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If Gilmore Girls was a season, it would be fall. As the nights get darker, nothing can fight the cold quite like a cup of coffee and a Gilmore Girls rewatch. There is something incredibly comforting and nostalgic about a familiar small town filled with quirky, loveable characters who always get into all manner of hijinks and misadventures.
Fifteen years after the show’s finale, fans are still divided about who Rory Gilmore’s best boyfriend is. Whether you’re Team Dean, Team Jess, or Team Logan, the battle of the boyfriends is bloody and controversial. It’s time to settle the debate once and for all. From his secret soft side to his unwavering belief in Rory, Jess Mariano is the best of the Gilmore guys for many reasons.
Updated on June 16, 2023, by David Caballero:
Gilmore Girls is still a beloved and influential show, with newer generations binge-watching it on Netflix and falling in love with Stars Hollow’s quirky and endearing characters. However, the debate about who Rory’s true soul mate remains, with fans divided between Dean, Jess, and Logan. Alas, looking at the evidence and the clues scattered throughout the show, it’s clear that Jess is Rory’s best boyfriend, and there’s enough material to prove it.
13 Rory and Jess Have a Lot in Common
While Dean struggled to keep up with Rory’s caffeine-induced pop culture rants, Jess and Rory traded obscure references like intellectual tennis matches. Although Dean’s promise to watch his girlfriend browse a bookstore for six or seven hours was thoughtful, she desperately needed an academic equal.
From the moment Jess stole her copy of “Howl” to write some notes in the margins, it was clear that Rory had met her match. Whether it’s debating the literary talents of Ayn Rand versus Ernest Hemingway, or Coldplay versus The Clash, there is never a dull conversation between these two.
12 Jess Understands Stars Hollow
The quirky and loveable town of Stars Hollow is a crucial part of Rory’s life. She loves being a part of it and participating in its oddities – from innovative festivals of living art to 24-hour dance marathons; what other people might find confusing or outright ridiculous, Rory finds endearing.
Jess shares Rory’s understanding of Stars Hollow. Despite hating the town when he first arrived, Stars Hollow eventually warms Jess’s cold heart; he even learns to enjoy the town meetings. Unlike Dead, who never quite fits, and Logan, who looks down on the town’s eccentricities, Jess is part of Stars Hollow, much like Rory.
11 Jess Inspires Rory
Rory is initially drawn to Jess because of his intelligence. She is attracted to his intellect and personality, finding him interesting and admirable even; he barely tries at school yet is far more knowledgeable than every other student. When Jess becomes a published writer, Rory feels genuinely impressed at his achievement.
Dean and Logan were never on par with Rory – they were less ambitious, less driven, and more complacent. Jess was the only one who could match her, and Rory admired his dedication to improving himself despite his troubled background. Jess inspires her to write the book about her life, showing how much he knows her and how good he is at bringing her out of her comfort zone.
10 Jess Challenges Rory
Although these two brainy bookworms have much in common, they don’t agree on everything. As Rory explains to Paris in Washington, people need someone compatible, “but not so compatible that they’re boring.” Jess constantly keeps Rory on her toes, which simultaneously frustrates and excites her.
While the rest of Stars Hollow treats Rory like a perfect princess who can do no wrong, Jess encourages her to let loose a little. She even skips school to visit him in New York! They wander around an eclectic record store together, sharing shy smiles, cementing their place as a fan-favorite TV couple.
9 Jess and Rory Have So Much Chemistry
After their day together in New York, Jess returns to the town he supposedly hates for her. Their reunion and first kiss are crackling with chemistry. They are like opposite magnetic poles that are inexplicably drawn together – a gravitational pull that cannot be resisted.
Dean may have been the perfect first boyfriend because he was safe. They largely stuck to hand-holding and simple pecks. However, as Lorelai begrudgingly admits, it was about time for a Jess. While Rory and Jess dance around each other and their feelings, the tension in the air is thick, which makes their first kiss all the more satisfying.
8 Jess Is a Secret Softie
Although Jess has been labeled the town bad boy, a regular Holden Caulfield (and a predictable TV stereotype), he has a sweet side. He regularly performs unexpected romantic gestures that he refuses to take credit for. When Rory is home alone, he brings her a care package, claiming it’s from Luke. When it’s revealed that it was Jess’ idea, he squirms in discomfort under Rory’s knowing gaze.
