Gilmore Girls is a classic feel-good show, with Rory and Lorelai sticking with each other through break-ups, college and everything in between. Rory comes across as the perfect child, she's kind, caring, and extremely smart, and she's definitely got a big future ahead of her, some of which we see in the Gilmore Girls: A Year In The Life special.
However, for every angelic thing that Rory does, she also makes a couple of mistakes. It's only natural, and she learns from most of them, but some of the things she does, from having an affair with Logan to sleeping with Dean when he was married, are really frustrating.
Best: When Rory Meets Dean
At the very beginning of the show, Rory meets Dean, who changes her life. It's also one of her cutest moments because they're both young and pretty shy yet she knows that she likes him. It's a really sweet introduction to Dean's character and the beginning of a really wholesome relationship.
Worst: Leaving Yale
Rory goes through a bit of a rebellious phase when she goes to college and decides to take a year off from studying. A lot of events lead up to that decision, but nobody around her is impressed with the idea of her leaving Yale, even if it's temporary. In fact, Lorelai is furious with Rory and it taints their relationship for a really long time.
Best: When Rory Kisses Jess At Sookie's Wedding
The whole dynamic between Rory and Jess is so good, especially when they're first getting to know each other. Things start to heat up a bit and Rory kisses Jess at Sookie's wedding. It's completely unexpected to both Jess and the audience but it's definitely one of her best moments.
They were a great couple on the show, even if they had their occasional issues, and Rory kissing Jess was long-awaited and one of the biggest moments of the series.
Worst: Having Sex With Dean While He Was Married
One of Rory's worst moments in Gilmore Girls was when she slept with Dean even though he was literally married to someone else.
It was a shocking moment because it's so unlike Rory to do something like this, which is why it caused a lot of drama. It was so out of character for her and the angry reaction was right for the moment.
Best: Her Friendship With Paris
After all they go through at Chilton, Rory and Paris seem like very unlikely friends. Once they leave Chilton and room together at Yale, they become very close, and it's hard to imagine that they were ever enemies in the first place.
One of the best things about Rory is that she sees the best in people, and that's definitely the case in her friendship with Paris. Their friendship ends up being one of the strongest on the show.
Worst: Her Friendship With Lane
Rory seems to forget about Lane at some point, and although it must be difficult to maintain a friendship when you live away from each other, Rory doesn't actually live that far away from Stars Hollow, but she definitely sees Lane a lot less in the later seasons that she used to. It doesn't seem fair on Lane's part, because she goes through a lot in the later seasons.
Best: Reconciling With Lorelai
After a tough period where Lorelai and Rory don't see each other, let alone speak to each other, they finally reconcile and it's a really heartwarming moment.
Lorelai and Rory have a mother-daughter bond unlike any other and was tough to see them on bad terms. Their relationship is literally the heart of the show, so Rory reconciling with her mother was absolutely was one of her stronger moments in the show.
Worst: Going On That Boat With Logan
Rory makes a lot of stupid decisions when she starts going to Yale and dating Logan, but one of the worst has to be when she stole that boat with Logan and his friends, prompting her to get arrested.
Her whole family was furious with her, and rightly so, because she's never acted so stupidly before. It definitely changes the relationship between her and Lorelai and her grandparents for a little while.
Best: Saying No To Logan's Proposal
When Rory and Paris graduate, Logan proposes to her. It's a big moment for them since Logan never really came across as the type to like commitment, and it's definitely the most serious relationship that Rory has ever been in. However, she says no, which makes a lot of sense and was probably the right thing to do.
Worst: Having An Affair With Logan
In the Gilmore Girls: A Year In The Life special, Rory isn't doing that good career-wise, but one person who she is still connected to from the original series is Logan. He's engaged and Rory has a boyfriend who she keeps forgetting about, so naturally, they think it's a good idea to have an affair.
Logan seems to be Rory's kryptonite in the sense that she can't think logically when she's around him. They aren't really found it, so fans will just have to wait and see what the future holds for Rory Gilmore - if they ever see her on-screen again.