Rory, Logan, and Dean Are Christopher. Jess Is Lorelai. Here’s why.

The Gilmore Girls love lives will probably be debated among fans until the end of time.
I think that’s down to good writing.

Each fan has their own opinion about which relationship they wanted for Rory or Lorelai.

I was ‘Team Logan’ when I first started watching the series at the age of 17.

Then, after a few rewatches, I began to be more ‘Team Jess’ because even though he left her heartbroken, without a word, and most of the time had a bad attitude, when he came back to visit for a bit, he was always able to read Rory so well.

He called her out on things she needed to hear, and she trusted that.

He really was like Rory’s compass. Encouraging her to go back north.

Also, the effort he had put into changing his life for the better was clear to see. And on some level, I admire that. It does take a lot of effort to become content in yourself.

However, now that I’m in my 30s, and have probably watched the main series about 8 or 9 times, and the sequel 3 times, I’ve come to the conclusion that Rory shouldn’t end up with any of them.

Let’s start with Dean…

He was a good first boyfriend. He seemed nice and sweet, and genuinely interested to know more about Rory when they were getting to know each other.

Also, in the first season Rory was shy, didn’t make friends easily, and was a bit of a people pleaser.

So, if we add the ‘timing’ thing that most relationships go through, the timing of them meeting then, while they were still at school, not quite sure who they were yet, was kind of perfect for them.

It was basically ‘right person, right time, but not their forever person.’

I say this, (sorry Dean fans) because if the timing were different and he had moved to Stars Hollow when Rory was at Yale, she probably would’ve thought he was nice and cute, but they would’ve been in completely different mindsets.

He clearly wanted a more settled life, with a wife and kids. A serious relationship that’s a bit more traditional.

Rory at that point was more ambitious. She would want something casual, not serious. She wouldn’t want kids yet. And she had aspirations of travelling the world. They probably wouldn’t have gotten together at all.

Dean thought his first love would become his wife someday. Much like Christopher with Lorelai, Dean always seemed to hold onto the idea that first love could become forever. Even years later, there was still an affection there that never completely disappeared.

Next up is Rory and Logan…

Most of this is based on their relationship in ‘A Year in the Life’. I was a bit surprised that they were secretly still seeing each other. I knew there’d be some sort of connection, but not this.

On my third watch-through of AYITL, during the scene where Rory is looking out of the window while Logan is still asleep in bed. You could tell by her thoughtful expression she had to end it with Logan, and that it would be the last time they’d see each other.

That whole scene had a bittersweet finale tone to it. And it suddenly clicked,
‘Oh. They’re both Christopher…’

Rory and Logan will always love each other, no matter how much time has passed. They’ll keep going back to each other, like magnets. Their ‘what if’ person.

In many ways, Rory has become Christopher too. She keeps returning to a relationship she knows can’t truly move forward, while struggling to find a direction that feels like her own.

She’s very much at a crossroads in her life, feeling lost and unhappy with how things turned out. And that is the exact point where I think she realised she can’t get over Logan, but she has to.

Just as Chris had to accept that he had to keep his distance from Lorelai when she got back together with Luke.

Logan was brought up by a strict father, much like Christopher did. Their dads had carved out plans for their futures. Things they expected from them.
And in one way or another they loosely followed the plan, but they made plenty of mistakes along the way.

They’re both cheeky and flirty. Charismatic and confident. They’re both in love with a Gilmore Girl.

Logan clearly wanted to keep seeing Rory in the last episode of AYITL. And when Rory implied they shouldn’t see each other again, he tried to find a way for them to carry on.

The subtle look and tone of ‘don’t do this Rory’ from Logan reminded me of a heartbroken Christopher.

And Lastly… Jess is Lorelai.

There are a few similarities I noticed between Jess and a younger Lorelai.

The more obvious parallel is that they were both angry at feeling trapped. The people around them often judged them without really knowing them, creating that same feeling of being an outsider.

However, Jess was clearly troubled and struggling. Basically, a big jerk when he first appeared in Stars Hollow. The disrespect to everyone but Rory, seemed like a built-in defence mechanism.
‘Don’t let them get too close, otherwise they might leave me.’

That insecurity reminds me a lot of Lorelai in season 1. She did a similar thing with Max.
When she realised things were getting too serious, her instinct was to bolt. To break it off, before he had the chance to break it off with her.

The inadequate feeling of, ‘if he knew the real me, he won’t like me anymore, and then I’ll be left heartbroken.’

I think that’s essentially what Jess did when he left town.
It was completely wrong, he should’ve been honest with Rory on that bus, but I think he was acting on emotion and insecurity, and felt like the only people who believed he could be a better person were Luke and Rory.

He needed to find his own way.
And it was interesting that he went to his estranged Dad first, but that’s what led him on the path to finding himself, and what he wanted to do, what he could achieve, without the judgement of family or the town of Stars Hollow.

Lorelai had Mia to look up to as a mentor, when she started working at the Independence inn.
I think her encouragement helped Lorelai to figure out what to do and who she wanted to be, while caring for a baby Rory.

For Jess it was slightly different.
I think having Luke as a role model, he did learn to appreciate what Luke had done for him.

Luke may be grumpy, but he’s also a gentle soul. I think Jess really needed to learn some life lessons from his uncle.

That might be why Jess reminds me so much of Lorelai.
– They both needed distance from the people and expectations that defined them.
– They both found mentors who believed in them.
– And they both eventually built a life that felt authentic to who they really were.

That’s also why I think Jess understood Rory better than anyone else. He wasn’t trying to tell her who she should be. He was trying to remind her who she already was.

I’m not in any way saying Jess and Lorelai are identical, but they both had to leave in order to find themselves.

Lorelai couldn’t become Lorelai while living under Emily and Richard’s expectations.
Jess couldn’t become Jess while being viewed as the troubled kid who’d never amount to anything.

Both had to step outside of the roles people had assigned them.

I don’t think Rory should end up with Dean, Logan, or Jess.

Dean represents the first love that was right for its time.

Logan is her Christopher. The person she’ll probably always love, but can’t quite build a life with. And vice versa.

And Jess is her Lorelai. The person who understands her and emotionally supports her when she needs it.

But understanding someone isn’t always the same thing as being ‘meant to be with them’. Jess is a good friend to Rory, and perhaps that’s where he works best.


Of course, that’s just my interpretation after far too many Gilmore Girls rewatches 😄

I’d love to hear your thoughts, whether you agree, disagree, or have a completely different perspective. Feel free to leave a comment below. And as always, let’s keep the discussion friendly and respectful.