The Guys of ‘Gilmore Girls’ Ranked, From Dean to Logan


Over Gilmore Girls’ seven-season run, the titular women have quite a few romances. The men Lorelai (Lauren Graham) and Rory (Alexis Bledel) date have caused a lot of controversies and have become part of the zeitgeist, but whether you’re “Team Jess” or “Team Dean” is really just scratching the surface of the debate. These are the Gilmore girls’ most important romantic partners, ranked from the worst choice to the best, including Emily (Kelly Bishop) since she is, of course, a Gilmore girl, as well.

Gilmore Girls

A dramedy centering around the relationship between a thirtysomething single mother and her teen daughter living in Stars Hollow, Connecticut.

Release Date
October 5, 2000

Main Genre


The CW

Honorable Mention: Paul from ‘Gilmore Girls: A Year in the Life’

This may be the first time Paul (Jack Carpenter) has ever gotten an honorable mention (or even a mention, at all.) Paul isn’t introduced until the lukewarm Gilmore Girls reboot, A Year in the Life. With the original series ending with Rory rejecting Logan’s (Matt Czuchry) proposal, it was easy to hope that in the time between the series finale and the reboot’s premiere, a new front-runner for the coveted prize of Rory’s heart would have taken the lead.

Unfortunately, the only new face introduced in the interim is Paul: a guy whom Rory cannot seem to remember she’s dating. It’s pretty clear, based on Rory’s opinion of Paul, that he’s not the one. And, while Rory is more than entitled to just not be interested in someone, Paul’s very existence begs the question: is Rory only invested in relationships that cause pain and worry? Paul seems like a sweet, committed guy, and yet, she finds him too boring to even remember. Either way, while he didn’t stand a chance with Rory, he still deserves to be acknowledged (and even get his name remembered.)

8. Dean Forester

Played by Jared Padalecki

Passionate members of “Team Dean” are sure to be horrified at Dean’s (Jared Padalecki) firm standing in last place. Sure – it’s clear why Dean has such appeal. He starts out as the handsome new guy at school, and he’s head over heels for Rory from day one. But, we meet Dean when he’s a high schooler, and he has a lot of growing to do before he becomes who he truly is. And who he truly is sucks. He pines for his ex on his wedding night, he cheats on his wife, Lindsay (Arielle Kebbel) with Rory, and then he proceeds to guilt-trip and yell at Lindsay when she may accidentally find out about his indiscretions. The list of reasons why Dean isn’t a good pick for a partner goes on and on, and that’s why he’s last on our list.

7. Jess Mariano

Played by Milo Ventimiglia

Those who aren’t Team Dean are usually Team Jess. Jess (Milo Ventimiglia) appeals to those who are fond of the brooding bad boy who’s deeper and more complex than other guys. But, folks who are vehemently Team Jess have managed to overlook some pretty damning evidence. Jess was very difficult at the start of their relationship. He later tries to pressure her into sex out of nowhere upstairs at a party, then promptly vanishes from Rory’s life without so much as a word. That’s enough to cause some long-lasting trauma, and Rory takes it like a champ. Sure, Jess returns many times to try to win Rory back. But, no matter what happens, Jess’s excuse for acting with cruelty and negligence seems to always be that he’s going through something that gives him the right to hurt other people through his selfishness. That’s not the kind of accountability we’re seeking for our girl, Rory.

6. Christopher Hayden

Played by David Sutcliffe

Lauren Graham as Lorelai and David Sutcliffe as Christopher walking arm in arm and looking into each other's eyes in Gilmore Girls Season 7
Image via The CW

Pretty much everyone (except Luke) was rooting for Christopher (David Sutcliffe) at one point or another. All the Gilmores, all of Stars Hollow, and pretty much all the viewers thought that Lorelai and Christopher could make it work. Christopher is Rory’s dad, and he has a laid-back coolness about him that adds to his appeal. Plus, it’s pretty clear that he always holds a torch for Lorelai. Still, while Lorelai and Chris’s undeniable chemistry persists for 20+ years and through countless major life events, so does something else: Chris’s inability to get his act together until it’s too late. And, we should really acknowledge that Chris must be, in large part, to blame for both Lorelai and Rory’s very bad dating track record.


