Gilmore Girls: 8 Times Jess Was Rory’s Best Boyfriend (& 7 When It Was Logan)

Fans of Gilmore Girls have remained invested in the series to this day thanks to its heartfelt relationships, especially the precious bond between Lorelai and Rory. But it’s not only the familial ties that keep viewers coming back for binges — it’s the love stories, too. While it would be safe to say viewers unanimously supported Lorelai and Luke, the fandom is a bit more heated over who was the best fit for Rory.

Team Jess or Team Logan is the question for most Gilmore Girls fans. They’re the only two men left standing at the end of the revival, Gilmore Girls: A Year in the Life. With Jess still carrying a torch for Rory and Logan likely being the father of Rory’s baby, it’s time to revive the age-old argument of who was the best boyfriend.

Updated on March 2nd, 2021 by Kristen Palamara: Although the main relationships in Gilmore Girls were between mothers and daughters and mostly focused on Lorelai and her daughter Rory — while also focusing on Lorelai’s relationship with her mother Emily — there was still a lot of room on the show for Rory to have three main romantic relationships throughout the series. Rory’s boyfriends included Dean when she was still in high school, then Jess, and Logan when she was fully attending Yale. Rory’s best boyfriend is a matter of opinion, but most of the time it is between Rory and Jess and Rory and Logan. 

15 Jess: Challenged Rory To Challenge The Rules

Jess and Rory began their relationship on tumultuous ground as Rory and Dean were still in a relationship when they started having feelings for each other. Rory had moments of rebellion, but it all escalated when she met Jess.

Jess was a character who was already breaking all of society’s rules like cutting class and trying to be independent of Luke. While these might not be the right choices, they still led Rory to start questioning her meticulous plans in life and whether they were right for her or just what was expected of her.

14 Jess: He Brought Rory Food

Rory was looking forward to a night on her own to do laundry and order in food when Lorelai was away for the night, but Paris and Jess crash her party. Paris needs support and comfort from her frenemy, which at first annoys her, but then Jess arrives with food.

Jess says that Luke was worried about her and told him to bring it, but it becomes clear that he had gathered the food on her own and brought it for Rory so he could check in on her. It’s a sweet gesture and the three end up having a great night together full of stimulating conversation and delicious eats.

13 Logan: Became Close To Her Grandparents

Although both Jess and Dean did somewhat attempt to become close with Rory’s family after realizing how important her mother and grandparents were to her, Logan was the one who tried the hardest to become close to Emily and Richard.

It was easier as the Gilmores already had respect for Logan and his family, but Logan did keep building a relationship with them on a personal level instead of just relying on his family name. Jess never fully tried to connect with Rory’s family even though they knew how close she was to them, and he even once showed up late to their dinner with a black eye.

12 Jess: Still Told Her The Truth After They Hadn’t Seen Each Other For So Long

Jess was back in town to have a promotion party for his book and Rory decided to go even though the two hadn’t been in contact for a while. They hadn’t seen each other in years, but Jess was still completely honest and real with her. He told her that being with Logan and dropping out of Yale wasn’t like her at all, and claimed that he knew her better than almost anyone.

It showed that Jess truly cared about her and her own happiness and didn’t feel like he was telling her Logan wasn’t the right match for her because he wanted to be in a relationship with her again. His intentions were pure and selfless.

11 Logan: Going Against His Family To Support Rory

Rory and Logan were a great match in her grandparents’ opinion, but the Huntzbergers felt much differently. They belived that Rory wasn’t good enough to join their family and thankfully, Logan immediately challenged them on it and stood up to them.

Logan supported Rory and went against his family when they claimed that the Gilmores didn’t compare to the Huntzberger family. He didn’t hesitate to express his true feelings for Rory and knew he wouldn’t break off the relationship just because of his family.

10 Jess: Left Her Notes In The Margins

When he first appeared, Jess was a love-him-or-hate-him type of character. The rebel of Stars Hollow, he left negative impressions everywhere he went. But there was one moment in his introduction that had fans swooning: when he stole a copy of Howl from Rory’s bookshelf and returned it freshly annotated.

Rory couldn’t help but fall in love with Jess when she read the notes he left in the margins for her, showing off his literati mind and highlighting their shared interests. It was one of the first times Rory connected with a peer — let alone a cute new boy — on that level. For a while, only Rory got to see this brainy side of Jess, and his little secret remained one of the series’ sweetest moments.

9 Logan: In Omnia Paratus Scene

The Life and Death Brigade sure had some fun during their run on Gilmore Girls, including the exhilarating umbrella jump. When Rory tagged along to her first Brigade as a journalist, determined to uncover their secrets, she ended up falling head over heels for Logan instead.

