The Age Old Debate of Dean, Jess, or Logan: Which Guy Was Really Best for Rory

Sydney Leahy, Editor

Gilmore Girls, a witty comedy-drama television series that follows main character Rory Gilmore from her early years of high school to her final days of college. Throughout the show, Rory has three major love interests: Dean, the caring first boyfriend and every mother’s dream; Jess, the school skipping rebel from a broken home; and Logan, the absurdly rich intellectual who loves to party. All three of these boys were suitable relationships for Rory at different points in her life, but only one, in my humble opinion, was her perfect match.

Let’s start with Dean. He seems like the perfect guy for young Rory. He’s tall, on the hockey team, and always responds to her calls. He helps with household chores, he plans romantic dates, and in season three, to celebrate their three month anniversary, he gives her a car he built himself. This incredible gesture quickly turns sour when Dean tells Rory he loves her in it, and surprised and overwhelmed, Rory isn’t able to say it back. Their break up, like many of young loves, doesn’t last long though. They get back together and everything seems perfect. Rory drives the car Dean made her and it appears that all has been forgiven, until Jess shows up. 

Jess immediately sparks Rory’s interest, and a friendship eventually forms between them. This friendship though evolves into infatuation when at the end of season two, while she is still in a relationship with Dean, they kiss. From that moment on, her relationship with Dean is only downhill from there. Dean, sensing that he’s losing Rory, begins to demand all of her attention, which becomes increasingly impossible when she begins preparing to apply to Harvard (her dream school since she could walk). With all of her extracurriculars and volunteer events, she begins having less and less time to spend with Dean. She eventually outgrows him. This is where Dean loses my favor. Instead of being an understanding boyfriend and allowing Rory time to achieve her dreams, he becomes clingy and needy, constantly complaining that she doesn’t spend enough time with him anymore. This, along with her growing romantic feelings for Jess, results in a sad but necessary breakup.

This brings us to Jess. Jess is the first boy to intellectually challenge Rory. He shares her passion for literature and is able to discuss complex ideas and theories with her. He’s not perfect though. He moved to the quaint town of Stars Hollow from New York to live with his uncle, because his mother could not take care of him anymore. He’s a broody teenager who is fed up with the world. His conversations with Lorelai (Rory’s mom) and basically anyone who is not Rory are curt, which does not help endear him to the close knit town of Stars Hollow where everyone knows everything about each other. He vandalizes property, barely goes to school, and rarely answers Rory’s calls. He leaves Rory constantly second guessing her self worth, which makes Lorelai disapprove of him even more. The town hates him and Lorelai hates him, but Rory is able to overlook these faults because she believes that she is in love with him. Their communication is abysmal which leads to numerous misunderstandings between Rory and Jess. He is known for running away from his problems, and after not graduating senior year due to an abundance of absences, he continues this trend. Without even so much as a goodbye, Jess gets on a bus and leaves for California where he recently found out his dad lives. And with that, Jess leaves Rory’s life. 

Now we can finally discuss Logan. He embodies all of the best qualities of the previous two. He’s intelligent, dependable, and truly listens and understands Rory’s needs. They meet at college. At first, he seems like a spoiled trust fund kid who cares more about his social life than his schoolwork, and for a while he is. He throws lavish parties and is constantly taking crazy and dangerous adventures just because he can. As Rory gets to know him though, she begins to discover the other side of him. Sure he was spoiled, but he came from the same world of privileged wealth that Rory was introduced to at 16 when she began to get to know her grandparents better. And sure he goes on a ton of unsafe adventures, but he’s able to challenge her and push her outside of her comfort zone in a similar way that Jess was able to. 

Unlike Jess though, he respects her, which allows her to regain confidence in herself. He gives her the opportunity to experience a multitude of exciting activities that she was always too busy or preoccupied to attend in high school. They are both incredibly smart and never run out of topics to discuss. Rory has finally found her intellectual equal. Logan does have his weak points though. His constant partying with his friends leaves him unavailable a lot of the time. His second weak point, though this is something he can’t control, is his family. The Huntzbergers disapprove of Rory because she wants to become a journalist and won’t be able to be a good house wife for Logan. After giving Rory an internship at one of his many newspapers to make up for the way his wife and father treated her, Mitchum Huntzberger (Logan’s dad) tells her that she just doesn’t have the skills necessary to become a journalist, a job that she has been working towards her entire life. This breaks Rory. She drops out of college, gets arrested, and moves in with her grandparents. After months of community service and being out of school, Jess comes back into the picture. 

Jess lives in New York now and works at a small publishing company. He’s even written a book. He comes back to town to give Rory a copy of said book, and after finding out that she has dropped out of school, is able to convince her to go back. Jess meets Logan, and after an awkward dinner with Logan and Rory, he goes back to New York just as quickly as he arrived. Some people believe that Jess at this age is the best pick for Rory. They romanticise his past relationship with Rory, completely forgetting how terribly he treated her. He was flaky and uncommunicative and overall a poor boyfriend. Logan on the other hand, has always been there for Rory and is able to discuss the problems in his relationship like an adult. As viewers, we have no reason to believe that Jess has changed his ways, and anyone who believes otherwise is too infatuated with his bad boy persona to accept reality. 

To conclude, clearly Logan is the best boyfriend out of the bunch and if you disagree with me you’re wrong.