Ranking Rory's boyfriends: Which of the 'Gilmore Girls' guys truly deserved Rory's heart?


Gilmore Girls inspired much good cheer during its seven seasons on the WB and CW, but its fanbase still found room to argue. Over what, you may ask? Over which of Rory Gilmore's boyfriends was best, of course.

Years after it went off the air, the debate rages on. Ahead of Gilmore Girls: A Year in the Life's debut on Netflix, let's settle it once and for all: Who was Rory's best love interest? To do that, we've rounded up every single guy she so much as flirted with — and included the different seasonal versions of her primary men. (Jess in season two is different than Jess in season six, after all.)

Who came out on top? Read on to find out.


17. Marty, season seven: Original recipe Marty, as you'll see later on this list, was a good guy! Last-season Marty was trash, a goon who was dating Rory's friend Lucy but insisted on lying about previously knowing Rory. His deceit screwed things up for Rory, Lucy and Logan, and he was never seen after his lie was exposed. Marty's split personalities were the onus for splitting the multi-season love interests up, because it's deeply unfair to judge his earlier persona against this horrible, unreasonable man.

16. Graham: Graham was a guy Emily tried to set her granddaughter up with at the end of season four after she had been single her entire freshman year. He turned out to be a jerk who invited her out, ignored her in favor of his friends and left her at the bar. Bye, Graham!

15. William: This was the guy who Rory decided to be bold and ask out in her dorm's laundry room. He said no, which is fine, and then told stories about a girl who was desperate to date him at parties. He wasn't talking about Rory, she found out too late (after confronting him publicly), but all things considered, he still seemed like a douche.

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14. Logan Huntzberger, seasons five and six: Ugh, early Logan sucks. He toyed with Rory's heart for a while, negging her and constantly calling her "Ace." Once they finally did date, he constantly dragged her out to get drunk and had a part in sapping her of all of her drive and passion. He got better, but hoo, he was rough trade at the start.

13. Dean Forester, seasons four and five: Dean was never great, but his last two seasons really served as evidence of how far he fell from grace. Getting married young to a woman you don't love, then cheating on her with your first love, then dumping that first love again when you get a little jealous? Bad look.

12. Sean: If you've forgotten (like I did before making this list), Sean was the guy Rory briefly flirted with while on Spring Break in Florida. He then witnessed Paris and Rory kissing and got straight-dude-pervy about it. It's a no for Sean.

11. Jess Mariano, seasons three and four: As much as I love Jess, even I have to admit these seasons weren't his finest hours. When he was first introduced, his bad-boy vibe worked because he was an idea for Rory, not an actual partner. When he comes back later, he's matured and grown. In these seasons, all his worst attributes are on display, and he suffers for it.

10. Dean Forester, seasons two and three: This isn't the worst Dean, but it's far from the best Dean. This Dean got jealous of Rory's friendship with Jess to the point of breaking up with her in front of her whole town at a dance marathon. Was she being unfair to him? Sure! But two wrongs don't make a right, and one could argue she was being unfair to him because he had gotten so possessive. Not a great boyfriend for Rory.


9. Tristan Dugray: In another life, I would probably rank Tristan higher. He was sort of a proto-Logan: troubled, blond, rich boy, albeit much younger and thus less reprehensible. He had a good exit, and he had irresistible charm (not to mention hair). But I have to acknowledge that under his good hair laid a real jerk, and that relegates him to the list's halfway mark.

8. Trevor: Trevor asked Rory on a date to a glorified Buca di Beppo, then sat on the same side of the table as her and failed to keep up any conversation with her. He was designed to be a bad date, but to be fair, he did try. He was just an awkward college freshman dating a girl who had never been in anything but serious relationships before. He was doomed to fail.

7. Robert: On the one hand, Robert seemed like a sweet guy who wanted to get to know his friend Rory better. He invited her out to a party, treated her well and didn't let awkwardness with Rory's semi-fling Logan get in the way. On the other hand, he chose to be friends with Logan and the numbskulls of the Life and Death Brigade, which can only speak poorly on his judgment.

6. Marty, seasons four and five: Poor Marty tried so hard to let Rory know he was interested in his initial run on the show, but when he finally got up the nerve to say it, she was already moony-eyed over Logan. Marty is a warning for sweet guys everywhere: There's no good reason to wait to communicate.


5. Dean Forester, season one: Early Dean is truly great Dean. He was the kind of nice boy with just enough edge to make a girl swoon. He read books (remember how, before Jess came along, Dean was a reader?) and tried hard to impress Rory's mother. He was a dream, a dream that was far too fragile to last. He wasn't perfect, but hey, he built her a car.

4. Tucker: Tucker, for those who haven't rewatched season seven recently, was the dreamy TA who replaced Richard after his heart attack. Rory developed a crush on him, and while Logan was very patient with Rory upon her confession of said crush, part of us wishes she'd just dumped him and run away with Tucker. Intellectual dreamboats don't come along too often, Rory!

3. Jess Mariano, season two: Jess in season two versus Jess in season three is a pretty good juxtaposition of what happens when you're trying to woo a person versus what happens when you've got them. In every way that Jess was an inattentive jerk later, he was devilishly invested in season two. He was still a weasel, but an attractive one, with his heart generally in the right place.

2. Logan Huntzberger, season seven: This was a welcome surprise: Gilmore Girls wrote Logan more effectively after Amy Sherman-Palladino left. He was still a flawed guy, but his maturation was evident, and his care for Rory grew in spades. Finally, just as the show was ending, Logan haters could understand why Rory was so attracted to this man — making it even sadder when she turned down his marriage proposal and broke things off for good.


1. Jess Mariano, season six: Speaking of maturation, no one showed how he grew on this show better than Jess Mariano. When he came back in season six for two episodes, he snapped Rory out of her reverie, getting her back on track at Yale, broken up with Logan (unfortunately temporarily) and back in contact with her mother (thankfully permanently). He also made good with his surrogate father Luke, and showed that he had great potential as a career author and publisher. It's sad that Rory eventually chose Logan, because her and Jess' connection when she visited him in Philadelphia was a clear sign that he was the right man for her. Perhaps A Year in the Life will give them a way back to each other.