As the release of Gilmore Girls: A Year in the Life gets closer and I embark on my (approximately) hundredth rewatch, I find myself revisiting the question so many fans of the show contemplate and discuss with great fervor: Which of Rory’s boyfriends was the best? Jess seems to be a fan favorite (and for a while, yours truly agreed), but upon further investigation – AKA my own personal opinions taking more solid form – I have decided that there is no good answer to this question. Rory Gilmore definitely had ups and downs in the series with her decision making, but let’s face it, she is the most treasured resident of Stars Hollow and deserves the best. And if we take a close look at all of the gents she chooses to spend her time with, I have to say, they’ve all got pretty significant vices. In my opinion, some vices are easier to deal with than others. But all in all, while Dean, Logan, and Jess all make Rory happy in their own ways, I personally think all of them strike out big time in winning the spot of who she should be end up with. Let’s discuss…
Oh, Dean. Keeping it completely real, I know that Dean was actually the perfect first boyfriend. He got along with Lorelai, he escorted Rory to the cotillion, he built her a car, and he listened to all the rules of movie night with the Gilmores. But the turning point of their relationship was definitely the 3-month anniversary “I love you”. In Dean’s defense, it’s not easy to express your feelings for someone and not have them reciprocated, especially when they’re that significant. And on the other hand, in Rory’s defense, Dean needed to calm down. Couldn’t he have given Rory a hot minute to let everything process? It was obvious she cared for him a lot, and being young and not entirely sure if you’re ready to say I love you is completely valid, so he should have respected that. End of relationship for the first time.
When they get back together, their relationship is threatened both by Jess moving to Stars Hollow and Rory getting ready to go to college. In my opinion, the way Dean handled the latter bothered me more than the way he acted toward Jess. While some of his overprotective behavior often left me rolling my eyes – get over yourself and be mad at Rory too, because she’s as much to blame – he was definitely justified in not liking the guy his girlfriend clearly had feelings for. But when it came to supporting Rory’s journey to an ivy league school, Dean did a really bad job. Sure, Rory was often blinded by her one track mind toward Harvard, but when you’re in high school and you’re working toward achieving a dream you’ve had forever, it deserves some support. The amount of times Dean got mad at Rory for prioritizing schoolwork over the two of them hanging out was super off-putting. Rory worked too hard to be punished with that bullshit guilt. And even though it was ugly and public and I don’t agree with Rory stringing Dean along for too long, they finally broke up for good. OR SO WE THOUGHT.
First of all, even if you didn’t recognize how dumb Dean was in the beginning, it was pretty solidified when he got married. Despite everyone having a different path in life, Rory was completely justified in being disappointed with Dean for giving up his spot in college when he had to deal with the responsibilities that came along with being married. And because we can’t enjoy nice things – like Luke and Lorelai finally getting together – Rory and Dean have to get back together again. While the demise of this third attempt at a relationship is not completely Dean’s fault, he still somehow manages to continue digging himself into a deeper hole with Rory that he can’t figure his way out of. Sure, they’re enjoying themselves and doing the sex and getting wrapped up in the nostalgia of their first loves, but they should have known the complications of getting back together while Dean was still married. I would even go as far to say that Rory’s third relationship with Dean marked the beginning of her string of bad decisions while in college. Fight me about it.
I know, I know, he’s beautiful. Hear me out, though. The entire Dean/Jess battle was dumb. I don’t think there is a couple in the history of the world that actually benefitted from playing games with one another instead of just using their words. In my opinion, you’re better off getting to the point or else it’s just going to cause more problems. So it was #NotCool for Jess and Rory to be doing the flirty stuff while she was still technically with Dean. Plus, Jess using that girl from his high school to make Rory jealous? #ReallyNotCool. Not only did that reinforce the idea that the only female character he bothered to be decent to was Rory, but it was also another unnecessary distraction from both of them needing to stop dancing around the fact that they wanted to be together. Seriously, folks, the best relationship advice anyone could ever give is use your words.
But okay, whatever, Dean finally made the move to step away and Rory and Jess were officially a thing. And things seemed to be okay, even though Jess could have made more of an effort to be chill with Lorelai. And he could have respected Luke more. And he could have been less paranoid about Dean, considering Jess had formally taken his place as Rory’s boyfriend and she proved pretty consistently that he was the one she wanted to be with. But other than those minor details (she typed sarcastically), the two seemed pretty happy. He was on board with Rory going to Yale and he attempted to meet the grandparents and their bond over books was unmistakably precious.
