Rory Gilmore: An In-Depth Analysis Of Her Career As A Writer Through Her 3 Main Romantic Partners – And Who Had The Biggest Impact On Her (*Hint, It’s Not Who You Think…)

I recently got to rewatch the entire ‘Gilmore Girls’ series, and yes, I’m excluding the Netflix revival, ‘A Year In The Life’, because it’s just terrible and I can’t believe it was ever made in the first place. It’s not like the fans ever asked for it. Nevertheless, I figured I’d finally write about it. After all, my previous post was about relationships and writing in the eyes of Carrie Bradshaw’s relationship with her most toxic boyfriend, Jack Berger on ‘Sex And The City’. If there was anyone who knew anything about writing and toxic relationships in the fictional world, it would be Rory Gilmore, played by Alexis Bledel of ‘The Sisterhood Of The Travelling Pants’.

Rory was introduced to us as the 16 year old daughter of Lorelai Gilmore, played by Lauren Graham of ‘Parenthood’, who had her daughter when she was 16 years old herself. Together they live in Stars Hallow, a small town Lorelei first moved to in order to get away from her very strict and very controlling parents, Emily and Richard Gilmore, who come from wealth. The series begins when Rory is accepted to attend Chilton, a prestigious private high school that Lorelai can’t afford to pay, so she goes to her parents in an effort to get them to agree to loan her the money. They agree, but only if Lorelai and Rory come over to eat dinner with them every Friday night. alas, the Friday night dinner tradition was born.

Throughout her time in high school, Rory has her heart set on attending Harvard University. This was always the future that Lorelai planned on giving her daughter; one that she didn’t get to have herself. Things, however, don’t go according to plan, and Rory winds up attending Yale University, where Richard also teaches, in season 4 of ‘Gilmore Girls’. And while Rory is very much motivated by school, books, and her writing aspirations, she’s also very much into boys. First she dates Dean, her perfect first boyfriend. She then dates Jess, Luke’s, Lorelai’s friend and future boyfriend, nephew, who’s just as much into books as Rory is, if not more. And finally, there’s her college boyfriend, Logan. Somewhere in the middle, there’s also Marty, but he doesn’t really count because Rory isn’t really ever interested in him in a romantic way. We’re also omitting Tristian for the very same reason.

All three boyfriends represented different phases in Rory’s life. Dean represented her teenage dream. He was the perfect first boyfriend when they’re teenagers, but a terrible one in adulthood. Jess represented toxic masculinity; someone Rory tried to save with her love and adoration for him, but couldn’t because it just wasn’t what he needed at the time. He was the right person, wrong time type of boyfriend. And Logan was her first adult boyfriend. He was player who actually turned out to be a good guy; even the marrying type. Rory played a vital role in all the three men’s lives in one way or another, whether she knew it or not.

Rory met Dean when she was 16 years old. He was her first everything, including her first sexual experience. It was always implied that Dean was looking for someone who’d be a stay-at-home-wife, an aspiration that Rory clearly didn’t have for herself. She wasn’t ever meant to be a housewife. Her path was always meant for the workforce from a very young age. That was how Lorelai raised her to be. Dean found exactly what he was looking for in Lindsay, who was also Rory’s old classmate when they were little before her move to Chilton. And yet, once he got married to the woman that was perfect for him only on paper, he realized it wasn’t enough for him.

Right from the start, it was evident that Dean was with Lindsay solely because he was trying to fill a void. He was still very much in love with Rory years after their relationship was over. Following their breakup that happened in season 3 due to Rory’s growing feelings for Jess that couldn’t be ignored any longer, Dean and Rory kept their relationship cordial. They still had to see each other because they lived in the same small town. It seemed as though their feelings for each other were over, but then, while drunk at his Bachelor party, Dean calls out Rory’s name and proceeds to ask Luke, ‘Why doesn’t she love me?’

Dean never revealed his feelings for Rory, and instead proceeded to marry Lindsay as initially planned. Nevertheless, Dean continues to see Rory. Their relationship grows and eventually develops into something more than just a platonic friendship as the two can no longer avoid their feelings for one another. Rory and Dean sleep together, while officially making Rory ‘the other woman.’ When confronted about it by Lorelai, Rory defaults the situation and tells her that he was her boyfriend first, and called him ‘my Dean’ as if he was her property of some sort.

