Jess Mariano joined Gilmore Girls in the second season as an antagonizing love match for Rory. The two were very different and yet had a ton in common. Stars Hollow pegged Jess as a bad egg from the start because of his teenage attitude and leather jacket, but did he deserve it? Sure, Jess stole from Taylor and spent most of his time trying to win Rory from Dean but deep down, Jess wasn't a bad guy.
He was a teenager who felt lost. School wasn't challenging enough for him, his dad was never in his life, and his mom passed him off to his uncle. All Jess needed was a little TLC and guidance to prove that there was some good in him after all.
He Was A Hard Worker
Everyone knows Jess shouldn't have skipped school. School may have not been challenging enough for Jess (he was far too smart for the classes he was taking) but he deserved a high school education. Nevertheless, if he wasn't going to make it in school then he had to get a job. He had two jobs working at Luke's Diner and Walmart. Jess' boss even made him employee of the month based on how hard he worked. His character proves that you can be a dedicated, hard worker without going to college.
He Came Back For His Mom's Wedding
When Liz came back to Stars Hollow to tell Luke that she was dating T.J. and wanted to start a life with him near town, Luke was shocked. His sister was always inconsistent and pulling stunts like this. When Liz and T.J. were ready to get married, all she wanted was for her son to walk her down the aisle.
Jess didn't want one part of his mom's wedding but after talking to Luke, he decided to do it to make his mom happy. Despite his inner comfort with fleeing, he fulfilled his mom's wish for the sake of her happiness.
He Helped Rory Whenever She Needed It
Because of Jess's unspoken love for Rory, there's nothing he wouldn't have done to help her or be near her. He ruffled some feathers between her and her then-boyfriend, Dean, but at the end of the day, Jess made Rory realize that she deserved more. Although Rory didn't understand Jess' random acts of kindness or his rebellion, she saw the good in him and tried proving that to naysayers.
He Loved Reading & Writing And Being Alone
Jess wasn't roaming Stars Hollow selling drugs or drinking at noon; he was a quiet kid who was misunderstood. He preferred reading and being alone. His penchant for solitude may have given him a loner reputation but that didn't mean he wasn't capable of making friends.
Whenever Jess was on screen, he was either reading or working. He wasn't terrorizing the city and making it a dark place to live. He had his screw-ups with the townspeople, but what teenager doesn't run into trouble here and there?
He Wanted A New Relationship With His Dad
Jess was too young to know his biological father when his dad abandoned him. It wasn't until Jess was in high school when his dad showed up in Stars Hollow. He sat at Luke's Diner watching his son at work in silence before leaving. Weeks later, Jess realized there's nothing for him in Stars Hollow and fled to California to be with his dad. It took a lot of guts to go across the country to be with a man who abandoned him and whom he barely knew. An empathetic person does this, not a bad one.
He Encouraged Rory's Higher Education And Future Career
Jess was always impressed by Rory's intelligence. Unlike Dean, Rory and Jess talked about literature and poetry, and her excitement about going to Yale.
Before the two got into that dreaded car accident, Jess asked Ror why she wanted to be a journalist or a correspondent and practiced interviews with her to prepare. Years later when Rory took a break from Yale, it was Jess who woke her up with his words, He made her realize that she was bailing on her career over a small bump in the road and that she was going downhill fast.
He Would Have Done Anything For Luke (Eventually)
Luke and Jess butted heads from the start. Luke tried to lay down the law and Jess wasn't having any of it. Funny enough, the two were incredibly similar. They were both bright, hard workers who preferred being alone (not to mention were secretly in love with the Gilmore girls). Jess broke plenty of Luke's rules but it became clear that there's nothing Jess wouldn't do for Luke. He was the only father figure Jess had. This bond is proven in the reboot, A Year in the Life.
He Followed Luke's Self-Help Example
When Luke knew he was ready for a change, he went to the book store and bought a self-help book and tape. He wanted to better himself and change his personal life. While listening to the tape, Luke realized he was in love with Lorelai and ready to start a relationship with her. When he was confident enough, he shared what he learned with Jess. At Liz and TJ's wedding, it was revealed that Jess listened to Luke and was secretly reading the book. Had it not been for that guidance, Jess would never have ever told Rory how he really felt.