Netflix Shows: Gilmore Girls-Dean, Jess, or Logan?

Screenshot from ‘Gilmore Girls’ Season 2 (2001) starring (left) Milo Ventimiglia and (right) Alexis Bledel. Copyright goes to Warner Bros. Television.

Hi! It’s Annie!

Though this show isn’t originally a Netflix show, that’s where you can watch it now! Which is exactly what I’ve been doing recently with my Mom. I grew up with this show because my Mom loved it, and the mother-daughter bond portrayed in the show really made this something special for me and my Mom. So as we’ve been talking about it as we re-watch it, we ended up on THE fan question. The question on the minds of the fans of this show has always been; who should Rory have ended up with? Obviously, we don’t really ask this question about Lorelai because we know she should have ended up with Luke, which is what happened. But the newest season of ‘Gilmore Girls’ threw the Rory question even farther into focus. So-who should Rory have ended up with? I think that if you actually look at the options, the answer is pretty obvious. But let’s look anyways!


The first candidate is Dean and he’s a pretty good one too. Rory’s first love and the absolute sweetest boy. At least at the beginning. When we first meet Dean, he’s absolutely perfect for Rory. He’s unassuming and gentle and just wants to make a good impression with her Mom. The way he handles Rory’s school bullies when he takes her to the Chilton dance is adorable too. He doesn’t pay them any mind and brushes them off, often finding ways to get Rory out of the situation in a safe way. Then everything falls apart after their first break up. Dean tells Rory that he loves her and freaks out when she’s unable to say it back. And though I do understand his heartbreak and the fact that they’re really young, Rory even explains why she’s unable to say anything back. It’s partly because of how divided her family is and because of that it takes her a while to get to the point where she can comfortably say it, even if she wants to. Dean does not understand this and breaks up with her. Then when they get back together, Jess gets thrown into the picture. Dean is immediately over-protective, even yelling at Rory for hanging out with Jess in front of her friends at some points. This definitely strains their relationship until it’s kind of a shadow of what it was. When Rory eventually leaves him, he’s still insanely jealous and tries to pick a fight with Jess several times. This all culminates into Dean jumping into a marriage very young and then him and Rory having an affair. Not to mention the episode where he says he’d rather have the kind of wife who makes dinner for him when he comes home from work. A little archaic. But their relationship did start out wonderfully before it crashed and burned.


The second candidate could be described as Rory’s bad boy phase at first glance. Jess is a troubled kid when he comes into town. He picks fights with kids from his school, seems very ungrateful to Luke who took him in, and plays pranks on the people of Stars Hollow. He quickly gains the reputation of being a delinquent. Rory is sure that he has some kindness in him, even though she doesn’t always get along with him. This portrayal is great! Rory doesn’t exactly hate him nor does she like him, which feels a lot more realistic than hating him outright or blindly believing that he’s a good person. As she gets to know him she realizes that he really does care, but his home life before this was so screwed up that he doesn’t really know how to show it. Jess softens up after spending more time with Luke and Rory. When they start dating, he’s still very troubled and kind of a jerk. He flaunts his relationship with her over Dean sometimes. But he’s much more understanding about Rory being friends with Dean than Dean was ok with her being friends with Jess. He also understand Rory’s hobbies and interests a lot more than Dean does. Jess leaves and comes back multiple times, often because he thinks he’s not good enough for Rory, until finally he leaves to find himself. When he comes back again, Rory has dropped out of college, is living with her grandparents, and is dating Logan. While Jess has matured, is a lot more chilled out and less troubled, and has even written a book; Rory has made so many mistakes. Jess reminds her that this isn’t her. And though he raises his voice, he doesn’t do it out of anger. He does it because he wants his friend back and even comfortingly puts his hand on her elbow before remembering her birthday. Jess also seems to still have a connection with Rory in the new season. But he didn’t start out that great.


The rich boy third candidate that might have been Tristan in an earlier season if he hadn’t left the show. Logan is certainly charming, but he’s also a massive jerk. Just like Tristan was! The thing is, he doesn’t mellow out. Logan consistently cheats on his girlfriends, gets everyone around him in trouble, and abuses his money and power. Often he pays no mind to Rory or her emotions. Let’s just say- Jess had a point when he said that Rory shouldn’t be dating a guy like him. Logan is a cautionary tale more than anything, despite his charms. A smiling face doesn’t necessarily mean a good heart. The new season just proves this as Logan is shown to have not changed in the slightest bit over the years. Logan will always be Logan. A frat boy with a tendency towards the awful. He should have never had a girlfriend in the first place. So, really, he’s out of the running for Rory in my eyes. When Rory admits to Jess that she loves Logan, you just can’t help but feel sorry for her after all he’s put her through.

Who should have ended up with Rory?

You might have already guessed, but I definitely think it’s Jess. Jess was definitely not the best boyfriend to Rory when they were first dating, but when he comes back he’s perfect for her. It’s almost like watching Lorelai and Luke. When one of them is ready to date, the other one isn’t. They just keep missing each other. But they will always have each other in their lives, and eventually you can’t help but wonder if that’ll lead to them finally getting together. Even when Jess wasn’t the best boyfriend, he was always a support for Rory that she needed. Dean was a nice boyfriend, but he didn’t completely understand Rory. Jess did. Jess was always unselfishly in love with Rory, sometimes even giving up habits in order to make her happy. Like quitting smoking and refusing to fight Dean. Though I believe that each of these three were integral to Rory’s growth, I think that, while watching the series, there is only one clear answer for Rory. Jess and Rory will always be endgame in my mind.

See you across the pond!

Sincerely, Annie

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