Who Should Rory Gilmore End Up With?

Photo: The WB Television Network/Photofest.
Is there any television debate more contentious than this one? It's the ultimate question for Gilmore Girls fans: Who should Rory Gilmore end up with in the end?

For those who don't know, there are three teams backing past boyfriends as strong contenders — Team Jess, Team Dean, and Team Logan. All claim that Rory Gilmore's heart has always belonged to one man. All claim that she is only compatible with one man. All claim that the proof is in the show's past seven seasons.

With Gilmore Girls: A Year in the Life coming to Netflix in November, we thought you might need a refresher on Rory Gilmore's past romances. Who knows? You may even realize that the boy of your dreams in the early aughts will never deserve the love and affection of Rory Gilmore.

Click ahead, and decide who's her perfect match.
1 of 5
Photo: Warner Bros/Everett Collection.
Team Dean
Dean Forester is an accomplished mechanic, an athlete (hello, hockey), and has a close relationship with Luke. Rory Gilmore met him at Stars Hollow High School.

Dean is her first everything: her first kiss and the first person she has sex with. Despite this, Rory doesn't know how to respond when Dean tells her he loves her; fortunately, they're able to bounce back when she admits, under her own terms, that she loves him too ("Because I love you, you idiot!").

But here's where things get janky: Dean breaks up with Rory because of Jess. They agree to be friends and Dean even marries another woman (Lindsay). But during his bachelor party, he tells Luke that he would rather be marrying Rory.

Later, Rory and Dean have an affair, and when Dean's wife finds out she very publicly kicks him out of their home. You might think that this would mean smooth sailing for Rory and Dean, but it doesn't. Dean breaks up with her and leaves Stars Hollow.

If Dean and Rory get back together it would be the culmination of their roles as high-school sweethearts, and hopefully a chance for them to mature together.
2 of 5
Photo: The WB/Photofest.
Team Jess
Jess Mariano is Luke's nephew. Sparks fly when Jess and Rory meet for the first time. Rory starts falling for him when she discovers his love of books and good sense of humor. She first kisses Jess while she's still dating Dean.

After months of Rory stringing Dean along, they finally break up. She and Jess begin their relationship, but Rory misses Dean's reliability — something Jess can't offer.

When Luke tells Jess he needs to finish school or leave, Jess chooses to leave town. He comes back a short while later and he tells Rory he loves her — before skipping town again. The next time he returns, he asks Rory to run away with him. She says no.

When Rory next sees Jess, he's written a novel. Their reunion is interrupted by a very jealous Logan. It all leads to Jess asking Rory why she dropped out of Yale and why she's dating someone like Logan. It's exactly the push she needs to get back on track with school.

In the end, they see each other again in Philadelphia. Rory kisses Jess, but also tells him she loves Logan.

A reunion for these two would mean that they were always soulmates thanks to their love of learning and literature.
3 of 5
Photo: The WB Television Network/Photofest.
Team Logan
Logan Huntzberger is Rory's last serious boyfriend on the show, but for Logan, Rory is his first serious relationship ever. He's been kicked out of multiple boarding school and has been in some trouble with the law, but Rory's grandparents love him.

When Rory first met Logan she was worried that he was exactly the kind of selfish rich kid her mother always warned her about. But she changes her mind when he helps her with an article. It doesn't hurt that he also comforts her when Dean breaks her heart for the last time.

First, they try a no-strings relationship, but it doesn't work out. Eventually, they become monogamous. But the return of Jess makes Logan very jealous; he and Rory take a break, during which he sleeps with someone else.

Every breakup leads to grand, romantic gestures and lavish gifts from this guy. Logan bravely asks Lorelai for help in winning back Rory's heart — and it works.

Sure, there's drama (the Marty-Lucy spat, Richard's heart attack, Logan's father's business), but the couple sticks together. Eventually, Logan asks Rory to marry him — and she turns him down.

A reunion for these two would mean that Rory had time to explore life on her own, but realized that at the end of the day, she needs Logan.
4 of 5
Photo: The WB Television Network/Photofest.
Team New Partner
Through the show's seven seasons Rory has cycled through every heteronormative TV-boyfriend trope: The artist bad boy, the nice guy, and the spoiled rich kid with a soft side. But these clearly aren't the only kinds of partner that exist.

When Gilmore Girls: A Year In The Life comes to Netflix, rather than revisiting old relationships that have run their course, maybe it's time for Rory to meet someone new. She's a nuanced, intelligent woman, and she deserves happiness. And maybe it's not with Logan, Dean, or Jess.

At the end of the day, maybe there's nowhere left for these relationships to go. Dean walked away, pretty definitively; Jess was hurt that she used him to get back at Logan, but understood that it was over; and Logan took his ring back and left her after she refused both of his proposals.

Maybe Rory Gilmore's soulmate isn't one of the guys she's already dated — maybe we haven't met him, or her, yet.
5 of 5
Photo: The WB Television Network/Photofest.
Team Solo Rory
Finally, maybe Rory Gilmore doesn't need to end up with anyone for our sake. We damn well know that she doesn't need to be with anyone to be happy with herself — please remember that she refused to marry Logan because she wanted her future to be free of any limitations. Talk about a smart woman.

Rory kicking ass in her career, still having the best mother-daughter relationship ever, and being there for her friends could be far more satisfying than a forced romantic arc.

Rory Gilmore isn't one of our favorite characters because she attracts hot guys; she's one of our favorite characters because of her intelligence, tenacity, and because she's so damn relatable!

Although we don't know what's coming in the Gilmore Girls revival, just remember that a romance not a necessity. Rory could end up with Rory — and it will still be a happy ending.

More from TV


R29 Original Series