11 things nobody wants to admit about Gilmore Girls

6. Jess wasn’t Rory’s best boyfriend (WAIT!)

Let’s all discuss this one calmly and rationally, shall we? Saying that Jess isn’t Rory’s best boyfriend is a hot take at face value, but it’s much more layered than that sentence can even express. So, with nuance and an open mind, let’s dive into it.

Throughout both iterations of Gilmore Girls, Rory had three Very Important Boyfriends. Yes, there were others along the way, like Marty and Paul (poor Paul…), but for the most part, it’s Dean, Jess, and Logan that fans spent the most time with and the most time debating. As more and more time passes, the popular consensus seems to be that Jess is the winner, and that’s an accurate conclusion to make.

Rory had three great loves. Three great boyfriends and three great love stories that had different conflicts and trajectories. But conflict is a keyword. None of them were totally perfect. Rory’s relationships with Dean, Jess, and Logan had their sweet and aspirational moments, but there were also huge red flags with all three of her boyfriends (and Rory, too, don’t think she’s getting away with anything here).

Having said all that, let’s circle back to the main topic at hand. Jess isn’t Rory’s “best” boyfriend. It’s probably just semantics, but Rory doesn’t really have a “best” boyfriend. Any of the three could be the best, and any of the three could be the worst. Dean was clingy and jealous and stepped on Rory’s agency. Jess didn’t communicate his feelings, pushed too hard sometimes, and could lash out. Logan was reckless and mysterious and made Rory insecure.

Undoubtedly, Jess would probably be the best bet of the three for Rory to end up with, which made Rory’s relationship and pregnancy with Logan (allegedly) in the revival frustrating for fans. Either way, the likelihood that you end up with one of the three great loves of your young life is slim. Jess moved away at such a formative time in such a horrible way and popped back up as “the one that got away,” teasing what could have been. Rory and Jess… It’s the greatest sigh of the century, the greatest love story never finished.