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A Deep Dive into Rory Gilmore’s Romantic Choices

The opinions expressed in this article are the writer’s own and do not reflect the views of Her Campus.

“Gilmore Girls” is without a doubt my favorite show in the whole world. Something about Stars Hollow makes me feel safe and comforted wherever I may be and Rory Gilmore has definitely had an influence on some big choices in my life (she may be the reason I’m a journalism major, who’s to say?). I have probably watched “Gilmore Girls” from start to finish at least five times, not to mention the revival, “Gilmore Girls a Year in the Life.” Through all of my Gilmore Girls binges, I have developed some strong opinions about Rory’s romantic choices. Here I will share my analysis and opinion on each of Rory’s relationships, and in the end, I will declare who I think she should have ended up with. 

Dean 

Dean was Rory’s first boyfriend. He appeared early on in season one and in the beginning of their relationship, he seemed kind and charming. Dean’s first day at Stars Hollow High was only a few days before Rory’s last day there. This complicated the beginning of their relationship and also served as the catalyst for Lorelai and Rory’s first major disagreement in the series. Rory became interested in Dean and decided that she no longer wanted to leave Stars Hollow High to attend Chilton. Lorelai refused to let Rory throw away her opportunity of going to an incredibly prestigious school for some boy she just met. In the end, Rory decided to still go to Chilton and she and Dean ended up dating anyway. Though this happens early on in season one, it already seems a bit out of character for Rory. Rory is incredibly driven and academically minded, so the thought of her throwing away the chance to attend such an amazing school over a boy is immediately off-putting. Luckily this side of Rory doesn’t last, at least for the next few seasons. 

At first, Dean is very supportive of Rory’s dream of going to Harvard and though he doesn’t share her academic drive, he doesn’t hold her back in any way. Dean’s true colors start to show, however, when he expresses that he doesn’t want to go with Rory to her formal dance at Chilton. It is clear that dances are not necessarily in Dean’s wheelhouse, but relationships are about sacrifices and supporting your partner in things that are important to them. Dean practically throws a fit about having to wear a tux and attend a dance with snooty rich kids, which would be understandable if it was a longer or more permanent sacrifice, but it was only one night. The dance was clearly important to Rory and eventually, Dean reluctantly agreed to go. 

Now, we move into something even worse. For their three-month anniversary, Dean builds Rory a car and takes her out to surprise her with it. This gesture is very sweet and Rory is incredibly grateful and excited about the gift. Then, Dean tells Rory that he loves her. Rory panics and doesn’t say it back, which is completely understandable since they had only been dating for three months and they were so young and still learning what love really means. When Rory doesn’t say it back, Dean becomes incredibly angry, yells at Rory, and tells her that since she isn’t capable of saying it back, he is breaking up with her. This moment is where I drew the line with Dean. In the beginning, I thought he was dreamy and romantic and I was able to ignore his annoying quirks and problematic approaches to situations, but this took his ignorance and selfishness to a whole new level. After this unfortunate event, Rory eventually decides to take Dean back and famously says, “I love you, you idiot!”, outside of Chilton. They reunite with a passionate kiss and their relationship seems to be happy and in the clear… until Jess gets into town. 

Jess 

Jess piques Rory’s interest from the moment he arrives in Stars Hollow. His bad-boy image and mysterious personality catch her attention and leave her wanting to know more about him. Dean notices Rory’s curiosity right away and becomes incredibly suspicious of and hostile toward Jess. Though Rory develops feelings for Jess, she tries to stick it out with Dean. Lorelai notices Rory’s interest in Jess and becomes hyper-aware of the time Rory spends with him and how she talks about him. Lorelai makes it very clear to Rory that she believes Rory should stay with Dean and forget about Jess. 

