Gilmore Girls: 10 times Jess was Rory’s best boyfriend (and 7 times it was Logan)

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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 June 21st, 2022, by Lynn Gibbs: Rory’s boyfriends on Gilmore Girls is a tough topic for many friends. Among Dean, Jess, and Logan, who could have been possibly good enough for Stars Hollow’s golden child. All of Rory’s boyfriends offered something to her life but Jess and Logan offered her the most for her future by the time the reboot rolled around. While Rory was still in love with Rogan in the reboot, Jess wasn’t completely out of the picture. With that being said, who was the perfect match?

Times When Jess Was Rory’s Perfect Match

Jess Challenged Rory To Bend 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.

RELATED: 15 Best Episodes To Rewatch If You Miss Rory & 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. Her rebellious moments led to some great episodes with Jess, however.

Did Lorelai Like Jess More Than Logan?

To be fair, Lorelai wasn’t fond of anyone Rory dated except for Dean. She was against Rory seeing Jess because of his bad-boy reputation and she hated the woman Rory became when she dated Logan because of her rebellious stage.

However, in the reboot, it became clear that Lorelai’s disdain for Jess left. He was in and out of their lives for years due to her relationship timeline with Luke, so she grew to care for him. Logan, to her knowledge, was out of the picture and was unaware her daughter was secretly seeing him. This was because Rory knew how her mother would feel about the situation since he lived abroad and was engaged to another woman. No one thought Lorelai would come around to Jess but she did with time.

Jess Never Cheated On Rory Like Logan Did

Jess wasn’t a perfect boyfriend to Rory but the one thing he never did that Logan did was cheat on her. There were plenty of times during their short relationship that Jess didn’t communicate well enough with Rory or include her in things, but those things were insignificant compared to the woes Logan put Rory through with other women.

At the start, Logan was honest about being interested in other women, which didn’t bother Rory at the time but it eventually took a toll on her. When they later had a rough patch in their relationship, Rory found out Logan told others that they broke up and he slept with multiple of his sister’s friends. Jess wasn’t an angel but he didn’t stoop as low as Logan.

He Surprised Rory With Her Favorite Food To Be Close To Her

Rory was looking forward to a night on her own to do laundry and order food when Lorelai was away for the night, but Paris and Jess crashed her party. Paris needed support and comfort from her frenemy, which at first annoyed Rory, but then Jess arrived with food.

Jess said that Luke was worried about her and told him to bring it, but it became clear that he had gathered the food on his own and brought it for Rory so he could check in on her. It’s a sweet gesture and the three ended up having a great night together full of stimulating conversation and some of the best foods mentioned in the series.

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

When Jess was back in town for the promotion of his book, 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 with her through their conversations. 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 future and didn’t think she was happy on that path. His intentions were pure and selfless.

The Sweet Notes Jess Left In Rory’s Margins

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

Rory couldn’t help but fall for Jess when she read the notes he left in the margins, showing off Jess’ smartest quotes and highlighting their shared interests. It was one of the first times Rory connected with a peer 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.

He Was Planning Their Future When Rory Got Into Yale

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 began shedding some of his tough layers. In one adorable instance, he came clean about looking up how far Yale was 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 went to the Ivy League institution. This wasn’t the only time Jess let his guard down for Rory, but it was one of the most endearing because he paid attention.

Jess Convinced Rory To Go Back To Yale

After Rory dropped out of Yale and began spinning out, Jess was the one who finally got 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 anything less. The effect they had on one another was mutual. As Jess told Rory, he couldn’t have published his book without her support either.

RELATED: 5 Reasons Jess Was Perfect For Rory (& 5 She Should Have Been With Someone Else)

Jess grew out of being an irresponsible, misunderstood teenager and into someone capable of loving Rory healthily and helpfully. Jess consistently proved himself to be the perfect boyfriend when he and Rory were not together because of the effect she had on him.

He Encouraged Rory To Write A Book When She Was Lost

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 visited her. 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 extramarital affairs, 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 and it felt like the two were were soulmates by the Gilmore Girls revival.

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 was the one for him.

RELATED: 5 Characters Who Got Fitting Endings (& 5 Who Deserved More) On Gilmore Girls

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 and Rory will eventually get fitting endings.

Times Logan Was The One For Rory

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

Logan Went Against His Family To Support Rory

Fans who felt Rory and Logan had a perfect relationship weren’t alone; Emily and Richard thought that way too. However, the Huntzbergers felt differently. They believed 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 his family disapproved.

The Omnia Paratus Scene That Changed Their Relationship

The Life and Death Brigade 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.

RELATED: 10 of Logan’s Most Romantic Quotes On Gilmore Girls

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. While they weren’t a couple quite yet, it was a seen with unintentional romantic quotes.

Logan Knew How Special Lorelai Was To Rory

Anyone determined to be in Rory’s life long-term had to understand how important Lorelai was to her. Logan was one of the few who understood it. When Rory was mad at him, he sought out Lorelai’s help in talking to her. 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. This meant Logan and Rory’s relationship timeline was about to accelerate. 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.

Logan Was By Rory’s Side 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. Lorelai luckily had Rory and Logan by her side but it was also an important episode for her and Luke.

Logan 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 needed at this time. Logan knew that Rory’s family came first and stayed with her during a difficult time.

He Gave Rory A Thoughtful Goodbye Gift

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 toy rocket. Not a plane ticket to London or a bouquet of roses… 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. Logan easily became one of Rory’s best love interests after this.

The Proposal

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 decided not to stay together, they eventually rekindled their romance in the revival while Logan lived in London. The only problem was that Logan was 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, which is why so many fans think Rory and Logan should have ended up together.