Rory Gilmore is flawed, her logic is flawed, and her decisions are flawed. Hence, the reason why her relationships with her boyfriends during the show never worked out is not just because of the general incompatibility between Rory and the men she chooses, but because of the huge amount of effort needed to actually maintain a relationship. During the course of the show, either Rory or her boyfriend would repeatedly put in too little effort to the point where they became downright neglectful. This would cause a power shift in their relationship where they were no longer equal and Rory has been taught from a young age to want the best for herself. It does not help that she hadn’t seen what a healthy relationship looked like in childhood until she started to visit her grandparents more often. Hence, even if they were perfect, these relationships would have failed anyway. No matter whose team you’re on.
Let’s begin with the first boyfriend: Dean Forester.
Dean was the typical nice guy and the perfect example of a first boyfriend. The idea that he could have survived a relationship with Rory past that first stage is laughable at best. He was the worst because he was overly self-conscious, overly attached, and spatially deficient. He was constantly jealous of every male she talked to, sulked when she would not respond to his messages or when she was too busy studying, and expected her to play a traditional housewife role in their relationship. Maybe he did not expect her to do it perfectly as that was resolved after Rory’s housewife freak out. Out of all the boyfriends, he was the least supportive of Rory’s goals. Beyond that, his goals were vastly different from hers. He dropped out of school and worked menial work while Rory had Harvard as a goal. Then, Dean goes and cheats on his wife with Rory and tries to rekindle their relationship after the divorce. Hmm.
Then comes the bad boy: Jess Mariano.
Out of all the boyfriends, Jess is the only one who was intellectually Rory’s equal even if he did not have the same formal education. Thoughtful, caring, and witty, there’s a lot to say about Jess that makes him look like the ideal choice. However, their relationship as kids was toxic on both sides. Jess goes through family issues and takes out his frustrations by leaving, ignoring, or dismissing Rory. Because of his issues he embraced the ideas of being a “bad boy” too literally. He basically become angry and disorderly to the point where he drops out of high-school because he is too “intelligent” for such plebeian activities. To top it off, before disappearing, he participates in an act of dubious consent with Rory, which is why he is the worst. However, they do meet again as adults and talk out many of their issues and he finally apologizes for all that he put her through. He shows the most character evolution of all the characters in the show (LITERALLY ALL OF THEM). So, Adult Jess is mature, but Young Jess needs loads of therapy.
Finally, we get to the rich kid: Logan Huntzberger.
Logan is the least problematic of all the boyfriends in my opinion, at least in the context of a college boyfriend and nothing more. Keeping him as a long-term boyfriend would be one of the most annoying and frustrating decisions in the history of the show. Logan is charming, fun, and rich (not by any feat of his own). However, his most remarkable attribute is the fact he went from playboy to a one-woman man, which is a mediocre accomplishment at best. I do admit that he supported Rory through her ups and downs, but it is hard to believe that he was doing it out of love and not a way to take the road of least conflict. He is the worst because of the way he treated Rory and her past interests. The latter he ensured felt inferior by focusing the conversation on how much more privileged he was by comparison. Besides that, he is portrayed as a self-entitled, debauchery enjoying, playboy kind of man. To top it off, his family treated Rory so badly that she was traumatized and dropped out of school for a while. The worst part is that he is so smart, so privileged, and so powerful, but throws it all away for the thrill of the moment and chasing the next high, even when he was working and when he lost all his money. Except what he decides is his next thrill is marrying Rory, who rejects him.
But let’s not rule out Rory Gilmore being her own woman.
In the revival, I hope Rory finally grows up and develops into her own self and chooses a man who is NOT on this list of past boyfriends. Hopefully someone new who would bring out the best in her and she would be able to bring out the best in him.
That is IF she still wants a relationship. When the show started, Rory was a teenager and she developed into a young adult, but she did not evolve in terms of self-discovery and experience, despite her mental breakdown during university. After graduating and after experiencing the working world, and hopefully after meeting different people, she could become less into the idea of a long-term relationship or maybe take her mother’s path of semi-solitude. She could surround herself with people who love her and support her while doing something she loves. She may go through some heart aches both romantically, familiarly, and psychologically, but she will be happy. Honestly, Lorelei Gilmore may be the most fulfilled, dysfunctional, and happy person I have ever seen on TV and Rory can be satisfied with that kind of life.