We Ranked Rory Gilmore’s Boyfriends So Fight Amongst Yourselves
Rory Gilmore makes some pretty awful romantic choices on Gilmore Girls.
From jealous boyfriends, to cringe-worthy dates, it can be pretty hard to watch — and let’s not forget that Rory isn’t perfect either. And while there are some really sweet moments, Rory’s dating life is (for the most part) pretty terrible. Especially due to the fact that Rory can’t seem to stop sleeping with men that aren’t hers to sleep with.
But throughout all the turmoil, treachery and love, who was the best out of Rory’s romantic partners on Gilmore Girls? And who was the worst?
Let’s find out!
Every one of Rory Gilmore’s boyfriends, ranked:
Dean worshipped Rory. And while Dean could be a kind and caring boyfriend, he could also be pretty full-on. Like when he gives Rory a CAR for their three-month anniversary, before confessing his love, then breaking up with her when she doesn’t feel ready to say ‘I love you’ back. Yikes.
Dean’s also quite cruel, jealous, and possessive — with both Tristan and Jess. And let’s not forget that Dean publicly broke up with Rory TWICE, including in front of the whole town at the 24-hour dance. Also, he takes Rory’s virginity while he is MARRIED TO ANOTHER WOMAN.
In my humble opinion, any cute moments between Dean and Rory just can’t make up for these pretty major issues.
Rory and Graham’s ‘date’ ends up being a pub crawl, where Graham pressures Rory to drink. She isn’t keen, but he doesn’t seem to care and eventually ditched her to go party with his mates.
Rory meets Trevor during freshman english at Yale and their date is painful to watch. He sits on the same side of the table as her, doesn’t laugh at her jokes, and the date ends up being rather boring and awkward.
This date shouldn’t have happened, mainly because Robert is one of Logan’s best mates, although Logan and Rory weren’t exclusive at this point — despite their obvious mutual feelings. Robert doesn’t seem super interested in Rory but she accompanies him to a party anyway, which ends up serving as a way to make Logan jealous.
Rory meets Tristan at Chilton, and for the most part, he’s a bit of an entitled dick. He makes fun of her, calling her ‘Mary’ (the virgin), and regularly picks fights with her boyfriend Dean, seeming to delight in making Rory uncomfortable and Dean jealous.
That being said, Tristan could be charming, and they do share a cute kiss. But then he gets sent to military school, so they never really get a chance.
Marty was smart, caring, humble and hard-working — not what I expected from ‘the naked guy’ who passed out in Rory’s hallway. He’s got a great sense of humour, and seems to have good chemistry with Rory and her grandparents, even joking about the naked hallway incident with Richard.
But by the time Marty confesses his feelings, Rory’s already into Logan. Marty also loses points later when he’s dating Lucy and lies about knowing Rory, and for the time he drunkenly compliments Rory in a way that’s a bit too much coming from ‘just a friend’.
If you don’t remember Paul, don’t worry — no one else does either. Paul, by all accounts, seems like a pretty great boyfriend. While he might appear to be a little boring, he was also really thoughtful, remembering small details about Luke and Lorelai, and even bringing them gifts.
But even though Paul is Rory’s boyfriend for most of Netflix’s four-part revival A Year In The Life, he’s barely in it. Their relationship consists of occasional texts, and Rory spends most of the season intending to break up with him — but forgetting. Of course, Rory was also sleeping with Logan for their whole relationship, so it was never really going to work out.
I wish Jess and Rory could’ve gotten together when they were older and wiser because teenage Jess had lots to work through. He had an attitude problem and didn’t tell Rory the truth about getting kicked out of Stars Hollow High School. He also MOVES ACROSS THE COUNTRY without even saying goodbye.
But Jess is also smart, funny and kind — and he loves Rory. He’s there to pick up the pieces after Dean humiliates her in front of the whole town, and even when they aren’t together, he encourages Rory to be her best. Like when she drops out of Yale, it’s Jess who helps her find herself again. And he does it again in A Year In The Life, by encouraging her to write a book when her journalism career is failing.
Sadly, by the time Jess gets his act together, Rory’s moved on. But even a decade later, it’s hinted that he still has feelings for his first love.
Rory is Logan’s first serious relationship and while it starts off rocky, they end up developing a really deep connection.
Logan isn’t always the best communicator: he felt like he couldn’t talk to Rory when his first post-college business venture goes bust, and earlier he interprets their “break” as “broken up” and ends up sleeping with other people. He can also be a jealous jerk, like when he baits Jess into a fight.
But for the most part, Logan’s there for Rory. He gives her a CAR to go comfort Lorelai after another Luke breakup. He gives her a place to stay when Paris kicks her out. And when Richard has a heart attack, Logan is there to support Rory — and Emily — however he can. He even flies from London to surprise her with a romantic rooftop date. Sure, romantic gestures are way easier when you’re filthy rich, but the good intent was there.
Logan even PROPOSES and even though Rory says no, ten years later in A Year In The Life, their love is clearly intact.
Every episode of Gilmore Girls can be streamed on Netflix.