During the seven seasons that Gilmore Girls was on The CW, fans watched Lorelai Gilmore (Lauren Graham) and Lorelai Gilmore Jr. (better known as Rory Gilmore, played by Alexis Bledel) deal with many challenges in their friendships, careers, and love lives. But while diner owner Luke Danes (Scott Patterson) is generally regarded as the boyfriend that Lorelai was meant to be with, Rory’s matches are a little more hotly contested.
To recap, there were three great loves of Rory’s life during the show’s initial run. First up was Dean Forester (Jared Padalecki), the floppy-haired boy-next-door (figuratively, not literally) who fell for Rory just as hard as she fell for him. Then there was bad boy Jess Mariano (Milo Ventimiglia), Luke’s wayward nephew who was sent to Stars Hollow by his mother in a last-ditch effort to correct his bad attitude and permanent scowl. Finally, Rory went to Yale and met rich kid Logan Huntzberger (Matt Czuchry), heir to a fortune and a newspaper company, who gets his kicks from the risky exploits of the Life and Death Brigade, a secret society at Yale.
Before getting into why, of these three, Logan was clearly the best boyfriend for Rory, here are a few honorable mentions of the guys with whom Rory had romantic brushes, but who never attained boyfriend status. There was Rory’s spoiled, obnoxious Chilton schoolmate Tristan DuGray (Chad Michael Murray), who spent most of his screen time getting on Rory’s nerves, but who eventually revealed that he had feelings for her. Tristan might have even become a boyfriend eventually, had he not been shipped off to military school (a.k.a. One Tree Hill). Then there was Marty a.k.a. Naked Guy (Wayne Wilcox), who earned his nickname when Rory found him passed out naked in the hallway, and who tried to be friends with her until it was clear that “friends” was all they were ever going to be.
With Gilmore Girls: A Year on the Life now available on Netflix, here’s a look back at the great loves of Rory Gilmore’s young life.
Runner Up #2: Dean Forester
Not many people end up marrying their high school sweethearts, and Rory’s relationship with Dean is a perfect example of why that is. While their early days of dating were sweet enough to give viewers cavities, it wasn’t long before they started to hit speed bumps. In the season 1 episode “That Damn Donna Reed,” it was revealed that Dean and Rory’s idea of a perfect married life didn’t quite match up; Dean liked the idea of “a wife cooking for her husband” in a ’50s-style marriage, which was jarring for Rory, who came from a household of junk food and take-out and was already planning hard for her career. Dean also demonstrated an insecure and possessive streak, breaking up with Rory for not immediately responding to his “I love you” with “I love you, too,” and getting in a fight with Tristan at a Chilton dance.
Dean’s clingy tendencies came to the fore when Jess came into the picture and Rory began falling for him, though to Dean’s credit he eventually broke up with Rory so that she could be with Jess. Dean and Rory’s final attempt at a relationship came in season 4, when Dean was already married to his other high school sweetheart, Lindsay. Long story short: Rory lost her virginity to Dean, Dean got divorced, and then Rory and Dean broke up anyway. What a mess.
Dean was definitely the best fit for school-aged Rory, who was romantic and often painfully naive, but as both characters grew older it was clear they were a poor fit for one another. Rory wasn’t the kind of girl to make her boyfriend the center of her life, and the chances of her becoming a doting housewife were slim (in any case, Dean had a doting housewife and ended up cheating on her). Rory’s relationship with Dean was a valuable part of her character growth, and the affair in particular was an important character arc that exposed Rory’s biggest flaws and helped her on a path to greater maturity.
Runner Up #1: Jess Mariano
If Dean was the boy next door, then Jess was that other most dreaded teenage girl fantasy: the project. Also known as a “fixer-upper,” a project is a guy who is tortured and angsty and angry, but who just needs the right girl to come along and “fix” him (see also: Beauty and the Beast, Fifty Shades of Grey, Pride and Prejudice, and a significant percentage of all romance literature). Essentially, Jess represented the next stage of Rory’s growth from a sheltered small town girl into a woman: he wasn’t a wide-eyed, floppy-haired schoolboy, but he also wasn’t a fully-grown and well-adjusted adult (not during their relationship, anyway).
Jess’ dreamboat status is understandable: he was from out of town; he acted like a thug but was extremely well-read; he skipped school; he wore a leather jacket; and when times got tough, he hit the road and went to places like Los Angeles and New York. His relationship with Rory was, understandably, a bit of a mess, but Jess did eventually manage to get over himself and pull things together. He published a book, ended up on good terms with Luke, and - most importantly - gave Rory the kick she needed when he came back and found that she’d dropped out of university and become an Emily Gilmore-in-training.
