Looking Back Now, Rory Was Actually The Villain On Gilmore Girls

Not many people are team Dean and there’s a reason for that. He was a boring boyfriend who was very jealous and ended up cheating on his wife, but we’ll get to that later. As much as he is very much in last place for Rory’s fave boyfriends, you have to admit that she wasn’t great to him either. She definitely had feelings for Tristan and then quickly started crushing on Jess all while dating Dean.

Throughout the series, Rory used Dean as a kind of safety net boyfriend. She knew how much he loved her, so she always knew that he would be there when she needed him.

A truly unforgivable act was when Rory ditched school to go to NYC to see Jess. While it may have seemed romantic to Rory and Jess shippers, it was reckless and selfish. Not only was she dating Dean at the time, but she also didn’t schedule her day correctly and missed her mom’s graduation.

Rory knew how important that day was for her mom, and still gambled by taking a late bus from NYC to Connecticut. She also left the signed Go-Go’s album on the bus that was supposed to be her mom’s sorry present. For someone so smart, she made a lot of poor decisions.

Remember when Rory kissed Jess at Sookie’s wedding, told him not to say anything, and then didn’t talk to him the rest of the summer? That’s extremely toxic behavior. Not to mention, she also cheated on Dean by kissing Jess, and got upset with Jess when he started dating someone else. What did you expect him to do, Rory?

Adding on to all of that, Rory is unjustly rude to Jess’ new girlfriend out of jealousy. She goes into her place of work and yells at her for no reason. Justice for Shane.

It’s hard to believe that Rory, who once lived with chatty Lorelai Gilmore, can’t seem to study anywhere but under a very specific tree at Yale. Instead of just studying at one of the 15 libraries on campus, Rory harassed a fellow student when she noticed her tree was taken in Season 4, Episode 6. Even if he was just reading a magazine, it doesn’t mean he has any less right to be there. He was there first.

Rory’s toxic relationship with Dean led her to sleeping with him at the end of Season 4, while he was married to Lindsay. This was when Rory’s “good girl” image was tainted for many fans. Not only did she sleep with Dean, but she got mad at her mom for calling her out. Then, she wrote a letter to Dean about the situation, and Lindsay saw it. Admitting to your infidelity in writing is never a good idea, Rory.

Dropping out of college is something that many people do for various reasons, but Rory’s excuse was pretty lame, TBH. For someone whose entire life was about getting into college and becoming a writer, she was quick to quit the minute Mitchum Huntzberger said she might not have “it” to be a journalist.

Honestly, Mitchum might be on to something, because Rory did cave pretty quickly after one person said “no.” She really thought life was going to be so easy. After all, she got into Chilton from her grandparents’ money, didn’t really appreciate all of the stress those Friday night dinners had on her mom, and never properly thanked her grandfather for getting her an interview with Yale. The road was pretty easy for a while, but the minute she hit one pothole, she ditched it all.

Stealing a yacht pretty much speaks for itself as far as villainous acts go, but it wouldn’t be a complete list without mentioning when Rory stole a boat in Season 5. Sure, she actually got arrested, which is one of the only times she’s forced to deal with the consequences of her actions, but she still dealt with it in a pretty terrible way.

She assumed she would get away with just 20 hours of community service for stealing someone’s yacht, because she called up her rich grandparents and they got her a good lawyer. Luckily, the judge saw through her privilege and sentenced her to 300 hours to complete within six month. However, Rory complained that 300 hours in six months would be a full-time job. It just shows that Rory’s never worked a day in her life if she thinks having to work roughly 12 hours a week for six months is a full-time job.

Rory knew her mother had an uneasy relationship with her grandparents. She used that to go behind her back, and stay with them after she dropped out of Yale. It was not only the ultimate betrayal, but also a conniving one.

While Rory used her grandparents’ love to go behind her mom’s back, she was quick to ditch them the minute things didn’t go her way. She moved out by Season 6, Episode 9 without a word, and instead, sent Colin and Finn to pick up her things for her. Cold! It truly is a privilege to continually avoid confrontation.

Rory cheated on almost every single one of her boyfriends, except Jess. However, she did cheat on Logan with Jess — unbeknownst to him. During a fight with Logan, Rory went to Jess in Season 6, Episode 18 and kissed him. She did immediately tell Jess she was still with Logan, but it didn’t change the fact that she cheated and led him on.

While some OG Gilmore Girls fans would rather ignore Gilmore Girls: A Year in the Life, it is canon — and probably where Rory is at her worst. Not only did she forget about her boyfriend, but she cheated on him the entire time with Logan. Logan isn’t off the hook either, because he was also engaged. Yikes! If there’s a Taylor Swift song that Rory Gilmore deserves to hear at The Eras Tour, it’s “High Infidelity.”

Mitchum sucks, but Mitchum was right. Rory did not have what it took to be a journalist in the digital age. In A Year in the Life, Rory exhibited her privilege once again by going into a job interview ill-prepared. She was also condescending, and said she didn’t even want the job when she was not offered it right away.

While everyone is entitled to having a bad day and making poor decisions, Rory Gilmore sure does fumble quite a lot throughout Gilmore Girls. For any Rory stans out there, I was once one as well. It’s OK to realize that you’ve been rooting for the anti-hero all along.