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Team Jess, Logan or Dean? An Analysis of the Best Couple on Gilmore Girls

By Nikie Yang


Spoiler Alert! Please don’t read it if you haven’t finished the show yet.


One of the most controversial arguments regarding Gilmore girls is which love interest was the best for Rory, so we’re finally going to settle this argument after 23 years (because I, a 15-year-old high school student, am extremely qualified to do this). Below is a rank of the most compatible couples throughout the show.



Rory and Dean

Dean: Rory's first boyfriend


Toxicity: 7/10

While Dean was a sweet first boyfriend towards Rory throughout their relationship, he was so toxic, misunderstanding and impatient with her e.g. when she didn’t reciprocate the “I love you” phrase to Dean, who then decided to break up with her. Like what? Any understanding boyfriend would’ve been a little more mature about that. To add to the situation further, he broke up with her in public the second time they got back together. The biggest red flag of all.


Compatibility and platonic-ness: 2/10

To be completely honest, Dean and Rory had nothing in common. They were just two kids who liked each other because the only other guys in Stars hollow were 30+. They just didn’t have a spark or connection like she had with Jess or Logan- it all felt very awkward.


Red Flags:

  • Insecure about their relationship

  • Broke up with Rory in public

  • Was extremely clingy to Rory

  • His hair (extreme bowl-cut vibes)




















Green Flags:

  • Willing to change the water cooler at the Gilmore house (ifykyk)

  • Tall

  • Built Rory a car

  • Respected Lorelai and her rules


Overall: 4.5/10

I’m sorry to everyone whose team is Dean, but the facts prove it. He was insecure and clingy throughout the majority of their relationship, and they had nothing in common or any sparks. He was a sweet first boyfriend for Rory, but their relationship would have never made it out of high school. Brownie points for building her a car though.


Rory and Jess

Jess: classic bad boy meets good girl, dating in high school after Rory leaves Dean for him


Toxicity: 5/10

While the two had an intense connection before they dated, Jess didn’t treat Rory the best during parts of their relationship. Such as when he just left Stars Hollow without telling his own girlfriend, or when the two of them would refuse to communicate with each other. Basically, when it wasn’t smooth sailing, things would get ugly quite quickly.


Compatibility and platonic-ness: 9/10

Jess was probably the only boyfriend of Rory’s who matched her intellectual capabilities, allowing them to have friendly debates about the “political and economic state of the world,” the two of them shared similar interests in books, music and movies. Jess and Rory were just a typical right person, wrong time cliche.


Red flags:

  • Left Stars Hollow without telling her

  • Filled with teen angst

  • Was rude to her family

  • Didn’t put as much effort into getting along with the people Rory loved

  • Smashed the car Dean built for her


Green flags:

  • Wrote in the margins of her book 🥰

  • Had lots in common with Rory

  • “Hated everyone but her” cliche


Overall: 7/10

Jess and Rory had so much potential together, and their chemistry before they dated was probably stronger than when they actually dated- but throughout the show, there were times I questioned being on Team Jess. If they pursued a relationship when Jess matured and they both grew as adults, they would’ve been endgame.



Rory and Logan

Logan: One of Rory’s more serious relationships, college boyfriend


Toxicity: 3/10

Throughout their relationship, Logan treated Rory right and made an effort for her- a new concept to him. But sometimes, he would let his privilege take over him and make him quite obnoxious to everyone around him. Their relationship did have a rocky start, but it bloomed into a deep connection between them.


Compatibility and platonic-ness: 8/10

Even though Logan and Rory didn’t share many common interests, Logan was always there for her when she needed him, no matter what. That’s what a good boyfriend does. He would encourage Rory to leave her comfort zone, and we saw her grow further with the help of Logan because the two of them were like salt and pepper.


Red flags:

  • Assisted in stealing a yacht with Rory

  • Slept with his sister’s friends on their break

  • Was rude to Jess when he came back into her life

  • Supported her decision of dropping out of Yale

  • He cheated on his wife in the revival (also Rory’s fault)


Green flags:

  • Was there for her when she needed e.g. when her grandpa was in the hospital

  • He was willing to do whatever to be with Rory who was his first proper girlfriend

  • Never idealised Rory, he loved her for who she was

  • He embraced her family and friends: he took Lorelai, Luke and Rory on a trip altogether

  • Surprised her with rooftop dates


Overall: 8/10

Even though I am Team Jess, all the little things Logan did for Rory were unmatched. The two didn’t have as bad communication issues, and he made Rory genuinely happy. Even though the two hadn’t seen each other in years, their spark was never lost in the revival series.



Rory and Tristan

I know Tristan and Rory never dated, and Tristan left suddenly throughout the show, but it felt illegal to not include him because those two had so much potential together. Tristan had such clear feelings for her and if Rory wasn’t blinded by Dean, they could’ve had a chance. They were the best “what could’ve been” couple in television history.




The verdict:

As much as I love Jess, Logan was the best boyfriend for Rory. He was sweet, and caring and prioritised her when she needed someone to lean on or talk to.



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