Gilmore Girls: 10 Saddest Things About Jess

Jess Mariano raised hell as soon as he entered Stars Hollow in the second season of Gilmore Girls. As the nephew of Luke, everyone in town expected Jess to follow in Luke’s footsteps and be a hard-working member of society. Sadly, Jess was offered a different path and didn’t know how to turn his life around.

This raises the question of whether Jess asked for these bad things to happen or if Stars Hollow was too strict for him to really thrive. Later in A Year in the Life, Jess appeared to have his life together in Philadelphia as a publisher and published author. But he sure did have a tough go of it before he found success.

10 His Dad Wasn’t In The Picture

There appears to be a discrepancy when it comes to Jess’ dad, Jimmy. When Liz called Luke to take Jess in, she said that Jimmy went out for diapers and never came home. But in another scene, it’s said that he left Liz and Jess at Der Weinerschnitzel just two years before he came to Stars Hollow. (Some fans think Liz refers to Jess’ former step-dad as the husband that left them a few years back.)

Regardless of when Jess’ dad left him and Liz, he was not a present figure in Jess’ life. They tried to connect before high school graduation when Jess went to California but that relationship seemed too far gone to be repaired.

9 His Mom Didn’t Know What To Do With Him

Liz Danes is Luke’s naive and flakey sister. As sweet as she is, she couldn’t control her son anymore and shipped him off to Stars Hollow to stay with his uncle. What Liz failed to realize is how that decision affected Jess.

Jess was going to a safe and stable home with a strong male figure but he was still being abandoned by his mother. Yet again, another parental figure in his life was leaving him. Whether Jess would admit it or not, he needed a consistent figure in his life — and his mother would have been an excellent start.

8 Rory Led Him On

Rory and Jess never seemed to make their love work. They started out on rocky terms and ended the same way. After Rory spontaneously kissed Jess at Sookie’s wedding, Jess assumed something was going to come from it. But nothing ever did. Rory went to Washington DC for the summer, never broke up with Dean, and never called or wrote to Jess once. Rory was frozen in time when Jess told her how much she led him on but he was willing to forget it if she broke up with Dean.

Years later in A Year in the Life, Rory led him on again when she showed up in Philadelphia to support him. They even kissed! Jess thought he and Rory would have a second shot at love but alas, she was still dating Logan.

7 He Never Felt Like He Belonged Anywhere

What’s upsetting about Jess’ story is that he felt like he didn’t belong anywhere. He had no home to call his own. The closest he ever got to a stable place in his life was with Luke. Liz was a nice woman but she traveled often for work and was too inconsistent to keep tabs on Jess.

Luke tried his best to make his little studio apartment a home for him and Jess. He gave Jess a job, helped him get his car, and pushed him through school. But even with all that guidance, Jess’ past caught up to him. He never felt like he belonged in Stars Hollow. He said the same thing when he went to see his dad in California. He had nowhere to go and no place to stay.

6 Hated School & Never Went To College

Liz, Luke, and Rory all encouraged Jess to go to school. He was an exceptionally bright kid who read books for fun and enjoyed intellectual conversation with Rory. Their conversations were far more intriguing than her conversations with Dean. However, Jess wasn’t good with following rules or even attending class.

Jess ended up spending more time working at Luke’s and Walmart than at school. By the end of the school year, his principal let him know that he wasn’t eligible to graduate. This, of course, is infuriating to everyone who cares for Jess. Instead of finishing school and going to college, he dropped everything and went on the run.

5 He Had An Entire Town Against Him

As soon as Jess moved to Stars Hollow the city had it out for him. To be fair, Jess didn’t make it easy for the townspeople to like him. He was rude to everyone, didn’t want to be there, and insulted everyone to their faces, but things never got better for him.

But it was weird to see grown adults like Lorelai and Taylor be so cruel to, realistically, a kid. Because at the end of the day that’s what Jess was — a kid. And yet he had adults going after him and pushing Luke to get rid of him. That couldn’t have been easy on Jess, especially when he tried getting his life on track.

4 The Car Accident That Drove Him Out Of Town

When Dean was out of town, Jess and Rory spent some time together and went for a drive. He asked Rory if she wanted to go home but she insisted they kept driving. A few minutes later, Lorelai got a phone call that her daughter was in the hospital after she was in a car crash with Jess.

Ultimately, Rory ended up with a few bruises and a cast on her arm. But Lorelai was incensed seeing her daughter in a hospital bed with Jess nowhere to be found. And once Stars Hollow found out that their golden child was injured at Jess’ hands, all hell broke loose. They essentially forced him out of town. Rory told everyone it wasn’t Jess’s fault but they already had their minds made up about him.

3 Jess Vs. Luke

Luke Danes was one of the best role models Jess ever had. He was hard on Jess when needed but soft when the situation warranted it. However, there were times where fans thought Luke was far too harsh on Jess. After all, Jess was just a teen who was going through a lot. Luke pushed him into a lake, hit him in a “joking” way that can be seen as abusive, and they got into a fight at T.J.’s bachelor party… Luke and Jess were close in their own way but even this relationship wasn’t safe.

2 He’s Always Down On His Luck

While living in Stars Hollow, Jess was always down on his luck. He was working two jobs but was also failing out of school and lying to his uncle. He loved Rory but she was with Dean, and when she broke up with Dean for Jess, he found a way to mess that up too. He bought a car but it was egged by Rory and her mother. He’s mocked when he tries to better himself. Jess is always down on his luck. There’s no winning with him.

1 Lorelai Was Exceptionally Hard On Him

As Jess’ guardian for the time being, Luke was allowed to be harder on Jess and demand certain things. After all, it was Luke who was giving him a place to live, a job, and a safe space to call home. However, Lorelai — who had no relation to Jess — was hard on him simply because he had a crush on her daughter. She was so attached to Dean that she was incredibly mean to Jess. Even when Jess and Rory started dating, she never fully accepted him. Jess never had a chance.

About The Author

Lynn Gibbs
(1657 Articles Published)

Lynn is a nomad who travels the globe on the hunt for her next adventure with her husband. A lover of being outside (and finding the best latte in town), Lynn is typically hiking, walking, or jogging when she’s not focusing on her love of writing. When it comes to shows streaming on Netflix or anything Bravo-related, Lynn’s your gal.

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