It’s officially fall and I don’t know about you but once October hits, I queue up the most autumnal-feel-good show I can think of: Gilmore Girls.
While I’ve exhausted all seven seasons more times than I can count, every time I start up the pilot again and get reintroduced to the characters of Stars Hollow, a quaint town I’ve always dreamed of living in, I still feel the same rush of excitement I did the first time. I’d do just about anything to be able to watch this show for the first time again.
I know I’m not alone in this fall-binge phenomenon. However, no matter how near-universally loved this show is, there remains a stark division within the fanbase: which of Rory’s boyfriends was the best?
I’ve seen this show so many times that I know the boyfriends as if they were my own. Today, I’m here to share my personal opinions on each of them and my ultimate rankings of each of Rory Gilmore’s loves.
Rory is by far not my favorite character in the show, but she somehow manages to be the favorite of basically every guy she meets. Her first boyfriend, Dean, played by the dreamy Jared Padalecki, starts out as an innocent little first love that we all want to experience at 16 years old. He is very romanticized and drawn up to be the “good guy,” especially in contrast to the Chilton Academy troublemaker, Tristan Dugray.
However, I could write a whole book on why Dean was the most toxic and manipulative of Rory’s boyfriends and was arguably the worst of the four main men. I can’t deny that I loved him at the start when I didn’t know about his anger issues, possessive tendencies, and gaslighting behavior yet. Don’t even get me started on that one episode where he expects Rory to be his 1950s housewife — cooking and cleaning for him while he goes to work. I rank Dean at number four on this list, with his only redeeming factor being how easily he can change a hot water bottle and the fact that he built her a car. Remember, material gifts don’t equate to healthy relationships!
Tristan never got his time to shine, mainly because heartthrob Chad Michael Murray left the show so early for one of my other favorite shows, One Tree Hill. However, he was just the right amount of snarky and sarcastic, always providing witty banter and dreamily delivered lines. I don’t know how Rory didn’t fall for him, especially after the Romeo and Juliet play, but he was rude to her from the start, though he had different intentions than how Rory took it. Plus, she was still under the haze of Dean. Still, I rank him at number three, which is honestly embarrassing for Dean, since Tristan had about two seconds of screen time.
Jess. When I first watched the show in early high school, I was a hardcore Jess stan. He reads. What more could a girl ask for? He was also snarky, funny, and exuded the “bad boy” energy from a 2014 cheesy Wattpad book. In contrast to Dean, he was every parent’s worst nightmare, as we see from Lorelai’s adamant hatred of Jess. I love Jess, but looking back on the show in my tenth rewatch has shown me that he was never going to be Rory’s endgame. I think they are much better suited as good friends, especially as they matured and became entirely different people. They’re the epitome of the “right person, wrong time” trope and my 15-year-old heart still aches for what they could’ve been.
Plus, I can’t forget that one episode where Jess crosses some really shaky boundaries and exhibits his morally gray character. Overall, I’d rank Jess second and will always love Milo Ventimiglia and mourn the loss of the Jess spinoff show we never got.
Finally, the pièce de résistance: Logan Huntzberger. I’m the most avid Team Logan stan out there. He fit Rory so well, especially the Yale and beyond version of her. He wouldn’t have been a good match for Chilton Rory, but he was the right person at the right time. He was also so perfect: he allowed her to face her fears, explore other opportunities, and supported her in any of her foolish endeavors. He also had the most self-awareness of any of Rory’s boyfriends: he knew who he was and wasn’t and never lied about it. Logan also forced Rory to face some uncomfortable truths about herself that were crucial to her own character development, and honestly what more can you ask for in a relationship?
AND he bought her a Birkin bag? The difference between this and the car from Dean is that Logan was actually a decent man apart from the bag, whereas Dean was seen as a decent man because of the car.
I will always love Logan. He’s a trust fund baby with daddy issues but still manages to come out on top. He was what Tristan was supposed to be and that honestly makes so much sense. I’ll never forgive Rory for the ending with Logan (which I won’t spoil).To be fair, no matter how much Logan deserves the number one spot on Rory’s boyfriends list, there was no better man in all of Gilmore Girls than Dave Rygalski.