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  • Writer's pictureSkyla Clarke

Who Was the Best Boyfriend in Gilmore Girls?

All too often I find myself arguing with girls my age about who Rory Gilmore should’ve ended up with at the end of the hit early 2000s TV show Gilmore Girls. Every single time it ends in mindless yelling and screaming, mostly because each girl is defending the boy that they fell in love with while watching the show. 


And so, I feel that it is necessary for me to break down my argument into points and publish it, so that I don’t get interrupted by people forcing their opinions in my face. In this article I will break my opinions down into the pros and cons of each boyfriend, with a summary at the end of which boyfriend was the best. 


I think the best place to start is with Tristan, seeing as he has the shortest time on the show. Played by Chad Michael Murray, Tristan is seen to be the most charming boy and Chilton, managing to have everyone wrapped around his finger except for Rory. He tries to get her attention by being irritating, and their romance only involves one single kiss, tainted by the fact that Rory had just broken up with Dean and was rather distraught about it. 


The only reason that Tristain pops up into the arguments of who is the best boyfriend is because he is hot. There, I said it. He had an annoying personality, and despite the fact that he did truly like Rory he went about it in the wrong way. He feeds into the idea that “boys are only mean to you because they like you” and that got him nowhere in terms of being able to start a relationship with Rory. In my opinion, he is the least eligible for the title of ‘Rory’s best boyfriend’ because he literally never was one. 


The next boyfriend I will discuss is Dean. If you are a serious Gilmore Girls fan, you would know quite a bit about Dean, seeing as he was quite a complex and prominent character throughout most of the show. At the start, he kind of stalks Rory as a way to get her attention, and eventually they do begin to date. Weird at first, their relationship shows typical teen love. And I do believe that during the first few seasons, Dean was the ideal boyfriend for Rory. He was kind to her, he listened to her and he was usually respectful of her boundaries. 


Usually. It was super awkward to watch when Dean told Rory that he loved her after building her a car, and she replies with “I love the car.” Sure, nobody should ever be forced into saying “I love you” especially if they don’t mean it. But the awkward thing about this conversation is that it was their one year anniversary, and Dean had done all of these super romantic gestures just for Rory to not give anything in return. I feel like it was the sheer teen awkwardness of Rory that led them to this position of breaking up, because when they meet up again a few episodes later she does tell him that she loves him. Dean was somewhat the victim of an awkward situation, and I feel like he just had a human’s response to the heartbreak of realising that a person you love might not feel the same way back. 


And Rory never failed in provoking Dean into multiple awkward situations. She would blow off their plans together, and then be upset when he got mad about it. She would flirt with Jess (whether she knew she was or not) and then get mad with Dean when he thought twice about it. Dean went out of his way to do things for her, by going to the ball at Chilton, going to her Debutante Ball, being respectful at her Grandparent’s house after they analysed him with intense scrutiny, and even helped her mum with different tasks that she needed done. We barely ever saw Rory do much for Dean in return. 


And so, I have huge respect for Dean in the first few seasons, as he was the best high school boyfriend Rory could have asked for. It was HER actions that caused Dean to get mad and upset towards the end of their (first) relationship, because she was too worried about Jess to see how her boyfriend actually felt. She pushed him to react in anger, leading him to get villainized by many members of the audience. 


However, I argue that he was acting like a human. Would you not be upset and angry that the person you love was falling for someone else? That they were pushing away all of your kindness and care for someone else’s? He had a valid response to the situation, despite the fact that he then became the ‘bad guy.’ 


In season four we see Dean fall in love with and very quickly get married to Lindsey. Rory is weirdly jealous of this relationship, despite the fact that she is together with Jess. The pair share a series of awkward interactions in Lorelai’s Inn, as Dean is a member of the construction team there. At the same time, Lindsey tries her hardest to earn Dean’s respect, by cooking him lunches and trying to become the perfect housewife. Their relationship dynamic is not the same as it was between Rory and Dean. Dean has limited respect for Lindsey, and he becomes a dictator of their household. 


It relates back to the episode “That Damn Donna Reed” in season one, which is one of the red flags that Dean did have in his relationship with Rory. They watch an episode of The Donna Reed Show together, and Dean shares about how he longs for a lifestyle where the wife stays home and cooks warm dinners for the husband to return home to each night—despite the fact that he knows well that Rory has large career ambitions. Eventually Rory folds, and produces Dean a home cooked meal while wearing a 1950s style housewife dress. 


Dean was trying to make his dream a reality in his marriage with Lindsey, and in doing so he seemed to respect her so much less than how he respected Rory. So much less that he ended up sleeping with Rory in arguably the most horrible episode of the whole show “Raincoats and Recipes.” Lorelai comes home to find the two of them together, and Rory tries to defend her actions in a way which would make any person with morals cringe. “He's not a married guy. He's Dean—my Dean.”  


Cheating on your WIFE, a.k.a the person that you told “‘til death do us part” is an inexcusable action. Therefore, I find the rest of Rory and Dean’s relationship from then invalid, because I lost all respect for them both. 


And so, I feel that while Dean was initially the perfect high school boyfriend, he was a horrible husband to Lindsey, and hence is nowhere near the best boyfriend in the show. 


