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

Rory’s (Alexis Bledel) love life is full of coming-of-age lessons for the beloved Gilmore Girls character, and Rory and Logan’s (Matt Czuchry) relationship at the end of Gilmore Girls represents the culmination of those lessons. After beginning her sweet relationship with Dean (Jared Padalecki) in season 1, Rory feels guilty about her romantic feelings for Jess (Milo Ventimiglia), 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.

The focus of Gilmore Girls is really on the relationship between Rory and her mother Lorelai (Lauren Graham), but how Rory navigates her different romantic relationships greatly affects her relationship with her mother as well. Lorelai doesn’t particularly like Logan, for example, but she understands that her daughter does. Rory’s romantic relationship with Logan falls at the end of the timeline of Rory’s boyfriends in Gilmore Girls, but it has a big impact on her storyline. 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.

Season 1: Rory Experiences Her First Relationship

Logan doesn’t make his grand entrance into Gilmore Girls until more than half-way into the series. As a result, most of Rory’s formative years are spent in a relationship with Dean, her very first boyfriend. Dean debuts in the pilot episode of the series, and so does Rory’s crush on him. It doesn’t take long for the two to become officially a couple.

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 later in the series, she realizes that she needs more from Logan.

Related

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

Dean Forester was Rory’s first love on Gilmore Girls. Her relationship with the Stars Hollow grocery boy wasn’t perfect but it had its sweet moments.

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

Jess, not Logan, makes his Gilmore Girls debut in season 2. He throws a wrench into the Rory Gilmore boyfriend timeline by turning her world upside down and making her question her relationship with Dean. When Rory meets Jess, it’s the first time she realizes she could be attracted to someone very different from her first boyfriend. 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.

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 for the long haul. She and Dean hit some bumps in their relationship in season 2 because of Jess, but ultimately, stay together heading into the next season.

Season 3: Rory Has Conflict With Jess

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. The two immediately enter into a relationship in season 3 of Gilmore Girls after Dean breaks up with Rory. Their chemistry has been palpable since meeting in season 2, much like the immediate chemistry between Rory and Logan in a later season.

Rory and Jess fight more and have more problems than Rory and Dean do, 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. She carries those observations from her relationship with Jess forward into the series.

Related

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

When it comes to Rory’s boyfriends, many Gilmore Girls fans are Team Jess. But they had a tumultuous relationship when they first met in Stars Hollow.

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

In season 4, Rory spends some time single, overwhelmed by Yale’s course load and becoming more comfortable living on her own. Rory tries to find her footing in her new world. She misses Stars Hollow and is still thinking about Dean, who is now married to Lindsay. Rory doesn’t meet Logan just yet in season 4 of Gilmore Girls, but instead, sees herself returning to her first love because Dean is familiar and comforting.

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. If anything, season 4 of the series very much foreshadowed the kind of conflict Rory would see in her love life another decade down the road.

This season demonstrates that Rory is someone who seeks the comfort of familiarity in her relationships. It’s why she and Dean break up and get back together more than once. It’s why she continues to see Logan even when they’re both dating other people.

Season 5: Rory And Logan Fall In Love

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. Season 5 features the debut of Logan, and the beginning of his relationship with Rory. The two don’t start dating right away. Instead, Logan doesn’t want a serious relationship, and Rory is willing to go with it in an effort to not repeat the mistakes of her past.

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. There is a spark between them early in the season, but nothing becomes serious until the end of the season as Logan admits he wants a serious relationship and Rory gets to meet his parents.

Logan, much like Jess before him, brings excitement into Rory’s life. He gets her to loosen up and take risks, something she doesn’t do with Dean beyond the risk of having an affair with him when he was still married. Logan initially appears like he might be a more mature version of Jess, but that’s not entirely true.

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

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.

Rory being a planner and her boyfriends not planning for their futures is something that Rory struggles with throughout the series. Dean struggles to connect with Rory when she focuses on school, Jess avoids discussing the future with Rory for most of their relationship, and Logan relies on the safety net of his family to secure his future, while Rory is constantly focusing her ambitions.

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. While their relationship is revisited in the Gilmore Girls revival series, they run into many of the same problems they have during Gilmore Girls all over again.

Related

Gilmore Girls: 10 Times Jess Was Rory’s Best Boyfriend (& 7 When It Was Logan)

Rory Gilmore found love on more than one occasion. That said, was Jess or Logan her best boyfriend in Gilmore Girls?

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

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. If the two want to stay together, they have to work at it, and that’s complicated when Logan gets a job that takes him away from Rory at the end of season 6. They try to make things work with visits when he’s in town, but their lives are being pulled in two very different directions.

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.

Of course, because Rory is a creature of habit when it comes to her relationships, it’s not entirely the end for them. The revival series revisits Rory and Logan’s love for one another in a way that sees Rory repeat nearly all of the mistakes she made in relationships throughout the main run of the series.

A Year In The Life: Rory And Logan Have An Affair

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

While some believe Rory and Logan’s affair to be out of character for her, it simply signals that Rory is repeating old patterns. Just as when becoming frustrated and overwhelmed in life at Yale, Rory got back together (and had an affair) with Dean, she does the same when her professional life is stagnating and has an affair with Logan. She seeks the comfort of someone she is familiar with and someone whom she shares love, but someone who isn’t necessarily right for her at the time.

The trouble here is that the affair with Logan doesn’t offer her the same level of comfort that her affair with Dean did when she was younger.

Here, she and Logan are both in other relationships. Rory doesn’t even remember that she has a boyfriend for much of the revival series. Logan is set to get serious in his relationship, and it almost seems as though Logan and Rory are turning into the very people that they found repugnant and tried to stand up to when they were in college. It’s good that things end between them in the revival series, seemingly for good.

Gilmore Girls: A Year In The Life allows Rory to revisit all three of her major relationships, but she only runs into Dean and pays a visit to Jess at work. It’s Logan to whom she devotes the most time and has her most romantic moments. It’s clear, however, that they no longer truly fit as a couple, and they go their separate ways amicably.

By the final episode, fans wonder if Rory is pregnant with Logan’s child. If the Gilmore Girls revival does come back, perhaps fans will see Rory and Logan as parents, but it seems likely they will not be getting back together again.