Gilmore Girls: Rory And Logan’s Relationship Timeline, Season By Season

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Rory’s love life is full of coming of age lessons for the beloved Gilmore Girls character. After beginning her sweet relationship with Dean in season 1, Rory feels guilty about her romantic feelings for Jess, and she leaves both partners behind to experience college life. When Rory meets Logan at Yale, she’s surprised to care about him so much since Logan is immature, and they quickly become a popular couple.

RELATED: Rory And Jess’ Gilmore Girls Relationship Timeline, Season By Season

From meeting and falling in love with Logan at Yale to experiencing many tough moments, Rory’s relationship with Logan is a wild ride, and Gilmore Girls fans love following along.

8 Season 1: Rory Experiences Her First Relationship


Dean and Rory's first kiss on Gilmore Girls

Season 1 has great Rory and Dean Gilmore Girls episodes as Rory finds love with the new kid in town who is working at Doose’s Market and who is polite, friendly, and incredibly kind. As Rory experiences her first relationship, it’s interesting to think about the lessons that she learns that she applies to her later romance with Logan.

Rory appreciates that Dean is there for her and compassionate and reliable, and when she experiences drama with Logan’s immature behavior, she realizes that she needs more from Logan.

7 Season 2: Rory Is Caught Up In The Dean/Jess Love Triangle


Rory’s love for Jess and Dean creates a lot of drama in her life for a long time. In season 2, Rory is still very much caught up in her high school life, happy to be dating Dean but wondering if she likes Jess more than she thought.

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

It’s interesting to look back on Rory’s Stars Hollow life at this moment. She has no idea that she will break up with both Dean and Jess and fall for someone else while in college. Rory still thinks that she and Dean will stay together.


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6 Season 3: Rory Has Conflict With Jess


Jess and Rory smiling at each other outside in New York City on Gilmore Girls

Jess creates issues for Rory on Gilmore Girls, and their relationship becomes tense in season 3, as Rory prepares to leave Stars Hollow for an Ivy League school and Jess doesn’t talk about the future.

Rory and Jess fight more and have more problems than Rory and Dean did, which shows Rory that love is complicated and that when strong emotions are involved, communication becomes even more crucial. In many ways, Rory is as different from Logan as she is from Jess, as Rory is serious about schoolwork and Jess and Logan don’t care much. Fans can see that Rory realizes that she can care about someone who isn’t the same as her and that she has to decide if there are too many issues to stay together.


5 Season 4: Rory Thinks About What Kind Of Partner She Wants


Split image of Dean and Rory talking outside on Gilmore Girls

In season 4, Rory spends some time single, overwhelmed by Yale’s course load and becoming more comfortable living on her own. She misses Stars Hollow and is still thinking about Dean, who is now married to Lindsay.

When Rory and Dean rekindle their relationship at the end of season 4, fans think that this is a mistake, just like viewers don’t approve of Rory and Logan having an affair in A Year In The Life. Rory still feels comfortable with Dean, and she still loves Logan in the revival, but in both cases, she needs to commit to someone without any cheating involved.


4 Season 5: Rory And Logan Fall In Love


Rory and Logan standing with umbrellas before jumping on Gilmore Girls

While Rory meets great supporting characters at Yale, it’s her relationship with Logan that fans love the most, and he has a huge impact on her experience.

In season 5, Rory and Logan fall in love, which definitely surprises them both. Logan didn’t think that he would want something more than just a casual relationship, and Rory isn’t looking for anything serious after breaking up with Dean. Fans like this stage of the show as the characters are getting to know each other and having fun.


3 Season 6: Rory And Logan’s Love Story Gets Complicated


Lorelai and Rory have lunch with Logan and Luke on Gilmore Girls

It’s in season 6 that Rory and Logan’s relationship shows signs of falling apart. After a brief break, Rory learns that Logan slept with other people, and Rory wonders if they can stay together since she has huge dreams for the future and Logan struggles to be responsible and mature.

RELATED: 10 Gilmore Girls Moments That Prove Rory & Logan Were Soulmates

While fans appreciate how much Rory and Logan love each other, it’s possible that Lorelai’s concern that they are too different is valid and that the relationship isn’t going to last beyond Rory’s time at Yale.


2 Season 7: Rory And Logan Deal With Serious Problems And Split Up


logan proposed to rory - gilmore girls

Rory’s Gilmore Girls journey from season 1 to 7 allows fans to see how much she changes. By season 7, Rory and Logan’s relationship is no longer easy breezy or that much fun.

While the characters still care about each other a lot, they’ve dealt with long distance and Logan’s horrible injury from a Life and Death Brigade stunt. When Logan asks Rory to marry him when her four years at Yale are over, fans know why she says no, as Rory still wants to accomplish a lot in her reporting career. Several Gilmore Girls fans are still sad at the way that this great relationship ends.




1 A Year In The Life: Rory And Logan Are Having An Affair


Alexis Bledel and Matt Czuchry as Rory Gilmore and Logan Huntzberger in Gilmore Girls A Year In The Life

Rory and Logan’s relationship continues in A Year In The Life, and fans are still frustrated by this storyline.

Viewers wanted to see Rory get back together with one of her three partners, and if Logan makes the most sense plotwise, it would work much better for the characters to be dating long-distance. Instead of Logan being engaged, Rory and Logan could see if they have what it takes to make things work again, this time as they navigate careers and the real world. By the final episode, fans wonder if Rory is pregnant with Logan’s child, and if the revival does come back, perhaps fans will see Rory and Logan as parents.

NEXT: 10 Behind-The-Scenes Facts About Gilmore Girls: A Year In The Life

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