The extramarital affair continues, and I personally couldn’t but feel utterly heartbroken for Lindsay. Rory made her seem like the bad guy, and even shamed her for the life that she chose for herself. The fact of the matter is, however, Lindsay never did anything to deserve such sh*tty treatment. The only thing she did wrong was love Dean the way that she did. Rightfully so, Lindsay ends her marriage to Dean when she finds out about his infidelity when she found the letter Rory wrote to him where she wrote about the affair and wanting to end it because of his marriage. Dean didn’t show any remorse for his actions, and neither did Rory, which makes me be even more heartbroken for Lindsay.

With that being said, Dean and Rory officially resume their relationship following the breakdown of his marriage to Lindsay, and Lindsay is never heard of or seen ever again. They could finally be out in the open without having to hide anything from the eyes of others. But once their relationship became official, the demise of their once loved-up relationship came to be. It became clear that they weren’t the people that they once were when they first got together as 16 year olds. The beginning of the end of Rory and Dean also marked the beginning of Rory and Logan.

Rory never cheats on Dean with Logan, which is more than anyone could say about her character from her teenage years back when she cheated on him with Jess. Rory was immediately drawn to Jess, mostly for their mutual love of books – something she lacked with Dean. Their mutual love of books was never a strong enough reason for them to stay together. Jess loved story, no doubt. But he was too troubled to be with someone like Rory. He lacked the parental support and guidance that Rory possessed. He wasn’t ready for someone like Rory when they were young teenagers.

Even though Rory never cheated on Dean with Logan, her attraction to Logan was evident right from the moment they meet in college. But Logan is a player. When he met Rory, he never had a single serious girlfriend. Instead, he opted for no strings attached type of relationships, as well as one night stands. He had no interest in committing to anyone. Rory wasn’t that type. She was a serious relationship type of gal. But because she liked Logan so much, she agrees to have a relationship with him that only revolved around sex.

But Rory wasn’t just someone who could continue to have a casual relationship with someone without feelings involved, so she ended their affair. When Logan realized he could lose her for good, he agreed to be her boyfriend. He ended up being a great boyfriend to Rory, especially considering she fact that she was his first ever girlfriend. Even when Rory was trying to make him seem like the bad guy, like she always had, with the exception of Jess, I just couldn’t be convinced that he actually was the bad guy. He was a good guy with his own set of laws. Many would argue that Logan represented the Christopher in Rory’s life, whereas Jess represented Luke, and therefore Jess was the right guy for Rory and not Logan.

I beg to differ. Firstly, I strongly disagree with, I think the entire ‘Gilmore Girls’ fandom, that Logan represents Christopher in Rory’s life. And second, I strongly disagree that Jess was ever meant to be the right guy for Rory. Though Jess played a vital role in Rory’s life, especially in her career path, I don’t think they were ever meant to be endgame. As much as I disliked Emily for meddling in Rory’s personal life when she found out Rory was back together with Dean, for the first time and only time, I thought she was absolutely right. Not for meddling in Rory’s personal life, but for not liking her relationship with Dean. The reason for her not liking Dean’s presence in Rory’s life was absurd, as it solely had to do with class and wealth. Nevertheless, Emily didn’t like Rory’s boyfriend, and I agreed with her.

By the time that Rory and Dean got back together again in season 5 following Dean’s divorce from Lindsay as a result of his affair with Rory, he and Rory were just too different for their own good. By that point, they were simply holding on to something that just wasn’t there in the first place. Dean stayed the same as he was when he was 16 years old. He was a typical small town boy who was happy in his comfortable life. Rory, on the other hand, was changing and evolving. She was gaining new experiences, and those experiences didn’t involve Dean. And that’s not to say that there’s anything wrong with being someone like Dean or someone like Rory, because there isn’t anything wrong with being like either like one of the two. But the two of them combined isn’t ever something to romanticize.

