I will start this essay by acknowledging my own bias in this conversation: I’m Zosha, and Logan is the best Rory boyfriend on Gilmore Girls.
At its heart the show was always about family, class, and the indelible ways those things inform our lives. But there were also boys and men, who each brought something different out in the incredibly close mother-daughter duo of Lorelei (Lauren Graham) and Rory (Alexis Bledel). It was inevitable that teams would form around pairings, particularly for Rory, and although it drove creator Amy Sherman-Palladino a little crazy, she acknowledged that “people love romance.”
Of the three relationships in Rory’s life, there was no contest who was the best. Really, the “versus” rivalry is a false one. The Gilmore Girls may be more than their men, and Gilmore Girls more than its love stories, but in the end, we’re all just pawns in Sherman-Palladino’s sick, sick game.
Longtime fans of Gilmore Girls will note that historically Rory had three prominent boyfriends during the original run: Jess, Logan, and Dean. But the game of “Best Rory boyfriend” is not a three-man race, so much as it is two men and a very tall baby. Dean is less of a competitor in these games and more the malformed first pancake you use to test the griddle temp but then inexplicably lose your virginity to years later.
Time and again Dean disappoints, whether it’s pressuring Rory to say she’s in love before she feels it or cheating on his wife. When he and Rory break up he acts sweet to her all while threatening Jess behind the scenes, explicitly because he knows Jess can’t do anything about it. By the time Dean makes his final appearance on the show he’s only there to be a jerk and get in Luke’s head. He’s either sweet and
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