Rory Gilmore was the goody two shoes of Stars Hollow. Her mother, father, and the entirety of Stars Hollow made it seem like Rory could do no wrong. She was brilliant and polite, which must have meant that she's perfect, right? With Rory growing up in a small town, her business was everybody's business and vice versa. When she reached her teenage years, no one expected her to mess up because she was seen as Little Miss Perfect (for whatever reason).
The reality is that Rory was no different from any other teenager and young adult. Just because she loved books and was Yale-bound didn't mean that she didn't make mistakes or do questionable things. In fact, there were several instances when Gilmore Girls fans questioned Rory's morals when she didn't learn from her mistakes.
Sleeping With A Married Man
When Rory became reacquainted with Dean during her college years, it was clear the fire between them was still burning brightly. There was just one problem: Dean was married. However, that ring on his finger didn't seem to bother Rory because she lost her virginity to him anyway.
In her eyes, she had Dean first. This is how she justified her behavior. She didn't once think about how this affected a marriage, a family, or even Dean's wife, Lindsay. All she thought about was herself and the moment feeling right. Shockingly, Rory learned nothing from this mistake because she continued sleeping with Logan when he became engaged, because why? She had him first!
Going After The Bad Boys
Rory had a thing for bad boys. As much as she told herself that guys like Tristan, Jess, and Logan were trouble, she sure did everything she could to stay close to them. Even Dean was viewed as a troubled kid in the eyes of Luke.
Rory sought Tristan out at the house party and kissed him, she hung out with Jess without telling anyone (and kissed him when she was dating Dean), and she somehow was able to tame the wildest of them all: trust fund baby Logan. Men like Dean and Marty were too safe for Rory, so she kicked them to the curb to chase the rebels.
She Stole A Yacht Because She Was Sad
Did anyone question Rory's morals more than when she stole a yacht? After a "hard day" at her internship, the owner of the paper — and her boyfriend's dad — told her that she didn't have what it took to be a journalist.
Hearing negative feedback for the first time in her life threw Rory down a black hole. She stole a yacht with Logan to feel better but she was arrested for her actions. To make matters worse, when Lorelai picked Rory up from jail, she was more concerned with Logan and blamed everything on Mitchum... She never took responsibility for her actions.
Is Your Grandparents' Vow Renewal Really The Place To Shoot Your Shot?
Rory went to Yale with Logan and could see him whenever she wanted to. They even worked at the Yale Daily News together. However, leave it to Rory to shoot her shot at her grandparents' vow renewal. What better time to win over a man than when your relatives are getting hitched, right?
Rory became jealous and salty when she saw Logan with another beautiful woman and decided to lure him away with champagne and kissing. The two were gone for so long that Lorelai, Christopher, and Luke all searched for her. Being discovered all messy from a kissing session was a bad move on Rory's part. It caused problems for her grandparents, her mom's relationship with both Chris and Luke, and made her look bad.
Living Rent-Free In Her Mind
Rory relies on plenty of people without realizing that they might not want to help her. When she moved into her grandparents' pool house, she became annoyed when they stored their things in her space, forcing her to move out of the pool house and into the main home with them.
She then moved in with Lane for a little bit and didn't seem to care that no one else in the house was okay with her staying there. Rory was later annoyed that Paris kicked her out for seemingly stabbing her in the back. And don't forget when Logan reminded her that she was living at his place for free. The only thing she could say to him was "Screw you, Logan" instead of taking ownership and doing her part.
Does Rory Forget What Her Last Name Is?
Due to growing up with a single mother who detested the wealthy lifestyle Emily and Richard led, Rory always thought the rich were too privileged for their own good, that they weren't living in reality and treated those less fortunate than them differently.
What Rory forgets is that she's a Gilmore. She may have grown up in a small town with her hardworking mom but she was able to go to private school, Yale, take a semester off from school, and never worked a day in her life. Things have always been handed to Rory. So, while she judged Logan's secret society and friends, she really should have looked in a mirror.
Why Couldn't She Accept That Paris Was Her Best Friend?
It was immoral of Rory to be one way with Paris to her face and another behind her back. In front of Paris, Rory is the best BFF a girl could ask for. She was one of the few who knew how to handle Paris' outbursts. But in front of others, Rory was anything but kind and didn't have Paris' back when others spoke poorly about her. Realistically, Rory spent more time with Paris than she did with Lane. Paris was there for Rory in her darkest moments, and yet she didn't consider her a best friend.
Her Treatment Of Christopher
To be fair, Christopher was not the best father to Rory. He abandoned her and Lorelai when she was born and was inconsistent while she growing up. He didn't become a stable presence in her life until she was in high school. However, Rory got in between her parents' relationship without her mother knowing. She warned her dad to stop coming around and to leave her mom alone. Rory had no right in going after her father or being disrespectful to him just because he got in a fight with her mother.
That Dreaded Sewing Kit
When Rory invited Logan over for Friday night dinner, he transformed into the ultimate gentleman that Richard and Emily would adore. But when he stole one of Emily's sewing kits and replaced it with another trinket, Emily realized the difference right away. She was so distraught at the disappearance of this sewing kit that she was about to fire the housekeeper because of it. But did Rory do anything to stop the situation? Nope! It was thanks to Lorelai that the housekeeper kept her job (for a little while longer at least) when she took the sewing kit from Logan and said she found it by the table.
She Started Treating Her Grandparents As Her Mother Did
There isn't a thing in the Gilmore Girls universe that Emily and Richard wouldn't do for Rory. She was the daughter they always wanted. She was brilliant and poised and noble — the complete opposite of Lorelai. Emily and Richard paid for her education, took her to Europe, refurnished the pool house for her, found her a job at the DAR, and so on.
Instead of recognizing these fortunes, Rory ran away without so much as a goodbye when she had enough of them. Emily was tortured that Rory was capable of being so callous. What's worse is that Rory blamed it all on the Gilmores.