BACK in October 2000, the first ever episode of Gilmore Girls was released, introducing the world to a sweet, wide-eyed Rory Gilmore and her spunky mother, Lorelai Gilmore, along with a handful of other eccentric characters.

The show was an instant hit and would continue to air until 2007 when the final episode was released on the CW. In 2016, Netflix created a four-episode miniseries of the show. 

Though this has been the last piece of material released from the show thus far, that hasn’t stopped the continued resurgence of the show afterward. 

Something that the masses have always loved about the show is Rory Gilmore’s relatability, considering that she’s a teenage girl who loves food and has crushes on cute boys, just like the rest of us.

Lorelai, Rory’s mother, comes from a rather affluent family background. Though it was never exactly specified how much her parents were getting yearly, their mansions and a small armada of servants are enough indications of their wealth. 

Feeling suffocated by the expectations forced onto her by being born into such a life, Lorelai eventually runs off to a small town called Stars Hollow after getting pregnant with Rory. There, she raises Rory to have a normal life, free of all the pressures she would’ve had to face in the world of Emily and Richard Gilmore. 

One questionable thing is whether doing so was the best choice for Rory. Or if perhaps doing so is what would, in the end, lead to her downfall. 

An illusion of normalcy

For most of her life, Rory has lived just like everyone else. But when she gets to high school, Emily decides to ask for help from her parents to pay for her tuition. They agree on the condition that they get to eat dinner on Friday night with both Lorelai and Rory. 

This is what soon opens the door to a whole other world for Rory. 

At first, Rory found it easy to fend off the advances of her grandparents when it came to their lasciviousness. She groans as she tries to get through her coming-out party and keeps her distance from the snobby people at Chilton High, not allowing herself to be so easily swayed by wealth and connections. 

This starts to change, though, most notably when she heads off to Yale. That is where most believe she began to give in to her privilege, as seen by how people say that Chilton Rory is better than Yale Rory.

Chilton Rory did her best to see the good in everyone, as seen in how she managed to become friends with Paris and Tristan despite how they treated her. 

She constantly proved her intelligence, even when she was falling behind with her subjects. 

She managed to work on the school’s paper, become vice president, and graduate as valedictorian of her batch even though others doubted her. 

Meanwhile, Yale Rory fought with someone just because they were sitting under her ‘study tree.’ 

She dropped out of school when she was told by one person that she didn’t have what it took to be a journalist, and then left her grandparents without so much as a thank you after living with them for an entire year.

She called people fat (the infamous hippo comparison) and made fun of those who talked about exploitation in class, saying, “I’ve never met anyone who likes the word ‘bourgeoisie’ so much.” 

She slept with her married ex-boyfriend, whom she had cheated on in the past. The list goes on and on.

It’s difficult to go into depth on all the bad things Rory did throughout her time at Yale. While, yes, she wasn’t perfect in the earlier seasons either, at least she was still nice.

A matter of upbringing?

It’s become quite common for fans to say, when looking at Yale Rory, that Chilton Rory would never have done the things that she did. Others may try to justify her actions by saying that they’re merely a result of her maturing and growing up.

To this, author Kuya Chhugera of The Teen Mag says it all: Rory seldom experiences any repercussions or remorse for the things that she does. Even when she stole a boat with her boyfriend, she felt that she was undeserving of the 300 hours of community service given to her. 

What makes things worse is that she has grown up thinking that anything and everything she does is without fault. When she stole a boat and her lawyer couldn’t get her out of it, her grandparents blamed her lawyer. 

When she helped Dean cheat on his wife, she gave Lorelai the silent treatment instead of confronting her problems. When her mother was unsupportive of her leaving Yale, Rory once again started to ignore her, going so far as to move in with her grandparents and stop talking to her mother entirely. 

Practically anyone who called Rory out or pointed out her wrongs was often villainized by the show. There were only a handful of instances—Jess asking her why she dropped out of Yale, for example—that worked in bringing her back to earth. 

The rest of the people on this show, though, coddle her, if anything. This is done the most by Lorelai. Even when Rory slept with Dean, all she got was a few hours of scolding, and then everything was right as rain. 

Yes, Lorelai succeeded in giving Rory the freedom that she never experienced in her own home. But perhaps the freedom she received from her mother was a tad too much.

A conscious choice

Eventually, Rory finds her way back to Yale and her mother in quaint little Stars Hollow, far from the likes of Emily and Richard. 

She even boldly breaks up with Logan when he asks her to marry him because she knows that she still has several adventures she wants to embark on before settling down. 

But that doesn’t erase the fact that, first and foremost, Rory has always had options.

Sure, drop out of Yale, because you know you’ll have your grandparents to go to when you do so. They’ll redecorate the entire pool house for you to stay in, and they’ll get you a job at the D.A.R., and sure, leave them without so much as a goodbye when you start to feel too suffocated by then.

Even then, you’ll be able to make up with your mother and go back to the loving citizens of Star Hollow, who have always looked at you as someone akin to an angel. Or when you and your mother aren’t okay, go and live with your rich boyfriend, who pays for the rent and groceries in full. 

Lorelai grew up to become a self-made woman, and her rise to success is surely something that her daughter has looked up to all her life. But the same cannot be said of Rory, no matter how successful we may all have hoped she would be. 

If anything, Rory is a representation of every other upper-class kid out there, feeling as if they are self-made while working in the offices of their fathers or making movies with their mothers. 

In an episode of the show titled Introducing Lorelai Planetarium, Logan is upset by Rory because he invites her to a party, and she writes an entire article mocking them for being rich and entitled. 

Amid their argument, Logan tells her: “Wake up, Rory. Whether you like it or not, you’re one of us. You went to prep school, you went to Yale. Your grandparents are building a whole damn astronomy building in your name.” 

Rory has faced a lot of hardships in her life; yes, nobody is saying that’s untrue. But the fact of the matter is that throughout all this, there has always been a cushion underneath her, whether it be her mother, her partner, her friends, or even the entirety of Stars Hollow. 

Yet, up to the end, she denied any semblance of privilege that she had in her, just like rich kids in real life do. 

“No, we’re not rich; we’re just comfortable,” they say, gallivanting around Europe for the month while still managing to get into an Ivy League school the following year. 

They will tell you it has nothing to do with connections, but you have been through enough hardship in life to know that’s not true.