Of Rory’s three major relationships on Gilmore Girls, her time with Jess is often seen as the most obviously toxic, but it’s also often the most popular with fans. Part of this credit has to go to Milo Ventimiglia, of course, who is incredibly charming in the role, but it’s also true that Jess is more than just a stereotypical bad boy, especially in later seasons.
Despite his popularity, though, it’s very clear that there were some huge problems with Rory and Jess’s relationship. A lot of this came down to Jess’s issues, and to their age, as they were teens at the time – and that’s not an age known for the best emotional awareness and perfect relationship communication!
- 1 10 Toxic: Terrible Communication
- 2 9 Perfect: Intellectual Equals
- 3 8 Toxic: Game Playing And Sparking Jealousy
- 4 7 Perfect: Challenged Rory
- 5 6 Toxic: Pushing Rory To Have Sex
- 6 5 Perfect: Amazing Chemistry As Adults
- 7 4 Toxic: Giving Rory’s Family Attitude
- 8 3 Perfect: Surprisingly Romantic
- 9 2 Toxic: Ghosting Rory
- 10 1 Perfect: Helped Each Other Grow
10 Toxic: Terrible Communication
Even for teenagers, these two really failed when it comes to communication. Whether it was Rory refusing to tell Jess that she wanted to actually make plans, and then leaving him a furious voicemail message when he didn’t figure it out on his own, or Jess giving one of his signature one-word answers that doesn’t actually explain anything, this was a couple that failed to figure out how to talk. A lot of this really did have to do with their inexperience in relationships, of course, but it was still an awful part of their partnership.
9 Perfect: Intellectual Equals
This was the thing that really attracted Rory to Jess in the first place (other than his brooding good looks, and rebellious attitude, of course). Both Rory and Jess were total bookworms (a far cry from Dean, who just tolerated Rory’s love of reading), and would spend time in spirited debate about their favorite authors. Jess was able to meet Rory on an intellectual level, and that made them a great pair.
8 Toxic: Game Playing And Sparking Jealousy
Both Rory and Jess were terrible at trying to push the other’s buttons and make them jealous, which is far from a healthy way to behave! Jess is particularly bad at this, intentionally bringing a date to the dance-off just to make out in front of Rory and Dean and annoy her, but they both love to play games.
Rather than just talking to each other, they spend too much of their time trying to manipulate each other, and it’s incredibly frustrating to watch.
7 Perfect: Challenged Rory
Rory grows up in a town that worships her, with a mother who thinks that she is the most incredible young woman in the world – which isn’t a bad thing, per se, but it does mean that Rory is incredibly sheltered and naive in a lot of ways. Jess is someone from a totally different upbringing, and who challenges her to really think about how she approaches life. Later on, he challenges her when she has dropped out of Yale, and pushes her to get back to what she really wants. It’s refreshing to see her with someone who doesn’t coddle or worship her all the time.
6 Toxic: Pushing Rory To Have Sex
One of the hardest scenes to watch in Gilmore Girls is when Jess is upset at a party, and Rory goes upstairs to talk to him… at which point they start kissing, and he pushes her to go further than she is comfortable. She ends up having to push him away, and runs off crying after he blames her for coming upstairs. It’s an appalling scene, and one that put a lot of fans off Jess completely.
5 Perfect: Amazing Chemistry As Adults
While the bulk of Jess and Rory’s relationship happens as teenagers, they do end up reconnecting as adults, when Rory is at Yale, and Jess has figured things out for himself and started working in the publishing industry, on a small scale.
At this point, it’s clear that the two have amazing chemistry, and that whatever spark began when they were younger has some serious potential now that they have both grown up a bit. A lot of fans were disappointed that they didn’t get a real second chance.
4 Toxic: Giving Rory’s Family Attitude
Jess is definitely a stereotype of a bad boy in many ways, and his attitude around authority figures is one of the most obvious examples of this. Unlike Rory’s previous boyfriend, Dean, Jess and Lorelai do not get along at all – and while she also has her part to play in this, he is often rude or surly with her, and doesn’t show her much respect. Similarly, when Rory asks him to meet her grandparents, he shows up late, with a black eye, and sulks and grunts through the dinner.
3 Perfect: Surprisingly Romantic
For all of Jess’s bad boy ways, he is actually quite romantic with Rory, and while he may not be the kind of big-gesture guy that Dean is, he shows how much he cares for her in a dozen smaller ways. It’s clear that both Rory and Jess really appreciate each other, and their day in New York is one of the most wonderful romantic episodes in the show (until she messes up her bus schedules, that is).
2 Toxic: Ghosting Rory
Possibly the worst thing that Jess did to Rory was simply leaving Stars Hollow after their big fight. He was dealing with a lot, admittedly. He found out he was flunking out of high school because of his lack of attendance, and Luke angrily told him that he would kick him out unless he attended summer school. Add that to the fight with Rory, and it’s easy to see why a troubled teen would just up and run. But leaving town without so much as a goodbye was absolutely terrible, and a fitting end to the toxic side of their relationship.
1 Perfect: Helped Each Other Grow
The early days of their relationship were definitely more toxic than perfect, but in the end, these two share something special. When they reconnect as adults, all the good things about their relationship are still there, but the worst parts seem to be something they’ve grown out of. The chemistry, connection, and shared interests outlasted the terrible teenage game playing – and perhaps, if there is a second revival, this can be allowed to play out.
NEXT: Gilmore Girls: Each Main Character’s First & Last Line In The Series
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