Which One of Rory Gilmore’s Boyfriends was the Best?


Rory Gilmore. We watched her grow from an adorable 15 year old to a successful young woman and we couldn’t be more proud if we tried.

She was clever, compassionate, and witty. And boy, could that girl eat!

But when it came to guys, Rory’s choices were a bit all over the place. Clingy Dean, Broody Jess, Reckless Logan. We came to love them all, despite their faults, but which one was actually the best? Before the new episodes arrive on Netflix this month (EEK!), let’s take minute to reflect on the ups and downs of Rory Gilmore’s dating history.

We’ll start with Dean, shall we?


Dean Forester (Jared Padalecki)

Ah, Dean. Rory’s first love.

He built her a car. A CAR. (I can’t even get a second look off a boy and Rory gets a car?!) He took her to events he really didn’t want to go to and he was nice to her best friend Lane.

As well as worshipping the ground Rory walked on, Dean also treated his little sister like a complete princess. (N’awwww!) Taking her to fairs and trick or treating, and generally being a complete cutie. I mean how many older brothers would want to be seen in public with their little sister?

And it wasn’t just his family Dean was good with. If you’re gonna date Little Gilmore, you have to get on with Big Gilmore. Dean wasn’t just polite to Lorelai, he helped her with household tasks and treated her with respect, even after he and Rory had broken up.

Okay, so far Dean sounds perfect, right? But things weren’t always peachy for him and Rory. Though he was clearly infatuated with Rory, he was also kinda clingy and jealous. (Yikes)

His paranoia wasn’t technically misdirected as Rory was clearly not as into him as he was to her. This was confirmed by her obsession with Jess, and when she inevitably got with Jess, no one was all that surprised.

Dean also let his short temper get the better of him when he broke up with Rory in public. Twice. (Ouch)

Even if Dean wasn’t jealous and clingy, there was still the fact that he and Rory didn’t have all that much in common. Sure, he read the books she suggested, and watched the movies she loved, but at the end of the day, they were worlds apart. She dreamed of Harvard and he went into manual labour. It was cute while it lasted though, eh?


Jess Mariano (Milo Ventimiglia)

Jess was always bad news in my opinion, but I guess everyone does love a bad boy. And Rory was no exception.

At worst, Jess was rude and indifferent. Flaky, even. He arrived in Stars Hollow a troubled mischief-maker, with no desire to do anything except get under people’s skin (and steal some gnomes).

He was disrespectful to Luke, and snarky with Lorelai, and did we mention Babette’s poor gnome?!

But his bad behaviour arguably made it all the more romantic when he actually got his act together for Rory.

They shared a love of literature and witty repartee. He definitely rocked that broody, misunderstood academic vibe. And the book in the back pocket gets extra points.

Jess and Rory certainly had a lot in common, but their views and ambitions were just too different to make it work. He matched her intelligence but lacked her drive and while Rory worked hard to get into college, Jess skipped classes and flunked out of high school.

When he was good, he was GOOD: taking Rory on an impromptu concert date and bringing her a big load of food when Lorelai was away. But the fact that he left town to find his dad and didn’t bother to tell Rory is a big thumbs down (and possibly a middle finger).

Jess was actually more romantic towards Rory when she was with Dean. After she became his girlfriend, Jess seemed to lose interest and reverted back to his indifferent manner. (*Sigh*)


Logan Huntzberger (Matt Czuchry)

Logan Huntzberger. Heir to the Huntzberger empire, and typical Yale playboy.

Or so we thought.

Logan charmed the hell out of all of us, (don’t even try to deny it), but also made us roll our eyes HARD.

Like when he thought being on a break was a break UP and slept with all his sister’s bridesmaids. Or when he and Rory had a falling out and he got drunk and jumped out of a plane. (Not his finest moments)

He was charismatic, clever and confident. He was respectful to Lorelai and adored by Emily and Richard.

Logan might have been reckless, especially when he was drunk, but he genuinely cared about Rory and her interests. He has a cheeky sense of humour and though he often teased her, he was never mean spirited towards Rory.

Also, Logan had THE BEST friends, (#FinnAndColinForever), and was a lot more sociable than Rory’s previous two boyfriends.


Okay so we’ve reflected on the evidence and we have to admit (as hot as Jared Padalecki is now), Logan was probably Rory’s best boyfriend.

While Jess had that enigmatic douchebag thing down, he was way too indifferent about life for wide-eyed Rory. Dean was as reliable and loyal as a golden retriever (Well, maybe not to Lindsay), but in the long run, he wouldn’t have been able to keep up with our high-flying Gilmore.

Logan got Rory in a way the others didn’t. He was laid back but immensely caring. He treated Rory with the respect she deserved and stood up for her in front of his family. Plus he looked GOOD in a suit – always a bonus.

Prefer Dean or Jess to Logan? Never fear – All 3 of Gilmore’s guys will be back for Gilmore Girls: A Year In The Life this month (25th November), only on Netflix!

Left to right: Dean, Jess, Logan

Left to right: Dean, Jess, Logan


Divya Soni


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