose’s Market is a fitting place for them to see each other again since this was the setting of their first kiss and where Dean used to work when they began dating. The two haven’t seen each other in years and only have a brief conversation. Rory thanks Dean for being so sweet to her and says that their relationship was a really good thing in her life. Dean is glad to hear that, but he has moved past Rory and Stars Hollow. He’s married, has his own family, and doesn’t seem to think about Rory anymore.

• Episode 4 “Fall”: Rory and Dean run into each other in Doose’s Market

In a nice touch, Dean mentions that he’s married to a woman named Ginny and has three kids as a nod to Padalecki’s real-life relationship with actress Genevieve Padalecki (formerly Cortese). The two met while working together on Supernatural and have three children. Dean’s time in the Gilmore Girls series is truly at an end, while Rory continues to figure out what she wants in her professional and romantic lives in Gilmore Girls: A Year In The Life.

How Rory & Dean’s Timeline Compares To Rory’s Other Boyfriends

Rory and Dean’s relationship timeline is more full than those of Rory and her other serious boyfriends throughout the show. While Rory has a flirtation with Tristan early in the series, her only serious relationships are with Dean, Jess, and Logan. Rory starts the series with Dean, but she ends the series with Logan, while she and Jess only have a few seasons together.

Logan might be who she ends the series with, but it’s Dean who has a more complete timeline when it comes to his relationship with Rory. Dean is who Rory experiences all of her firsts with. He isn’t just her first boyfriend, but her first love. In fact, Dean is the only boyfriend Rory repeatedly goes back to after years apart. She and Jess meet up after a long separation, but nothing happens between them other than Jess giving her advice. With Dean, Rory rekindles a romance, making their on-again-off-again relationship last over five years.

Dean and Rory also get a measure of closure, something that isn’t truly felt with Rory’s other relationships. She and Logan never feel finished since they have an affair in Gilmore Girls: A Year In The Life. Likewise, Rory and Jess have brief moments in one another’s lives as adults that feel as though their could be more to come from them. Dean’s relationship timeline with Rory is the only one that truly comes to an end in Gilmore Girls.

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

Writers

Amy Sherman-Palladino

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

Showrunner

Amy Sherman-Palladino