It’s important to understand the way Rory was raised and the circumstances that she was raised in to contextualize her actions.
At the end of season four, Rory sleeps with her ex-boyfriend Dean Forester, who is married to another woman.
Rory is under the false impression that Lorelai will support her and Dean.
However, Lorelai is greatly disappointed in Rory’s decision. In defense, Rory claims that Lorelai should be happy she is with Dean again, as Lorelai constantly praised him and their relationship.
The constant interjection of opinions made by Lorelai to ‘protect’ Rory from becoming her shaped Rory and made her unable to make rational decisions herself.
After this, Rory and Lorelai rekindled their relationship, but Rory continues to make bad decisions.
The perception from viewers towards the mistakes made by Lorelai versus Rory differ immensely.
While Lorelai’s mistakes are glamourized and deemed as a sign of rightful independence, Rory’s mistakes, although still wrong, receive much more backlash.
Many high school students can relate to the feeling of being drained and burnout. This is especially true for Rory, a student from whom perfection is expected, as, to her grandparents, she is the perfect daughter they never had and to her mom, she is the perfect daughter she never was.
In addition, many of us can relate to an immense and exhausting fear of failure.
We, as viewers, don’t want to recognize the human mistakes Rory made, as many of us strongly relate to her and don’t want to accept our own mistakes.
We aren’t denying that Rory made irreversible mistakes throughout the show.
She cheated, commited a felony and gave up on her education. These were all terrible decisions on her part. However, many viewers argue that Rory’s actions in the later season are out of character, which is false.
Rory’s traits progress throughout the show. Even in her first relationship, Rory is shown to make rash decisions based on limited circumstances and cheat.
Many viewers overlook this initial behavior as they saw the actions as beneficial to Rory.
Part of the reason for the rapid progression of Rory’s more negative characteristics is the new sphere of influence from her grandparents’ high-society world.
Rory is met with even more entitlement, is expected to meet higher standards and to fill the shoes of what being a Gilmore means in her grandparents’ societal circle.
Her grandparents, although loving, obviously view Rory as the golden child they never had. They strategically formulate a relationship with Rory that allows her to shield herself from the real world problems under their wealth and protection.
This causes building tension between Lorelai and specifically Emily, with Rory caught in between two warring worlds.
One of small life simplicity within an idyllic town with little room for growth and one with vast amounts of advantageous resources to achieve endless possibilities.
Once again, many viewers can relate to this, as many people wish to leave behind their small town lives to move on to bigger and better things.
However, with the amount of praise and adoration Rory receives from the citizens of Stars Hollow, it seems to be the perfect life.
When Jess arrives to Stars Hollow, he brings the outsider perspective that Rory partially grew into.
Jess repeatedly complained about how Stars Hollow is suffocating and that there is little to no privacy because it seems like everyone is aware of any controversies or conflicts. This environment limited Rory’s potential to experiment with different opportunities and to grow into womanhood.
It also didn’t help that Rory was labeled with being the ray of sunshine that Stars Hollow raised, causing added pressure for her to not make any mistakes.
Although Rory undoubtedly made mistakes that are inexcusable, many viewers cast ignorant and unfair judgment upon Rory without fully considering her character development and what contributed to her “downfall.”