Ranked: Every single one of Rory Gilmore’s romantic interests
Is Jess or Logan coming out on top?
Though Gilmore Girls at its core is a show about a mother and daughter relationship, it doesn’t stop multiple romantic relationships forming over the years and becoming a heavy focus of the show. The relationship between Luke and Lorelai features in all seven seasons as a constant “will they? Won’t they?” storyline. Spoiler alert, they will. However whilst fans generally agree Luke and Lorelai are soul mates, there is heavy debate over which of Rory Gilmore’s boyfriends was right for her.
Across the seven seasons Rory has three serious boyfriends – Dean, Jess and Logan. They all have their strengths and a lot of weaknesses. However they’re not the only men Rory is interested in. Throughout the series Rory goes on a number of dates and experiences multiple flirtations with a number of different guys.
But who is the worst of all these guys? And which of the boyfriends is the best for Rory Gilmore? We’ve ranked all her romantic interests across the seven seasons and the Netflix special “A Year In The Life” to truly decide once and for all.
Just a note, Marty will not be included in this, as to be a love interest, the other person has to at least express some sort of romantic interest and Rory could not have friendzoned poor Marty harder.
These are all of Rory Gilmore’s love interests ranked from worst to best:
A fuckboy if ever I’ve seen one. Looks as interesting as a plank of wood. He was definitely only going to be interested in sleeping with Rory and probably wouldn’t have remembered her name.
Extra bad points for fetishising her kiss with Paris.
This man has zero self-respect. He’s essentially a grown up Dean. He follows Rory around like a little puppy and has no problem being walked over and forgotten.
She literally abandons him at a restaurant? We shouldn’t be surprised at Rory walking over guys at this point but c’mon Paul you need to up that self worth.
They literally went on one date that was arranged by Emily and it wasn’t really an actual date. He took her along for some drinks at the pub with his mates which wasn’t great form but he probably only invited her out of obligation so I can’t hate him too much.
Also look at his shirt, a guy like that was never going to get on well with Rory.
If you want a real life example of a tragically awful date then watch season four, episode five of Gilmore Girls where you will see Trevor take Rory out.
They met in an English class and like many of the men Rory dates he was a total suck up. He completely agreed with her point in the class just to get her on a date.
And then the actual date, god it was painful to watch. His blazer was hideous, he sat next to her rather than opposite and he was just plain vanilla. Granted Rory told a joke about breath mints so he didn’t have loads to go on but still Trevor and the date were a dud.
Like his attitude to life Robert’s relationship with Rory was there for a good time not a long time.
He didn’t seem deeply interested in her or any other women on more than a surface level. However he was decent to Rory at the party they went on a date to and Rory was literally only using him to make Logan jealous.
I doubt they would have gone further than one or two dates, but he was nice enough.
Ah Tristan Dugray, he was exactly the kind of boy you fancied when you were 14 years old, apart from Rory who did not fall under his spell.
He was charming, a serial flirt and had a killer smile. However you just know you couldn’t trust him and apart from Rory he didn’t really appear to see girls as anything other than potential conquests.
It’s also hard to know if Tristan was genuinely interested in Rory or just the challenge of trying to get her. He had moments of kindness and seeming human, however given his actions in the Netflix episode he doesn’t seem to have learnt any lessons in life and is just a bit of a man-whore.
Dean started off great. He was kind, respectful and he genuinely enjoyed spending time with Rory’s family aka Lorelai. He practically worshiped the ground Rory walked on and that was kinda the problem.
He was intense – who says I love you and makes their girlfriend a car after three months together? And then he pressured Rory to say it back, which is understandable when you’re a teenager with your first love but it was just too much and incredibly off putting.
He had anger streaks and by the time Jess came around he was possessive, clingy and basically had no self-respect. In fairness he had a right to be worried about Jess and Rory and yet after a week of sulking around after their breakup he is more than happy let Rory into his life again and walk all over him.
And then we have to address the Lindsay situation. Dean was definitely not over Rory by the time he married Lindsay as evident by starting a fight with Jess at the house party, saying Rory’s name whilst drunk the night before his wedding and of course when he slept with Rory whilst being married.
He started off as a lost puppy and by the time the series ended he was just a spineless young man.
Look it pains me to not put Jess as number one because by the Netflix special he is practically perfect and if anything, too good for Rory. However as the majority of his appearances were in the original episodes this is what we’re going off.
Jess begins as a bit of a dick. He’s moody, argumentative and has zero respect for anyone, which when you’re 16 is attractive but in reality it’s just a bit pathetic. Yes he may have been a great match for Rory intellectually but he was a pretty terrible boyfriend. He didn’t call and just assumed she would be available for him, which is kinda the energy she gave out. He lied a lot to her throughout their relationship about his job and school, which whne you’re 16 is pretty big. He just left without warning or even a goodbye. He was clearly afraid of his emotions which is one of the reasons he had to run away to the other side of the country.
He tried to pressure her into sex and couldn’t let his feud with Dean go despite being the one who ended up with Rory.
However in the later seasons Jess is far a better match for Rory due to his maturity and they actually would have had a great relationship had Rory not been in love with Logan. Jess is calmer and would have been encouraging of Rory’s dreams. But it was too little too late and Jess learnt the hard lesson that timing is a real bitch.
Truthfully no one is deserving of the title of Rory’s best boyfriend because they all have a LOT of faults, however Logan is the best match for Rory by the end of the show.
Logan is cheeky, flirty and always the centre of a party and these personality traits actually worked to bring Rory out of her shell. He adored her, always saw the good in Rory and was an intellectual match for her. They seemed to have a real friendship as part of their romantic relationship.
He appeared to be deeply in love with her – the rocket, the surprise trip back from London and being by her side when Richard had a heart attack.
Though he didn’t want an exclusive relationship at the start he was always honest with Rory which he can’t be condemned for. And yes he could be considered a rich trust fund kid but hey so are Rory and Lorelai despite acting otherwise. He didn’t always have the best influence on her, stolen boat anyone? Logan didn’t always respect her dreams – when he proposed, sure it was nice but at the end of the day he wasn’t prepared to give up his goals and so he wanted to Rory to move across the country for him.
Logan did sleep with someone else after he thought they had broken up however he thought they were over so only the true Rory fans can hate him for that one.
Ultimately Logan is the only one who will fit with a grownup Rory – he pushes her out of her comfort zone, cares for her, they can resolve arguments without a dramatic breakup and he’s got those great journalism connections Rory just can’t give up.
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