Is Rory Gilmore A Ruined Character Or Cautionary Tale?

The 2000-2007 television show Gilmore Girls is a beloved staple of television for a good reason. The seven-season show follows Lorelai Gilmore and her daughter Rory (played by Alexis Bledel of The Handmaid’s Tale fame), whom Lorelai had at age sixteen. After running away from her wealthy parents’ home in Hartford, Lorelai got a job at an inn and raised her baby in Stars Hollow, Connecticut, an idyllic and idiosyncratic small town. Gilmore Girls begins when Rory is sixteen years old and has just gotten into Chilton, a prestigious prep school that she believes will help her fulfill her dream of going to Harvard. In order to pay for the private school, Lorelai begrudgingly asks her parents for money, agreeing to the condition that she and Rory will come for dinner every Friday night.

At the beginning of the show, Rory is a studious, somewhat socially awkward teen who loves reading classic literature and aspires to be a journalist. While some of this may sound like a young adult trope, female teenage characters like her weren’t terribly common in the early 2000s. The main focus of the Gilmore Girls was Rory’s best friend bond with her mother, as well as her growing relationship with her grandparents and their world, the world Lorelai had left behind. Lorelai and Gilmore Girls itself paint Rory as the perfect girl, calling her an “angel” and telling the audience that she is “special.” In later seasons, however, Rory makes regrettable decisions, including sleeping with her married ex-boyfriend and stealing a yacht for a joyride. I, like many other viewers, used to see Rory’s later actions as out of character. Upon rewatching (and rewatching, and rewatching again), however, I believe that Amy Sherman-Palladino, the creator of Gilmore Girls, may have had this character arc in mind for Rory all along.

Rory + Relationships

Rory’s various romantic relationships are, unsurprisingly, a hotly debated topic within the fanbase. Her behavior in her early relationships is sometimes overlooked, but it provides a clear foundation for her later, more controversial actions. Rory displays two patterns regarding dating that are crucial to notice here: her tendency to cheat or be involved in cheating and her willingness to throw important facets of her life away for a guy. Both of these patterns are fully evident in the later seasons, but their foundation is laid early on.

Dean

Dean is Rory’s first boyfriend, arriving at Stars Hollow from Chicago in the first episode. He and Rory quickly begin a relationship that Lorelai is initially wary of but later wholeheartedly approves of. In the first episode of Gilmore Girls, Rory meets Dean and immediately tells Lorelai that she no longer wants to switch schools but wants to continue going to the local Stars Hollow High, where Dean goes to school, rather than Chilton. Though Rory changes her mind by the end of the episode, this conflict illustrates her tendency to make rash, life-altering decisions for a boy.

As Rory and Dean’s relationship begins to stagnate, a new character named Jess moves to town. As the show sets up a contrast, forgetting that Dean is from Chicago, between Dean’s clean-cut small-town persona and Jess’s “bad boy,” intellectual nature, Rory finds herself increasingly drawn towards Jess. Rory eventually kisses Jess while still dating Dean. Dean breaks up with her not long after, at which point she begins officially dating Jess. At this time in Gilmore Girls, kissing Jess can be put down to a youthful mistake on Rory’s part, particularly given Dean’s controlling and manipulative nature. Though Lorelai is upset when she finds out that her daughter kissed someone other than her boyfriend, she understands that Rory is seventeen and bound to make mistakes. Dean, however, is not gone from Gilmore Girls, and Rory has never left Dean’s thoughts. Both Rory and Dean’s behavior in the early seasons lay the foundation for what is perhaps the most infamous moment in Gilmore Girls.

Raincoats And Recipes

The season four finale, titled “Raincoats and Recipes,” tends to be either adored or despised by fans. By this point, Rory is in college, and Dean is married. It has been a significant amount of time since they have dated, but they have spent season four developing a “friendship,” which they both try to deny means anything more. There are several momentous events that occur in “Raincoats and Recipes,” but the most notable is the episode’s conclusion, where Lorelai comes home to discover that nineteen-year-old Rory has lost her virginity to the married Dean and confronts her about it. In trying to defend herself, Rory repeats Dean’s manipulative and untruthful assertions that his marriage is over and that neither he nor his wife, Lindsay, are happy.

