THIS CONTAINS SPOILERS so if you haven’t watched or finished the series, I suggest you stop here!!
Gilmore Girls is literally my favorite show of all time and I have seen it about five times or so and it brings me so much comfort and an immense amount of joy. Throughout the years of watching it, I have had an internal debate about which of Rory’s three boyfriends is in fact the best. My opinion for the longest time was that obvious answer was Logan, but maybe that was just because I found him the most attractive! I have finally decided though, to go into it a little more and see if the facts would back that up.
I have compiled many pros and cons for Dean, Jess and Logan, so let’s get into it.
Dean- Rory’s First Boyfriend
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Pros:
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Tall
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Got along with Lorelai
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He loves intensely
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He is willing to do things for her
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Changing the water cooler
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Building a car (!!!!)
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He enjoys movie nights with her and Lorelai
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Cons:
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Kind of has a temper, jealousy, and insecurities
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Got mad at Rory when she didn’t say “I love” back right away
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Not really his fault, but, not as ambitious as Rory- they were on different paths, and it was hard for Dean to keep up with her
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Cheated on his wife with Rory
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Overview of Dean: He was an okay first boyfriend- not completely awful. He was definitely too jealous to have a healthy relationship with Rory, although some of his rage was rightfully so- like when Jess came into town. He didn’t seem to be interested in all of the things that Rory was, but he definitely put in effort.
Jess- Bad-Boy Boyfriend
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Pros:
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He brought Rory out of her comfort zone a bit
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He has the same intellect as Rory and shared many of the same interests
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He helped her get back on track when she wanted to drop out of Yale
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Cons:
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Didn’t have the best relationship with Lorelai
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Doesn’t show emotions all of the time
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Not super emotionally available due to past traumas- partially absent mother and father
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Angry, flaky/not attentive
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Pushes people away even if they offer to help him, mainly because he is scared of getting hurt
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Caused fights and trouble
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Overview of Jess: If Jess was better at communicating and didn’t get up and leave when any inconvenience arised, he would’ve essentially been perfect for Rory. They were on the same intellectual level, and they shared so many of the same interests. Jess in his early stages was not emotionally available or ready for a full, healthy relationship with Rory. In his later years, he matured so well and was able to aid and guide Rory with some of her own issues.
Logan- Rich, College, Party Boy
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Pros:
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Romantic and mostly kind
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He always wants to take care of Rory- in terms of living situations and financial stability
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Helped her to get out of her comfort zone and introduce her to more fun activities
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The relationship itself was mature (Logan, not so much)
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Cons:
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Reckless
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Low self-esteem due to his father
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Doesn’t really work hard for anything he gets- it is all handed to him
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Doesn’t fully stand up for himself- he lets his dad dictate everything in his life
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(He did try to start his own business, from his dad’s money, which ultimately failed, but he did try.)
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Flaunts his wealth
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Also cheats on his fiance with Rory
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Overview of Logan: He was my favorite RG boyfriend, and now… it seems like there may just be too many cons. He seemed to genuinely care about Rory but the way he was brought up and his mindset got in the way of that a lot of the time. He was immature and while he had the ability to live life with little to no setbacks, he really didn’t have to bring that into Rory’s life. She didn’t have the financial freedom that Logan did, although he did help her pretty often. He let his father run his life even when that was not the path he wanted to be on himself.
The fact that Dean and Logan go on to cheat on their veryyyyy exclusive significant others, shows that they were not in the right area in life to just be honest and end their relationships, and some part of them is just trying to hold onto the past, aka Rory. I do think that Logan and Rory could’ve been very successful with each other, however, it still seemed like there was some sort of blockade keeping them from being together wholly. His life was set up for him and he seemed to dislike that the majority of the time, yet didn’t really change it. Overall, the three boys have many issues they need to work through but, they weren’t completely awful people. With that being said, based on my list, I think that I have to side with Jess being the best of Rory’s boyfriends. However, I am not going to do that.
When Jess and Rory were dating, he was very emotionally distant and he left when things got hard. I personally wouldn’t be able to deal with my significant other just getting up and leaving out of the blue quite frequently with little to no explanation. While Jess in his later years grew into a good man, the way he acted while in with in the relationship with Rory was just unfortunate. Therefore, I really think Logan is the best boyfriend. He was always there for Rory, and despite the hardships with his father and his future, and his sometimes childish behavior, to me, he didn’t emotionally harm Rory at all. He introduced an excitement into her life that she hadn’t really had in the past, and although his father made her want to drop out of Yale, that wasn’t entirely Logan’s fault.
In my eyes, he always made an effort to show Rory that she was loved and that he valued her; even when he was working in London they would truly try to talk on the phone when possible- he also wanted to marry her so if that doesn’t say “I love you”, then I don’t know what would! I do think their relationship was mature and could’ve lasted a long time but while Logan was ready to work at a serious job and get his life together, Rory wasn’t quite there yet. If there were to ever be additional episodes after “A Year in the Life”, I would hope that they would be together though.