The entire point of Rory and Dean resuming their relationship again when she was in college was to showcase how much Rory had changed since she first got together with Dean, and how much Dean stayed the same and expected Rory to stay the same too. He wasn’t interested in her life as much as he used to be. He had his own ideas for what he wanted Rory to end up to be and their life as a couple to look like, which was exactly what Lindsay was willing to give him wholeheartedly. Rory, on the other hand, had different plans for herself; ones that didn’t involve Dean or anything that interested him about her. For example, her writing aspirations. He was never interested in her writing, and it was more evident than ever when he gave Rory a not-so-subtle hint when she bluntly asked him what he thought of an article she wrote during a long-awaited date and he couldn’t give her an answer.

Logan was different. He read everything that Rory ever wrote. Unlike Dean, he was actually interested in her work. He was invested in her work. Rory’s relationship with Logan was entirely different than her relationship with Dean, and there were numerous clues that Rory the mistakes she made in her relationship with Dean and learned from them in her relationship with Logan. For example, when she told Logan she loved him and he didn’t say it back, she didn’t take offence to it like Dean did when he first told her he loved her and she couldn’t say it back to him immediately. Instead, she completely understood where he was coming from and agreed to be patient with him. Rory’s relationship with Logan represented everything that her and Dean’s relationship wasn’t – a mature and a loving relationship where both parties support one another unconditionally. Dean was right for Rory, but he was right for her at 16; not in her 20’s. They always had an expiration date; even if Rory didn’t end up cheating on him with Jess, they would’ve still broken up eventually. It just would’ve happened later rather than sooner.

Logan represented a pivotal time in Rory’s career and path to success…or the beginning of the end of her success. Rory got an opportunity to work as Logan’s father’s assistant at his publishing firm after he met her. But after witnessing her work ethic, he didn’t have anything nice to say about it, and didn’t leave anything out when telling her about it. Rory made a great assistant, but not a great journalist- in the words of Logan’s father. Suddenly, that comment alone shattered Rory and her dreams of her future aspirations to be a journalist. It made her question everything about herself, and with that, she quit Yale. She became estranged with her mother due to her decision, as Lorelai felt that Rory was giving away her future due to one man’s option which shouldn’t have mattered in the first place; a future for which Lorelai practically risked her own life for. They even spent Rory’s 21st birthday estranged, a milestone that they had planned for since Rory’s childhood days.

While she and her mother were estranged, Rory lived with her grandparents. Logan was a constant presence in the house. Richard and Emily liked Logan for Rory, and were even friends with his parents, which made it hard for them to believe Lorelai when she told them Logan’s father was the reason for Rory’s fall from grace. And unlike Lorelai, Logan supported Rory’s decision to quit university even though he didn’t agree with it, and it caused great conflict between him and Lorelai. What Lorelai failed to realize, however, was that Logan wasn’t that much different than her. Out of all of Rory’s boyfriends, Lorelai only had a liking to Dean, mostly because he was the dream boyfriend; one that would never intentionally hurt her daughter. But Logan wouldn’t hurt Rory intentionally either. Lorelai just couldn’t believe that Rory could make such bad decisions all on her own. She believed that Logan always whispered things in her ear to get her to do all the bad things that she did just because the two were in a relationship. The reality is, however, that Rory made all those bad decisions like steal a boat and quit Yale solely on her own. She wasn’t as perfect as Lorelai made out her to be after all.

Though Lorelai keeps trying to blame Logan for Rory’s failings, she fails to see the bigger picture and put the blame on Rory herself. And through her endless game of blaming Logan for Rory’s wrongdoing, she fails to see that the person standing in front of her is actually the male version…of her! Yes, you read that correctly: Logan was the male version of Lorelai. And I know that it might be hard for you ‘Gilmore Girls’ Stan’s to believe, especially considering that so many of you see him as Rory’s Christopher, so let me explain myself. You see, Logan wasn’t happy with his life. He wasn’t happy that he didn’t actually had to work for everything that he’d achieved. It was all practically handed to him. But it was all at a cost. The thing with parents never help their children just for the sake of helping them. There’s always some sort of agenda that they seem to be hand, and that was Logan’s father in particular, just like Lorelai’s mother in particular. At one point, when his father publicly humiliated Logan in front of Lorelai and Luke, Lorelai even told Logan that no one knew what it was like to feel like a disappointment to their parents better than her; and I think that was the moment where Lorelai really connected with Logan on a much deeper level.

