If Gilmore Girls were a time of year, it would be fall. As the nights get darker, nothing beats a cup of coffee and a rewatch of Gilmore Girls to get rid of a cold. There’s something very comforting and nostalgic about a familiar small town full of quirky, likeable characters who are always getting into all kinds of hijinks and misadventures.
Fans are still divided 15 years after the show ended about who was Rory Gilmore’s best boyfriend. No matter if you’re on Team Dean (wrong), Team Jess (right! ), or Team Logan (very wrong), the battle between the boyfriends is a bloody one. It’s time to end this argument for good. Jess Mariano is the best of the Gilmore guys for many reasons. He has a secret soft side and never stops believing in Rory.
Both Rory and Jess share a lot.
Rory Gets a Howl from Jess
Dean had a hard time keeping up with Rory’s pop culture rants fueled by caffeine, but Jess and Rory traded obscure references like they were playing intellectual tennis. Dean’s promise to watch his girlfriend look through a bookstore for six or seven hours was sweet, but she needed a smarter friend more than anything.
Rory knew she had met her match the first time Jess took her copy of “Howl” so she could write in the margins. Whether they are talking about Ayn Rand vs. Ernest Hemingway as writers or Coldplay vs. The Clash as bands, these two never have a dull conversation.
But He Also Challenges Her
Gilmore Girls’ Jess and Rory
Even though these two smart bookworms agree on a lot, they don’t always see things the same way. In Washington, Rory tells Paris that you need to find someone who is compatible with you, “but not so compatible that they’re boring.” Jess always keeps Rory on her toes, which frustrates and excites her at the same time.
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 smile shyly to each other as they look at records in an unusual record store.
They get along so well.
The First Kiss of Rory and Jess
After spending the day with her in New York, Jess goes back to a town that everyone says he hates, just for her. Their first meeting and kiss is full of chemistry. They are like opposite magnetic poles that are drawn together by a force that can’t be stopped, like gravity.
Dean might have been the perfect first boyfriend because he was safe. Most of the time, they just held hands and pecked each other. Lorelai reluctantly agrees, though, that it was time for a Jess. There is a lot of tension in the air as Rory and Jess dance around each other and their feelings, which makes their first kiss all the more satisfying.
He Has a Secret Weakness
At the Bracebridge Dinner, Rory and Jess
Jess has been called the town’s bad boy and a Holden Caulfield look-alike, but he also 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 and says it’s from Luke. When he finds out that it was Jess’ idea all along, he moves around awkwardly as Rory looks at him.
At the Bracebridge dinner, Jess destroys the snowman that was in the lead so that Rory’s snowman, which was inspired by Bjork, can win. Again, he doesn’t say that he did it. He doesn’t want the praise; all he wants is for Rory to be happy.
He researched it.
Rory asks Jess how far it is.
When Rory decides to go to Yale, Jess says that it is only “22.8 miles” from Stars Hollow, which shows that he looked it up by accident. He tries to explain it away by saying, “I just pushed a few buttons on a computer,” but Rory is already proud and in love. He finally gives up, pulls Rory in, and kisses her on the head.
Even though Jess left town before he went to Yale, this shows that he was already thinking about their future together. Lane says that Rory and Jess are like “a really sweet, old, agoraphobic couple” who met when they were too young and immature. Wrong place, wrong time.
He never cheated on her. Jess and Rory cheat on Logan.
Although this seems like the bare minimum, Jess is actually the only boyfriend that never cheated on Rory or used her to cheat on someone else. Logan cheated on Rory with a few of his sister’s bridesmaids, and then he cheated on his fiancée with Rory in the revival. Dean also liked Rory even though he was still married to Lindsey.
Rory has also never cheated on Jess, even though she has cheated on other people before. She cheated on both Dean and Logan with Jess, which is bad, but it shows that she was most happy with him and couldn’t stay away. The most important thing was that Jess was always true to her.
He got her to agree to return to Yale.
Rory is persuaded by Jess to go back to Yale.
Jess is the one who talks Rory into going back to college after she loses confidence and quits. As they sail out to sea on a stolen yacht, Logan encourages her downward spiral, while Lorelai freezes her daughter out in an attempt to be tough. Neither way works, so Jess has to clean up the mess.
Jess tends to come back into Rory’s life just when she needs him the most. He has never been afraid to tell her the truth, and luckily, she listens. After he talks to her about it, Rory comes to her senses and goes back to Yale to get her life back on track.
Rory has always had faith in him.
Rory gets his book from Jess.
Rory believed in Jess from the moment he showed up in Stars Hollow with a book in his back pocket and a lot of teenage angst on his mind. She stood up for him against everyone who couldn’t see past his cocky smile, and she constantly reminded him of his potential.
When Jess shows up years later as a published author, she is happy but not surprised. She tells him that he has a great brain and that she always knew he could do something like this if he would just sit down and stop moving around. When Jess tells her that he couldn’t have done it without her, it’s clear how much her steady faith changed his life.
And He Believed in Her Right Back
The Revival is about Rory and Jess.
Rory Gilmore’s life is falling apart when the new season starts. She is 32 years old, has no job, no money, and no underwear. History seems to be repeating itself now that she is back in her hometown and having an affair with her college boyfriend, who is already taken.
Just like ten years ago, when Jess showed up at the right time to persuade her to go back to Yale, he shows up again to persuade her to write a book. Even though they don’t see each other very often as adults, they can still talk to each other with ease. Again, it is Jess’s help that gets Rory back on track.
He Still Loves Her
Jess in Autumn
In the last shot of Jess in “Fall,” he is looking longingly at Rory through the window. Even though he tells Luke it’s an old story, that look says something else. Things are stable in his personal life, but they never stay that way. Why bother with new people if you can’t get over someone from your past?
Even though it took Rory a few months to figure out how she felt about Jess at first, he had been in love with her from the start. When you look at it that way, you can see that nothing has changed. He’s loved her since the beginning, and he always will.