Whether you are a fan of Jess, Logan or Dean, there is no denying that each boy offered something to Rory's life, causing her to grow or, maybe sometimes, shrink as a character. We all have our favorites, and for many, that is Jess--the brooding, book-loving, resident James Dean of Star's Hollow.
Then again, maybe you'd argue that title goes to Dean himself. Either way, Jess and Rory's relationship is a substantial part of the Gilmore Girls series and gave way to many ups and downs.
Toxic: Idealized
Their relationship is built on the ideas they built up of each other the entire time that they weren't together. Rory is the pretty small-town girl, awkward and adorable and brainy. She is mysterious and endearing through her bashfulness.
Jess comes off as edgy and also emits a mysterious energy, constantly having his head in books yet never going to school. These are the things that attracted them to each other, but they are superficial.
Not Toxic: Encouraging
Without each other, they may have been less likely to persist in their goals to live lives outside of their small-town familiarity.
Whenever Rory gets stuck in a rut and doubts her goals, Jess will often appear as the voice that reminds her of what she is capable of, pushing her to reach for more than is safe. Rory coaxes Jess to believe in himself as well, always reminding him to resist giving in to his tendency for despair.
Toxic: Wanted What They Couldn't Have
Rory and Jess began liking each other while Rory was still with Dean. The fact that she was with someone else only heightened the drama and excitement of flirting with each other and playing with the possibility of being an item.
If Dean hadn't been an obstacle between them, they may not have been as obsessed and romanticized their situation less.
Not Toxic: Adoring
As the show goes on we do see that Jess sees past his initial superficial value of Rory and that he seems to genuinely admire her as a person.
Rory was possibly hit hardest by her relationship with Jess, and this is likely because he's the one who got her more than anyone else. They respected each other enough to always be straightforward with the other, which speaks to the quality of their care.
Toxic: Indirect
The early days of their relations with each other, after Rory has left Dean, are marked by absolute flakiness.
One would think that being kept apart so long would mean they valued being together, but instead, Jess takes Rory for granted. He is never open about how he feels about her and doesn't communicate his intentions, leaving her wondering if he cares at all.
Not Toxic: Challenging
Rory and Jess are similar, yet come from very different backgrounds at the same time. Both have unconventional upbringings, but Rory has a devoted mother, while Jess's parents both abandoned him. These differences cause both of them to challenge their understanding of life and expand their empathy.
Rory challenges Jess to consider that there is hope beyond his bad experiences, and Jess reminds Rory to appreciate her good fortune.
Toxic: Dishonest
Dishonesty comes in many forms, it isn't always explicitly telling a lie. Jess has a habit of omitting information from Rory--he doesn't tell her how he feels about her for a long time, knowingly leaving her believing that he doesn't care.
He also leaves town without telling her, when she thought they were together. But their relationship itself also began in dishonesty, in the fact that Rory had feelings for Jess and continued to be with Dean.
Not Toxic: Balancing
They two did a good job of balancing each other out. Jess could be hot-headed and impulsive, and Rory helped to mellow these behaviors through her example of being more calm and logical.
Conversely, Rory could let her imagination run away with her and cause her to fall into a spiral of self-doubt--Jess was good at bringing her back to earth and instilling a sense of practicality and simplicity.
Toxic: Immature
Their relationship began when they were in their early teens, so it's no wonder they both had their bouts with immaturity. Hiding how they felt from one another and playing with each other's feelings is a classic sign of an immature relationship.
Their immaturity in their own lives also affected their relationship, what with Jess walking around with a chip on his shoulder and Rory being naïve.
Not Toxic: Creative
One of the main things that brought them together in the first place was their common passion for art. Rory and Jess both have inquisitive minds.
Until Jess, Rory has never met anyone who loves books as much as she does. She finds in him her intellectual match, and they feed each other's hunger for ideas and conversation. Any healthy relationship requires good conversation, and this is something Rory and Jess never lack.