Gilmore Girls Relationships Ranked

Gilmore Girls is an amazing TV series featuring Lauren Graham and Alexis Bledel. The premise of the show is that Lorelai Gilmore (Lauren Graham) was a teen mom to Rory (Alexis Bledel) and left her extremely wealthy parents to raise Rory on her own in a small (fictional) town called Stars Hollow in Connecticut. The show follows Rory, 16, and Lorelai, 31, in their small town lives, highlighting their extremely close relationship.

Rory is very smart and her whole life has lead up to her attending Harvard for college, even though when the series starts she is only a sophomore in high school. The show ends when Rory graduates college, and the remake takes place 10 years later, when Rory is in her early 30s and Lorelai is around 46. Throughout the series, Rory has three serious relationships: two in highschool, and one long-term relationship in college. Because no two relationships are created equal, here are the Gilmore Girls relationships ranked worst to best:

3) Out of all three of Rory’s relationships, Jess was the most promising but overall also the most disappointing. The relationship started with her cheating on her first boyfriend, Dean, so it was sort of doomed from the start anyway. They portray the “will they, won’t they” stage while Rory is still with Dean in a way that makes you root for Jess. He gets her in a way Dean doesn’t. They read the same books, he can keep up with her intellectually, and he has dreams bigger than Stars Hollow. He’s troubled and angry, so Rory feels special to have him open up to her.

However, the biggest flaw with Jess was the thing Rory liked most about him: he was edgy and sort of “bad”. In the end, Jess couldn’t commit to Rory. He leaves her abruptly and won’t say he loves her, even though he does. He runs away from her and skips town, then comes back months later after she’s already moved on and begs for her forgiveness. Ultimately, Jess was a flop and a waste of her time.


2) Next is Logan, her first really serious boyfriend who she meets in college at Yale. It was a hard decision for me when ranking them, but Logan probably takes second place because he is so pretentious. In the beginning, you hate Logan for being rude to wait staff and extremely stuck up because of the massive amount of money he has. Even though he grows on you through him and Rory’s relationship, she just can’t relate to him. He couldn’t commit to her for over a year and that really lowered her self esteem when he was seeing other women while they were spending most of their time together. This would’ve been fine if they were both fine with it, but it was clear Rory was only going along with it to please Logan, and Logan only wanted to continue dating other people because he was scared to be in a relationship and wanted to hold on to his playboy persona for as long as possible.

But there were still many pros to Logan. He brought her out of her shell, and taught her it was ok to be a little out of the box sometimes. He was also her first really serious adult relationship, so she learned a lot about how to coexist with someone in real life, not just high school. He challenged her and kept her on her toes, but ultimately I just don’t think he was the best for her.


  1. Not that Dean really deserves top spot, but I think he does more than Jess or Logan. Dean was Rory’s first boyfriend and first love. They meet in sophomore year of high school, and so watching their relationship grow from a young age was really sweet. For their anniversary, Dean built Rory a car, and gave it to her so she doesn’t have to take the bus to school every day. He bonded with her family, and did the best he could to make  Rory happy. You could tell he really admired her because of her wit, intellegence, and ambition and she inspired him to want more out of his life.

In the end, Rory outgrew Dean and left him for Jess, who challenged her more. Dean got married at 18 and dropped out of highschool, and made himself really unhappy in his life and marriage. He ended up cheating on his wife with Rory after she had gone to college, which wasn’t very cool. He was pretty possessive over Rory, but he truly did the best he could at such a young age. Their love was really sweet and pure, which is why I think he deserves the top spot.


Rory certainly has her faults too and is not a perfect character, and neither were any of the boys she dates. After all , they’re all really young and make mistakes. If you want a heartwarming series filled with sweet moments, a mother-daughter bond like no other, and a coming-of-age story, Gilmore Girls is perfect for you, and I suggest you watch it as soon as possible.

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