In the 2nd season of Gilmore Girls, a new face arrived. Jess Mariano, the new boy in town and the bad boy of Stars Hollow. Since he’s come to live with Luke, his uncle, he must work at Luke’s Diner in order to earn his keep. From the first moment he saw Rory, there was a connection between the two of them. Rory already had a boyfriend (Dean) but there was something about Jess that sparked curiousity in her.

From the moment he arrive in Stars Hollow, he created bad first impressions with everyone. The town didn’t trust or like this newcomer and although Luke defended his nephew, he too came to realise that Jess was no angel. He pulled pranks for amusement and some were in order to impress Rory. He showed no respect for Lorelai or Luke and the only person he showed any decency towards was Rory.

Although he was the ‘bad boy’, Jess had a softer side too and this was a side that usually came out when he was around Rory. He was a book fanatic like she was and they had the same taste in music. Rory felt that Jess could relate to her in more ways then Dean could and she was attracted to him. The attraction was mutual, as Rory had caught Jess’ eye from the first time he saw her. Rory enjoyed the excitement and the not knowing of what would happen next. One time when they were getting ice-crem, Jess crashed her car by accident and Rory fractured her wrist. Lorelai was livid and blamed Luke. Jess split and went back to New York. On the day of Lorelai’s graduation, Rory failed to show and instead, hoped on a bus to New York to see Jess. They spent the day together and after Rory returned to Stars Hollow, Jess soon did too and they kissed at Sookie’s wedding. Rory freaked out and run off, leaving Jess stunned and a little confused.

In the 3rd season of Gilmore Girls, Rory returns from her time in Washington DC and Jess has already moved onto another girl. He was hurt that Rory hadn’t contacted him during the summer and that she appeared to be back with Dean. Every encounter between them was heated and emotional, the chemistry between them was blindingly obvious. Dean could see it too and broke up with Rory at the national town dance.

Jess and Rory finally got together but their relationship was short-lived. Jess began working at Wal-Mart and was skipping school in order to work shifts. He missed too many days and was unable to graduate with his year level. Moodiness got the better of him and at a party when he and Rory was kissing, he went too fast for her and she told him to stop. Already in a foul mood, he yelled at her and she was stunned and hurt by his words. She ran downstairs in tears and bumped into Dean. Jess followed her down and saw her with Dean. He was jealous and Dean was angry that Rory was upset so they got into a fight. The police came and broke the party up. Jess walked away as Rory was helping a very drunk Lane.

Jess and Rory both avoided each other afterwards, each wanting to see the other but couldn’t bring themselves to do it. Jess’ father showed up for an unexpected visit and soon after, Jess left Stars Hollow without saying goodbye to Rory. She was hurt and Jess went to California to get to know his father. Rory graduated and moved on to university. In a telephone call, Rory told Jess she thought she had loved him but he left so she would have to move on. He listened in silence without saying anything to her at all.

Jess returned to Stars Hollow in search of his car, which Luke had hidden. He was stuck in town for a couple of days and continually was running into Rory everywhere. He kept leaving whenever they would cross paths and she was annoyed that he wouldn’t even talk to her. When they finally did talk, face-to-face for the first time in a year, Rory angrily demanded to know what he had to say for himself after everything that had happened. He paused, told her he loved her and then left. Rory was left stunned and very surprised.

The next time they met, Jess had come back to Stars Hollow for his mum’s wedding to her boyfriend, TJ. Luke had come to Jess’ apartment and yelled at him to come. He did come and patched everything up with Luke. They reached an understanding and Jess told Luke that he was greatful for everything that Luke had done for him, even if he wasn’t the easiest person to get along with. Jess walked his mum down the aisle, much to her delight, and tried to keep a straight face during their slight ‘unorthodox’ wedding. On his way out of town, he stopped by Yale to surprise Rory. Dean was with her but Rory told him to leave. Jess asked Rory to come away with him so they could be together but she turned him down. He still wanted to be with her but not in Stars Hollow. She refused and again, he left. There was no real closure between them though and *hopefully* Jess will came back someday soon and Rory will say yes.