In fact, Jess is the runner-up here not because Rory is too good for him, but because he ended up being a little too good for Rory. Rory “fixed” Jess in the way that a person might try to fix a broken tap because they don’t want to pay for a plumber: inexpertly, and ultimately doing more harm than good. Ultimately, Jess worked things out for himself and ended up maturing the most when he was apart from Rory. When they eventually saw each other again, Rory kissed Jess in a premeditated attempt to get revenge on Logan, and Jess was appropriately annoyed at discovering he’d been used by the girl he used to love. There may be a perfect partner out there for Jess, but it’s not Rory.
The Best Boyfriend: Logan Huntzberger
Let’s get this out of the way: Logan is kind of a jerk. Then again, so is Rory. Despite Lorelai’s frequent proclamations that her daughter is the nicest, smartest, most perfect creature on the face of the earth (actually, this might be part of the problem), Rory has definitely had moments of being self-centered and spoiled and irresponsible. After all, she wouldn’t be such a relatable character if she was too perfect.
Logan made a poor first impression when he ran into Rory and Marty and spoke to Marty like he was a servant (which, Logan would later argue, he was). Rather than falling in love at first site, Logan paid little attention to Rory and didn’t even remember her the next time they met. However, between Rory’s investigative reporting into the Life and Death Brigade and Logan’s token position at the Yale Daily News, the two soon grew closer and Logan came up with an affectionate nickname for Rory: “Ace.”
Though Logan had a reputation as a notorious playboy, it’s notable that he didn’t pay much attention to Rory until she began scolding him for the way he treated Marty - perhaps because Logan was so used to people sucking up to him. In any case, he fell for her personality rather than her pretty face. In him, Rory found her match in more ways than one; not only did Logan have a quick wit and a wicked sense of humor (with Dean and Jess, Rory had to do a lot of conversational heavy lifting), he had also mastered the art of fast talking, making him a comfortable fit for a Gilmore girl. His friends Colin (Alan Loayza) and Finn (Tanc Sade) were also an added bonus, with the three of them forming a comedy trio that was funny and obnoxious in equal measure.
Like Dean and Jess before him, Logan is very much a classic romance trope: the hedonistic playboy who is so dazzled by the romantic heroine that he agrees to go exclusive. Logan has easily the most businesslike mind of all the boyfriends, even when it comes to romance. When Rory says she no longer wants to casually date him, he interprets it as an ultimatum and makes an immediate counter-offer of exclusivity. His cool-headedness was a valuable foil for Rory’s flashes of irrationality, and he was able to weather the toughest hurdles of their relationship, including Rory getting them both arrested for stealing a boat.
While some fans were unhappy with Logan’s acceptance of Rory’s decision to drop out of Yale (compared to Jess’ intervention), there’s a certain merit in the fact that Logan always treated Rory like an adult, capable of navigating her own crises and making her own decisions. During his early appearances on the show, Logan was beloved by Emily and Richard Gilmore but got off on the wrong foot with Lorelai, which didn’t exactly help endear him to fans (especially after he stole one of Richard and Emily’s trinkets, and seemed ready to let the maid take the blame).
In many ways, each of Rory’s boyfriends was the perfect boyfriend for her at the time: Dean was the puppy love boyfriend; Jess was the angsty teen boyfriend; and Logan was the coming-of-age boyfriend. But while Logan and Rory’s relationship may have had fewer dramatic highs and lows, it also weathered a lot of bumps in the road and survived, with the two of them only breaking up when Rory (wisely) declined to move to California and marry Logan, at the end of the show’s much-maligned seventh season.
Amy Sherman-Palladino has said that Logan’s character was based on Rory’s good-natured but unreliable absentee father, Christopher (David Sutcliffe), explaining that, “We wanted Rory to date her father. Every girl has a father issue, and Logan was Christopher. Logan was charming, smart, and not quite the dependable soul that you need.” Certainly Rory’s adventures with Logan and the Life and Death Brigade are reminiscent of the flashbacks to Lorelai and Christopher’s youth, but Logan always seemed to have his feet a little firmly on the ground than Christopher did. Speaking to EW, Matt Czuchry disagreed with Sherman-Palladino’s comparison of Logan and Christopher, saying:
A boyfriend who wants his girlfriend to be the best person she can be, rather than the best girlfriend she can be, is a worthy boyfriend indeed.
“I saw this character as somebody who is going to push Rory to be the best that she could possibly be in her personal and her professional life, and to live life in this kind of carpe diem way… That’s always the way that I came at it."
Dean, Jess and Logan are all set to return in Gilmore Girls: A Year in the Life. Will Logan still be the best possible suitor for Rory, or will time have changed things? You can find out by watching the Gilmore Girls revival on Netflix now.
