Rory Gilmore is a big part of what makes Gilmore Girls so special. As Lorelai's only daughter, Rory is seen as the prodigy child in Stars Hollow, destined for bigger things. She is incredibly bright and has her eyes set on Harvard and Yale while she's in high school but along the way, Rory's flaws intensify.
Not content to make garden-variety teenager mistakes, Rory goes out of her way to be her own worst enemy without even realizing it. She grows increasingly whiny and entitled when things don't go her way, which is not how Lorelai raised her. And if Gilmore Girls fans learned anything from the revival, it's that Rory has only continued her streak of self-sabotage.
She Hates Entitlement (But Is Totally Entitled)
Part of the reason why Lorelai left home at a young age to raise Rory on her own was because she didn't want to live the cookie-cutter, entitled life her parents laid out for her. She didn't raise Rory with a sense of entitlement due to her last name because that's not who they are. Rory emulated her mother's outlook through her Yale days and even judged Logan for his entitlement.
However, Rory too becomes entitled. She thinks she's too cool when she gets to college and that she deserves a job at Mr. Huntzberger's newspaper just because she interned there. Rory becomes everything she detested.
She Sympathizes With Her Mom's Disdain For The Gilmores (But Moves In With Her Grandparents Anyway)
Rory has always ed and understood her mother's arguments against Emily and Richard. The youngest Gilmore listened to her mom vent and complain about them for years, and soon realized what her mom was protesting about.
But as soon as Rory gets into an argument with mom over taking a break from Yale, she moved out of Lorelai's house without a peep and into her grandparents' house. Pulling this after complaining about them for years only complicated things for Rory.
She Breaks Up Dean's Marriage (And Then Ruins Her Relationship With Him)
According to Rory's logic, if she had something first then it's her's forever. After breaking up and moving on from Dean, the two become friendly again after Dean has been married. The problem is, the attraction between the two is still strong. The two end up sleeping together and Rory has no regrets.
Rory thinks she and Dean belong together and is happy she lost her virginity to him. Sadly, her selfishness showed up when she chose to drink with Logan and his friends over go on a date with Dean. When Dean saw a tipsy Rory surrounded by men, he knew they were over. Rory, however, is shocked that Dean left her and cried into the arms of Logan.
She Wants Her Dad Around (And Then Tells Him To Stop ing Them)
Rory is so close to her mother that she never felt like she needed her dad, or that she missed out on moments with him. However, when he does show interest in being a part of Rory's life when she's in high school, she welcomes him with open arms.
It's when Christopher plays around with her mom's heart and cancels trips that Rory pushes him away. She even told him to stop calling Lorelai and mes their lives. What Rory doesn't realize is that she too is playing yo-yo with his feelings.
She Worked Her Butt Off To Be Successful (But Quits After One Negative Comment)
Rory is a hard worker who studied for most of her youth so that she could go to an Ivy League school. With the pressures of a private school and Yale, one would assume that Rory had thick skin to get through the harshest of criticisms.
But as soon as Mr. Huntzberger says she doesn't have what it takes to be a journalist, Rory crumbles, steals a boat, gets arrested, and takes a break from Yale. How is Rory supposed to be a professional journalist if she can't handle negative ?
She "Needs" Her Friends (But Treats Them Poorly)
Rory doesn't care to be popular at Chilton but she does need the of her friends. Lane is her best friend in Stars Hollow and Paris is her best friend (even though she doesn't say it) at school. Without someone—who isn't her mother—to vent to, Rory would fall apart.
However, she doesn't always treat them the way they deserve to be treated. And when her pals get annoyed at Rory for being treated like garbage, Rory gets defensive and confused. She creates more problems for herself when her selfishness takes over and she forgets her friends.
She Stole A Yacht (And Got Mad At Her Mom For Overreacting)
Rory got through high school unscathed but by the time college rolled around, her efforts in independence took a tumble.
After she was denied a position at the local newspaper, the only thing Rory felt like doing was going to the sea, apparently. With Logan's help, she tried stealing a yacht and was arrested for it. Lorelai was petrified and showed up at the station to bail Rory out. Instead of leaving jail apologetic and upset, Rory was defensive and would rather talk to Logan instead of her mother. Unsurprisingly, this caused a rift between the Gilmore girls.
She its Dean Is The Best Boyfriend (And Then Sabotages Their Relationship)
Rory always knew Dean was the perfect guy for her but she ruined it time and time again. In A Year In The Life, she told Dean she always felt safe when she was with him and never felt that way with another person again.
But if she really had these deep feelings for Dean, her actions never followed suit. She had a lingering eye for Jess and later, for Logan.
She's Praised For Her Brilliance & Independence (But She's Totally Sheltered)
Some fans don't understand where all the love for Rory comes from. Sure, she's adorable, sweet, and incredibly smart but she also has flaws that make her unlikeable.
She's been told her entire life that she's "special" and unlike the others, and she insists she's just like Lane or Dean. But as soon as something doesn't go her way, she whines. In the back of her head, Rory really does think she was above the others and should be treated differently. Being unprepared for failures only made her life more difficult.
She Doesn't Want Handouts (But Expects Things Without Earning Them)
Rory learned from her mother what hard work looks like. And like her mother, Rory also didn't want handouts because of her family name. But when she's in Yale, her last name and good family totally go to her head and place her on another planet.
Later in A Year In The Life, Rory is confused when she interviews for a job and doesn't get it. She was not prepared nor was she qualified for the job but expected it to be given to her based on her degree. The same thing happened when she applied for a fellowship at a smaller paper. Rory declined the offer because she thought better things were coming but when they didn't, she called the paper and backtracked. Sadly, they already fulfilled the position she arrogantly turned down.