Make no mistake, though, Rory didn’t let her potential future father-in-law’s toxic, manipulative and demeaning behaviour slide. When Logan almost died after he was involved in an accident with his friends, which happened after his remark to Rory had her decide to quit Yale, his father didn’t even have any intend to come to visit him at the hospital to see if his own son was okay or even alive. Rory, already in a lot of distress, suddenly got enraged with her boyfriend’s father, enough so for her to leave an angry voicemail (this was 2006, might I add; a time for voicemails), where she told him to take his pride up his a** and visit his son at the hospital. I think that was the moment Rory actually got a little bit of respect from his father, as he ended up showing up at the hospital to his son thereafter. When his father saw Lorelai and Luke at his own cottage when he came unannounced, during the same incident where Lorelai told Logan no one understood what it was like to feel like a parent’s biggest disappointment, Logan’s father told him he’d be swinging him to London for work as soon as he graduated Yale so he could get his sh*t straight. Immediately, Rory assumed it was to break her and Logan up, and she almost seemed disappointed when Logan’s father told that not everything was about their relationship.

Though Rory didn’t want to let her love with Logan go, she knew she’d be holding him back if she’d asked him to stay for her. So she didn’t. Even when he asked her to tell him not to go the night before his departure, she didn’t tell him to stay; though that was all she really wanted. The two decided to continue on with their relationship long-distance, and they ended up standing the test of time. That was the time that Rory really gained her independence. She knew that she could it all on her own; that she wasn’t with Logan because she needed him or his money, but rather because genuinely loved and cared for him. She lived in his apartment rent-free during the time that he was in London, but moved (back) in with her roommate and high school and college nemesis, Paris, as soon as he moved back to town because she didn’t want to feel like she depended on him.

This was also the time of confusion for Rory. This was the year she was graduating from Yale and embarking on an entirely new adventure as a journalist. But this was also the time where her and Logan’s relationship was getting more and more serious. They’d been together for 3 years, and the mere talk of marriage and their future together was inevitable. She’d always had her life goals set for her future from a young age, but those goals didn’t include a man in her life, nor did they include sharing a life with a man. Logan, on the other hand, though he never had his sights set on sharing a life with a woman, planned to marry Rory and make a life-changing move with her that would disrupt her own plans. Instead of asking for her father’s blessing as usually done for old time’s sake, Logan asked Lorelai for her blessing in marrying her daughter.

Logan proposed to Rory in front of her entire family at her graduation party. She was caught off guard. She couldn’t give him a straight answer. It mirrored the exact moment Dean told her he loved her for the first time, except there was much more at stake this time around. In the end, however, Rory decided not to marry Logan. She chose her career instead. But as we saw in the 2016 ‘Gilmore Girls’ revival, Rory’s career had failed. It didn’t go according to her plan, and she was back home. She was also engaged in an affair with Logan, who was back in London and had an affair with girlfriend on the side, while she herself had a boyfriend she kept forgetting about. Judging by the looks of it, she would’ve been much better off had she married Logan and took her career as back burner. But that’s also life, and she needed to learn that sometimes she can’t control her life and everything that happens in it. That was the biggest lesson she needed to experience and witness herself.

Also in town was Jess, another one of her ex-boyfriends. He was in town because his uncle, Luke, and Rory’s mother, Lorelai, were finally getting married after years of being a couple. Jess was Rory’s shortest-running boyfriend, and yet, he was the most significant one when it came down to her career. He was the one that encouraged Rory to go back to Yale. He was obviously someone Rory respected a lot, especially considering since she listened to absolutely no one when they told her to go back to school, and yet when Jess came along, it only took him a mere second to get her into her senses. They weren’t even together by that point as a couple and hadn’t seen each other in years. When they reunited again in the revival, he was the one that encouraged her to write a book about her and Lorelai’s life as mother and daughter that would eventually become ‘Gilmore Girls’.