She also claims that Dean “was [her] boyfriend first” and that this gives her the right to sleep with him despite his marriage. Eventually, Rory leaves the house in tears while Lorelai stands stunned. Rory’s choice to sleep with a married man is considered extremely out of character by some, including Lorelai. And just like the incident with Jess, her youth is occasionally used to mitigate the severity of cheating. Though I do think nineteen-year-olds should be held to rather higher standards than this view implies, I might largely agree with this if Rory learned from her mistake and refrained from infidelity for the rest of Gilmore Girls. However, this is not the case, which points to the conclusion that a tendency towards affairs is a part of Rory’s character.

Too Many Affairs To Remember

Rory continues to cheat in big ways and small ways throughout the course of Gilmore Girls. She kisses Jess once more while dating a different boyfriend named Logan, in what might be seen as an act of small revenge for his cheating on her while they were taking a break. And in the 2016 revival of Gilmore Girls, titled A Year in the Life, which takes place when Rory is 32 years old, she is consistently and casually cheating on her boyfriend, Paul, with Logan, who is engaged. By this point, neither she nor Lorelai seems to see anything wrong with Rory’s actions.

For longtime Gilmore Girls fans, Rory’s romantic choices are disappointing, to say the least. She displays a complete lack of empathy and morals in the revival, and it can no longer be put down to her age. Willingness to cheat or be a party to cheating is a consistent character trait that Rory displays throughout the show, which may be correlated to the sense of entitlement she slowly develops over the course of the series.

Rory + Wealth

The fundamental conflict within Gilmore Girls is the struggle between Lorelai and her mother, Emily, and to a lesser extent, her father, Richard. More broadly, the struggle is between their respective worlds, with Rory caught in the middle. Having fled from the world of elitism, wealth, and high society in which she was raised, Lorelai firmly believes her daughter will appreciate the same small-town life she does. While this is true to some extent, as Rory loves living in Stars Hollow and is very similar to her mother in many ways, she is also increasingly drawn to her grandparents’ world of luxury and class.

Richard + Emily

When Lorelai and Rory begin coming to their house for Friday night dinners, Emily and Richard are thrilled to find that their granddaughter is in many ways the daughter they always wanted. Rory is quiet, well-mannered, and appreciative of their world. At the same time, Lorelai rebelled against her parents’ controlling, stifling nature, eventually getting pregnant and dropping out of school, thereby derailing all their plans for her. To Richard and Emily, their granddaughter is their second chance, another opportunity to watch a bright young woman carry the Gilmore name through a prestigious university and marry someone with similar good breeding. Since their desires, at least in terms of going to college, match fairly well with what Rory wants, there isn’t too much friction between them in the early seasons. Rory doesn’t experience nearly as much of the dark side of Richard and Emily’s behavior the way Lorelai did growing up and thus has a very different impression of and relationship to them than her mother.

While Richard and Emily clearly love and care for their granddaughter, they also clearly and strategically position themselves as the alternative–the alternative to Rory’s life with Lorelai, the alternative to life in Stars Hollow, and the alternative to facing the consequences of any poor choice that Rory might make. When Rory has a fight with Lorelai and is fed up with Stars Hollow, she runs to her grandparents, who gleefully welcome her, delighted that she has run from Lorelai to them. When Rory gets into legal trouble late in the series, they provide a lawyer who, they incorrectly insist, can get Rory off practically scot-free. And when Rory drops out of Yale, where she is attending college, they allow her to live with them instead of working with Lorelai to help get her back on track.

