Rory Gilmore's Love Interests: Who Was Mr. Right?

Welcome to MsMojo, and today we’re exploring the question that “Gilmore Girls” fans still have a lot of feelings about. Which of Rory’s boyfriends was the best?

The Many Romances of Rory Gilmore

Was Dean the first boyfriend who should have been the last? Would Jess’ bad boy attitude soften over time? Did Logan have the upper hand because he and Rory came from the same world? Aside from April Nardini, there’s one topic that’s sure to make an entire section of the “Gilmore Girls” fandom want to throw hands. Debate over who was Rory Gilmore’s perfect match still rages to this day. While none of her boyfriends, crushes, and potential suitors were perfect, we’re going to give each one their due to decide once and for all who should have been the one.

Dean Forester’s Pros

When we first meet Dean, he’s a nice new kid from Chicago who is immediately charmed by Rory’s enthusiasm for reading. Although he initially mistakes her inexperience for disinterest, he quickly falls for her. He may not have been as smart or ambitious as Rory, but Dean was generally supportive of her aspirations. His best quality, though, was how giving and attentive he was. There was a sweetness to him that made us root for him at first. The guy even built her a car for her birthday. As far as romantic gestures go, that’s hard to beat.

Dean Forester’s Cons

Although Dean is devoted to Rory, it sometimes verged on too much. As he felt her slipping away, he became more insecure in their relationship and acted out in anger and jealousy. It’s not as if Rory handled it well either. She lied about her closeness with Luke’s nephew, Jess Mariano, further eroding their trust. A shared commitment to mess led to their doomed second attempt at a relationship and the breaking up of Dean’s marriage. Ultimately, he just didn’t fit in Rory’s world once she went to Yale. The prevailing perception of Dean among fans seems to be either outright hostility at his flaws or an acknowledgment that he was a good first boyfriend for Rory but not her endgame.

Tristin Dugray

Although he didn’t stick around long, the Chilton student spent much of the first season teasing Rory. Of course, this turned out to be a cover for his crush on her. While Tristin’s teasing verged on the cruel at times, he eventually starts to show Rory the real him. Could they have had a future together? Unfortunately, we’ll never know. Their enemies to lovers storyline was cut short when Chad Michael Murray decided to leave the show after the first season. Some fans have even theorized that the snobbish rich boy with a softer side storyline was later reconfigured for Logan Huntzberger but more on him later.

Jess Mariano’s Pros

The second season sees Rory falling for Luke Danes’ nephew, the surly, sullen, and sharp-witted Jess. Unlike Dean, Jess was Rory’s intellectual equal, and he shared her interests in literature and creative expression. Throughout the series, they inspire each other to be better. When Rory decides to leave Yale, it’s Jess who is able to give her the tough love she needs to hear. At the end of the day, fans love Rory and Jess for their incredible chemistry. The sparks are constantly flying between these two, even when they’d rather not admit it. It’s the push and pull that makes them so irresistible.

Jess Mariano’s Cons

Jess’ bad boy attitude has its drawbacks. From the very beginning he has an issue respecting boundaries. This culminates in an unforgivable moment in season 3 that sees him trying to pressure Rory into a more physical relationship. He’s often mercurial, disrespecting the people Rory cares about because he doesn’t feel like being nice, even for her sake. Jess also seems to find it unnecessary to let people in or communicate how he’s feeling or what he’s doing. He even leaves Stars Hollow, and Rory’s life, without saying goodbye. The timing never seems to line up for these two. When Rory had her life together, Jess was a mess. When Jess finally seems like he’s on the right path, Rory is lost in an identity crisis. This might be a case of mismatched growth.

Marty: The Naked Guy

Some of their first interactions had the makings of a rom com meet-cute. Marty was a working class Yale student who felt out of place due to his social and economic standing. That feeling only intensifies when Rory finds him lying naked on the floor of their dorm. Alas, it isn’t meant to be. Their friendship doesn’t last that long, as Marty’s feelings for Rory clearly aren’t reciprocated, and he quickly leaves the picture. His final arc on the series sees him pretending not to know Rory in front of her friend Lucy, who is also his girlfriend. That doesn’t stop him from hitting on Rory later though. Like many things that happened in the last season, it’s totally weird and really out of character. Still, Marty never had a chance.

Logan Huntzberger’s Pros

Where Rory is someone who frequently worries too much about her place in the world and what she wants to do with her life, Logan is the perfect antidote. He is as supportive of her happiness as he is her ambitions. He even stands up to his family when they ambush Rory at family dinner. Perhaps most importantly, despite her skepticism of him and the posh, moneyed world he represents, he respects Rory’s mom, Lorelai. While he can be an immature and often reckless rich boy, Logan is charming, charismatic, and genuinely eager and willing to change for Rory. What’s more, he was an equal match for her on practically every level. This duo has true power couple potential.

Logan Huntzberger’s Cons

On the surface, it’s easy to dismiss Logan. He’s a snobby rich kid with a rude, elitist family who doesn’t feel the need to be responsible or mature. His entitlement is everything Lorelai hates about her parents’ world. You could make the case that Logan was partially the reason Rory stole that yacht and ended up dropping out of Yale for a while, though Rory herself bears the brunt of the accountability there. Although Rory leaves Logan at the end of the original series finale, their relationship in the 2016 revival series sees the two sneaking around behind their partners’ backs. We could consider this a major step backward for both their characters, but it’s a step backward they’re both making together.

Oh, we almost forgot Paul! Unfortunately, Rory did, too.

Logan Is Mr. Right

While many fans are certain that Jess is The One, this might be a case of wishful thinking. Their parallel arcs just made them better off as friends. By the end of the series, only one suitor truly fit Rory for the journey she’d been on, and the person she was: Logan Huntzberger. Over several seasons, Logan grew in a way that made him a match for Rory. He is the only boyfriend who showed that he was willing to be what Rory needed, and his own flaws complement hers. It helps that of all her love interests, he was the only one who never puts her on a pedestal. To Logan, Rory is a complete human being, with many qualities he admires and aspires to equal, and faults he doesn’t hesitate to call out. Their relationship is a true partnership in a way none of her others were. That’s not to say they weren’t a mess in the show’s limited revival season. Maybe someday we’ll get an update that sees them learn from their mistakes.

You’ve heard our reasoning. Who gets your vote for Rory’s best match? Tell us in the comments.