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5. Logan Huntzberger

Played by Matt Czuchry

Alexis Bledel as Rory smiling at Matt Czuchry as Logan in Gilmore Girls: A Year in the Life
Image via Netflix

Logan Huntzberger (Matt Czuchry) may not be the greatest guy in the world, but he’s the best match for Rory out of the men she dates. These two complement each other well and (usually) bring out desirable sides of each other. Logan is the classic playboy, and Rory seduces him into monogamy: a tale as old as time. This change of heart adds to Logan’s desirability. The fervor with which he fights for Rory anytime the going gets tough is impressive, and the fact that he proposes on the night of her graduation seems to be further proof that he has transformed into the perfect commitment-loving partner. But, when the reboot rolls around, he’s blatantly cheating on his new fiancée with Rory, which proves that he never really changed — and nor did she. Logan has since been revealed to be the father of Rory’s child, which she announces at the end of Gilmore Girls: A Year in the Life, adding another layer of complexity to this sordid romance.

4. Luke Danes

Played by Scott Patterson

Though this may be a hard pill for many Gilmore Girls fans to swallow, Luke (Scott Patterson) is actually very lucky to be this high on the list. Luke loves Lorelai; this is for sure. But, when it comes time for Luke to really give Lorelai what she needs, he keeps coming up short. Luke is a good guy, and he’s reliable, but what good is reliability when you still end up keeping major parts of your life hidden from your partner? Not a lot.

3. Jason Stiles

Played by Christopher Eigeman

Christopher Eigeman as Jason Stiles eating dinner at the Gilmore house in Gilmore Girls
Image via The CW

Jason’s (Christopher Eigeman) (or should we call him “Digger?”) placement as number 3 among heavy hitters is sure to cause controversy. But, the list is backed up by science. Unlike some others (cough cough… Jess…), Jason acknowledges and works past his issues in order to be with Lorelai. Plus, the two have amazing chemistry. While Lorelai is in the right when she ends things because Jason is suing her father, Jason is in the right as well. He’s doing what has to be done, and that doesn’t stop him from fighting for Lorelai long after she leaves him. Admit it: if Lorelai hadn’t already moved on, Jason’s appearance at the opening night of the inn would’ve been romantic and game-changing. Digger deserved a second chance.

2. Richard Gilmore

Played by Edward Herrmann

Emily and Richard Gilmore (Kelly Bishop and Edward Herrmann) dancing at their vow renewal in Gilmore Girls
Image via The CW

Richard (Edward Hermann) is the only true Gilmore guy (that is, until Rory has her baby, perhaps.) And, he does the Gilmore name proud. Richard is a wonderful patriarch and a stable, committed husband to Emily. Sure, he has a pretty big indiscretion that causes a serious rift in their relationship, and he isn’t always the easiest person to be with. But, Richard sees Emily for who she really is, and he stays truly in love with her for his entire life. He even has a vow renewal after their time apart that he treats like a real second wedding and makes an incredibly thoughtful and romantic toast. These two are meant to be, and Richard is a real keeper.

1. Max Medina

Played by Scott Cohen

Lauren Graham and Scott Cohen as Lorelai Gilmore and Max Medina, talking seriously in Gilmore Girls
Image via The CW

None of the Gilmore Girls men is truly perfect. But, Max Medina (Scott Cohen) gets pretty close. Max is a true romantic, and he fights so hard for Lorelai that she never has to wonder what his true feelings are or if he’ll be there for her. Lorelai really screws Max over in the end, and even though she may have her reasons, he definitely deserves better. Lorelai only has to dream up the idea of 1,000 yellow daisies, and he makes sure she gets them. What more could a (Gilmore or otherwise) girl ask for than that?

Gilmore Girls is available to stream on Netflix in the U.S.



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