The next boyfriend that appears in the show is Jess. He starts off being quite a hostile troublemaker, and before you attack me, I KNOW he had a hard life, but I don’t really think that is any excuse for treating everyone poorly. When, for whatever reason, Rory does fall for him, she doesn’t act in the way that she usually does, sacrificing things that she usually wouldn’t for him. For example, she let him drive the car that Dean built for her, and then, he crashed it. Later on, she goes to visit him in New York resulting in her missing her mother’s graduation that SHE wanted her to go to. Rory’s personality and decision making changed for the worse when she was with Jess. 


But not only that, but when they were together, Jess was far from the ideal boyfriend when they were together. His poor communication skills as well as his disrespect for many of the important people in Rory’s life was upsetting to see after the way her relationship initially was with Dean. Speaking of, Jess was super jealous of Rory’s friendship with Dean, and although Jess’s fans often bring up Dean’s jealousy in their arguments, they fail to mention Jess’. I wonder why. 


Jess also treats Rory poorly on a number of occasions. Unlike Dean, he seems basically unwilling to do anything for Rory, and gets very grouchy when he has to go anywhere for her, including her grandparent’s house or the party that Lane’s band was playing at. Is it really a healthy relationship if one party is mad all of the time? 


Another incident which I must bring up is the fact that Jess literally tried to force Rory into giving consent, and then got all mad when she didn’t. Like excuse me? That is an action which is beyond justifiable. It is an example of manipulation and there is really no excuse for it.


Again, I must say that there are only limited reasons why any Jess stans are Jess stans. 1) He’s good looking, 2) The pair shared a common interest in literature, which apparently makes Jess a better boyfriend than Dean, and 3) He listened to Rory like twice so that makes him a good boyfriend right? 


And then, he packs up and leaves for California without saying anything to her. All he does is play with her emotions, and yet people seem to think that he is the perfect match for her. I will agree that Rory did make him grow as a person, but that’s not the goal of a relationship. The goal of a relationship is for both parties to benefit and become better people from being around each other. That certainly wasn’t the case with Rory and Jess, as it was almost like their whole relationship was just Rory being a good influence on him. 


The last boyfriend that I would like to bring up is Logan. Logan appeared later in Rory’s life as they met during her second year at Yale, but he did have a large influence on her. In his first scene, he appears as a cocky rich guy as he torments Rory’s friend Marty about working at his parties. He continues to act like a bit of a jerk throughout their early interactions. However, as he gets to know Rory they warm up to each other, and he and his friends do appear to be very humorous at times. 


They end up committing to a non-exclusive relationship, but they both start to become frustrated when they get into relationships with other people, so Logan agrees to become more of a “commitment guy” unlike he was before. They become a super cute couple until Logan meets Jess and becomes insanely jealous of him (just like all of the other boyfriends did—what’s it with jealous men on this show?). This leads to an argument between Rory and Logan, which Logan sees as a breakup and Rory does not. This leads to an event not dissimilar to “WE WERE ON A BREAK” in Friends, and we all know how that argument began. Logan sleeps with one of his sister’s friends, but doesn’t consider it cheating because he thought that they were broken up. Eek. 


He also doesn’t tell her, until she finds out herself through his sister. Double eek. However, as Rory is holding the grudge over his head, he gets into an accident after pulling a stupid stunt with the Life and Death Brigade. It is here when she realises how important he is to her. 


The thing about Rory and Logan’s relationship is that it went both ways. Both of them genuinely cared so much about the other. Logan made a terrible mistake, and there’s not much justifying that, but when he works for Rory’s forgiveness and they stay together you can see how important they are to each other. 


Another thing about this relationship that I think is important to discuss is the fact that Logan isn’t afraid to bring Rory back down to earth. To me, Dean and Jess spent all of this time putting Rory up on a pedestal making her believe she is so fantastic—which of course isn’t a bad thing! However, Logan wasn’t afraid to call Rory out when she was acting like a bit of a brat, because let’s be honest, she did at times act really spoiled. “Yeah well, you’re not exactly paying rent either” is one of my favourite quotes from Logan, because he really made Rory realise that her life is not as hard as she portrays it to be, which I definitely got sick of at times. Even though he might seem a bit harsh in saying it, he’s not wrong, and that’s one of the other qualities that I think was quite good about Logan, is that he was very blunt but had good intentions. 


And so, when it came to the second to last episode of the entire series and Logan proposes to Rory, I was dumbfounded when she said no. He was ready to do whatever it takes for her, but she denied him because she wanted her future to be “free”? They had been dating and living together for so long, and they were a really great match, but Rory rejected him because she wanted freedom? And not only did she reject him, but she totally ended the relationship that had been a great part of her life for so long. 


To conclude, I will never understand why Rory rejected Logan’s proposal. They were the best match out of all of the boyfriends in Gilmore Girls, because their relationship actually went both ways. I feel that with every other relationship one party cared more (or showed their care more) than the other, and this led to turmoil and eventually a tragic ending. Overall, I do think that Logan was the best boyfriend due to his great communication skills, his willingness to own up to his mistakes, and because of how much he genuinely cared for Rory. Tristan, Dean, and Jess all had good traits, but there were things that happened or ways that they acted that just put them in a really bad light when it came to being in a relationship with Rory. And so, whether you like it or not, Logan is the best boyfriend in Gilmore Girls.

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