Spoiler alert warning

Over twenty years later, Gilmore Girls continues to be a staple show for viewers who enjoy comedy along with endless love triangles. The controversy surrounding who Lorelai and Rory should end up with prompts heated debate even two decades later. Here, I will evaluate the suitors for the women and explain why they should or should not be with their respective Gilmore girl.

First up: Rory’s men and boyfriends that never were.

Dean
As Lorelai said, Dean was the perfect first boyfriend. It was the quintessential puppy love that’s portrayed in every coming of age movie or show. Dean was reliable, kind, and treated Rory well. Despite this, when Dean was upset, his temper was uncontrollable, to a point where it made me, as a viewer, a bit afraid. Especially since it is near the beginning of the show when Rory is still naive, Dean’s good nature matches her personality, but the fact that he would be upset so easily over Rory studying for one of her prestigious classes at Chilton shows that they are not meant to be. Overall, Dean is a good guy, but his borderline anger issues bump him down in the ranking, at least the first time around.

When Dean and Rory rekindle their relationship during Dean’s separation with his wife, Lindsay, the whole thing becomes a train wreck. I fault Rory for the majority of the damages, but Dean is far from innocent. Dean and his wife were clearly in a rough patch, which left Dean vulnerable to poor decision-making. Rory acted completely selfishly in returning to Dean especially with him still technically married. She put him in an impossible position, contributed to his long-term misery, and should have been the responsible adult in this situation. Once again, this relationship was terrible to begin with.

Jess
Jess, the classic bad boy which screenwriters chose to match with the seemingly angelic, studious girl was actually an exciting match for the first bit. Jess pursuing Rory at the tail end of her gradually failing relationship with Dean added an exciting aspect to the show. Jess’s persistence and the tension between the two made the show nearly addicting. Jess’s love for books and intellect equal to Rory’s was refreshing to the show. That being said, Jess’s recklessness time after time made it blatantly obvious that Rory and Jess don’t belong together. A little impulsivity added into Rory’s life was okay, but the regular endangerment that Jess didn’t even hesitate around was too much for Rory in her character development.

I didn’t mind having Jess linger around after the couple broke up. I understand how some people might see it as a bit irritating, but I liked having the potential that Rory and Jess might get back together. When Jess came back and knocked sense back into Rory when she was taking a hiatus from Yale, Jess gained many points in my book.

Marty
Poor Marty never really got a chance. Marty was friend-zoned from the first minute upon meeting Rory, but never deserved to be. Attending Yale with Rory shows he is of equal intelligence to Rory and it is established that he works, once again similar to Rory who understands the vitality of working to support themselves. Marty is kind and clearly cares about Rory. Meanwhile Rory is jumping between Dean and Logan while Marty, an arguably perfect guy, is right there. Marty deserved better.

Logan
Jess’s persistence is nothing compared to Logan’s. Not many people would rent an entire coffee cart to follow someone around to win them back. Despite Logan’s somewhat romantic persistence and suave demeanor, Logan created many issues between helping Rory steal the yacht or spoiling Rory to an unhealthy degree. He is very similar to Jess, but more condescending and rich instead of angry and broke. I liked Logan when he was trying to win Rory over, but when his family became involved, he changed a bit into not being as patient and being aggitated easily. Logan matches Rory’s new upper-class lifestyle with the dangerous nature Jess possessed. If Logan stayed the same the throughout his pursuit of Rory and relationship, I would be in full support. That being said, he didn’t–and his endless back and forth with Rory became exhausting for viewers.

Now onto Lorelai.

Max
Poor Max Medina: he deserved better. Max patiently waited for Lorelai to be okay with her dating Rory’s teacher. Once they did date, Max was courteous of the relationship with Rory as a student and guy dating her mom. Though it was difficult, they found ways because of Max. They were even engaged and Lorelai jilted him the day of the wedding. Max was such a good guy, and he truly cared for Lorelai and Rory. But per usual, Lorelai’s commitment issues caused her to miss the opportunity with a great guy. And when she tried to rekindle things later on, nothing but infuriation filled viewers’ minds. Lorelai was the problem here, not Max.

Christopher
Christopher and Lorelai’s timing was always a disaster. Between Lorelai’s relationships and Christopher with Gigi, I didn’t mind Christopher and Lorelai together as they came from the same world and both loathed it. The stunt where Christopher tried to break Lorelai and Luke up was not cool whatsoever, but other than that he was a good guy. I don’t think they loved each other quite as much as Lorelai and Max, but the companionship between Christopher and Lorelai was unmatched.

Jason
Jason and Lorelai also never worked because he was so type A. Jason was structured and serious which was just so not Lorelai, who is bouncing off the walls. Plus, the whole thing with Jason, Richard, their company, and it all going under was terrible, so it was bound to never work out. I also hated how he came back and wouldn’t leave even when Lorelai asked emphatically. Overall, a terrible match.

Luke
Here’s where the controversy will come in–I don’t like Lorelai and Luke. He was a great friend to her over the years, undoubtedly. But the chemistry wasn’t developed enough throughout the entire show. Only in the few episodes before did the writers start having Lorelai and Luke develop feelings for each other. And once they started dating, it was a train wreck. Even before they were engaged and April came into Luke’s life, Luke and Lorelai’s lives just didn’t fit. Again, they are great friends but the friends to lovers arch just doesn’t work for them.