Jess Mariano was added to the Gilmore Girls cast in the second season to stir the pot between Rory and Dean. And he certainly succeeded, as Dean and Rory broke up and she started a relationship with Jess in season 3. But a love story with Rory wasn’t all Jess was known for; he was seen as the town’s bad egg. He didn’t like school and he’d rather have read books alone than conform to what Stars Hollow found acceptable.
Sadly, Jess was painted as a villain when he was simply dealt bad cards. With an absent father and a mother who didn’t know how to parent, Jess felt alone and deserved more out of life.
10 His Big Moment Was Overshined By Logan’s Jealousy
Rory had to deal with two of her love interests when Jess came back to Connecticut to talk to her. With Logan out of town, Rory promised Jess they could go out to dinner as friends so he could tell her more about a huge life moment for him — he wrote a short novel. Jess didn’t graduate from high school and it’s assumed he didn’t go to college, so it was extraordinary that he was able to chase his dreams and write a book.
Unfortunately, Logan came home early from his work trip and joined Rory’s dinner with Jess. Logan acted out and treated Jess poorly due to jealousy and soured Jess’s big moment. Not only was his news squandered, but so was his time with his old friend.
9 His Dad Turned Him Away When Jess Traveled Thousands Of Miles To California
At the end of Rory and Jess’s relationship timeline, he left Stars Hollow and traveled thousands of miles to California. His dad, Jimmy, (whom he met briefly) lived there, so Jess was hoping for some kind of fresh start with him after Jimmy abandoned him as a child.
Jimmy and his girlfriend were startled to see Jess and didn’t know how to react. Instead of taking Jess into their home and getting him on the right path, his dad told him he couldn’t stay there. Jimmy explained that he didn’t know how to be a dad and it was best that he left. But as Jess bluntly reminded him, he had nowhere to go and nothing to his name. At that moment, he deserved a place to stay and some guidance.
8 Does Liz Realize How Much She’s Hurt Jess?
When Jess showed up on his doorstep, Luke had no idea how to be a parent or what being a dad even entailed. However, his sister, Liz, told him that she didn’t know how to control her son. Luke had no choice but to step up and become a father figure to his nephew.
Liz eventually started coming around Stars Hollow more once she found stable work, but she never thanked Luke for all that he did for her son — nor did she take accountability for the pain she caused Jess as a detached parent.
7 A Town Meeting Regarding A Minor?
How Stars Hollow treated Jess was shocking. It’s hard to believe that Jess was the first kid in town who disliked school and liked causing mayhem, but they proceeded to have a town meeting dedicated entirely to him, which is a little dramatic.
Considering Jess was just a teen, Luke felt it was ruthless to have a room full of adults attacking his nephew. Jess deserved a chance from the likes of Stars Hollow but was never given one, simply because he had a troubled upbringing.
6 Rory Assumed Jess Got Into A Fight
Rory and Jess could never fully get their relationship off the ground because of how they started. With them slowly dating after Rory broke up with Dean, they were trying to start fresh without the entire town judging them. And sadly, Rory could never fully trust Jess because of his issues with commitment.
On the night that Jess was supposed to meet Emily Gilmore for the first time, he showed up late and with a black eye. Rory immediately assumed Jess got into a fight with Dean because they were always getting into arguments, and was disappointed in him. In actuality, the storyline of Jess’s black eye was more funny than dark: he was attacked by a swan and was embarrassed to tell Rory. Nevertheless, Rory should have had more trust in her boyfriend.
5 Luke Picked On Him For Working At Walmart
Before Jess and Luke created a solid relationship where they both respected and cared for each other, they both picked on each other from time to time.
In one scene, Luke was concerned as to where Jess got the money to fix his car. At the time Jess was only working at the diner and Luke knew how much he was paying him. Jess eventually told Luke he was working at the local Walmart. Instead of commending Jess for working so hard and saving his money, Luke belittled him. He asked if Jess greeted people and mocked him for wearing a vest. Considering Jess was being responsible, he didn’t deserve this.
4 Jess Shouldn’t Have Been Involved In T.J.’s Bachelor Party
When T.J. and Liz’s wedding was around the corner, T.J. threw a bachelor party with his brother, a few friends, Luke, and Jess. It seemed odd that Jess was invited to his soon-to-be stepdad’s bachelor party, but he couldn’t get out of it. Jess wasn’t an outgoing kind of kid and he didn’t feel comfortable in a strip club.
Jess tried sitting alone at the club and read his book but when T.J. began berating him about walking Liz down the aisle, he became annoyed. He didn’t want to walk his mom down the aisle and wanted to be left alone. Instead, T.J. slapped Jess’s book out of his hands and started a fight with him. Yet again, Jess looked like the problem when he was interrogated by T.J.
3 Rory Played With His Heart
Jess and Rory weren’t always kind to each other and they were awful at communicating. They could never find their footing in their relationship. Those emotions were multiplied when Rory spontaneously kissed Jess at Sookie’s wedding — even though she was still dating Dean. While it was a great episode for Jess and Rory fans, it also hurt Jess because he knew she wasn’t going to leave Dean for him. Rory didn’t intentionally try to hurt Jess, but their kiss didn’t help matters.
As long as Dean was in the picture, Rory wasn’t ready to end that relationship to start an uncertain one with Jess. Rory did this again years later with Jess when she traveled to Philadelphia for his book reading, kissed him, and then dropped the bomb that she had a boyfriend. Jess was yet again sitting there disappointed that Rory had kissed him while in another relationship.
2 Brilliant, Independent Young Man With No Structure
Jess wasn’t a bad kid; he was just misguided. With no parents around to guide him and no real friends, Jess became a man of independence. The only person he could rely on was himself.
Like Rory, Jess read a lot of books on his downtime. He’d rather read and learn in his own way than being bored at school with kids he didn’t like. All Jess needed was an adult who understood him and gave him some time.
1 Lorelai Was Unnecessarily Rude To Him
Considering Lorelai was known as the “cool mom” in Stars Hollow, it was shocking how rude and cold she was to Jess. They got off on the wrong foot when she caught him taking a beer from her fridge but she never gave him a second chance.
Like the rest of Stars Hollow, Lorelai saw Jess as the black sheep and made his life difficult. With Lorelai also having been a misunderstood teen, it was contradictory of her to not see where Jess was coming from.