Top 10 Times Rory Was the WORST on Gilmore Girls

Rory starts showing her true colors in the pilot episode. Since she was little, it’s been both her and her mother’s dream that she go to Harvard. Her attending a preparatory school is a huge step towards achieving that goal. However, the 16 year old is willing to throw away her spot at the prestigious institution Chilton for the sake of a crush. She tries telling Lorelai that she’s being considerate of their financial circumstances. But, the former teen mom knows a thing or two about making reckless decisions for the sake of a guy. It’s not often that the older Gilmore has to play the mom card, but this is one of those times.

As an only child, Rory grew up always having the time and space she needed for her intense study habits. However, with college comes a whole new environment and plenty of new challenges to adapt to. With her dorm suite not being a conducive habitat for school work, Rory had found comfort studying outside under a tree. However, another thing only child life didn’t prepare her for was sharing. She is unhappy when she returns to the spot on a different day and sees that it's already been claimed. When Rory appears to make amends later, it seems like she might be accepting that she won’t always get her own way. Instead, she ends up bribing the guy to leave.

The aspiring journalist develops her voice while writing for the Yale Daily News. When she’s tasked to review a ballet, Rory transcribes all of her harshest observations about the show. Her article is so scathing, it makes her an enemy of one of the ballerinas. As Paris reminds us, we’ve been told repeatedly that Rory is an inoffensive angel. However, this episode shows that’s not necessarily the case. And Rory is rightfully called out for spreading her negative opinions so thoughtlessly. We get that she’s a critic, but the university student wrote comments that were totally unnecessary. It seems like Lorelai never taught her daughter the idiom, “if you don’t have anything nice to say, you shouldn’t say anything at all.”

We’re going to say it: Rory doesn’t make the smartest decisions professionally. In the original series, she turns down a salaried position at a reputable publication for a fellowship she doesn’t even end up getting. In the miniseries, she’s struggling as a freelance writer. When she finally lands a meeting at Condé Nast with help from Mitchum Huntzberger, the Yale graduate has nothing to pitch. She eventually considers accepting a position at an up-and-coming internet publication, but isn’t prepared when she meets with the CEO in person. She does a terrible job selling herself and demonstrates that she hasn’t done her homework. The interaction is embarrassing, and ends with Rory getting rejected over the phone while standing in the lobby.

Throughout the series, Rory isn’t always a great or even a good friend. Remember when she dragged Marty to a Chinese restaurant with Logan’s gang? That wasn’t cool. We feel especially badly, however, for Rory’s supposed bestie from Stars Hollow, Lane. The show begins with the teenage Gilmore changing schools and therefore having less opportunity to spend time with Lane. The protagonist also starts dating in season one, and her childhood pal is often reduced to a third wheel. In season two, Lane’s too embarrassed to tell Rory that she’s joined the Stars Hollow High cheer squad. The girls’ paths cross less and less as the show goes on. Lane goes through a lot over the series, and Rory can rarely be counted on as a source of support.

Rory’s biggest mistakes often involve her love life. Over the course of the original series and its Netflix revival, she commits plenty of romantic faux-pas. The miniseries shows the thirty-something freelance writer in a relationship with a guy named…He’s presented as chronically forgettable; neither Lorelai nor Luke can remember his name. However, rather than the situation reading as funny, it comes off as rude. Rory never gives Paul the respect he deserves and is surprisingly okay with committing infidelity. She doesn’t even have the decency to break up with him before sleeping with other people. In the end, it's he who calls off the relationship via a text message. Honestly, good for you, Paul.

An Ivy League education for Rory is the goal of both Gilmore girls from the beginning of the show. Although Lorelai is initially opposed when Rory shifts her focus away from Harvard, in the end, all parties are pleased when the teenager enrolls at Yale. This is why it's such a big deal when Rory decides to leave university. Now, we’re not saying taking time off is bad in general, but in this case, it’s probably not for the best. Rory is letting her doubts, sewn by Mitchum Huntzberger, get in her way of success. Her choice causes a divide between mother and daughter when Rory goes to her grandparents for support behind Lorelai’s back.

Rory’s relationship with her boyfriend Logan’s dad is a tense one. Mitchum Huntzberger is a newspaper mogul who offers the aspiring journalist an internship. At first, this seems generous, but then, Mitchum takes the protagonist aside and undermines her confidence. Rory is wrecked by what Mitchum says, and lets the weight of his words affect her mood. She decides to do something reckless with Logan, suggesting they take a yacht that doesn’t belong to them. What Mitchum tells Rory is harsh, but in no way does it justify an action as entitled and chaotic as this. Logan is never one to say no, and both characters wind up in jail.

Sharing is apparently not one of Rory’s strengths. Neither is fidelity. Despite his status as a married man, Rory pursues a flirtationship with her ex Dean that evolves into a full blown affair. She loses her virginity to him, and then tries to convince her mother that it's a good thing. Her outburst is surprisingly entitled considering she’s the “other woman” in this scenario. Lorelai, who’s made plenty of her own mistakes, doesn’t fall for her daughter’s logic. She pushes back against Rory’s denial and things escalate. A rift develops between the two Gilmore girls that Rory allows to fester when she chooses to go to Europe with Emily.

Before we unveil our top pick, here are a few honorable mentions.

Sleeping With a Wookiee, “Spring”
There’s a Lot Going on With This One

Forgetting Her Privilege, “Gilmore Girls” (2000-07)
Rory Needs a Wake Up Call From Her Trust Fund Baby Boyfriend

Many of Rory’s mistakes can be excused because of her age. However, her sustained affair with Logan while he’s engaged to another woman happens when she’s in her thirties. The two refer to their relationship as “Vegas,” implying that what they do together stays just between them. Meanwhile, their respective partners, Odette and Paul, have no idea. Logan’s French fiancée is never seen on screen, but that doesn’t stop us from feeling for her. The affair is hypocritical, especially considering how upset Rory got when she found out Logan slept with someone else while they were broken up. We’re not opposed to Logan and Rory as a couple. However, their relationship as depicted in the miniseries is problematic.