The Mainsheet


Gilmore Girls: Ranking Rory’s Love Interests

by EMILIE ALDEN

Gilmore Girls is a show with comfortable fall vibes that follows the relationships and adventures of Lorelai Gilmore and her daughter Rory as they navigate the small-town life in the fictional town of Stars Hollow, Conn. Originally aired on the WB network, then the CW network, the hit TV show is now available on Netflix.

One of the most debated topics in the show’s seven-season run (2000-2007) is the ranking of Rory’s boyfriends: Dean Forester, Jess Mariano and Logan Huntzberger.

Dean is a walking red flag. He is controlling, impatient and manipulative, and his toxicity only increases with Rory. Dean chronically disappoints, whether it’s getting into fights at Rory’s school dance or breaking up with Rory when she couldn’t say, “I love you.” Dean, knowing Rory’s dream is to go to Harvard, gets annoyed when Rory has to study. When Rory and Dean break up, Dean acts sweet to her face while threatening new boyfriend Jess behind Rory’s back. One of the worst parts about Dean is that he thinks he’s a nice guy when he is really obsessive, often disregarding Rory’s feelings. Dean is either sweet and innocent or jealous and possessive; either way, he is definitely Rory’s worst boyfriend.

Jess–with his leather jacket and troubled, sad-boy attitude–has captured the hearts of many, including Rory. Though Jess appears to be a careless “bad boy,” Rory immediately sees through his facade and they develop an intense connection. From the margin notes in shared favorite books to Jess bringing Rory a feast from Luke’s diner completely out of the blue, Jess admires Rory from the moment he comes to town. Their chemistry is so powerful that they eventually have to act on their feelings, but their actual relationship is far from perfect.

When they get together, the only spark Rory and Jess have is confined to their shared interests. Jess actively ignores Rory, making her wait for days before calling and standing her up whenever something goes wrong in his life. Rory has to beg Jess anytime she wants him to do something for her, like meet her grandmother. Even then, Jess won’t put in any effort to be respectful to Lorelai or Emily, and it’s honestly hard to watch. Yes, Jess is only 17, but his lack of communication and effort beyond doing what he wants is what makes him a bad boyfriend. Jess ends up abandoning Rory and moves to California without notice, ending their relationship.

Jess and Rory’s relationship is the definition of “right person wrong time.” If they had pursued a relationship after Jess had matured, it probably would have been endgame. Though they had shared interests and undeniable chemistry, Jess ultimately missed his shot.

Logan, the charming, smart, “old money” Yale man is undeniably Rory’s best boyfriend. Though they have different backgrounds, Logan and Jess’s characters are actually very similar. They are both incredibly intelligent; Logan challenges Rory to push herself beyond her limits and has similar interests. They could also both be jerks when something wasn’t right.

Fans’ biggest grievance against Logan came after their massive fight in the season-6 episode, Let Me Hear Your Balalaikas Ringing Out, when they don’t talk for weeks and Logan rebounds with his sister’s friend. Rory eventually finds this out and accuses Logan of cheating, but Logan defends himself by saying he thought they were broken up. Even in their biggest fight, however, Logan makes space for Rory’s feelings and they eventually make up.

Though Logan is presented as pretentious and spoiled, his communication skills and love for Rory make him the best boyfriend.

Logan always assures Rory’s needs are being met, consoling Rory about family issues at a party he was throwing, and even saving the Yale newspaper when Rory couldn’t. As their relationship flourishes when Rory is at Yale, Logan proves to be a considerate, mature, intelligent boyfriend who fights for their relationship. Logan provides the most stable and mature relationship for Rory.

Though Gilmore Girls doesn’t solely follow Rory’s love life, her infamous love triangles have captured viewers’ attention for over 20 years. Through adventure, romance, and heartbreak, Gilmore Girls has stood the test of time, as generations of fans continue to debate the controversial topic of Rory’s love life.