Though widely understood as holding an aesthetic monopoly over coffee, oversized knits, and the season of fall, Rory Gilmore is actually not a dependable source for romantic and academic advice. Gilmore Girls, in addition to being a charming show about a mother and daughter navigating life, supplies many moments of low-stakes drama, primarily related to Rory and her relationships, whether those be with boys or the classroom. Starring a mother-daughter duo and taking place in the fictional town of Stars Hollow, Gilmore Girls offers the television equivalent of a fall afternoon spent sipping coffee and reading classics, with a script largely made up of wicked-fast banter and pop culture references. It is the kind of show enjoyed by so many because what conflict exists is largely detached from reality — it’s kind of hard to relate to someone whose problems and ‘big life choices’ include picking between a number of Ivy League schools and boyfriends.
It’s early October at the time of writing this, so I’m going to hazard a guess that many people are either restarting the classic 2000’s show, or selectively picking out delightful fall episodes that don’t make you cringe with how poorly Rory handles a situation. This article contains spoilers, as I’ll be hashing out some of Rory’s more dramatic moments of shortsightedness and bad decision-making. That being said, I do love Rory for her constant rotation of reading material, dedication to print journalism, and general need for coffee at all times. I also love her wardrobe, and her hair in season seven. She is, after all, merely a made-up character in a popular show, and can you really fault her for getting back with her ex or ending up in jail after a night out? You can, actually, and here’s why.
As you probably know, or else can infer from her general disposition of ‘beautiful and innocent lamb,’ Rory has a steady rotation of men in her life. This ranges from high-school sweetheart Dean, to bad-boy Kerouac aficionado Jess, to rich college boyfriend Logan. Naturally, there is a great deal of overlap between these boys, and this causes problems. Multiple breakups pepper Rory and Dean’s relationship in the early seasons, but the damning event is Rory’s kiss with Jess at a wedding in season two, while she’s dating Dean. Beyond the jealousy, communication, and immaturity issues, the reality of Rory cheating on Dean is pretty obviously not role model behavior.
The Rory-Dean-Jess love triangle instigates a seasons-long feud between Dean and Jess and results in more than a few punches being thrown, after Rory and Jess’s constant flirting pushes Dean to very publicly break up with her. There are a variety of ways Rory could have dealt with the love triangle, but instead she forces the boys to duke it out — the first in what will become a habit of avoiding her problems. Further exemplifying what not to do, Rory misses her own mother’s graduation simply to be with him, before they ever even officially begin their brief but tumultuous relationship.
Perhaps the greatest of Rory’s romantic errors comes in the form of a one-night stand with Dean in season five, who, at the time of their tryst, is married. Disillusioned with Yale and her studies, Rory flees to Stars Hollow and seeks comfort where she knows she’ll find it. Beyond the obvious problem of Dean initiating it, Rory showcases an inability to respect that Dean is married and an unwillingness to recognize that she was also at fault. One of the biggest issues with this series of events is Rory’s use of Dean — and her hometown — as a crutch when things get tough.
This night is also the source for one of the biggest series fights between Rory and Lorelai, who cannot understand (finally, some sense) why Rory would want to be ‘the other woman’. In classic Rory fashion, she avoids this conflict by jetting off to Europe for several months with her grandmother and refusing to speak to Lorelai — continually attaching herself to people who enable her ability to skirt her issues. In spite of having plenty of time (and probably views of Athens) to give her some clarity, Rory decides to date Dean after his wife kicks him out. The biggest lessons here? Don’t sleep with your married, high-school ex-boyfriend just because it’s convenient, and if you’re using a tour of Europe to escape your problems, stop and reconsider some things — your privilege is showing.
But nowhere does Rory’s privilege show more than when she drops out of Yale in her junior year. One of the most iconic lines from the show comes from Jess’s outburst after Rory runs into him on a night out: “No Yale! Why did you drop out of Yale?!” Truer words have never been spoken, or more aptly emphasized. In my opinion, Rory’s choice to drop out of Yale is one of the most unforgivable decisions she makes in the entire series, regardless of the fact that she eventually does go back and graduate from the college. The principle of the situation, her reasoning, and what she chooses to do instead (read: joining the DAR to be surrounded by 50-year-old high society women and living in her grandparents’ pool house) is so antithetical to her intelligence that it temporarily ruins her character.
Her decision to leave Yale (the number four school in the United States, by the way) in the fall of her junior year is due to her complicated relationship with Logan and her failed internship the preceding summer. There are three major takeaways here: relationships should not dictate the entirety of your academic career, open relationships almost never work, and internships are not as big a deal as they seem. Also, Jess was right about pretty much everything. The only, and I mean only, good thing to come out of Rory’s break from college was the Birkin bag Logan buys her for apparently no reason at all.
The internship as a reason for her dropout is a moment that made viewers across the world want to take Rory by the shoulders and shake some sense into her. After receiving a journalism job offer from Mitchum Huntzberger (coincidentally, Logan’s dad), participating in said offer, and being told she doesn’t have what it takes, Rory decides to straight-up quit. No big deal, it’s not like it’s been her dream career since she was 5 years old. Like any of us would do if we found ourselves facing a devastating rejection, Rory steals a yacht and spends the night in jail before Lorelai bails her out. Her yacht-stealing is partially Logan’s fault, making this yet another instance where her Bonnie and Clyde tendencies are not model behavior. Have any of us had a rough night and gotten ourselves into trouble after a few too many glasses of champagne? Probably! Have any of us ended up in jail after said trouble? Not likely, but I wouldn’t rule it out! There is something to be said for protecting your peace and knowing when you’re beat, and stealing a yacht simply is not the answer.
Logan, though my favorite of Rory’s boyfriends, has never been known for his impeccable record and thought-out approach to decision-making. Logan skates through his life knowing that money and family name excuse him from most everything, though his only real fault is being blonde. Rory, though cognisant of Logan’s financial leg up, fails to take this into account unless it benefits her. She lives alone in Logan’s insanely nice apartment for the entirety of her senior year at Yale, initially refuses the internship his dad offers her, and starts several fights when Logan takes a job in London that he’s worked legitimately hard to get. In sum, it tracks that their relationship ultimately ends and Rory is left to make some necessary career choices, on her own this time.
Despite her actual genius and capability for dedicating 95% of her life to studying, Rory made some seriously questionable decisions throughout her time on the show. But few of these transgressions are entirely Rory’s fault — relationships take two to function, whether romantic or familial or platonic. Almost all of the other characters mess up in ways big and small and generally contribute to Rory’s problems in some capacity. She has many redeemable, lovely, and genuinely kind moments, but I won’t dwell on these, since Rory attempted to do the same thing in her infamous scathing Yale review of the ballerina, and as I’ve just argued, we’re not modeling our lives off of her.
Rory’s decisions often come from a place of insecurity, having grown up lauded for her intelligence and regarded by every Stars Hollow inhabitant as the town’s golden child, and she fails grandly at recognizing her privilege, most notably the lengths others in her life go for her. It’s understandable that in her late teens and early twenties she would be influenced by boys, have a rebellious streak, and make decisions she regretted. These things are normal, these things are okay. But that doesn’t necessarily justify all of her actions, and it certainly doesn’t mean that as an audience we can’t see where she went wrong and perhaps wonder if there wasn’t an obvious alternative to the situation, as opposed to idolizing every element of her life. She very well might be the secret villain of the show — her actions certainly do not always correlate with the path of least destruction. Lest we forget, this is a fictional piece of media, and though she is one of television’s biggest self-proclaimed perfectionists, perfection doesn’t make for good TV.