To the residents of Stars Hollow, Rory Gilmore has always been smart, careful, and determined. The Gilmore Girls character always planned to leave after high school, no matter how much she loved the small town she grew up in.
Even though Rory was intelligent and always had a pile of books that she was reading, she made decisions that seemed out of character. Whether she was dealing with her Chilton classmates or her current boyfriend, Rory sometimes stood on a moral high ground that she didn’t deserve.
In the season one episode “The Deer Hunters,” Rory got incredibly upset after sleeping in and missing an important English test. She was mean to Paris and Tristan as she was super frustrated by the whole situation.
This was hypocritical of Rory, as she had been mad that Paris made her enemy number one and Tristan wouldn’t stop teasing her. She felt alienated and like she would never fit in with them. But instead of taking the high road and treating them politely, she acted just like they did.
Dean said he was a fan of The Donna Reed Show so Rory decided to make him dinner in the season one episode “That D*mn Donna Reed.”
While this was a sweet moment for the couple, it was also a time when Rory was a hypocrite. At first, she acted like Dean shouldn’t like Donna Reed because she was a housewife who took care of the home. She acted totally above the whole thing and like no one should cook for their family. Later, she did research and saw that Donna Reed was impressive, and she felt bad about being so judgemental.
Rory felt that her story was always going to include Harvard, and succeeding at Chilton seemed like a necessary step on that path.
Yet Rory was a hypocrite because she had Ivy League dreams but didn’t seem to think that she had to get involved with any school activities. It was only when she was told that she wasn’t showing any school spirit that she agreed to take up some extra-curriculars. This seems odd because if she was so ambitious and determined to succeed, wouldn’t she have come to that conclusion on her own?