With that said, despite most of the ‘Gilmore Girls’ fandom being Team Jess when it comes to who they think Rory should’ve ended up with, I just don’t think he was meant to be a romantic partner for her long-term. Sometimes, the most important people in your life are in your life for a short time, and that was Jess for Rory. He played an important role in her career path; the most pivotal role I’d say. I also think that way about Dean. He was meant to be her perfect first boyfriend. They were the teenage dream. But as adults, they never would’ve work. He didn’t show any interest in her writing at all. He didn’t care for it. Rory needed a partner that showed an interest in her writing. She needed someone to come to for advice and such. She needed someone to go to so they’d tell her whether she was good or not. Dean didn’t want that for himself. He didn’t even want his perfect woman to have a career in the first place. He would’ve been the happiest if she didn’t, and that was part of the reason why he and Rory didn’t work in the end. He didn’t fit into her world anymore.

And Logan was the love she missed out on. Many fans believe that she made the wrong decision in turning down his marriage proposal and choosing her career over him – a career she ended up failing in the first place. I think it’s unfair to say that turning down Logan’s marriage proposal was a mistake. Maybe that’s just how her life was meant to turn out, and maybe her greatest blessing was actually none of her former boyfriends, but Logan’s father instead. I related to Rory’s character in more ways than one. Firstly, I related to her in her struggles as a writer. And second, I related to her in her relationship with Logan’s father. My father-in-law had made it very clear that I wasn’t good enough for his son, and those reasons were more than just about me not good enough for just one reason. The main reason was that I have cerebral palsy, and his view of cerebral palsy is very much what you read about in textbooks. He’s a very by-the-book kind of man, and therefore, refused to see me as a person. Instead, he saw me as the textbook version of cerebral palsy. Therefore, when it comes to work, he not only said I wouldn’t be a good writer, but that I wouldn’t be able to work in the workforce in general. At least Rory’s boyfriend’s father said she’d make a good assistant.

With that said, my father-in-law wasn’t ever this special person by any means that I necessarily cared for. Practically the whole entire world thinks of me the same as my father-in-law. Any time I get out the door, there’s an entire circle of doubters. But as a writer, as well as a woman, and a disabled woman, having such a person in close proximity to me was my biggest blessing, because it made me want to prove to myself that I could do everything he said I couldn’t. Having him in such proximity to me made me want to do more and achieve more in my life. And I did. I achieved literally everything he said I wouldn’t be able to do and more – both in my personal life and my professional career. If I didn’t have someone like him in such a close circle, maybe I wouldn’t have been so motivated to silently just say to him, as well as the entire world, ‘F*ck you and your assumptions, I’ll show you what I’m capable of!’ She ny silently saying it, I mean not saying it literally, but f*cking doing it.

As a writer, as a woman, and as a disabled woman, there will always be people that will doubt you and your capabilities. I believe that these doubters, especially when ones who are at such close proximity could be the best thing for you. Instead of finding a partner that would motivate you in your aspirations and capabilities, finding your biggest hater and doubter should be seen as your greatest goal in your life – that’s the biggest lesson that we learned from witnessing Rory’s life. It’s not a romantic partner that could have the biggest impact and influence on your entire life, but rather someone close to you that doubts you. And the best part was that slogans father ended up offering Rory an opportunity years after he doubted, which gave us an even bigger lesson to learn from: your doubters will come around and you’ll prove them wrong, and that will be the greatest feeling in the world. And f*ck yes, those opportunities NEED to be accepted; no doubt about that.

And so, though the three men in Rory’s life had their own individual impact on Rory’s life as a writer in one way or another, the one biggest influence wasn’t someone she was romantically involved with. Logan’s father was actually the one person she needed most in her life. In hindsight, he was the one that changed everything for her. He was her greatest reason to aspire to succeed; just like my father-in-law aspired me to succeed. I can honestly say that when it comes to Rory, I’m not Team Dean, I’m not Team Jess, and I’m not Team Logan. I’m Team Mitchum Huntzberger – Logan’s father.