At the Bracebridge dinner, Jess destroys the front-runner in the snowman competition so that Rory’s Björk-inspired creation can win. Once again, he avoids owning up to it. He doesn’t want the recognition; he just wants to see Rory happy.
7 Jess Cares About the Little Things
When Rory decides to go to Yale, Jess points out that it is only “22.8 miles” from Stars Hollow from him, accidentally revealing that he looked it up. He tries to play it off, claiming that he “just a hit a couple of buttons on a computer,” but Rory is already smug and smitten. He eventually stops resisting, pulling Rory in and kissing her head.
Although Jess left town before Yale, this shows he was planning their future together back then. As Lane observes, Rory and Jess are like “a really sweet, old, agoraphobic couple” who met when they were too young and immature. Right person, wrong time.
6 Jess Never Cheated On Rory
Although this seems like the bare minimum, Jess is the only boyfriend who never cheated on Rory or used her to cheat on someone else. Logan cheated on Rory with several of his sister’s bridesmaids and then cheated on his fiancée with Rory in the revival. Similarly, Dean pursued Rory while he was still married to Lindsey.
Furthermore, while Rory is something of a serial cheater, she never cheats on Jess, either. She did cheat on both Dean and Logan with Jess, which is not great, but it proves that she was happiest with him and couldn’t resist coming back. Rory and Jess had issues but were always committed to each other, cementing them as one of the TV couples robbed of their happy ending.
5 Rory Always Believed in Jess
From the moment Jess stumbled into Stars Hollow with a book in his back pocket and a head full of adolescent angst, Rory believed in him. She stood up for him against everyone who couldn’t see past the arrogant smirk and constantly reminded him of his potential.
When Jess turns up years later, a published author with his life together, she is pleased but not surprised. As she tells him, he has such a wonderful brain, and she always knew that if he sat down and stopped shaking it about, he could do something like this. When Jess tells her that he couldn’t have done it without her, it’s clear how much her steady belief changed his life.
4 Jess Convinced Rory to Go Back to Yale
Unlike the driven and exceptional Paris (who should’ve been a more prominent Gilmore Girls character), Rory is more unstable and insecure. A crisis of confidence leads her to drop out of college, and Jess is the one who convinces her to go back. Logan encourages her downward spiral as they both sail off into the sea on a stolen yacht, while Lorelai freezes her daughter out in an attempt at tough love. Neither approach works, leaving Jess to pick up the pieces.
Jess has a habit of reappearing in Rory’s life when she needs him most. He has never been afraid to call her out and can get through to her. After he confronts her, Rory snaps out of it, going back to Yale and getting her life back on track.
3 Jess Always Believed in Rory
When the revival kicks off, Rory Gilmore’s life is falling apart. At 32 years old, she is unemployed, broke, and lacks underwear. Back in her hometown and having an affair with her engaged college boyfriend, history seems to be repeating itself.
Just like a decade previous, when Jess showed up at exactly the right time, convincing her to go back to Yale, he reappears again, this time convincing her to write a book. While they clearly don’t get to see each other much as adults, there is an ease to their interactions that never left. Once again, Jess’ intervention is what sets Rory back on track.
2 Jess Still Loves Rory
The Gilmore Girls revival received mixed reviews, but Jess’s role was universally acclaimed. The character’s final shot reveals him wistfully looking through the window at Rory. Although he tells Luke it’s ancient history, that look tells a different story. Things in his personal life are stable but never permanent. Why waste time on new relationships if you’re still hung up on someone from your past?
While it took Rory a few months to realize her feelings for Jess in the beginning, he was pining after her from the start. After that look, it’s clear that nothing has changed. He has always loved her and always will.
1 Jess Is Rory’s Luke
Rory and Lorelai have one of the best mother-daughter relationships on television. They are connected on a deeper, more meaningful level, sharing every crucial aspect of their lives and always supporting each other. Rory and Lorelai’s journeys also mirror each other, with the revival going so far as to have Rory pregnant by a wealthy, immature man who won’t be a prominent figure in her child’s life.
In every way that counts, Jess is to Rory what Luke is to Lorelai. The revival even hints that Jess will fulfill the same uncle-like role in Rory’s child’s life that Luke fulfilled in Rory’s. It’s a poetic and beautiful similarity that cements Jess as the best man for Rory, someone willing to adapt to her circumstances and build a future together.
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