Real Gilmore Girls fans know the crux of the show isn’t about Rory and Lorelai, but about Lorelai and Emily. It’s about issues of class, generational trauma, and the vast complexities of the mother-daughter relationship as much as it is about the wacky happenings of small-town Connecticut where everyone just so happens to make rapid-fire pop culture references in normal conversation.
Nevertheless, the ranking of Rory’s boyfriends has long been the show’s most hotly debated topic, with dozens of articles and Reddit scholarship on the topic, all of which resurfaced for the Gilmore Girls: Year In The Life Netflix special in 2016. It’s been more than two decades since the show’s premiere, and if you bring up Gilmore Girls in a crowded room, you’ll still see a chorus of people swoon, clutch their hearts, and utter, “Jess!” to nobody in particular.
Obviously, there is a right and wrong answer (Logan was the best boyfriend for her, Dean is a psychopath), and we’ve taken it one step further and broken down a definitive ranking of every man on Gilmore Girls. Because for a show primarily about the relationships between three generations of women, there’s an annoying amount of men roaming around Stars Hollow — maybe even more than women?!
Dean Forester 0/10
Despite being Rory’s first boyfriend, this man is a walking red flag. From getting in fights at Rory’s school dance, to being stoked on her dressing up as 1950s housewife Donna Reed to cook him meatloaf, to cheating on his wife with Rory — he is toxic, toxic, toxic. The worst thing about him, of course, is that he thinks he’s a nice guy. Enough!
Tristan Dugray 1/10
This smooth-talking, spiky-haired prick calls Rory “Mary” (as in the Virgin Mary) when she transfers to Chilton, which is not only gross, but unoriginal. He’s also rude to Paris and pulls a textbook bad-boy move and gets into a fight with Dean at a dance. His only redeeming quality, you might wonder? He’s played by Chad Michael Murray in his 2001 prime.
Christopher Hayden 1/10
Like Dean and Tristan, Christopher has almost no redeeming qualities. A spoiled rich kid, he doesn’t help raise Rory and then sporadically comes back into her and Lorelai’s lives, promises he’ll stay, and then takes off again. He fails at almost every business venture, and even his uptight wife Shari leaves him, but he gets one point for looking kind of hot on a motorcycle.
Zack Van Gerbig 3/10
How Zack is able to bag the drummer goddess that is Lane Kim we will never understand. He can’t cook, clean, or take care of himself. He’s not that good of a guitar player! He’s only mildly cool and doesn’t understand how lucky he is that Dave Rygalski moved to California so Adam Brody could be on The O.C., because that’s the only way Lane would be with him. Let’s not forget Mrs. Kim’s unbridled disgust toward him either — you don’t call just anyone a “wild pig of filth” who will “swim in the sludge with Satan’s hell dogs.”
Jackson Belleville 4/10
Jackson and Sookie have their cute vegetable chemistry: There are no other two people in the world who would sleep with their vegetables to make sure they don’t get frosty overnight. But never forget that this man lied to her about getting a vasectomy — points had to be docked!
Max Medina 5/10
Besides it being wildly inappropriate for a teacher and the parent of a student to date at a school as gossipy as Chilton, Max is actually a good teacher. He gives Rory the first D of her life, which she needed to get taken down a few notches. He probably would have been good for Lorelai too, but right before their wedding she decides she doesn’t love him, because she rejects stability over and over again. (Sorry to those who relate!)
Taylor Doose 6/10
Let’s get the collective groan out of the way. Taylor is the worst, but that freaky dude is the backbone of Stars Hollow. Basically the de facto mayor, he makes sure the town has their silly events wherein 90% of major plot points happen. Rory and Dean’s grocery store kiss and the 24-hour dance marathon where he breaks up with Rory? Thank you, Taylor!
Richard Gilmore 6/10
Sure, he has a lot of toxic masculinity and some very antiquated upstairs-downstairs ideas about the world — but this man makes Emily Gilmore happy and ultimately only does the best for his family, and for that we are in awe. Plus, we love his little bow ties.
Michel Gerard 7/10
Name a worse employee than Michel, who is constantly rude to guests and refuses to do basic job duties. But we appreciate his love of chow chows and let’s face it: Someone needs to roast Lorelai every once in a while, who doesn’t do that much work at the Independence Inn either. (Literally — Sookie does everything!) At least they could finally make him openly gay in the Gilmore Girls: Year In A Life Netflix miniseries.
There’s something immensely comforting about flannel- and backwards hat-wearing Luke Danes, the only attractive adult male in Stars Hollow. He might have a secret daughter who is smarter than him, not know how to express his feelings, and throw adult temper tantrums, but this king is always there, giving Lorelai the safety and consistency she needs to complete her character arc, so we’ll allow it. Plus, he built her a chuppah and made her an ice skating rink! A man in men’s business.
Dave Rygalski 8/10
Dave gets major points just for being played by Adam Brody, but he’s also the sweetest boy on Gilmore Girls. This king pretends to be in a Christian rock band, eats Mrs. Kim’s fake egg sandwiches, and plays at church just to gain Mrs. Kim’s approval because he has a massive crush on Lane! He also doesn’t drink soda because the carbonation “freaks him out” — he’s so gentle. It’s too bad Brody had to go be Seth Cohen, but we like to think that in an alternate universe, Lane moves to Orange County and starts a band with Seth and they fall in love forever.
Logan Huntzberger 8/10
It’s a controversial opinion, but Logan is Rory’s best boyfriend. Obviously, our hearts will always be with our little literary bad boy Jess (more on this soon), but Logan was by far the most compatible with Rory. Logan is the only boyfriend who can give Rory the East Coast media elite life she wants, and as much as we all wish Rory would move to Philly and run a lit mag with Jess, we know that girl is going to get a staff writer job at New York Mag and live in the Huntzberger penthouse, or maybe in Park Slope if she has a bohemian-lite phase. Plus, Logan’s Life and Death Brigade antics at Yale aren’t not hot. Rory needs to loosen up, and nobody else could get her to jump off five-story scaffolding wearing a ball gown and carrying a parasol.
Jess Mariano 9/10
Logan may be Rory’s best boyfriend, but Jess is why half of us watched the show at all. Jess’ hotness is undeniable: his leather jacket, his tortured, sad boy attitude, how his flirting style is gifting dog-eared copies of Moby Dick, and spontaneous trips to Washington Square Park. It can’t be denied: Jess is the blueprint. Even though he ultimately abandons Rory and moves to California without telling her, he makes up for it by convincing her to write a book in the Netflix miniseries.
What more could you want in a man than drive, passion, and consistency? Kirk’s got it all: He can write, direct, and star in avant-garde performance art that rivals David Lynch; he can carry the expansive vocal range of Tevye in Fiddler On The Roof; he has had literally every job that exists in Stars Hollow. He’s a man of the people, and the people are lucky — especially Lulu. It’s just too bad he and Lorelai never dated.