Created by Amy Sherman-Palladino, Gilmore Girls, is a comedy drama from the early aughts that has received widespread popularity over the years for its depiction of a healthy mother and daughter bond and for the quaint and cozy vibe that the show exudes. Starring Lauren Graham, Alexis Bledel, Milo Ventimiglia, and others, the show is a comfort watch for many. While the show focuses on the tight-knit community in the town of Stars Hollow, there is the brash and abrasive character of Jess Mariano, who is a rebel. Therefore, here are 10 of his most uncomfortable realities as a character in Gilmore Girls.
Jess's habit of pushing everyone away, his habit of not communicating, and other uncomfortable realities about Jess in Gilmore Girls
1. Jess didn’t make any efforts after getting Rory

After competing with Dean to get Rory’s affections and being hell-bent over her, it was confusing for the viewers of Gilmore Girls to notice that Jess wasn’t interested in putting any interest anymore after he finally got Rory. For example, in the show’s third season and the 10th episode, Jess refuses to go with Rory to the Winter Carnival. He does this not only because he isn’t interested in being a supportive boyfriend, but also because he thinks he is above everyone in Stars Hollow. Interestingly, when Rory remarks that he used to go for such events when he was trying to woo her, Jess directly accepts that he did that earlier because he was trying to win her and now, he doesn’t have to do it because he has her. Therefore, there is a clear difference between how he treats Rory when he is trying to woo her and when he actually gets together with her. This is just one of the points about Jess that make him a controversial character in Gilmore Girls.
2. Jess pushes everyone away

Jess is one of those characters in Gilmore Girls who comes from a controversial family background and he is therefore the talk of the town for his reputation. While it is understandable that one would not like to mix with the same people who are talking about you behind your back, Jess’s problems was that he was abrasive towards everyone. He always replies sarcastically and that makes matters worse. Further, even when he found a good-natured mentor in Luke, who was patient with him and wanted Jess to make something for himself by finishing school, Jess rebuffed him. Even when Luke offered to pay off Jess’s damage, Jess rejects his efforts to help him. While it is true that Jess had a lot of past baggage, it was still no excuse for him to treat others the way he did. Therefore, this is another example of how Jess became unlikeable in Gilmore Girls.
3. Jess pursued Rory when she was with Dean

As mentioned above, Jess had his sights set on Rory in Gilmore Girls, even though she was committed to Dean. For Jess, everything was a matter of competition and he wanted to compete against Dean to win Rory’s affections. Jess’s meddling disrupts Rory and Dean’s relationship and it doesn’t help that Rory thinks of this lightly and even dismisses Dean’s concerns over Jess’s increased involvement in their relationship. Rory even begins to spend time with Jess afterwards and does not let Dean know about this. Therefore, this is one of the prime examples of how Jess became a controversial character in Gilmore Girls. He was a rebel and wanted a girl who was already committed, disregarding Dean’s feelings entirely. However, when Jess finally wins Rory over and the two are together, Jess cannot handle the continued friendship between Rory and Dean and gets jealous. Therefore, this instance reflects Jess’s hypocrisy and immaturity.
4. Jess was rude to everyone except Rory

As mentioned above, Jess had a strained relationship with everyone in Stars Hollow, the town where Gilmore Girls is set. Jess is more than eager to establish himself as an outcast and loves to rebel against everyone and everything. He feels like he doesn’t belong there and is therefore rude to everyone. While there is a sad backstory as to why Jess turned out this way and that is because his father abandoned him and his mother was unable to control his rebellious nature, it still did not give Jess the license to behave the way he did. However, he likes Rory and does not behave meanly towards her. Even though he does not like Dean and is unable to make small talk because of his introvertersion, he tries to woo Rory by being good to her. And in Gilmore Girls’ second season’s 13th episode, Rory notice this and directly asks him why he is only nice towards her. While Jess admits that he doesn’t like anyone else, the fact that he displays kindness selectively is not the mark of a mature man.
5. Jess didn’t know how to communicate with Rory

