As a Gilmore Girls enthusiast, I had a period of time where all I did in my free time was binge the show. In the process, I developed some fairly strong opinions about the show, specifically, which guy is meant for Rory Gilmore, the main character. Before we get into that, we need to talk about what makes the show what it is.

The scene is set in Stars Hollow, a small town in Connecticut. Lorelei, Rory’s mom, got pregnant with her as a teen and named her Lorelei (and gave her the nickname Rory). They have a tight relationship within their community, and an even tighter relationship with each other. They get breakfast at Luke’s Diner almost every morning, and Luke Danes (who is the owner) has a close bond with Rory and Lorelei. What makes the show so comforting is the small town community, the color pallet, and the distinct personalities of each of the characters. 

Throughout the 153 episodes, there are three main romantic interests that Rory has. First was Dean Forester, followed by Jess Mariano and Logan Huntzberger. The only true way to see who is best for Rory is to break down each personality and match it with Rory’s.

Dean was a great first love. He was humble and took care of Rory while also being fun and up for anything. He took time to make her thoughtful gifts and was never shy when it came to going on adventures. However, as soon as Jess came into the picture (before Jess and Rory started dating) Dean started to become overprotective and jealous even though Rory wanted nothing to do with Jess at the time. There are times when all Rory wants is to be independent and Dean tries to hover and once again becomes jealous of the time Rory wants alone. Over time, with the shift in Dean’s attitude and the entrance of Jess into the series, Rory and Dean end up breaking up.

Shortly after the break up, Rory and Jess begin dating. Jess’s character is supposed to be a rebellious teenager who gets shipped off from New York to Stars Hollow by his mom to have a fresh start with his uncle, Luke Danes. Jess didn’t have enough parental guidance at home, so the hope was that by giving him a new town surrounded by new people would give him a fresh start and put him back into place. We quickly begin to see that this mischievous shell isn’t all that Jess is. He turns out to be very intelligent and loves reading, something he finds in common with Rory. This intellectual similarity between Rory and Jess is part of what makes them click so much. Despite being so intellectual, he likes to push people’s boundaries and disobey his authorities. This leads the town’s people to not like him and want him gone, but Luke pushes for him to stay. When Jess and Rory were together, he liked to push her out of her comfort zone and get her to do things she wouldn’t normally do. His immaturity led to an eventual break up despite the fact that their personas complimented each other.

Logan and Rory didn’t meet until Rory went to Yale. Logan began charming Rory when she started interning for the Yale Daily News. Despite his charisma, Logan was from the opposite background as Rory. He was wealthy and privileged, whereas Rory was more humble. Similar to Jess, Logan also wanted Rory to leave her comfort zone, just in different ways. While this was the most mature and stable relationship that Rory had, it was not the best one for her.

While it may have been conflicting in some ways, Jess was definitely the best for Rory. They both had their independent streaks while still having enough in common. Intellectually they suited each other and they both bonded in being misunderstood. There was never a dull moment between these two characters and their dynamic suited each other best. 

So while it may not be the absolute best relationship ever, Jess and Rory compliment each other and fit together like puzzle pieces. I know this may be a controversial topic for other Gilmore Girls fans, but Jess and Rory were definitely meant to be from the start.