When I was a teen, I loved Rory Gilmore. She was one of my biggest fictional role models, along with Hermione Granger and Veronica Mars, a smart, driven, ambitious bookworm who wanted to learn everything there was to learn and then go out and change the world.
So it's weird to rewatch the show's later seasons as a 28 year old and wonder: how did Rory become to unlikeable to me?
At least, why did she become temporarily unlikeable. I made some notes for this post while watching Season 4, and I was so irritated by Rory that I almost quit the rewatch. Now I'm in late Season 6, and my feelings about Rory have changed again, back to far more positive ones, despite her privileged behavior.
And I think the difference is all about perspective. When her grievances seem legitimate (at least, for her age) and her efforts seem genuine, it's easy to root for her. At Chilton, Rory was the outsider studying hard to achieve her dream. But the moment she steps into Yale, she loses that outsider status. She moves into a privileged position and yet acts like the things that were handed to her still aren't enough, and it's this, rather than the ambition and privilege itself, that makes her suddenly hard to like.
There's the mattress incident, and the chaos it causes, because the Gilmore Girls can't accept the idea of using the university-provided mattress that everyone else uses. There's Rory being rude and ungrateful to her grandmother after Emily fits out her dormroom, like there's no greater burden than getting great furniture and technology in your dorm, and her roommates are going to resent having a good TV. There's a whole plotline about Rory needing to study against a specific tree, and asking another student to move because it's hers and she needs it. Rory's shifted in the narrative, from a Chilton newbie to a legacy Yale student with all the inherent advantages of that. She's no longer the underdog, but the entitled one, the person who thinks she has more right to things than others.
But the biggest problem, for us as an audience, is when her unlikeable traits are targeted at others. Like the ballerina incident, where she's horrifically rude to a dancer in a review, and then is shocked when the dancer reacts badly. She publicly insults someone else's talents, weight and looks, and destroys everything they've worked for, and yet seems unable to recognize that she did anything wrong. She "wrote what she thought," but it's the fact that that's what she thought that's the problem.
It creates the feeling, as you're watching, that Rory might make fun of you if she came across you. It's a problem that comes up every now and again with Lorelai and Rory, but more and more as the series continues. They make fun of people for being overweight, hairy, unfashionable... on and on, and it makes it harder to connect with them, because, wow, what horrible thing might they think about you if they met you?
This is also, I think, why, although Rory continues in this entitled world, she becomes more sympathetic again later in the show, when things go wrong. I can sympathise with Rory having her dreams crushed by Mitchum Huntzberger and panicking so much that she drops out of Yale. Maybe she's privileged, taking a step back from that great chance at an education, but she's the one in pain, and her decision hurts her, so it's easier to sympathise with her, especially since she eventually comes back and fights for what she's missed. She's on the back-foot again, and that's far more compelling than plotlines that attempt to suggest that her privilege isn't privilege at all.
And then there's the revival, where Rory becomes more unlikeable again. She's struggling, but she seems to approach that struggle from a position of privilege, upset that this headstart isn't giving her all that she wants, rather than hustling and just not succeeding. She's a lazy journalist, falling asleep when interviewing people and not preparing story ideas for interviews. She jets back and forth from London constantly, and it's hard to sympathise for her difficulties when she's constantly travelling abroad to hook up with her engaged ex-boyfriend. Worse, that sense of privileged mockery and disdain returns. She and Lorelai mock people by the pool. She finds the Thirty-Something Gang pathetic and laughable, when she's in the same position as them, only with an apparent trust fund to support her. She's better than the nerds at Comic Con. She's better than Logan's rich fiancee. Her story isn't "my hard work isn't working out," but "why isn't the world treating me like I'm better than everyone else?" And if we get the sense she feels she's better than us, it becomes really hard to connect with her.
So, the problem isn't necessarily that Rory is ambitious, or rich, or whatever, but about her perspective. If we feel like it's us and the Gilmore Girls against the world, they remain sympathetic, even when they do occasionally terrible things. But once it feels like the Gilmore Girls are in a separate category, against us as well as the rest of the world, then it becomes hard to sympathise with them.