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Today is a big day in Stars Hollow. It's the kind of crisp, autumnal day when the quaint little town looks like a real-life New England paradise. The gazebo is covered in bunting and fairy lights, the town band is out in full force, Luke's diner is bursting at the seams, and Kirk has taken on about 12 new odd jobs to keep the whole affair running. No, it isn't the Autumn Festival or the Firelight Festival… or even Bid on a Basket day. It's October 8, 2024, Rory Gilmore's 40th birthday. And naturally, the entire town has come together to celebrate.
Rory's birthday has always been a momentous occasion for the townspeople of Stars Hollow; just take her 16th birthday way back in season one of Gilmore Girls. Luke surprised her with balloons and coffee cake. Sookie baked another cake with Rory's literal face on it. And her mother, Lorelai, invited the whole town over for what honestly seemed like the greatest birthday party ever. It was so cute and so wholesome, it left every little girl watching dreaming that their 16th birthday party would also see them wearing a pink boa and birthday tiara as they chatted happily with their middle aged neighbours.
That party was just another example of how, back in the early days, Rory Gilmore was the unlikely pop culture heroine for Millennial girls everywhere. We were all inspired to straighten our hair, obsess over our grades, guzzle down gallons of coffee, and spend our weekends having marathons of The Godfather movies with our mothers (naturally, they were thrilled in our choice of role model). After all, Rory's life was perfect and so was she. Or so we all thought.
Somewhere between the ages of 16 and 40, Rory transformed from hopeful, promising young woman into selfish, uninspiring flop. I hate to bring this up (on her birthday of all days!), but over the course of seven seasons and a reboot, Rory Gilmore proved that she was kind of the worst.
A quick recap of some Rory's low moments:
- When she kissed Jess while dating Dean.
- When she got annoyed with Jess for dating someone new even though she was still with Dean.
- Oh yeah, and when she strung Dean along despite spending all of her time staring at Jess, thinking about Jess and talking about Jess.
- When she missed her mother's graduation because she went to New York to hang out with Jess.
- When she continually asked her grandparents for money, ignoring her mother.
- When she got irrationally angry at a random guy for (checks notes) sitting under a tree in a courtyard at Yale because (checks notes again) she had decided it was “her” study spot.
- When she slept with Dean when he was married. And then called him “my Dean.”
- When she ran away to Europe with Emily after fighting with Lorelai.
- When she wrote that scathing review for the Yale paper.
- When a tiny bit of criticism sent her spiralling and led to her stealing a literal yacht.
- When she dropped out Yale and moved in with her grandparents.
- When she cheats on her new boyfriend Paul (in the infamous Gilmore Girls reboot) with Logan.
- When she shows up at a job interview with absolutely zero ideas and expects to land the gig based on — well — the fact that she has always got everything she has ever wanted.
So, yes, we could declare Rory to be the worst and call it a day.
After all, at this point, the Rory hate has been well-documented. Numerous articles (like, so many) and even more Reddit posts have meticulously noted her many character flaws and missteps. But on her 40th birthday, perhaps it's worth reassessing whether it's really so bad if Rory is the absolute worst Gilmore girl?
We see you, Miranda Priestley.
While Rory's downfall may have disappointed and even repelled some viewers, there's no denying that it was, as a character study, really, really interesting. Rory's journey began with a childhood that could only be described as wholesome. She was raised by a young single mother who, although she had next-to-no money, brought her up on a diet of junk food and a curriculum of classic movies and novels – in a town filled with colourful but kind characters who took the young family under their wing.
By the time Rory was a teen, the pair had a plan. She would go to Harvard! She would become a foreign correspondent! And, above all, they would always be best friends first, mother-daughter second!
But as the seasons progressed and Rory got older, their simple little life and their innocent plans became more complicated. Rory became a teen girl with teen girl problems. She wanted to date. Suddenly, having a best friend for a mother didn't seem to serve her so well. Then, she was drawn into her grandparents' lives. Emily and Richard introduced her to a world of debutant balls and golf clubs and cocktail parties. Although this world had been a restrictive one for Lorelai, Rory saw it not as a prison, but rather as a gift.
In hindsight, Rory's downfall was even a little prescient. With Rory, we got the chance to watch a millennial girl grow up practically in real time. And, as it turns out, show creator Amy Sherman-Palladino absolutely nailed a few things about her generation.
In recent years, a social media trend has seen millennial women contemplating what they now see as the curse of being a gifted child. “If you were a gifted child in the 90s, how's your ADHD, high-functioning anxiety, and perfectionist-based procrastination going?” one viral clip says. Essentially, there's a theory that young women who were seen as academic prodigies as children in the '90s are now struggling to actually get stuff done.
Rory fits the description perfectly. She was the smartest kid in her town — so smart, she got to go to a fancy private school. After being valedictorian, she got into every college she applied for. After sailing through school getting nothing but encouragement and praise (along with what was essentially a free money tree, courtesy of her grandparents) it's no wonder she couldn't handle failure when it came — it's no wonder the first sign of criticism from her editor on the Yale student paper sent her spiralling into stealing a yacht, dropping out of school, and taking refuge with her grandparents.
This brings us to the infamous 2016 reboot, Gilmore Girls: A Year in the Life. Here, we got to see Rory's natural progression from gifted kid to dysfunctional adult. At 32, none of Rory's plans had come to fruition — but her sense of entitlement was still just as strong as ever. She had a bad relationship with a guy named Paul, on whom she was casually cheating with Logan. She had no job, no motivation, no direction, and, seemingly, no home. She was practically unrecognisable from the hopeful girl at her 16th birthday party. But looking back, it's a journey that makes sense.
So, yes, Rory may have been the “worst” in Gilmore Girls. But while her fall from grace may make our favourite autumnal cosy show a little less cosy, it's also what makes the show so rich, so nuanced, and so good.
When we last saw Rory, she was dealing with a surprise pregnancy. It's now her 40th birthday, eight years later. By now, Rory has presumably had her child (another Gilmore Girl, naturally). I like to think she has learned a thing or two after becoming a mother during her low point back in 2016. Perhaps, she's done a little self-reflection and faced up to the fact that whatever she wants from life, it's ultimately up to her to get it. And us millennials who idolised her way back in 2000 might learn a thing or two from her journey, too.
Rory made mistakes. She could be selfish. She was certainly entitled. In a word, she was flawed. But maybe that's actually a reason to love her. Because guess what: we've all grown up to have our own flaws, too. Maybe it's time we embraced female characters like her in all of their messy, unappealing complexity.
No, Rory is not perfect. And yes, Gilmore Girls is a better show for it. So with that… happy 40th birthday, Rory, the relatable, flawed queen of Stars Hollow.
