In that spirit, here are the best moments from the black sheep of Stars Hollow, Jess Mariano.
The Bracebridge Dinner (Season 2, Episode 10): When Loralei and Sookie host a big dinner at the Inn, the whole town’s invited…including Jess.
Jess and Rory meet each other at a very uproarious time in Jess's life.
He is unhappy with and disorientated at having been unceremoniously sent to live in Stars Hollow by his irresponsible mother.
The shocking hook-up -- which occurred in the season four finale (and is shown in a little more detail in the season five premiere) when a married Dean cheats on his wife and Rory loses her virginity -- is certainly one of the most memorable moments in "Gilmore" history, but as Bledel and Padalecki tell it, they'll always remember filming the scene in question for an entirely different reason: trying to fit together on Rory's ridiculously small bed.
"It was like a miniature twin," Bledel recalled to EW.
Rory is much less direct in her actions, unwilling to face her instant attraction to and strong feelings for Jess, which leads her to continually, unapologetically flirt with him, while staying in a relationship with Dean.
That being said, he was also a giant douche at least 50% of the time.One day she said to eel Tuna that she was going out to fetch food for them.Then she travelled far away, to find a new man for herself.Once Lorelai invites him into her home to a welcome feast, Jess meets Rory and his interest seems peaked, although he throws a lot of attitude her way all the same.Even realising Rory isn't really like him, emotionally, he still attempts to talk with her when seeing her in town, in spite of his disastrous conversation with her mother.