15 Times Gilmore Girls: A Year in the Life Gave Us All the Feels

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5. Jess Sets Rory Straight (Again)

Jess was a pretty terrible boyfriend, but he is one of the few characters throughout Gilmore Girls who shows development of any kind. Last time we saw Jess he was a successful author trying to convince Rory to get her life together and go back to Yale. Now he returns in a similar capacity as a friend when Rory is doubting her future once more. He is the one who gives her the idea to stop writing other people’s stories and to instead write a book about what she knows: her relationship with her mother.

Despite all of his faults, Jess knows Rory. He encourages her the way no one else can and believes and supports her. This is the kind of relationship she needs in her life. Not people who enable her, but people who push her. It is nice to see that Jess and Rory still mange to have a relationship after all these years.

This moment is full of feels because it is just so nice seeing Rory and Jess together again. Although Jess isn’t in a lot of A Year in the Life, his presence is felt as an important character in both Rory and Luke’s lives. And for all the Team Jess fans there is a particularly squee worthy moment where Jess looks longingly at Rory from her porch window proving they are keeping hope alive with more than one of Rory’s former beaus.