As Rory grows ever more involved in her grandparents’ world, she transforms from the quiet, down-to-earth girl from the beginning of Gilmore Girls and into a more self-involved, entitled, and impractical person. Richard and Emily are certainly not the only ones to blame for coddling Rory and giving her unrealistic expectations and opinions of herself, as I will discuss shortly, but they do provide a strong shield between their granddaughter and the real world. Because of the part the elder Gilmores play in Rory’s development; I believe the change in her character was a well-crafted examination of a child raised with high expectations of herself and the awareness that if she doesn’t meet these expectations, she will be a disappointment to her family, just as she was when Lorelai first got pregnant with her.

Logan

Rory’s college boyfriend, Logan, should also be mentioned when discussing the way wealth impacts Rory’s character. Logan comes from a world of even more wealth and privilege than the Gilmores to the point that Rory is stunned when seeing his house for the first time. Logan is a charming playboy figure who uses his wealth to get away with stunts that would send most people to jail. Along with the grandparents, he helps pull Rory towards the high-society world. After a disastrous dinner with his family, during which Rory is demeaned for her social status and illegitimate birth, Logan’s father, Mitchum, offers her an internship at the newspaper he owns. When Mitchum later tells Rory that she doesn’t have what it takes to make it in journalism, Rory, distraught by the first real criticism she has ever received, steals a yacht with Logan for a joyride.

Once again, Rory’s actions are considered by Lorelai, as well as some viewers, to be out of character. It certainly is hard to reconcile the bookish, school-loving teenager with the young adult who commits a felony and drops out of college. But right from the first episode in which she considered quitting her new school over Dean, Rory has shown a tendency to take drastic actions when she feels trapped or upset. This trait, combined with the rapidly expanding world of luxury and privilege she has been introduced to since beginning dinners with the grandparents and especially since meeting Logan, leads to the downfall of the “perfect Rory” image.

Rory’s Career

The most disappointing aspect of Rory’s arc is, in my opinion, her career trajectory. At the beginning of Gilmore Girls, she has dreams of being a foreign correspondent and is a diligent student. She has a real passion for literature and schoolwork that comes through in her achievements.

And while she hits a few rocky places during the later seasons, as mentioned above with dropping out of college and getting arrested, the original series ends with her about to set off on the campaign trail, covering then-Senator Barack Obama–a job that should have panned out even better than could have been anticipated in 2007 when Gilmore Girls ended. But the optimistic note on which the original series ends turns sour in the revival.

A Year In The Life

The audience never gets to see Rory as a successful journalist or successful at anything. In A Year in the Life, Rory is floundering, unable to find a job, and seemingly unmotivated. Now, it’s more than reasonable for a 2007 graduate in such a rapidly shrinking field as journalism to struggle to find work. However, Rory’s difficulties seem to be almost entirely of her own making. She falls asleep while interviewing sources and sleeps with one of them (once again cheating on her boyfriend, Paul). Gone is the dedicated reporter Rory used to be. The reporter who in high school turned an article about the repaving of the school parking lot into a tearjerker, the editor who in college rallied her team to get a paper out in time in the face of challenging odds. Adult Rory, as it turns out, can’t even pull off a single story.

It’s disheartening, and Rory never gets back on track within A Year in the Life, ending the revival with plans to write a book about her life with her mother. As many fans have pointed out, journalism and foreign correspondence may never have been the right choice for Rory, even if she sometimes had a knack for writing good articles. There’s nothing wrong with realizing the path you’re going down isn’t the right one for you and course-correcting. But Rory seems to lack such self-awareness, even deciding to write the book solely on the advice of Jess, by then an old ex and friend. The audience gets the sense that Rory could succeed if she would only get out of her own way.

In short, Rory’s arc is one of disappointment and unfulfilled promise. It leaves a bad taste in the mouth of many viewers and leads to no end of hatred for Rory’s character. For many girls like me, who grew up idolizing and relating to high school Rory Gilmore, her ending is unnerving and feels almost like a slap in the face. But, as many viewers have realized, it’s entirely possible that her arc, or one like it, was intentional from the start.

