Like every other suburban white girl, Gilmore Girls is one of the loves of my life. I have watched the entire show at least four times and the revival twice, and I rewatch my favorite episodes more often than I’d like to admit. It’s the mashed potatoes of TV shows: warm, comforting, and predictable.
But for any Gilmore Girls fan, it is widely known that the debate over who Rory should end up with is one of serious controversy. The choice boils down to three serious contenders: Dean (tall, protective boy next door), Jess (alternative, sarcastic writer), and Logan (charming, bad boy socialite). All the boys have their own merits, and I myself wouldn’t mind ending up with any of them (wink wink, Milo Ventimiglia). However, when looking at the broader context of the show, it’s clear that the answer is, in fact, none of them.
So, curl up with your coffee and your coziest sweater as we navigate the romantic turmoil of Stars Hollow’s finest!
Warning: Spoilers ahead!
Dean
Initially, Dean appears to be the perfect match for Miss Rory Gilmore. He is patient and understanding of Rory’s innocence, devoted to learning about her interests (even reading Anna Karenina twice) and eager to shower her with gifts. He even wins the Lorelai stamp of approval fairly early on, which can’t be said for the other boys on the show. However, when taking a deeper look at some of the episodes, Dean’s controlling nature rears its ugly head. I first noticed this in episode fourteen, “That Damn Donna Reed.” Rory, Lorelai, and Dean are sitting on the couch watching The Donna Reed Show, and Loreali and Rory laugh over the unrealistic expectations set for wives within the show. Dean quickly defends it, arguing that it’s nice when women put in the effort to create a good home for their husbands. A fight between Dean and Rory quickly ensues, but Rory makes it up to him by, I kid you not, dressing in 1950s attire and cooking an entire dinner (despite the fact that Rory’s cooking skills are mostly limited to putting takeout onto a plate).
To me, this episode perfectly captures the fatal flaw of Dean: He is attracted to Rory’s intelligence and independence, but does not actually appreciate it within the relationship. Dean’s controlling nature to not only change Rory but keep her to himself is also a huge red flag. He doesn’t trust her and instead goes out of his way to fight with boys she says she has no romantic interest in at the time (Logan and Jess). Not to mention the fact that they end up in an extramarital affair after Dean gets married, and then have a relationship largely consisting of sad car sex. Gross and enough said.
Jess
First off, let’s think about this through a basic family tree. Lorelai and Luke end up together in the revival. Jess is Luke’s nephew (but they really have more of a father/son relationship), and Rory is Loreali’s daughter. Therefore, Jess and Rory are basically step siblings. Ew. But, even for those of you willing to look past this, Jess is just too emotionally immature for Rory. He leaves her waiting for his call for hours at a time and is often cold and distant with Rory for no reason. He also takes his issues with his mom and Luke out on Rory in a dangerous way. For example, in “Keg! Max!” Jess tries to pressure Rory into doing something physical with him even though she is obviously not ready. And let’s not forget, he straight up left Rory and moved to California with absolutely no warning.
To be fair, Jess does partially redeem himself in other seasons, like when he helps Rory get out of her rut while she’s taking a gap year from Yale, and in the revival when he comes back as a put-together author. Still, I think Rory and Jess’s relationship is past viability. Rory is obviously still not over Logan in the revival and doesn’t seem to view Jess in a romantic way at all. Although Jess undoubtedly has the most character growth of the three boys, he simply missed his shot with Rory.
Logan
Logan is a risk-taker. I mean, he literally jumped off a cliff. While I actually think that this quality of Logan’s is important in getting Rory out of her shell, it does prove to be toxic and unsustainable for the two of them. Logan’s risk-taking leads Rory to steal a boat and get arrested, derailing her image as the next Christiane Aumanpour. His drinking habit gets rather out of hand, and Rory spends one too many nights helping clean him up. Logan leads Rory to reject an offer from a solid job opportunity in favor of a chance at a prestigious internship that Rory doesn’t ultimately get, and the list goes on.
In very consequential ways, Logan’s risk-taking behavior lands Rory in quite a bit of trouble that outweighs the positives of their relationship. He’s also a representation of everything about the elite class that Lorelai worked her whole life to escape: He owns a ridiculous amount of property, can depend on his dad to pay off anyone that causes him trouble, and can travel pretty much anywhere in the world at the drop of a hat. In one word, Logan can be described as entitled, and that simply is incompatible with the way Lorelai worked so hard to raise Rory.
All three boys have flaws that cannot be rectified within their individual relationships with Rory, all of which end up proving to be too toxic to continue. But beyond the toxicity, Rory simply could not end up with any of these boys because it would go against the show’s arc and major themes. From the very beginning, Amy Sherman Palladino (the show’s creator and writer for all but one season) said she knew what the last four words of the show would be. For those of you who have finished the revival, they are:
Rory: Mom?
Lorelai: Yeah?
Rory: I’m pregnant.
In this way, Gilmore Girls ends the way it started. Lorelai and Rory both seem fated to be single mothers. If Rory were to end up with any of the boys above, it wouldn’t be staying true to the cyclical nature of Gilmore Girls and one of its major themes: Despite one’s attempts to change others, their past, or their family history, it is impossible. Lorelai works for pretty much the entire show to create a different life for Rory than she had, and she tries to shape Rory’s actions in the way Lorelai sees fit. However, as proven by the fact that Rory ends up in the same place as her mother, the sooner one stops running away from their past and instead accepts others as they are, the sooner one can find peace. It’s a beautiful message, and one that would be completely lost if Rory ended up with Dean, Jess, or Logan. So ultimately, I’m on team Rory: a fierce single mother, raised by a fierce single mother, ready to take the world by storm.