Throughout Gilmore Girls, Jess Mariano was one of the most memorable, loved and hated characters of the entire series. He was loved partly because of his turbulent friendship and eventual relationship with Rory. Conversely, he was hated because of the way he acted around everyone in Stars Hollow, including Luke and Lorelai, and how he managed to hurt Rory several times by doing a lot of really stupid things.
Whether someone loves him or hates him, Jess has had a lot of good and bad moments on Gilmore Girls. Therefore, here are five times Jess was the best, and five instances when he was the worst.
Best: Jess’s Fight With A Swan
The time where Jess was attacked by a swan is one of the funniest moments of Gilmore Girls. It seemed so out of place because the expectation was that Jess got into an actual fight, however, it turned out that he actually just got attacked by a swan.
Jess felt so embarrassed over what happened that he refuses to tell Rory, who cannot help but assume he got into a legitimate fight. He ended up telling Luke though, and his sheepish embarrassment was so wholesome that it provided another reason to love him.
Worst: Crashing His Car With Rory
Jess is known to do a lot of impulsive things, and while crashing his car might not have actually been his fault, it definitely didn’t make him look good. While on a break from studying, Rory and Jess go to get ice cream and end up in a car accident that leaves the former with a broken wrist.
Of course, this makes Lorelai furious, especially since she was never a big fan of Jess anyway, and Luke was just as angry and disappointed as anyone would expect him to be. While things worked out fine by the end, this was definitely not one of Jess’s best moments.
Best: Convincing Rory To Go Back To Yale
Despite his problems, Jess really did grow up and come into his own in the later seasons of Gilmore Girls. One of his better moments was when he met up with Rory and tried to convince her to go back to Yale after she decided to take a year off.
It was sweet that even after all the time they were away from each other, Jess was one of the only people that really understood Rory and what she was going through. At this point in the show, Rory was in a relationship with Logan but that didn’t stop Jess from caring about her.
Worst: Leaving Without Telling Anyone
One of the worst things Jess ever did was to leave Stars Hollow without telling anybody. It was a sad moment on the show, and a sad moment for fans because Rory and Jess had an iconic relationship that had taken ages to build up to.
Jess had always hated Stars Hollow but leaving Rory heartbroken was an awful thing to do. It just solidified the fact that, no matter how many good things Jess did on Gilmore Girls, he was a fairly problematic character.
Best: Buying Rory’s Picnic Basket
Technically, depending on whether someone is Team Jess or Team Dean, this was a bad move on Jess’s part. However, the moments that come after it were sweet, because Jess bought Rory’s basket in the Stars Hollow charity auction just so he could spend time with her, and maybe spite Dean a little bit in the process.
Dean and Jess fight over Rory a lot throughout the show, and this was just one of those examples. This is one of those times where viewers really got to see how much Jess likes Rory and that he’s really just a soft person at heart.
Worst: Jess Constantly Trying To Make Rory Jealous
Rory and Jess have a relatively on and off, will they or won’t they, relationship, where they tend to make the other jealous by doing ridiculously petty things. Jess tries to make Rory jealous dozens of times throughout the show, especially when she’s back together with Dean, who also has jealousy issues.
Honestly, after all the things that Jess did, it shouldn’t be surprising that Rory and Jess never really get over each other. When she is with Dean, Jess gets jealous, and when Jess is dating another girl, he tries to make Rory jealous. Either way, it never ends well.
Best: Publishing His Book
Once Jess left Stars Hollow for good, he does a lot of growing up, including going to live in New York, where Rory visits him. Eventually, Jess publishes his own book, marking a great development for his character.
As someone who doesn’t really accomplish anything in Stars Hollow except annoying almost every town member, it is moments like this where Jess proves that he’s actually a good person who wants to achieve a lot, and that is admirable. It was a great moment for fans to see how well Jess was doing.
Worst: When Jess Ruined Dinner With Rory & Emily
A time where Jess was the absolute worst was when he was invited to Rory’s grandparent’s house to meet them and have dinner. It was massively important to Rory, and she wanted him to make a good first impression so that they would like him.
Ironically, this is also the same episode where Jess gets attacked by a swan, causing him to turn up late for the dinner, with a black eye and a terrible attitude, all because of the fact that he was embarrassed. Rory ended up being humiliated by his actions and her grandparents weren’t impressed at all, and all because of a swan.
Best: Rory & Jess’s First Kiss
Another example of Jess at his absolute best, and a moment that also happens to be one of the greatest in the entirety of Gilmore Girls, is Rory and Jess’s first kiss.
At Jackson and Sookie’s wedding, the two see each other after a long period of flirting and almost becoming a thing but then not becoming a thing, and Rory decides to pull herself together and kiss Jess. Naturally, he’s very surprised, but it’s a very sweet moment that will always be remembered as the start of an iconic relationship.
Worst: When Jess Tells Rory He Loves Her (& Then Runs Away)
Jess Mariano is probably the character with the worst timing on Gilmore Girls, as he constantly seems to say things at the wrong moment. No other instance better illustrates this fact than when Jess tells Rory that he loves her, only to proceed to leave Stars Hollow without telling her.
The worst thing about it is that he probably knew that Rory felt the same way and that telling her and leaving would be a pretty massive jerk move. However, he did it anyway, because he’s Jess and that’s what he does best.
