I will start this essay by acknowledging my own bias in this conversation: I’m Zosha, and Logan is the best Rory boyfriend on Gilmore Girls.
At its heart the show was always about family, class, and the indelible ways those things inform our lives. But there were also boys and men, who each brought something different out in the incredibly close mother-daughter duo of Lorelei (Lauren Graham) and Rory (Alexis Bledel). It was inevitable that teams would form around pairings, particularly for Rory, and although it drove creator Amy Sherman-Palladino a little crazy, she acknowledged that “people love romance.”
Of the three relationships in Rory’s life, there was no contest who was the best. Really, the “versus” rivalry is a false one. The Gilmore Girls may be more than their men, and Gilmore Girls more than its love stories, but in the end, we’re all just pawns in Sherman-Palladino’s sick, sick game.
Longtime fans of Gilmore Girls will note that historically Rory had three prominent boyfriends during the original run: Jess, Logan, and Dean. But the game of “Best Rory boyfriend” is not a three-man race, so much as it is two men and a very tall baby. Dean is less of a competitor in these games and more the malformed first pancake you use to test the griddle temp but then inexplicably lose your virginity to years later.
Time and again Dean disappoints, whether it’s pressuring Rory to say she’s in love before she feels it or cheating on his wife. When he and Rory break up he acts sweet to her all while threatening Jess behind the scenes, explicitly because he knows Jess can’t do anything about it. By the time Dean makes his final appearance on the show he’s only there to be a jerk and get in Luke’s head. He’s either sweet and innocent, or dopey and possessive; either way he’s played himself out of a win here.
Let’s go to the tape: Jess and Rory had an instant heat to it, as two reserved nerds who love books. He saw and admired her impressive intellect; she saw through his whole act and called him on his bullshit. Their cutest moments would happen when she was dating boyfriend-at-the-time Dean, The margin notes, the conversations, the bringing her a feast of Luke’s completely unbidden. Ultimately that chemistry was powerful enough the two eventually had no choice but to act on their feelings for one another, it was getting rude (even to Dean, a human wet saltine).
But once Dean is out of the picture and Jess and Rory can finally date unencumbered by any sort of flippy-haired tree, their relationship is far from rosey. In fact, it’s bad! There’s simply no way around this.
Whatever spark they had seemed confined to their shared interests, and season 3’s Jess is actively uninterested in expanding their connection beyond that. Most of their relationship is spent one of three ways: not talking, strained talking, or making out. Rory cajoles him into doing something with her (like meeting her grandmother); he acquiesces but is still kind of an ass about it. Jess worries about Dean, and Rory tries to get him to remember that she’s trying to be friendly with her ex and his furrowed brow.
It’s not that anything Jess does is unforgivable — he’s 17! He’s definitely not a strong communicator as a boyfriend, and is even less interested in ever being vulnerable. But it’s certainly not fun to be around, particularly as a girlfriend. In season 3’s “Face Off,” their communication falls apart, leaving both of them sullen and unable (or unwilling) to broach any of the obvious cracks under their feet. Instead they sheepishly paper over concerns starting to drill through their hearts, a pattern that comes to define their brief relationship.
It’s true of almost any love triangle that your OTP says a lot more about you than it does about the people within the relationship. Jess likely appeals to those who love a bad boy, a person struggling to be their best when every deck seems stacked against them. He and Rory clearly care for each other in a lot of the ways that matters. I don’t begrudge the kid. But unlike Riverdale, I don’t think anyone should be doomed to date the people they dated in high school for the rest of their lives.
You can chalk it up to circumstances — almost as soon as Rory and Jess were together and WB announced a spinoff for his character to go get to know his estranged father. Maybe the powers that be had to tank his character so he could leave for his (ill-fated) spin-off. Either way, the text just doesn’t support Jess being a good boyfriend.
Like I said, I get the appeal of Jess among the constellation of Rory’s boyfriends (and certainly we can all join hands in judging those who root for Dean). In many respects Logan’s and Jess’ characters overlapped: Both were incredibly intelligent, even sharper when they felt threatened; they challenged Rory to grow beyond the bounds of what she thought she was capable of and dream bigger; they were prone to being assholes when the vibes were off.
But within the seven seasons of Gilmore Girls, Logan is the one who actually puts in the work as a partner. While him and Rory have a rocky start — an early prototype of the now much-more-common “casual” relationship that one side secretly hopes is more — even their fights are more productive than her and Jess’. The most egregious strike leveled against him by fans was their painful fight (after Logan gets jealous at a dinner with Jess) in “Let Me Hear Your Balalaikas Ringing Out,” after which they don’t talk for a few weeks. The initial argument is nasty, with neither party really at their best. He assumes they’d broken up, she thinks of it as a “hiatus” (at least, until she hears that he believes otherwise). Once they’re back together and Rory finds out he slept with his sister’s friends during their break, she accuses him of cheating on her.
Logan disagrees, but he doesn’t shy away from the conflict: he understands why the information would wound her (it’s why he didn’t play it up!), but in his mind it’s truly not cheating — he genuinely thought they were broken up, so he was just depressed and rebounding. He makes space for her feelings in a way she won’t, and is unable to until he’s in the hospital recuperating from a near-fatal Life and Death Brigade stunt. (If this article is how you’re choosing to enter the Gilmore Girls fandom just know it’s not as strange as it reads.)
