As the leaves turn orange and the school year kicks off, the season of binge-watching Gilmore Girls and pretending to be Rory Gilmore at Chilton for academic motivation has commenced. From excelling at all aspects of school to a balanced social life, it’s safe to say we all look up to high school Rory. So where did it all go wrong? How did Rory Gilmore go from the girl we wanted to be to one we feared becoming? We’re here to dissect how Rory went downhill and why it all went south. 

At the start of the show, watching how Rory navigated this prestigious and cutthroat private school was simply astounding. Viewers admired her determination and how she was able to adapt to the competitive environment after growing up with a much different background than her peers. From failing her first tests to garnering the valedictorian title, Chilton was a test of Rory’s grit and she certainly took it by storm. Being able to witness her win student council elections, bolster her journalism career at the Franklin, and get accepted into Ivy League universities felt rewarding not just for her but for everyone watching the show. As viewers delved into the world of Gilmore Girls, they felt so seen by her soft-spoken and diligent character, as well as this spark of motivation to accomplish things just like Rory. They looked up to her. But reflecting back on the show, moments of Rory’s extreme selfishness and entitlement were evident even before she went to college.   

 Rory Gilmore’s downfall began in Season Three of Gilmore Girls, specifically in the episode “Let the Games Play”, in which she does not attend Lorelai’s graduation and instead takes a trip to New York with Jess.  This was a tremendously selfish move since she knew just how much Lorelai had worked and struggled for her degree. While Rory might have been missing Jess since he had gone to live in New York and it was perfectly fine to go visit him, why did she choose this day specifically? She knew it was Lorelai’s graduation and she knew how much she wanted her there. This marked a turning point for our beloved Rory. 

Ah yes, college Rory. A time of not-so-good hair decisions, unreasonable and irrational rebelliousness, selfishness, and academic burnout. All throughout her freshman year, Rory displayed such horrible behavior that was almost hard to fathom. How could Season One’s organized, bookish, sweet Rory turn into a cheating, ungrateful, selfish, irrational, and not to mention annoying monster? Her freshman year was definitely a test of just how horrible she was about to become. She prioritized herself over her roommates and family and friends time and time again and expected everyone to do the same. When she deemed her roommates as too loud, instead of retreating to the library or a coffee shop like a normal person, she decided to venture outside onto the lawns of Yale and reserve a random tree as her “Study Tree”, even paying a man and forced him out of sitting under “her tree”.  She began a relationship with her now married ex-boyfriend Dean and excused it by claiming that “he was my boyfriend first!” She was beginning to burn out academically, ignore her friends and family, and was overall not herself at all.

Also seeing as she did not appreciate the sacrifices her mother and grandparents made to get her there, not to mention the fact that Emily and Richard paid for her schooling. After this, she went to live with them at their pool house, when she knew just how much this would hurt Lorelai. 

She then proceeded to become the perfect ideal American debutante, and just who Emily and Richard wanted Lorelai to be. She began to attend her grandmother’s parties, became enrolled in the Daughters of the American Revolution (DAR), became completely estranged from her mother, attended many irresponsible parties, and became somehow even more disrespectful and irate to her family, who was giving her a place to stay. 

Rory had become exactly who she and Lorelai had feared she would become. Let’s face it- Rory Gilmore became an insufferable, whiny, quitting person. But why? 

Her whole life, Rory was constantly praised by not just her family but the whole town of Stars Hollow. Being able to make it out of Stars Hollow High and to go to this prestigious private school and then to a reputable university like Yale was astonishing to the town. Rory epitomized Stars Hollow’s pride and joy. Carrying this title, it seemed like Rory could do no wrong as she was put on this pedestal by everyone around her. This facade of perfection made it incredibly difficult for her to handle any criticism. While Mitchum Huntzberger’s feedback in Season Five was relatively harsh, Rory’s response to it was simply unjustifiable. Getting arrested and dropping out of an ivy league university? That isn’t the Rory viewers looked up to as a little girl who wanted to achieve just as much as her. She had spent her whole life working towards being a world-renowned journalist and to see her throw her dreams away after criticism seemed so out of character for Chilton Rory. 

Rory is the epitome of “Gifted Kid Burnout.” She spent her childhood being nothing short of a perfectionist in her academic career. However, we can see that this need for perfection was a price to pay as she entered Yale. These high expectations she set for herself resulted in her feeling burned out with the workload she had as a college student.  

Another major flaw of Rory’s that broke our hearts was the mere entitlement she had. The cherry on top was the fact that she acted as if she wasn’t entitled and didn’t have the same privilege as the rest of her peers — when in reality, her entire education was funded by her grandparents, she was given so many opportunities due to a plethora of connections, and she had a whole building being named after her. She was so tone-deaf towards the end of the show, and frankly, it was painful to watch. It’s safe to say Logan putting Rory in her place in Season Seven definitely made viewers support Team Logan even more (if that’s even possible.) At the end of the day, Rory was one of the privileged kids whether she liked to admit it or not. 

Well, the real question is: did Rory Gilmore redeem herself as an adult? Absolutely not. In Gilmore Girls: A Year in the Life, Rory’s career was disappointing, to say the least, after all the potential she had, she has an affair with Logan who’s engaged after rejecting his proposal at the end of Season Seven, and her entitlement continued to make an appearance 10 years later. Rory was still a 16-year-old in her adult years and therefore never made a comeback.