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Gilmore Girls 101: Ranking Of Rory Gilmore’s Boyfriends

Gilmore Girls fans have tons of strong opinions about Rory Gilmore’s boyfriends. Here is why it’s good that she never ended up with any of them.

For a show that tells the story of a fast-talking and fun mother and daughter, Gilmore Girls is all about the romance. For seven years, we loved watching this duo chat about their lives over tons of junk food, make pop culture references like they were going out of style, and oh yeah, fall in love. Rory Gilmore, in particular, has three serious boyfriends over the course of the series, and fans have some pretty serious thoughts about who she should have ended up with. This important topic has been

Rory Gilmore, in particular, has three serious boyfriends over the course of the series, and fans have some pretty serious thoughts about who she should have ended up with. This important topic has been getting more headlines lately with the upcoming Netflix revival that will start streaming on Friday, November 25.

In my opinion, Rory is exactly where she needs to be, and that’s single. She should never have ended up with Jess, Logan or Dean. While we all love these characters and think they are adorable and sweet – which they are, for the most part – there’s a reason that she is still on her own.

Read on to find out why Rory never ended up with any of her three boyfriends.

1) Dean: The Small Town Boy

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It’s hard not to love Dean. When we first meet him, he’s got that super floppy and adorable hair, and he can’t stop staring at Rory. He’s bagging groceries at the local market and he’s amazed by the concentration that she has when she sits under her favorite tree and reads. It doesn’t take long for these two lovebirds to start talking, start hanging out, and eventually, fall in love.

But because Dean is her first love, that mean that out of all of Rory Gilmore’s boyfriends, he is the one who should definitely not end up with her. That’s kind of the way that it goes with first loves, right? First loves hold a special place in our hearts, but we don’t end up with them.

First loves need to stay in the past. That’s because you grow up, become older and wiser, and you become a totally different person. Judging from the Netflix revival trailer that shows Rory as a single woman who is “rootless” and traveling around as a journalist, Rory is definitely different from who she was back in high school. She and Dean would have absolutely nothing in common now. He’s a small town boy and she’s definitely meant to live in a big city.

Yeah, Dean is very sweet, but he’s way too innocent for her.

2) Jess: The Bad Boy

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Ask Gilmore Girls fans who their favorite one of Rory Gilmore’s boyfriends are and we’re most likely to say Jess. First of all, he’s hot. Second of all, he’s a bad boy. What more could we ask for in a TV boyfriend?

The problem with Rory and Jess is that they always feel more platonic than romantic. They bond over their shared love of reading, but that doesn’t necessarily mean they’re meant to be together.

Jess needs to be on his own and come to terms with his past. He’s reeling from an unhappy childhood and he’s definitely a pretty angry teenager. He and Rory are ultimately polar opposites: he’s a bad boy, she’s a good girl, and that’s never going to change, no matter how old they both get.

Jess is in her Rory’s life for a good reason: to help her transition away from her first love, the super innocent Dean, and to help her begin the process of growing up. One prime example? When they get into a car accident. This proves to Rory that bad things do happen.

He is good for Rory because he showed her that she needed to stop being so sheltered. But it’s hard to imagine the two of them ever ending up together, especially considering the fact that they never fell in love with each other.

3) Logan: The Preppy Boyfriend

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Out of all of Rory Gilmore’s boyfriends, Logan is definitely the most complicated, and even the most controversial. Seriously, ask any fan and you will hear that they absolutely hate him or absolutely love him. It’s difficult to like him when he first comes onscreen, and sometimes it’s even harder as time goes on.

That’s because at the end of the day, Logan is an immature rich boy who really doesn’t deserve Rory. He’s mad at his dad for never loving him enough, which is fair enough. But he acts in such a childish way that it’s hard to imagine him ever being a good enough boyfriend for anyone, let alone the lovely Rory Gilmore.

When the two of them first start dating, it’s really hard as a super fan (or any kind of Gilmore Girls fan at all) to root for them. That’s because while Rory may think that she knows Logan’s background because he is wealthy and sophisticated like her grandparents, she’s actually wrong. He’s from her grandparents’ world, sure, but that’s not her world. Her world is Stars Hollow with its quirky people and junk food and comfort.

Ultimately, the two of them are living in two totally and completely different worlds, and that becomes even more obvious toward the end of the series. Logan really doesn’t understand Rory at all. He proves that when he proposes to Rory. Fans all over were scratching their heads, totally confused. Why would he do that? Of course she was going to say no.

If we know anything about Rory, we know that she is determined to make it as a journalist and that she has a work ethic like no other. She would never, ever throw that away to get married, and that’s just the way that it goes.

4) Rory: The Single Girl

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According to the recently released trailer for the Netflix revival, Rory is totally and completely single. There are absolutely zero references to her having a boyfriend or even a kind-of boyfriend.

Instead, the focus is on how she keeps moving around and can’t seem to find a place to land, both physically and metaphorically. Her grandma Emily seems really upset about this, but Lorelai just shrugs it off, acting like it’s super exciting.

What’s so awesome about Rory Gilmore is that while she’s definitely open to love and having a serious boyfriend, she’s totally okay with who she is. She is pretty much the definition of a confident and cool single girl since she would never let her solo or relationship status define her. She wants to be defined by her career, her smarts, her effort and her life.

Out of any of Rory Gilmore’s boyfriends, it seems like Jess is the most likely for her to still have a bit of a crush on… at least from what we can tell from the trailer. That’s because there’s a scene of them having coffee and joking about what a mess her current life has become. But that still doesn’t seem super romantic, so it’s more likely than not that nothing is going on between them.

5) The Boyfriend Yet To Come

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Ultimately, I believe that Rory’s true love is still out there. We will see what happens in the Netflix revival. There don’t seem to be any hints of her falling in love again or even meeting another cute boy, but maybe they didn’t want to show us too much. Given her smarts and good looks and charm, I don’t think Rory Gilmore will be single for long. Her guy is still out there, and he’s going to be much more perfect for her than any of her three boyfriends.

That’s because at this point in her life, Rory has had three boyfriends. Sure, she wasn’t super serious with Jess, but she definitely learned a lot from her time with him. She knows enough about who she wants to be with to be able to recognize him when he comes into her life, that’s for sure.

She’s grown up, she’s gotten out of Stars Hollow, she’s seen the world, and maybe now she’s really ready to fall in love… and make it last this time. Sometimes it’s even better to fall in love later in life since you have enough time and space to find yourself, to figure out your career, and to ensure that you don’t have to give anything up.

The world has always been Rory Gilmore’s oyster. Now she just has to find the guy. And we will all be watching the Netflix revival very, very carefully.

Do you think that Rory is meant to be with Dean, Jess, Logan, or none of them? Share your thoughts with us in the comments below!

About the author

Aya Tsintziras

Aya Tsintziras is a freelance lifestyle writer and editor. She loves coffee, barre classes, 90s television and pop culture. She is a food blogger at A Healthy Story and shares gluten-free, dairy-free recipes and personal stories.

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