Countless fans of Gilmore Girls think that the romance between Rory (Alexis Bledel) and Jess Mariano (Milo Ventimiglia) couldn't be more perfect. After all, these two bookworms meet cute in adorable Stars Hollow, and they immediately connect over their love of banter and intellectual discussions.
While Rory often acts like a grown-up, she doesn't always know how to act in a serious relationship, and she makes many mistakes along the way. While Rory and Jess are shipped by many fans, there are definitely some moments in their love story that need a second look.
10 Jess Pressures Rory
Jess can be an immature bad boy but he takes things to another level in the third season episode "Keg! Max!"
Jess gets upset and mad when Rory tells him to stop when they're making out. He doesn't handle her saying no very well, which is something that would never fly today. She lets him know that she doesn't want to sleep with him, but he has a hard time dealing with that news, which is uncool.
9 Jess Doesn't Even Break Up With Rory
While breaking up is always going to be tough, no one deserves to be randomly abandoned. Ghosting is an unfortunate reality of dating these days but, of course, that doesn't mean that it's the right thing to do.
Jess doesn't break up with Rory properly. It would be bad enough if he called to say that things are over, as an in-person ending is the way to go, but instead, he just leaves.
8 He Fights With Dean Too Much
Many people may be on Team Jess but he doesn't act in a mature way when it comes to Rory's other love interest, Dean (Jared Padalecki).
Jess fights with Dean way too much, and this suggests another side of him that people would be wary of today. He has a dark side, for sure, and he gets too angry.
7 Rory Flirts With Jess While In A Relationship
While Rory and Dean's romance isn't necessarily perfect, that doesn't mean that Rory should flirt with Jess while she's still got a boyfriend. She can be pretty naive and innocent at times, but even Rory should take a step back and think about what she's doing.
This isn't the best behavior on Rory's part, and it's strange and confusing that she wouldn't stop herself from behaving this way with Jess when she claims to be in love with Dean.
6 Jess Wants Rory To Leave Yale
Jess may have some awesome and smart lines, but he doesn't always act like someone who is worthy of Rory. One example is when, in the fourth season, he wants Rory to leave Yale and be with him.
This isn't something that would fly today, as an education is very important, and Jess should realize that Rory would never say yes. She's always been logical and responsible, and leaving everything behind isn't be her style.
5 Rory Kisses Jess While With Logan
Logan (Matt Czuchry) and Rory have their own problems, and one of them is the fact that he sleeps with someone else while they're taking a break. Rory has trouble getting over this, so when she visits Jess in the sixth season, she kisses him. She wants Logan to know that she can be with someone else, too, and that's the only reason why she does it.
Rory really messes up here, and it's more proof that their relationship wouldn't seem so great today.
4 They Never Plan For Their Future
Rory has some ups and downs in her life but one thing is for sure, she was always going to pursue higher education. Both Rory and her mom Lorelai (Lauren Graham) have always believed that Rory was destined for greater things.
But when Rory dates Jess as she's finishing off high school, they never talk about the future, at least not in a proper and real way. It's clear that they're going off in different directions as Rory is college-bound and Jess has no clue what to do, but they should have some honest conversations.
3 Their Romance Starts Right When Dean And Rory's Is Over
Dean and Rory had a lot of good things going for them, but unfortunately, they broke up in the third season. During the Stars Hollow 24-hour dance marathon, Dean realized that Rory was hopelessly in love with Jess and that things couldn't continue that way.
Rory messes up by not giving herself time to grieve the end of her romance with Dean. They had been through so much and he meant a lot to her, and yet she just jumped into things with Jess.
2 Lorelai And Luke Don't Approve
Lorelai and Luke (Scott Patterson) definitely don't approve of Jess and Rory's relationship. It makes sense that they would feel that way, as Lorelai has seen how immature and lazy Jess can be, and Luke feels that Jess is too experienced and fast for Rory.
It doesn't seem like a lot of Stars Hollow residents have thrown their approval behind this relationship, and that proves that something is wrong with it.
1 They Never Communicate
Rory and Jess definitely have a communication problem, and it's something that can't be overlooked today.
Rory disappointed fans sometimes and one of the worst things that she did was to become a passive victim in her relationship with Jess. Instead of demanding that he talk to her, she seems to just float along, making excuses for him with her mom and other people. These two don't communicate the way that she and Dean did, and it's a major flaw in their love story that wouldn't fly now.
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