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Gilmore Girls: 14 Saddest Things About Jess

Jess Mariano raised hell as soon as he entered Stars Hollow in season 2 of Gilmore Girls. As the nephew of Luke Danes, everyone in town expected Jess to follow in Luke’s footsteps and be a hard-working member of society. Sadly, Jess was on a different path and didn’t know how to turn his life around.

This raised the question of whether Jess asked for these bad things to happen or if Stars Hollow was too strict for him to 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.


His Dad Wasn’t In The Picture

jess dad - gilmore girls

There’s some 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. Regardless of what happened, Jess was abandoned by his dad.

RELATED: 10 Reasons Why Fans Are Team Jess, According To Reddit

They tried to connect before high school graduation when Jess went to California but that relationship seemed too far gone to be repaired. Fans soon became Team Jess after seeing how difficult his childhood was.

The Epic Battle Against The Swan

If fans missed watching Rory and Jess-based episodes, they should stay clear from ‘Swan Song.’ In the episode, Jess and Rory were dating but encountered a few hiccups. Rory realized their relationship was struggling but thought it was time for Jess to meet her grandparents.

Jess was anything but thrilled to meet Emily and Richard and fought against it, which only made things worse for the couple. Jess did eventually agree to the dinner but showed up late with a black eye. Emily was displeased by Jess’ appearance and lack of respect, which made Rory tense. In the end, Jess left the dinner early and told Luke he was attacked by a swan, which was why he had a black eye. However, he was so embarrassed that he didn’t have the confidence to be honest with Rory about the accident.

Jess Vs. Dean

When Jess met Rory, she was dating Dean. But the more Rory got to know Jess, the stronger her feelings were for him instead of her boyfriend. Dean saw how threatening Jess was to his relationship and got into public arguments with him — even though Jess wasn’t doing anything harmful; he was just being himself.

When Dean broke up with Rory and she started dating Jess, the arguments between the two men continued. It wasn’t the best decision for Jess to continue these fights with Dean, but when he was antagonized he felt a need to defend himself. As long as Jess lived in Stars Hollow, Dean was going to be a problem.

His Dad Didn’t Want Him In California

Jess Mariano in California in Gilmore Girls

When Jess dropped out of school and his relationship with Rory got worse, he bailed without saying a word. No one really knew what happened to Jess but as viewers saw, he was in California.

His biological dad lived in California and he thought that maybe he could have a fresh start with him in a new city. Unfortunately, Jimmy was still unprepared to be a father and didn’t was Jess staying with him. This was so upsetting because Jess had nothing and it was eye-opening that his dad didn’t see that and was still turning his back on him.

His Mom Didn’t Know What To Do With Him

Liz and Luke did not have the best relationship in the series. As his naive and flakey sister. they were very different. As sweet as she was, she couldn’t control Jess anymore and shipped him off to Stars Hollow to stay with his uncle. What Liz failed to realize was 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 yet another parent. Whether Jess would admit it or not, he needed a consistent figure in his life — and his mother would have been an excellent start.

Rory Led Him On

Rory and Jess’s relationship timeline never seemed to 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, Rory led him on again when she showed up in Philadelphia to support the release of his book. Jess thought he and Rory would have a second shot at love after a brief kiss but alas, she was still dating Logan.

He Never Felt Like He Belonged Anywhere

dean and rory in nyc - gilmore girls

What’s upsetting about Jess’ story is that he felt like he didn’t belong anywhere. This led to poor decisions, which made fans think he got worse and worse. The closest he ever got to a stable place in his life was with Luke.

RELATED: 10 Ways Jess Got Worse & Worse On Gilmore Girls

Luke tried his best to make his studio apartment 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 had nowhere to go and no place to stay.

Hated School & Never Went To College

jess in stars hollow

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 literary references and conversations were far more intriguing than her conversations with Dean. However, Jess wasn’t good at 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 was infuriating to everyone who cared for Jess. Instead of finishing school and going to college, he dropped everything and went on the run.

He Had An Entire Town Against Him

luke talking to jess - gilmore girls

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.

What was strange was seeing 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.

The Inappropriate Town Meeting

Taylor talking about Jess at the Town meeting on Gilmore Girls

After a few weeks of living in Stars Hollow, Luke was stunned when he found out there was a secretive town meeting that he didn’t know about. As it turned out, it revolved around Jess.

In the meeting, Taylor got everyone on board with hating Jess for the harmless pranks he pulled around town and for his non-school spirit around Stars Hollow. Considering these were adults going after a teenager, many found it disturbing. Taylor even said the town would be better off if Jess left, which was shocking considering Jess was basically a kid being bullied by a sea of adults.

The Car Accident That Drove Him Out Of Town

Split images of Jess and Rory on Gilmore Girls

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. Once Stars Hollow found out that their golden child was injured at Jess’ hands, all hell broke loose. They essentially ran him out of town. Rory told everyone it wasn’t Jess’s fault but they already had their minds made up about him. How this situation was handled was a problem Rory and Jess fans still have with the series.

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 when 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 aggressive, and they got into a fight at T.J.’s bachelor party… Luke and Jess were close in their way but even this relationship wasn’t safe.

He Was 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 him, he found a way to mess that up too.

RELATED: 10 Most Annoying Things Jess Mariano Ever Did

He bought a car but it was egged by Rory and her mother, he was mocked when he tried to better himself — Jess was always down on his luck. There was no winning with him because Stars Hollow was annoyed with anything Jess Mariano did.

Lorelai Was Exceptionally Hard On Him

As Jess’ guardian, 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, Lorelai never fully accepted him. Jess never had a chance despite being a better fit for Rory in some instances.

NEXT: Who Was Better For Rory On Gilmore Girls, Jess Or Dean?

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