And then the honeymoon period fizzled out and, look at that, Jess returned to being a closed off, low-key boyf. And with Rory getting ready to transition into college, this wasn’t complementary. Plus, he did so much lying. Yall, he lied to EVERYBODY!!!! I don’t know how Rory put up with it for as long as she did. Jess became so obsessed with the idea of getting out of Stars Hollow that it became his only priority – behind school, and behind his relationship with Rory. What started out as a few lies about where Jess spent his time ended up being a big mess for the people in his life who cared about him. Among the excitement of Rory’s Chilton career coming to an end and a new one beginning at Yale, she had to deal with the fact that her boyfriend was constantly disappearing and refusing to open up about what he wanted in life. And after the entire Kyle’s bedroom debacle, Rory decided she’d had enough. Or maybe Jess decided, it’s still unclear, as are all of Jess’s motivations for the decisions he makes. We get a few answers about Jess as the series continues, but it’s pretty certain that he was too unpredictable for Rory. Which might be a good enough justification if it wasn’t for…Logan.
Full disclosure, Logan SUX. Okay, moving on. If you watched through season four and thought Jess was the “bad boy”, your definition was about to be refined. Considering Logan was rich and took the Richard and Emily route in life, he was incredibly spoiled. It wasn’t surprising that these experiences influenced the way he treated women, as well as people in general. Everything was Logan’s for the taking. In Rory’s defense, she did not go after Logan at his immediate beck and call. She challenged his behaviors in a way that was clearly intriguing to him, and Logan eventually decided to commit to relationship rather than lose Rory completely But that didn’t mean he was suddenly about to change all of his ways. Even if you were to ignore the awful way his family treats Rory – which is pretty difficult to ignore, but hypothetically – their relationship is still built off morals that are clearly not Rory. Stealing the yacht; duh. Dropping out of Yale; duh. Giving up on her dream of becoming a reporter, and instead, working for the DAR…DUH. Before Logan, just the thought of all of these scenarios would have had Rory laughing in your face. It was beyond out of character for her to do all of these things, and rather than Logan supporting what was clearly the best decisions for Rory – as they were her decisions – he just goes along with the derailment of her future. Had he actually cared about her, he would have made more of an effort to encourage her to go back to Yale and continue pursuing her dreams. Let’s not forget Logan’s analysis of Rory’s situation: “It’s all temporary, just have a drink.”
As for their first “break up”, as all of you Friends fans know, there is always confusion with the idea of taking a break vs. breaking up and how that affects whether or not you can/should sleep with other people. According to Rory, the two were taking a break, during which she THANKFULLY didn’t go back to Dean (lol). But Logan took the first opportunity he had to go back to his old ways, which he was not honest about with Rory until she heard it from his sister’s friends. WHAT EVEN!!!! With all of the struggles Rory and Logan went through to reach a common ground about their relationship being exclusive, Logan should have been more conscious about how that behavior would reflect on him according to Rory. Come on, dude, she practically spelled it all out for you. Keep up.
And THEN. Yall. The proposal. WHAT THE HECK. I understand the desire for spontaneity with that sort of thing, but the two had never even discussed their future beyond Yale or the idea of marriage. And then he proposed to her in front of an entire audience and put her on the spot. Think about it. He had clearly been thinking about this decision for a while, but in the moment, Rory only had about 10 seconds to make up her mind. And thankfully she handled the situation as best as possible by saying, “Uh, no thank you, but let’s chat about this.” Especially because Rory had made such strides in getting her life back on track to where she wanted it, it made sense that marriage would be the furthest thing from her mind. She was focused on finishing up at Yale and getting a reporting job and repairing her relationship with her mom; once again, because it was the world according to Logan, he didn’t take this into consideration and simply did what he wanted. All of his behaviors and the way he viewed his relationship with Rory were affected by being endlessly spoiled. From Logan’s point of view, he could never quite understand why Rory didn’t agree with the way he made decisions for his life. And if I could make a bold assumption, he never really figured it out. Up until the very end when Rory chose her career over Logan, I would bet anything that he just found another girl to take her place and fulfill the Huntzberger plan.
It’s no doubt that we’re all interested to see how these dudes fit into the story of Rory’s life beyond season 7. But I’m going to be honest, I don’t think Gilmore Girls: A Year in the Life should settle the Dean vs. Jess vs. Logan debate by writing one of them to live happily ever after with Rory. Maybe Rory has a brand new dude that’s perfect for her. Maybe her and Marty cross paths again and realize they were meant to be together. Maybe she doesn’t want to get married. I guess we’ll have to wait and find out what happens. And until November, I’ll keep my fingers crossed that we get some satisfying answers.