Rory had three major relationships on Gilmore Girls, and Logan may be the most controversial of them... especially after the events of A Year In The Life. At first, it seemed that Rory and Logan were total opposites, and couldn't stand each other. But of course, this is just sitcom preamble to a romantic relationship, and sure enough, the two got together after a while. For some, though, the issues they had at the start are impossible to overcome, and this will always be a toxic relationship for Rory.
For others, though, that first impression faded, and it became clear that Logan and Rory could actually be perfect together. It's interesting to think what might have happened if Rory had accepted Logan's proposal in the end - could that have been the thing that made this pairing perfect, or were they always destined to be toxic?
Toxic: Based On An Immediate Dislike Of Each Other
It might be a trope in movies and TV, but usually, an instant dislike of someone isn't the precursor to a lovely romantic relationship. Especially given that Rory's instant dislike is based on the fact that Logan is rude to people that he sees as 'below' him or as having a serving role, and seems arrogant and spoiled. He also seems to find her intriguing... but a bit stuck up, and her own kind of arrogant, judging him for hiring someone to bartend a party. Neither of them should really have wanted to start a relationship with someone they thought so badly of.
Perfect: Intellectual Equals
Possibly Rory's most defining trait is her intelligence - from the very first episode, her academic abilities are front and center. So a relationship with someone else who is just as smart, and getting a similar education, fits her perfectly. It would be important for both Rory and Logan to be with someone who was an intellectual match, and they definitely found that with each other.
Toxic: Game Playing
Neither Rory nor Logan is particularly good at being upfront with what they want, at least at the start. Logan dates her, but then leaves her hanging, refusing to commit to anything, and usually leaving her wondering. He invites her over for what she thinks is a date night, and what turns out to be a poker game that she can sit on the sidelines of.
It's classic gameplaying, and it's not a great look. Of course, Rory is no better, scheming to try and make him jealous by taking his friend to a party, so perhaps they deserve each other on this one.
Perfect: Fit In Each Other's World
As the show goes on, Rory becomes more and more connected to her grandparent's world, and the world of Ivy League privilege. It's something that both Dean and Jess find uncomfortable, but it's where Logan fits in perfectly. He wouldn't find it remarkable at all that Rory had a 'coming out', and his parents know her grandparents already. While it may seem like this isn't that important (and in the grand scheme of things, it isn't) coming from the same kind of background definitely makes life easier.
Toxic: Total Lack Of Communication
Neither Rory nor Logan are that great at saying what they want to say, and this is connected to the game playing issue with their relationship. Rather than simply tell Logan what she wants, Rory drops hints and then sulks when they aren't picked up. Logan makes huge plans without even really mentioning it to Rory (even after they live together), and struggles to talk about his issues with his father - or tell Rory that the plans they are making can't happen because of that. Even in the revival, he fails to mention that his partner is moving in with him - which, even given their 'arrangement', is a pretty huge omission.
Perfect: Challenged Rory
Logan was supportive of Rory when it mattered, but he challenged her when it mattered, too. In many ways, Rory grew up surrounded by cheerleaders, and people who thought she was the best thing ever to happen to Stars Hollow. Then, when her grandparents came back into her life, she was told by everyone around her that she was brilliant, beautiful, and from a 'good' family with a lot of money.
Logan, in many ways, stopped her from getting arrogant, and gave her a little perspective. He was willing to challenge her and to call her out when she started to get too wrapped up in herself, as well as push her to try new thing and step out of her comfort zone, and she did the same for him, which was what both of them needed from time to time.
Toxic: Patronizing And Arguing
The issue with these two challenging each other was that it could often move past a healthy and loving reality check, and into patronizing territory. While some fans enjoyed Logan's nickname for Rory, most felt that calling her 'Ace' was just plain rude, and that he often treated her like a naive little girl, compared to his worldly self. Rory, for her part, did the same to him, considering him out of touch due to his money, and often snapping at him and putting him down. Neither are a particularly good sign of a healthy relationship.
Perfect: Clear Respect (In The End)
While they got off to something of a rocky start, by the end of the series, it was clear that Rory and Logan found a real mutual respect for each other. They listened to study and career woes, they supported each other, and they even managed to learn how to communicate (most of the time). By the time of the revival, Logan made it clear that he fully supported Rory's desire to write a book, and never lost faith in her - in the end, they found the mutual respect that was needed.
Toxic: Cheating
Of course, the revival also included one of the most toxic elements of the series: cheating. Rory is, in fact, something of a serial cheater. She cheated on Dean with Jess, then had an affair with Dean while he was married, and in the revival, was having an affair with Logan and cheating on her boyfriend, Paul. Logan isn't much better, telling her initially that he wants to keep seeing other people, then upsetting her by sleeping with his sister's bridesmaids (almost all of them), and then cheating on his partner. And while it's possible that there is some kind of ethical non-monogamy arrangement between Logan, his fiancee, and Rory in the revival, it seems like this is just some straight-up cheating going on... which is absolutely toxic.
Perfect: They Grew Together
Had Rory and Logan not been having an affair in the revival, it had the potential to be a fantastic end for the two of them, as it was clear that they cared deeply about each other, wanted to support each other, and that they had grown into something that really worked. It was a long road from two college students who weren't ready to commit, to the point that Logan proposed, to them still loving each other in adulthood - and in many ways, it could have been a perfect ending, too.