Even though Jess didn’t show his mean side to Rory, he did plenty of other things that would eventually break Rory’s heart. In Gilmore Girls, while Dean is someone who is extremely obsessive about being attentive, Jess is the opposite. Even when Rory wanted Jess to talk to her and discuss things, Jess was unable to do so. Even though Jess didn’t mean to hurt Rory, he eventually did by not taking her feelings into account. There are many instances, for example, instead of talking about feeling low, he wanted to get intimate with Rory and came on too strongly, which scared her. Interestingly, even when he did confess to Rory about his love for her, he flees from Stars Hollow and does not leave any note or message for her. Therefore, Jess had a lot of growing up to do as he escaped his emotional problems by running away from them. Further, Jess used to call Rory but didn’t say anything when he was on the line. Therefore, he always had cold feet when expressing himself. All these instances showcase Jess’s harsh reality as a character in Gilmore Girls.
6. Jess was dishonest with people

Another recurring problem about Jess’s nature was that he was frequently dishonest in Gilmore Girls. For example, Jess refuses to admit that a swan attacked him and that caused him to miss a family dinner with Emily and Richard. Even when Rory pushes him to speak the truth, Jess ends up lying and gets defensive, creating a rift between them and insulting Rory’s grandparents. One of the major faults of Jess is that he lies and withholds the truth from the few people who care about him. Jess always had Luke’s protective hand over him and rather than being grateful for it, Jess took it for granted. The worst part was that he lied to Luke about still going to school, even though he had stopped showing up. Luke gave Jess a place to stay and a job under the condition that he would finish school. However, rather than communicating as to why he felt that school was pointless and was struggling with his grades, he simply stopped going and withheld this truth from him and everyone. Therefore, this proves that Jess from Gilmore Girls, loves to self-sabotage even when he could just have a real conversation.
7. Jess and Lorelai had a lot in common

Even though Lorelai liked Rory’s first boyfriend Dean, she was immediately suspicious of Jess in Gilmore Girls. However, the interesting thing is that Lorelai and Jess had a lot in common. No wonder that Rory was therefore attracted to Jess. Both Lorelai and Jess are smart, witty, and independent. Both of them have a problem letting other people inside and both speak the same language of fast and dry humor. Even though Jess is more introverted than Lorelai and does not care about Stars Hollow, both of them are just as stubborn when it comes to authority. Lorelai and Jess are therefore the mirrors of each other, even though both of them don’t want to acknowledge it. Further, both have a rebellious streak within them and believe in finding their own paths through hard work. While the common ground between Lorelai and Jess would have made Jess a good partner for Rory, there were many drawbacks to Jess’s character in Gilmore Girls, which did not make him the right choice for her.
8. Jess and Lorelai never got on good terms

While Jess and Lorelai had a lot in common, it seems that instead of bonding over their similarities, the two drifted even further. When in season 2, episode 6, Lorelai invites Jess over for a small family dinner and wants to make him feel welcomed in Stars Hollow, Jess begins to immediately showcase his disdain for the small town. He responds with sarcasm and attitude and mocked the town. However, when Lorelai suggests the Jess could always count on Luke and ask for his guidance, Jess was quick to respond and asked her if she was seeing him. Jess’s response was totally uncalled for and he therefore did not make a good impression with Lorelai. No wonder then that Lorelai never liked Jess afterwards. While the two have a somewhat sweet conversation later on in the same season, it is only because Rory requested Jess to be nice to her mother. Therefore, Jess’s abrasive nature is another faulty aspect of his personality in Gilmore Girls.
9. Jess matched well with Rory but he never aligned with her

The unfortunate aspect about Jess and Rory’s relationship is that the both of them had to do a lot of self-work and therefore, the two were not compatible for a relationship. Even though Jess was good for Rory academically, as he always encouraged her to pursue her academic goals and wanted her to remain authentic to her values, Jess also had to do a lot of character development himself. Jess was the right boy at the wrong time as both him and Rory had to grow up and mature a lot. While Jess is the one who intellectually challenged Rory and brought out the best in her, he also had to set his own life right. Over the years, Jess became an emotionally mature character and not only did his set his life right, but he also published a book. However, Jess was someone in Gilmore Girls, who could always be Rory’s best friend and not her partner.
10. Jess improved but that doesn’t make him a good fit for Rory

Similar to earlier point, whereas Jess began showing real growth and became more mature, grounded, and self-aware as the years went by, Rory was still stuck in her old ways. While Jess was already smart, witty, and understood Rory, Rory was at that stage in her life, where she was repeating old patterns and was still emotionally confused and had commitment issues. Even though Jess was Rory’s match intellectually and challenged her to become better, Rory was on a different trajectory. Therefore, Rory and Jess were never meant to be in a relationship with one another. Even though fans of Gilmore Girls might want to see Jess and Rory together, the fact is that Jess is better suited for Rory as a friend, one who can hold her accountable.