In Hindsight is a series dedicated to revisiting old shows, movies, books, and music that impacted us when we were younger and exploring how we connect to it now. Beware spoilers! 

When Rory Gilmore’s character was first introduced through Gilmore Girls into the households of impressionable viewers twenty years ago (feel old yet?), she quickly found home within the folds of many introverted, pop culture-obsessed bookworms with a penchant for caffeine and junk food. 

And why not? Rory was constantly shown (and praised) to be intelligent, dedicated, witty, tenacious, and more. Heck, even I wanted to be her when I grew up and I was already grown up when I watched it the first time! 

It’s when I watched it the second time, though, that made me pause.

Maybe the global-wide quarantine has me feeling cynical but Rory kind of sucks folks, and not just in a “I am flawed like every human being” way but in a “every part of her life is tainted by her suckiness” way. Rory Gilmore had me pursing my lips the entire eight seasons; I was practically channeling the collective disapproval of every Desi woman in my ancestry. 

There’s a lot to be said on the levels of ways she sucks (I didn’t even touch friendships in this piece) but here are the four that majorly pissed me off.

1. Monogamy is the one word Rory Gilmore doesn’t know the definition of. 

Dean Forester, Jess Mariano, and Logan Huntzberger stand at the milestones of Rory’s romantic journey throughout the seasons. And while each relationship had its ups and downs, one characteristic of Rory’s remained consistent throughout – her cheating.

Her first kiss with Jess? While she was dating Dean.

Rory Gilmore, a brunette girl, leaps toward Jess Mariano, a dakr-haired boy, and kisses him.
[GIF description: Rory leaps toward Jess and kisses him.] Via GIPHY
The first time she had sex? With Dean, while he was married.

Rory and Dean in bed.
[GIF description: Rory and Dean in bed.] Via GIPHY
Another kiss with Jess? While she was with Logan.

Jess leans into Rory for a kiss.
[GIF description: Jess leans into Rory for a kiss.]
Jess is the only one Rory hasn’t cheated on though I chalk that up more to the fact that their relationship didn’t last long enough to introduce ample opportunity. 

Time and again, as Rory grew up, her “indiscretions” worsened but each time she walked away with zero guilt and repercussions. When we were reintroduced to Rory in Gilmore Girls: A Year In The Life at the age of 32, we found her in Logan’s arms before learning he’s engaged (!!!) and that Rory herself has been in a two-year relationship (!) with a man named Paul who she just kept forgetting to break up with – classy.

"I've gotta get going," say Logan to Rory who's in his lap. "But you're my pillow!" she responds.
[GIF description: “I gotta get going,” says Logan to Rory who’s in his lap. “But you’re my pillow,” she responds, hugging him close.] Via GIPHY
Is it even worth mentioning that she had a one-night stand off-screen as well during her relationship with Paul?

2. Self-centered, on the other hand, is a word she’s all too familiar with. 

Ditching her mom’s graduation to chase after Jess. Ignoring Lane, her best friend, whenever in a relationship. Not even considering her mom’s feelings when she decided to pen a book laying out every nook and cranny of the Gilmore Girl clan… Rory made it abundantly clear that her feelings reigned over others’. For a girl who was constantly praised for her maturity, there’s a laundry list of examples trailing behind her that beg to differ.

Yes, her grandmother Emily can be stifling, manipulative, and overbearing but if Rory is keen to have a relationship with her, should she respond in kind or call Emily out on her bullshit like an adult?

If Rory suspects a guy to be spreading a rumor about her in college (which he wasn’t FYI), should she verbally attack and abuse him in a classroom debate or speak to him… like an adult?

When she so easily fell into bed with Dean, did she even pause to think about Lindsey, his wife? No, because Dean was hers first apparently. Yes, of course, it was his decision to cheat, but… we have seen, time and time again, that for Rory Gilmore, it only matters when she’s the one being wronged.

3. Excuse me, I wrote for The New Yorker. 

We all have ambitions we’re working towards in life and for Rory, that’s to be a journalist. It’s a certainty she’s been living with since her childhood so one would think she’d be prepared to jump on every opportunity presented to her and be moderately versed in how things operate in the fickle world of freelance writing. 

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Yet, when we meet her a decade post-graduation, she seems to have regressed and it’s all sorts of depressing. A few bylines in some well-established publications and Rory finds herself entitled to similar opportunities. But when given the chance to pen a piece for Condé Nast’s GQ, our girl falls asleep during an interview and sleeps with a source (big no-nos). 

After finding herself fired from a book project, she lashes out at her client effectively burning that bridge, and when she finds herself hitting her version of rock bottom, she decides to “graciously accept” a position at the up-and-coming lifestyle publication, Sandee Says, that had been head-hunting her only to show up unprepared to the interview, expecting to be handed a job that she was openly showing disdain for.

If you’re looking for ways to make a mark in journalism, take her steps as a guide of what not to do. 

4. But I’m a Gilmore!

Privilege and entitlement run rampant in Rory Gilmore’s life. In fact, the premise of the show has very much been that she’s privileged but not as privileged as others. Her third beau, Logan pretty much nailed it when he told her: “Wake up, Rory, whether you like it or not, you’re one of us. You went to prep school. You go to Yale. Your grandparents are building a whole damn astronomy building in your name.” 

Rory may not have been born with a silver spoon but it was always waiting for her on the sidelines – fees for Chilton, for Yale, a car, a pool-house-turned-apartment, and so much more.

And when she wanted something, she felt entitled to have it – be it Jess despite being in a relationship with Dean (let’s not forget how she treated Shane, Jess’ beau) or Dean (“he’s my Dean”) when he was married to Lindsey. 

Let’s also not forget that when Logan’s family disrespected her and thought her beneath them, her response was that she’s a Gilmore! instead of expressing indignation at the blatant classism at play. 

The bottom line with Rory is that she never truly learned or cared for the consequences of her actions because she grew up sheltered, being told she was special, and that she could do no wrong. It’s how she justified stealing a yacht, it’s how she justified her cheating, her dropping out of university, and her poor relationships between friends, family, and romance.

There’s no denying that Rory Gilmore’s ambitions, work ethic, and quick-wittedness carved a sweet spot in the hearts of many. There’s also no denying the other, darker, facets of her character, the one’s which over time have made many a viewer realize that Rory Gilmore kind of sucks.

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  • Sana Panjwani

    Armed with a journalism degree and a passion for reading, Sana is on a mission to find her voice, gives Would You Rather? questions a little too much thought and is a recovering procrastinator.