While Rory and Dean are still together, Jess becomes more curious about Rory and antagonizes Dean in an attempt to steal her away. His persistence may come off as charming to some, but to me, it seems creepy and invasive. Jess’ efforts to break Dean and Rory up are incredibly immature and unproductive, despite how much he may like Rory. He tries a variety of things, like outbidding Dean at the picnic basket auction to win a date with Rory, he steals the bracelet that Dean made Rory which causes her to go into a panic about Dean noticing her not wearing it, he gets into physical altercations with Dean, and he asks Rory to tutor him so that they can spend more time together. This kicks Jess off with an immediate red flag, even before the relationship officially begins. When Jess realizes that Rory and Dean aren’t going to break up so easily, he begins a relationship with another girl, his only motivation being to make Rory jealous. This makes it obvious how little respect Jess has for women and how low he will stoke to get what he wants. He ultimately breaks up Dean and Rory, hurting both of them, and hurts the girl he used to make Rory jealous. 

Once Dean and Rory break up, Jess swoops in to comfort Rory almost immediately. He dumps the other girl and swoons over heartbroken Rory. Soon after, Rory and Jess begin their relationship. Immediately, Jess is unwilling to participate in much of Rory’s life. He refuses to go to the town carnival until he learns that Dean will be going. Most of Jess’ motivation comes from the desire to possess Rory as if she is some kind of prize to be won. He doesn’t show much interest or make an effort in having an actual relationship. 

A couple of months into Rory and Jess’ relationship, he tries to initiate sex with Rory and when she declines, he gets mad at her and storms off. This drew the line for me with Jess. Later, he apologizes and they make up, but it doesn’t take long until he leaves Stars Hollow, without even telling Rory. 

Dean… Again…

While Rory is dating Jess, Dean begins seeing Lindsey. Their relationship appears casual at first, but a lot happens when Rory goes away to college. Dean and Lindsey get engaged and eventually married. After only about a year of their marriage, Rory finds herself single and Dean claims that things aren’t working with Lindsey. They end up having sex, while Dean is married. This is one of the lowest points for both Rory and Dean. It shows how unloyal and deceitful Dean is and how naive and selfish Rory is. Once Lindsey finds out and she and Dean separate, Rory and Dean get together again. Their third try doesn’t last long and they don’t receive any support from the town. 

Logan 

Logan doesn’t enter the scene until Rory is at Yale and has been single for what seems like the longest period of time throughout the entire series. At first, he seems mysterious and charming, but after observing him more, it becomes clear that he is a pretentious prick riding on Daddy’s money. He is incredibly rude to people who don’t come from money and he leads Rory on in the beginning. He tells her that he likes her but he isn’t the relationship type. At first, she accepts this and tells him that she can handle it. She quickly realizes, however, that she doesn’t want something casual. Once she tells Logan this, he decides that he wants to commit to a serious relationship with her as well. It seems all sunshine and rainbows at first, but Logan doesn’t end up being a good influence on Rory. 

While with Logan, Rory becomes more stuck up, reckless, and selfish. Not all of the blame can be placed on Logan, but he definitely doesn’t help. While with Logan, Rory steals a boat, gets arrested, and drops out of Yale. Somehow, their relationship lasts… at least up until Rory’s graduation from Yale. 

In the series finale, we see Rory graduate from Yale. All seven seasons have led up to this moment. After she graduates, Logan pops the question. Rory becomes frazzled and unsure, but ultimately says no. She tells him that she wants to be with him, but she isn’t ready to get married. Logan gives Rory an ultimatum and says that they either get married or break up. Rory chooses to break up. By Logan doing this to Rory, he lost any ounce of respect I possibly had for him. 

Who wins?

In short, every choice presented is a horrible choice. I would choose none of these men for Rory. I wish with all of my being, that Rory would have ended up with Paris, but alas, it wasn’t written in the stars.

Jadeyn Dugger

CU Boulder '25

Jadeyn is currently a freshman studying journalism and Spanish. She loves to read, write, sing, act, and spend time outdoors. You can find her writing about social issues, her own personal experiences and stories, and whatever else sparks inspiration.
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