Find out who takes the number one spot!
What do we think of when we hear the word “fall?” Pumpkins, crisp air, sweaters coming out of hibernation. But what says “fall” better than an annual rewatch of Gilmore Girls?
I am not ashamed to admit that when September 1st rolled around, the first thing I did was lay in my bed and put on Gilmore Girls. I don’t know what it is about fall that makes everyone and their mother want to return to the town of Stars Hollow, but Gilmore Girls is without a doubt the epitome of fall. But can we even talk about Gilmore Girls without debating who the best boyfriend for Rory is? The answer is no, and I am here to answer that question.
The first of Rory’s boyfriends that we meet is Dean. Dean gets last place in my eyes. Sure, Jared Padelecki looked great, but he has very few redeeming qualities after that. I remember the first time I watched Gilmore Girls, I thought Dean was okay; he really seemed to care about and love Rory. But when I got to the “That Damn Donna Reed” episode, I was done with Dean forever. I could not believe that Rory, such a strong independent woman, was submitting to this 1950s housewife stereotype, just to please Dean. I was FUMING. Then, he finally gets the “perfect” wife that he always wanted in Lindsay, and constantly belittles her for not doing enough to support their family, and then he cheats on her with Rory! Dean is a possessive, backward-thinking, horrible person, and no matter how you feel about Rory, it is clear that she deserved better than him.
Time to talk about Jess. Ah, Jess. The mysterious bad boy that we all want to come into our lives and break our hearts. The ranking of Jess is complicated because his character evolves so much throughout the series. If we look at the Jess that first arrived in Stars Hollow, who was angry at the world and hated all authority, he does not seem like the best match for Rory, who is a straight-A student on the way to the Ivy League. Then, Jess comes back to Stars Hollow and starts to get his act together a little bit more, but still lacks direction. Then Jess fully leaves Stars Hollow for Philadelphia and becomes the best man in the entire series. He has direction, he has passion, he has purpose, and he is doing good work. What more could anyone want? Now, that Stars Hollow Jess, while a menace to the town, was so good to Rory. He understood her in a way that no one else did, and intellectually matched her more than any other person in the show, besides maybe Paris. However, at that time, Rory needed someone who was going to match her ambition in life, and Jess just couldn’t do that for her. Philadelphia Jess is a different story. This version of Jess had such a clear path in life and was doing so well, but at that point, Rory was evolving into the entitled girl who had everything handed to her in life. At that point, Jess needed more than Rory. Jess is my personal favorite boyfriend, but I don’t think he and Rory were meant to be.
Logan Huntzberger. Logan is hands down the best match for Rory. He may be entitled, and a jerk at times, but he loved Rory and pushed her to be the best version of herself, most of the time. He challenged her to take risks, and to step outside of her comfort zone, because he could see the potential that she had. Logan wouldn’t be my first choice for a boyfriend, but he was absolutely perfect for Rory. It seemed like both Jess and Dean were jealous of something that Rory had; Dean was jealous of her intellect and Jess was jealous of her direction. Logan just genuinely admired and cared about Rory. He was also the only person to call her out and say that she too came from money and had the same privileges that she resented him and others for. He was the only one to see Rory for who she was and make her see herself for who she was. I don’t think Jess or Dean could ever love Rory the way that Logan loved her.
There you have it. A definitive ranking of all of Rory Gilmore’s boyfriends. Number one is Logan, number two is Jess, and number three, all the way at the bottom, is Dean Forester.