Logan always pushed Rory to venture beyond her comfort zone — albeit a little too far sometimes — and this was a moment of major growth for her. It’s clear even in the “In Omnia Paratus” scene that Logan would be a boyfriend who could lead Rory into a life of adventure and a little magic, too.

8 Jess: Looked Up How Far Yale Was From Star Hollow

The bad boy with a heart of gold is an archetype that’s been done before, but few were better than Jess Mariano. After he and Rory become “a really sweet, old, agoraphobic couple,” Jess begins shedding some of his tough layers. In one adorable instance, he came clean about looking up how far Yale is from Stars Hollow.

Rory was touched that the normally closed-off Jess had taken the time to map out exactly how far she would be living from him when she goes went to the Ivy League institution. Of course, this isn’t the only time Jess let his guard down for Rory, but it was one of the most endearing. Only the best boyfriends would pay such close attention.

7 Logan: Got How Special Lorelai Was To Rory

Anyone determined to be in Rory’s life long-term has to understand how important Lorelai is to her. Logan got it. When Rory was mad at him, he sought out Lorelai’s help in talking to her, although Lorelai couldn’t believe it at first. That’s not the only time he went straight to the source.

When Logan decided to propose to Rory, he asked Lorelai for her blessing, even before telling Rory about his big move to San Francisco. Lorelai’s opinion meant a lot to Logan, and he wanted to talk to her first about it. On the other hand, Jess and Lorelai just could not get along.

6 Jess: Convinced Rory To Go Back To Yale

After Rory dropped out of Yale and began to spin out, Jess was the one who finally gets through to her and inspired her to get back to school. Even Lorelai wasn’t able to do that. Unlike Logan and Dean, Jess pushed Rory to be herself and not settle for anyone less. The effect they have on one another is mutual, as Jess told Rory he couldn’t have published his book without her support, either.

Jess grew out of being an irresponsible and misunderstood teenager and into someone who was capable of loving Rory in a healthy and helpful way. It might seem strange, but Jess consistently proved himself to be the best boyfriend when he and Rory were not actually together.

5 Logan: Was There For Rory During Richard’s Heart Attack

While lecturing Rory’s class at Yale, Richard suffered a heart attack. The ensuing arc was one of the show’s most devastating. The Gilmore family rallied around Richard as he recovered at the hospital. And, in an important show of support, Logan made sure he was there for Rory.

Logan actually arrived at the hospital via helicopter, having dropped everything as soon as he heard about Richard’s condition. That’s the kind of partner Rory needs at her side. Logan knew that Rory’s family came first and stayed with her during a difficult time.

4 Jess: Encouraged Rory To Write A Book

Jess reappeared in the revival during another wayward moment in Rory’s life. While she was a struggling writer working at the Stars Hollow Gazette, Jess paid her a visit. Rory felt she was floundering, but Jess recognized she was in a rut, proposing just the right idea to break her out of it: write a book about her and her mother. And Rory did just that.

On the other hand, Dean and Logan incited an extramarital affair, the grand theft of a yacht, and a much-maligned angsty drop-out arc. It’s hard to argue with the results; even when they’re not together, Jess proved to be a steady presence in Rory’s life.

3 Logan: Gave Rory The Most Romantic Gift Ever

In the final season premiere, Logan took off for London, but not before leaving a mysterious present for Rory. At first, she was just as confused as the audience — it was a rocket. Not a plane ticket to London or a bouquet of a hundred roses or something else ritzy and romantic. A rocket.

As it turns out, the rocket had a special meaning: it was a representation of true love from Logan’s favorite episode of The Twilight Zone. In a fit of excitement, Rory recalled watching the episode on the couch in her grandparents’ pool house. Knowing how much it meant to Logan, Rory declared it the most romantic gift she’s ever gotten. That’s extra boyfriend points for Mr. Huntzberger.

2 Jess: THAT Look

It was the look seen around the fandom. After Luke noticed there was something between Jess and Rory, Jess gazed longingly at her through the window on his way out. It seemed he still had feelings for her after all this time. The swoon-worthy scene confirmed without a doubt that she really was the one for him.

And there may be hope for them after all. Just like Luke pined after Lorelai before she returned his affections, Jess and Rory appear to be following a similar trajectory. Keeping that in mind, perhaps Jess is the one for Rory, too.

1 Logan: Proposed To Rory

The boy who never wanted to be a boyfriend was ready to become a husband for Rory. After three years of dating, Logan asked Rory to marry him at her graduation party. While the moment divided fans, there’s no denying it was an earnest effort on his part.

It was the best way he knew how to express his commitment and devotion to Rory, the one woman who truly captured his heart. Even though they decide not to stay together, they eventually rekindled their romance in the revival while Logan lived in London, engaged to a French heiress, and Rory was getting her bearings as a writer. After all those years, they just couldn’t let one another go.