Though Logan was initially set up as a spoiled heir, it’s those incredible communication skills and a big heart that make him different. He pushes through trepidation about a serious relationship with her to find that he actually does want one, and joyfully pulls out all the stops whenever he can. Whether it’s acknowledging she’s having a hard time processing family stuff at a work party he’s throwing or jumping into action to help her get the college paper out, he’s a dream partner for the day-to-day stuff. As a Huntzberger, he has his petulant blindspots, but hey, so does Rory, as a Gilmore.
Ultimately, Logan benefits in the main way Jess was held back: Logan’s not a brash 17-year-old kid, he’s a reckless 20-something on the precipice of coming into his own. So they get to make much more adult choices together like sleeping together, moving in, getting back together with something more than a shrug. And over time, he lives up to the promise, proving to be a considerate, intelligent, and mature boyfriend. He is exactly the sort of boyfriend character I like to see in the world: part of a dynamic relationship, not perfect but always making sure his partner’s needs are being met. Logan earned the mantle of not only Rory’s best boyfriend, but also being able to sneak a penis joke into the WB in the 2000s (depending on how you interpret Matt Czuchry’s line reading there).
No matter who wins … we lose
But then again, what did Logan’s two years of character growth have when pitted against A Year in the Life?
What started as a sweet thing (more Gilmore Girls!) quickly soured into … actually watching Gilmore Girls: A Year in a Life. Pretty much no one comes off great in the Netflix revival. The four episodes are turgid and unfocused as they struggle to recapture the Gilmore Girls magic. While Amy Sherman-Palladino said the controversial seventh season of the show would be canon, she didn’t watch it. And much of the show’s timeline reflects a creator uninterested in diving into where the characters were then, with Luke and Lorelei still idling down the aisle, and Rory being published in The New Yorker without having figured much out professionally since we last saw her.
Growth for almost every character seemed nonexistent, but in particular Logan. Having broken up with Rory in the penultimate episode, he’s apparently spent the last few years deteriorating: In A Year in the Life, he’s a busy professional who still parties with his Life and Death Brigade friends when he’s able, and cheats on his fianceé with Rory. He’s still clever and full of banter, but (like much of the revival) it all takes on an air of tragedy. This isn’t the match we once knew, but rather a bad plot dressed up like a media heir.
Take this however you want, but it felt like character assassination. Worse yet, I was aware of how my rejection of the new character came off. Now I was the one leaning into a selective memory when it came to my boyfriend of choice. The text no longer backed up a lovely and loving relationship, but instead something that was doomed and gutted of what once made it so compelling. It’s a devastation not unique to Gilmore Girls when TV reboots are a dime a dozen. But there was only one group of people who could really understand what I was going through: Jess fans.
A Year in the Life is the sort of revival that’s so odiously bad it makes it hard to revisit the sweetness of the original. And as part of that, it forces us to acknowledge the twisted way the Palladinos were always filtering the Gilmore Girls narrative for themselves: not as characters but echoes of the past. Amy Sherman-Palladino said there were four words she always envisioned to end the show. When A Year in the Life finally showed us them — “Mom?” “Yeah?” “I’m pregnant.” — it solidified the guardrails Gilmore Girls had always been on. This was always going to be a show about how Rory’s choices mirrored her mother’s, from the final pregnancy beat back to the types of men she’d choose between.
It’s impossible to unsee the way the show is constantly setting her up with her own version of Christopher and Luke’s class differentials: Tristan and Dean, then Jess and Logan. And you start to see this play out across all of the Palladinos’ shows. The Marvelous Mrs. Maisel can’t let Midge be vulnerable, so it instead makes her impenetrable. Bunheads would rather torpedo towards a Woody’s Roundup conclusion than give the story some sort of closure. And when big changes need to happen on Gilmore Girls they happen because a character tanks. Jess was wanted for another show so he suddenly doesn’t care about taking care of Rory; Logan was Rory’s version of Christopher so he regresses into a life of privilege; even Luke has to do a total 180 and doubt his and Lorelei’s relationship once he finds out he has a daughter.
Through that lens, the problems of Gilmore Girls come into sharp focus, and extend much further beyond season 7 changeups or good boyfriend material. The truth is, both Jess and Logan could likely make ideal partners, were they not hamstrung by Sherman-Palladino’s larger machinations on what they needed to be, and instead were allowed to just be true to the characters they became. After all, one of the few bright spots of A Year in the Life is Jess’ seemingly very-real glow-up, coming across as a man who has led an unorthodox but much more caring life than the ne’er-do-well teenager he once was. Logan, unlike Christopher, is in a much better position to step up in the open-ended finale of the revival.
It’s time both sides came together, acknowledging that if Gilmore Girls feels worth revisiting at all, it’s because it’s worth more than its boyfriends or endgames. At its best, the show was a masterclass in imperfect characters attempting to love each other in spite of that. The show can get a bad rap for protagonists that come off as spoiled or selfish, childish or unthinking.
But when Gilmore Girls is peaking it’s in exploring how these choices are informed by a characters’ past; the entire premise of the show is characters challenging themselves (and, yes, often failing) to deal with hard situations to the best of their abilities. Almost every relationship is messy and flawed, but unlike other shows it doesn’t think flawed love is worth giving up on. Jess, Logan, Rory, Emily, Richard, Lorelei — they’re all marvelously consistent and contradictory, all at once. As they bounce off each other at Luke’s or Friday night dinners, it’s not a question of simple misunderstandings so much as it is deep-rooted differences in how they show that love. For some, that’s Jess and his cool street smarts; for others (me), it’s Logan and his constant caring. Either way, I think it’s a pull strong enough to return to Stars Hollow again — and to blot the revival out from my life entirely. The heart wants what it wants!