Every Gilmore Girl’s junkie knows the ins and outs of Rory Gilmore’s many relationships over the six seasons of the classic saga. Whether you’re team Dean, Jess, or Logan - you know young Miss Gilmore left a trail of jilted lovers. I mean, who needs a man when you have Lorelai Gilmore as a best friend.
However, in hopes of making some sense of all of these failed past relationships, here is an analysis of why Rory’s relationships didn’t work out.
Era #1: Rory and Dean.
Dean represents the classic example of the first boyfriend. He’s plays that typical “guy next door” who’s new to town and ready to make his mark. Dean ends up charming the innocent Rory and they make it official in Season 1. In my most unbiased opinion, Dean was the boyfriend that I hated the most. Dean was an overly needy, jealous, and immature high school boyfriend that Rory should’ve dropped after the first breakup. We all remember the horribly awkward first “I love you” and I’m pretty sure we all cheered when Rory finally moved on. Dean suffocated Rory and was unable to understand Rory’s grand visions for her life. Goodbye, Dean.
Era #2: Rory and Jess.
Jess is the perfect example of the mysterious bad boy. He’s quintessential leather jacket and clear disregard for authority intrigues the impressionable Rory. Jess is unorthodox making him irresistible to a girl who always played by the rules. Jess pushes Rory and challenges Rory to step out of her comfort zone and be the best version of herself. The only reason that Rory and Jess didn’t make it is the age-old problem of timing. The reason why Jess and Rory are made for each other is that Jess is the flame that never died for Rory. Every time that Jess comes back into her life, Rory can’t help but fall a little bit more in love with him all over again.
Era #3: Rory and Logan.
Logan represents the classic example of that guy you know you never thought you could get, but suddenly end up with. Logan is a pretentious and insensitive frat boy that is incapable of acting his age. Even though his arrogance can be directly connected to the terrible Mitchum Huntsberger, Logan has a good deal of maturing to do before he’d ever be worthy of Rory. Logan is never going to be able to escape the control of his overbearing father. Logan is a carefree rich boy and shares all too many characteristics with the infamous Christopher Hayden. Sure, Rory could probably have a happy life with Logan - but there will come a day that his career, his ego, or his father get in the way of her future. The fact that this is the only Gif where Logan even makes an appearance speaks for itself.
In anticipation of the newest release, fans everywhere are on the edge of their seats wondering how the writers will pair up our favorite characters. Only time will tell who our favorite Yale graduate will end up with during the next season finale. I know my fingers will be crossed for Rory and Jess to finally end up together at last.
