Why Rory belongs with Jess

The Gilmore Girls revival is this Friday, as we all know. I’ve been avoiding reading about it as much as possible to avoid spoilers, although I can see all three ex boyfriends are making an appearance. Which made me think about who Rory belongs with, if any of them.

That’s important – it might be be someone else, or no one. But what if it is one of them? Who would it be?

I’ve given this a lot of thought, and I am landing on Team Jess.

Note: If you haven’t gotten all the way through Gilmore Girls, this does contain some spoilers.

Let’s look at the other two contenders first, with a brief recap of the relationships.




Rory’s first boyfriend. They date and are super cute together, but then she gets eyes for bad boy Jess, and ends up leaving Dean for Jess.

After Rory and Jess have broken up, Dean marries Lindsay at a very young age, then cheats on her with Rory – this is how Rory ends up losing her virginity to Dean. Dean gets divorced and Rory and Dean get back together.

The break up is epic. Dean comes to pick her up at her grandparents’ house and Rory comes stumbling, tipsy, out of the pool house with a gaggle of Yale guys behind her, wearing a cute dress and a freaking tiara.

Dean says, sadly and without anger, “I don’t belong here. Not anymore. Do I?”

And it’s true. He doesn’t. Rory has been swallowed up by Yale life, by the upper class society of Hartford, and small town Dean does not fit into that world.

My thoughts

I like Dean. I like Dean a lot. But, he’s the kind of guy who will live in the same town he went to high school in, forever. Staying in the same job, forever. Admittedly, a decent job, moving up in management and making okay money kind of job, but still.

His kids will go to the same high school he did. His family will have dinners at his parents’ place every Sunday. They will never leave Stars Hollow. It’s a very decent and even admirable life, but it’s not for Rory.

And not because she’s too good for him, part of the elite class now – it’s because Rory has bigger dreams than that, and Dean would have held her back.

The thing is, is that Dean would be a really great choice for a lot of women.  And it’s really tempting to pick Dean, because that would mean Rory would stay in her Stars Hollow bubble forever. Which would make all of us happy and we could continue to watch the show play out forever and ever in our favorite town.

But would it make Rory happy? Isn’t she destined for bigger things than the small town life?



Ah, Logan. The college boyfriend, the final boyfriend of the series, and arguably the most significant. Logan is the ultimate pretty boy, party boy, spoiled rich kid with a trust fund kind of boy. Logan and Rory actually date for three years, most of her time at Yale.

There is a point where they have a fight and Logan thinks they’re breaking up and Rory doesn’t realize this. Logan sleeps with several of his sister’s friends during this time, which Rory doesn’t find out for quite awhile, and then it’s quite awhile still before she’s able to let that go. But they move on, even surviving long distance for awhile while he’s in London.

At the end of the series Logan proposes to Rory at her graduation party in front of her parents, grandparents, and friends. Rory is stunned and tells him she has to think about it. She ultimately says no, and I can’t blame her.

Not necessarily because of the age thing – she was 22 at this point – but because they had never even talked about marriage before. I mean, what was he thinking?

My thoughts

As with Dean, I do like Logan a lot. I don’t think badly of him for the playboy reputation. I can forgive him for those slew of girls he slept with, because he was young and in college and drinking a lot, and probably genuinely did consider him and Rory to be broken up at the time.

But he is absolutely not the right guy for Rory. I would definitely pick Dean over Logan, if it were between the two of them.

I mentioned before that Rory should be destined for great things and not be constrained to a small town – this is admittedly something Logan could provide for her. She could travel the world with him. He can afford it.

But she’d always be something of a trophy wife. She’d always be standing behind him, not next to him, so to speak. Case in point, he wanted her to give up trying to find a job after graduation and join him in California. And follow his dreams, putting hers on hold. That’s not Rory.

Even though he wouldn’t mean to, Logan would darken Rory’s special Rory glow. He’s too big and powerful and has too large of a personality. Rory needs to shine, and Logan would outshine her.



Forgive me for going out of order, because I wanted to save my choice for last.

Luke’s nephew Jess is the quintessential bad boy who comes to town when Rory is still in high school, dating Dean. Although dark, moody, and an all around jerk, Jess exhibits a soft side with his surprising love of books. And, shocker, Rory also is a huge bookworm, and this is how they bond.

She tries to fight her feelings for him, but they finally come to a head when Rory kisses Jess right before Sookie’s wedding. She and Dean call it quits, and she begins a new relationship with Jess.

They effectively break up after Rory refuses to sleep with him at a party, resulting in a fist fight between Jess and Dean. Shortly afterwards, Jess abruptly leaves for California without telling Rory where he’s going.

Fast forward a couple of years, and Rory and Jess see each other again. He comes to town and goes out to an awkward dinner with Logan and Rory, during which time Jess and Logan throw a bunch of testosterone around. He pops up again when Rory goes to Philadelphia to see his new bookstore/art gallery/publishing house.

Because yes, Jess owns his own business now and has gotten his shit together.

My thoughts

Even though he comes on the show as kind of an ass, Jess proves even then and going forward that he loves Rory. Like when he looks up how far away Yale is, because he wants to stay with Rory when she goes away to college, and isn’t threatened by her dreams and ambitions. When she later drops out of Yale, Jess is the voice of reason. I could go on.

But the main thing that sells me is when Jess has his own bookstore – and has written his own book. And no, not just because I heart books. But because it shows that he’s not the immature drifter he once was.

Jess has his own ambitions, his own dreams, and he accomplishes them – he just doesn’t do it in the same linear fashion everyone else does, with high school then college then the Big Job. He really genuinely changes for the better.

Rory, too, grows a lot over the course of the show. Her high school years depict a shy, reserved young girl, and then she transforms into this take-charge, bad-ass young woman, who can run the Yale Daily News, coordinate DAR events, and stand up for herself when the situation demands it.

Final Note

Jess and Rory have both showed they can change and evolve overtime, growing into the people they’re meant to be. Dean and Logan, while great guys, will almost certainly never change. They would hold her back; Jess would let her blossom.