Lorelai’s Influence

Lorelai generally does an excellent job in a complicated situation, considering that she has raised a child by herself from the age of sixteen. But she certainly comes with significant baggage, namely the intense desire not to be like her own controlling, emotionally distant mother. In doing so, she fosters an extremely close, perhaps codependent relationship with her daughter, wherein Rory is often the first one to witness and try to ameliorate Lorelai’s worst moments. The patterns of behavior Rory repeats lend credence to the idea that her arc was planned to be disastrous from the start. While Rory is still in high school, Lorelai sleeps with Christopher, Rory’s father, while still dating his girlfriend, Sherry. Like Dean does much later, he tells Lorelai it’s over between them (though since Sherry is actively looking for a new apartment, there seems to be more truth to this than when Dean said so to Rory. It turns out that Sherry is pregnant, and Chris leaves Lorelai and Rory once again to be with her.

When Lorelai confronts Rory about sleeping with married Dean, Rory throws this example in her face, erroneously claiming that Chris was already engaged to Sherry and knew she was pregnant when Lorelai slept with him. Despite her inaccurate retelling of the events, the writers seem to have been drawing a parallel between the two. Both are quite willing to believe what their exes tell them about their relationships, even if Rory commits a far greater wrong than Lorelai. These parallels are further emphasized by the famed and oft-maligned, final four words of A Year in the Life, which, not to give too much away, all but confirm the creators’ desire to tell a “full circle” story with Rory and Lorelai. This full-circle being planned from the start strongly suggests that Rory was always intended to go down the path she ultimately did, or at least one similar to it.

The Dangers Of Overpraising

Some viewers say that Rory is extremely privileged, and while this is certainly true in the later seasons, it is important to note that this was far from the case at the beginning of her life. Rory spent the first years living in a potting shed at the inn where her mother worked as a maid, moving into a single-family home when she was a preteen. Her forays aggrandize the sense of entitlement she displays into the world of wealth, but that isn’t where it originates from. From the beginning of Gilmore Girls, Lorelai tells her daughter that she is “special,” that she is an “angel,” and that she is “the sweetest kid in the world.” Stars Hollow itself also contributes to Rory’s sense of uniqueness. The townspeople, feeling as though they helped raise both Lorelai and Rory after the former showed up at sixteen with baby Rory in her arms, cosset, and practically worship Rory. Once Rory begins regularly seeing her grandparents, her self-conception as “special” is cemented by their clear jubilation that she is different from her mother.

With this sense of specialness comes a subtle but crushing sense of responsibility. Rory has to be the perfect, special girl because that’s who everyone important in her life has told her she is. She has to be the Gilmore daughter Lorelai wasn’t for her grandparents, and she has to be the emotional support Lorelai never got from Richard and Emily. And because of her studious nature and genuine adoration for her mother and grandparents, she is able to pull this off for much of her life. But as she starts entering the real world, facing losses and dealing with criticism, it begins to fall apart. Rory is special; therefore it’s only natural that her married ex-boyfriend would still be in love with her.

The sense of ownership she seems to feel towards her ex-boyfriends may have its roots in the idea of her on a pedestal, superior to any other woman in the world. Rory is special; therefore, she should be able to make it in journalism despite not quite having the drive. And if she realizes that she has messed up and thereby shattered her image of perfection, she acts out in an attempt to cope and regain control. None of Rory’s actions are out of character, as disappointing and infuriating as they may be.

To this day, I don’t know for certain if the creators of Gilmore Girls actually planned Rory’s arc this way. There will always be a part of me that longs to see a powerful, inspiring Rory Gilmore setting the journalistic world on fire and sticking to her values when it comes to relationships. But it’s impossible to deny that the foundation for her later disappointments was there from the very beginning. As it is, perhaps Rory serves more as a warning against raising children with the idea that they are special than anything else.